10 Amazing Destinations for Solo Travelers

One thing I get asked about a lot is solo travel. I hear a lot of “I could never do that. I am not brave enough.” I don’t consider myself to be brave or particularly adventurous to be honest. So why do I travel solo? I do it because I don’t have someone to travel with regularly and I refuse to sit at home and let life pass me by while I wait for a travel companion that may never come.

To date, I have traveled on my own a couple dozen times and have some amazing and funny memories from these trips. I have found a peace in traveling solo, problem solving on my own and not having to please anyone else along the way.

If you find yourself contemplating taking a solo trip but are not sure where to start, I have some ideas for you! Below, I list 10 amazing destinations for solo travelers.

Three Things to Consider Before Booking a Solo Trip

In general, there are three things in particular that I consider before booking a trip as a solo female traveler. They are:

  1. Is the destination “safe” and how does the country treat women?
  2. What is the native language and will I encounter people on a regular basis who can speak some English?
  3. What is the transportation situation? Is renting a car or driver necessary or is public transportation easily accessible and reliable?

10 Amazing Destinations for Solo Travelers

Hawaii, USA

I know that Hawaii doesn’t seem like it would be an amazing destination for solo travelers but it is my favorite place to go as a solo traveler. I have been to Hawaii four times, three times solo. Yes, you will be surrounded by lots of couples and families. However, there is plenty of beach and pool space for everyone.

I like Hawaii because I feel very safe there. The weather is almost always nice. You will get the occasional rain shower but it means there is likely a rainbow to follow.

Renting a car in Hawaii is necessary but the rental process is easy and most of the driving is small towns and paved so it is easy. If you do go somewhere you are not comfortable driving (ie. the Road to Hana), join an organized tour and let an expert do the driving.

There are lots of restaurants with great food and the Hawaiian people are wonderful. I do encourage you to learn about the Hawaiian culture before you travel so you understand Hawaii’s history. It is key to respecting that culture while you are visiting.

Traveling the Road to Hana in Maui


I booked a trip to Greece in 2014 to meet up with some friends who were visiting there. While I spent several days with them on the island of Skiathos, I traveled through Athens, Santorini and Mykonos on my own.

I found exploring Athens and then traveling to and around the islands to be fairly easy, other than one evening when all of the ferries were canceled as I was trying to get from Mykonos to Santorini. The islands were small enough that I felt like I could walk around and see most of what I wanted to see, even without a car. There were restaurants everywhere with delicious Greek food.

Amazing Destinations for Solo Female Travelers
Oia in Santorini, Greece


Australia is a GREAT option for solo travelers. There is so much to see and do. The one thing to keep in mind is that Australia is a huge country, so you will need to pick and choose what you want to do.

I started my trip in Sydney where I met up with a couple of friends. We toured the opera house, climbed the Sydney Harbor Bridge and did the Coogee to Bondi Beach coastal walk. After a brief stop in Canberra to see a friend and her mom, I spent time on my own visiting Uluru and then scuba diving at the Great Barrier Reef.

I flew from place to place within Australia since the country is so big but when I was in different areas of the country, I was able to walk to restaurants for dinner each evening with no problems.


While I traveled to and from Croatia on my own, I traveled through the country as part of an organized tour with Trafalgar. This was my second time traveling as part of an organized tour. I was much more comfortable with splitting off and doing my own thing this time. I did a lot of my own exploring and ate meals at restaurants I wanted to try this time.

I liked that my transportation around the country was taken care of. Croatia is filled with great people and good food. It has an interesting history as well. Dubrovnik. Split. Hvar. These are just a few of the places you should check out while you are there. While you’re at it, add Slovenia to your Croatian itinerary. Slovenia is one of the most beautiful countries I have visited.


This one definitely isn’t a secret. I have been to Italy twice and definitely think it is a good option for solo travelers. Rome, Florence and Venice are all easily accessible by train. All of them are easily walkable too.

I would recommend going during the shoulder seasons (April and September or October) if you can to avoid the massive crowds. Also, make sure to plan ahead. I am all for going to a place and then deciding when to do things but Italy is not the place for winging it. If you want to check out the Colosseum, the Vatican and the museums in Florence, make reservations ahead of time so you don’t waste hours of your trip waiting in lines.

London, UK

London is my favorite international city to visit and definitely one of the most amazing destinations for solo travelers. It is also the first city I visited solo. I landed in London in 2013 to meet up with my Contiki travel group. It was my first time abroad and I never felt uncomfortable or unsafe, even with minimal travel experience.

There is so much to see and do in London. This is one city where the hop on and off tours buses are popular. I recommend joining one of them to start you visit so you can get the lay of the city and then plan to hop off and on accordingly.

New York City, USA

New York, New York! One of my favorite cities to visit. I have been there several times and still don’t feel like I have even scratched the surface on all there is to see.

Go to a Broadway show. Check out Times Square. Walk through different neighborhoods. Visit the Top of the Rock. Meander through Central Park. Explore the museums. Take the subway.

Your feet will be sore when you leave but it will all be worth it.

Chicago, USA

I can’t write an article about amazing destinations for solo travelers and not mention my favorite city – Chicago. Obviously since I live here, I love it and think it is a great place to live and visit. I admit to my biases.

There is so much to do here! Take an architectural cruise via a boat on the Chicago River. See the Bean in Millennium Park. Have a drink at the Signature Room in the former Hancock Tower. Step out on the ledges at Willis Tower. Go to a baseball game a Wrigley Field. hang out at one of the many beaches along Lake Michigan. Enjoy delicious food all over the city.

Chicago is also a great place for a girls’ weekend if you are looking into destinations for that as well.

A view of Millennium Park from Cindy’s Rooftop in downtown Chicago

Grand Cayman

There are a lot of great places to visit in the Caribbean. However, I am very picky because I do not like staying at all inclusive resorts. I think they are the worst for solo travelers to be honest because options are so limited and I tend to feel trapped on the resort. While many islands in the Caribbean are full of all inclusive resorts, one that is not is Grand Cayman. And therefore, I think it is a good option for solo travel.

I flew to Grand Cayman to finish my open water scuba diving certification. It seemed like a much more pleasant way to do it than in a local quarry in rural Illinois.

I stay at the Sunshine Suites, which was across the road from Seven Mile Beach. Seven Mile Beach in Grand Cayman is one of the nicest, most picturesque beaches I have been to. The sand it white and the water was clear. I did not rent a car but was able to use the buses to get around. They have some great restaurants worth checking out too. Diving was great too if you are a fan of scuba diving.

Alaska, USA

I visited Alaska as part of my quest to visit 50 states that I finished in 2018. I spent a week in Alaska, visiting Anchorage, Kenai Fjords National Park, Denali National Park and finishing my trip in Fairbanks (where it was 90 degrees F the day I left!).

I did not rent a car, instead choosing to utilize organized tours and the Alaskan Railroad to get around. I LOVED LOVED LOVED taking the Alaskan Railroad through the Alaskan countryside. I splurged and got a seat on the first car where food and drinks were included. The best part was the little balcony off the back of the train car. I spend a lot of time out there during the trip admiring the Alaskan scenery as it went by, looking for moose and breathing in the fresh air.

If you are going to Alaska, I highly recommend taking the train for at least part of your journey. You won’t regret letting someone else do the driving while you relax and gaze at the scenery.

Amazing Destinations for Solo Female Travelers

There you have my list. I hope it inspires you to go for it! Solo travel can be so rewarding. There are many benefits to traveling solo. You can check out some of them here.

As for me, I can’t wait to keep traveling solo. Some of the places I hope to visit soon include Switzerland, Scotland, Iceland, New Zealand and Japan!

I cannot wait to start planning and take off!

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Amazing Destinations for Solo Female Travelers

Life Lately – A Preconfinement Recap

Tulips in Chicago

Do you remember the song “How Bizarre, How Bizarre” by OMC? That is the song that keeps running through my head whenever I take a moment to think about life lately. I almost get whiplash when I realize how drastically life has changed for everyone over the past ten days.

From a work perspective, we went from being told to continue working in the office 100% on Friday, to splitting into A and B teams that would rotate weeks in the office on Saturday to everyone working 100% from home for the foreseeable future on Sunday.

Chicago is now under a “shelter in place” order. Only essential businesses are open. Over the past seven days, I have only been outside to get the mail, walk the dog and go to the grocery store.

And there is no end in sight. How bizarre!

To pass the time, I started working on a puzzle. You should have seen the look on my mom and sister’s faces when I told them I was working on a puzzle. I didn’t like puzzles growing up. Turns out, I still don’t really like them but for the record, I did finish the one I started. They recommended working on a blog post to pass the time instead. That’s sound advice so that is what I am doing. Here is a recap of some of the things I have been working on so far in 2020. 

Work Life

Our department is on the move!

Two weeks ago, my team moved to a temporary floor at work so our regular floor can be rehabbed. They will be changing our permanent floor over from cube life to “high performance” life.

What does “high performance” mean you ask? Well, it means we will be sitting at tables with long rows of workstations on them. The seating will be open, meaning that we won’t have an assigned seat and will sit wherever there is an open workstation each day. We will have a small locker for our personal stuff. Moving to high performance means they can get twice as many people on our floor.  This will save them money, which is always the goal.

Lucky me, I’m part of the group that was moved to a floor already set up for high performance. We are now sitting on a floor with the tech team. We finished one week in the new format and I survived. Is it ideal? No. But I will adjust.

Life Lately
My cube in our old office space. I miss it already. 🙁

New Office Space
Our new office space.

Public Transportation Life

If you’ve seen me within the past few months, you’ve probably heard me gripe about the construction the Chicago Transit Authority is starting along the north part of the red line. The plan is that beginning in late 2020, they will be closing two stations completely along the route and closing two others but building temporary stations in their place during construction.

Of course the station I use almost everyday is one that will be closed with no temporary station. And how long do you think it will be closed for?

I figured 12 months, maybe 18 months.

Nope! I was way off.

Originally they said three years.

Yes. Three years.

Since then, they’ve upped it to four years.

I’m not even sure what to say to that. Will it ever be reopened? And more importantly, how will I get to work in the meantime?

The second question is the one I’m trying to find the answer to. I can walk to the next station. It’s not a terrible walk at about 10 minutes. Easily doable when it’s nice and light outside.

But what about when it’s super cold or raining or dark?

Then I’m not sure. There’s a bus I can take that I will likely be frequenting more often when I work late or go out in the loop after work. Of course Lyft, Uber and cabs are available. And driving too. But none of them are ideal.

The Nightmare Nonprofit Situation

Another thing I’ve been working on is trying to resolve an issue with a nonprofit I used to be on the board for. There were unauthorized withdrawals made from the bank account by the executive director. The funds were used to pay for personal expenses. I won’t go into the specifics. I do believe it was a mix up (they have multiple accounts at the same bank and used the wrong card). However, to date, the ED has not been able to reimburse the account as I have been asking her to do.

It is such a mess. The situation has been going on for about a year and a half. Attorneys and CPAs are now involved. The Attorney General is next. It has caused a lot of anxiety and sleepless nights for me. I am hoping that we are finally getting close to a resolution. Once the funds are repaid, the nonprofit will be dissolved.

Overall, while I am very frustrated and angry about this, I am mostly just sad and disappointed. I consider the ED to be a good friend. She inspired me with her vision and ideas and is one of the most caring people I know.

There are so many lessons I have learned from this situation and so many things I will do differently before joining another board. I am trying my best to find the silver lining in this situation. I look forward to having it resolved so I can move on.

App Life

For the past year or so, I have been exploring an idea I have for an app. It turns out that being a female tech founder is really hard…for many reasons. It is also really lonely. Finding people who have done what I am trying to do and who understand what I am talking about when I discuss it is rare. There are so many decisions to be made. So much money is required. It is overwhelming a lot of the time. I spend all of my downtime thinking about it. 

Currently, I am still in the early stages of this process. I am fortunate to have made some great connections recently that have been very helpful. We are currently working on market validation and then I have to figure out how to fund development of the app. Hopefully, it will keep moving forward and I will be able to share more in the future. Stay tuned.  

It is Almost Tulip Time

In exciting news, on my last day in the office a week ago, I noticed that tulips are starting to pop out of the ground in the beds downtown. This makes me SO HAPPY! Chicago plants thousands of tulips and it beings me lots of joy to see them blooming in the spring. There are so cheery and colorful. I can’t wait until they are blooming (hopefully, we will be back to working in the office by then. Fingers crossed!). 

Tulips in Chicago
Tulips along State Street in Chicago, May 2019.

Life in Confinement

As I write this post, I am hunkered down at home like most other people I know. I spend Monday-Friday working from my dining room table with breaks to take Stella for walks. I find that I don’t walk away from my computer much when working from home so I make a point to schedule walks in to get some movement into my day.

Maltipoo in Chicago
My at-home assistant is quite lazy sometimes.

On the days I am not working, I have been cooking, napping, chatting with friends and family, watching “The Voice,” reading and being lazy. 

Several people have asked me if the current situation has impacted my travels. So far, it has not. Other than a quick weekend trip to Toronto in January for the app, I haven’t traveled in 2020. I do have a trip planned for June but at this point, it is likely to be canceled. That is okay. I can wait to travel until it is deemed safe for everyone (not just me). 

I want to end this post by thanking everyone who has reached out to me to make sure I am doing okay. The messages and texts have been very appreciated. The good thing is that I am comfortable being alone. I like my home so I am happy here and I have Stella to keep me company. That being said, if you need someone to talk to, please reach out to me. Feel free to email me at carmen[email protected] I would be happy to connect and chat. 

Until next time, stay healthy and safe. And stay home! 

If you would like to keep reading, I recommended three good books to read while being confined to home in my last post. You can check it out here

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Life Lately


Tips for Women Traveling Solo

Last Tuesday night, I had the opportunity to go to an event featuring a panel of solo travel experts. The event was held at the Away store in the Gold Coast Neighborhood here in Chicago. The purpose was for the panelists to share their tips for women traveling solo.

The panel included the following women, all of whom have traveled solo extensively and have lots of fun stories and recommendations to share.

  • Lori Rackl, a travel editor for the Chicago Tribune who moderated the discussion
  • Leanna Lee and Sofia Martin from Wanderful
  • Natalya Grabavoy, a Copywriter and Digital Strategist
  • Kehinde Smith, a Travel and Lifestyle Influencer.

Panel for tips for women traveling solo

I didn’t really know what to expect but the discussion was interesting and I learned a few things along the way. There were three items from the discussion that really resonated with me as a solo traveler. I thought I would share them with you here.

Three Tips for Women Traveling Solo

  • Travel with a door stop so you can stop doors from the inside. I do not stay in AirBnBs or VRBOs often when I travel solo because I always wonder who else has keys to the unit I am staying in. Staying in hotels with room doors that do not have a chain or deadbolt on the door also makes me nervous. I had never considered bringing a door stop so I could easily block the door from the inside until it was mentioned at this event. It would solve the problems for all of the above so I think this is a brilliant idea! A small rubber doorstop like this are easy to throw into a suitcase. They are cheap too! I know there are things to consider with this – like what if there is a fire and I need to escape quickly? But I think the risk of that is small compared to the risk of someone unwelcome entering the unit. I plan to use this the next time I travel because I think it will be a great way to ease my mind.
  • When staying at a hotel, make friends with hotel staff. Do the same with wait staff at restaurants. This is something else I hadn’t considered. I usually try to stay anonymous and incognito when I travel (and in Chicago too, likely the result of growing up in a small Iowa town where everyone knew me). But after listening to the conversation about this, I realize I have it all wrong. Making myself known to the hotel staff means they are more likely to look out for me. This could be especially helpful in places I may not be as comfortable in. They are likely to remember me going in and out. They also applied this getting to know people idea to the wait staff at restaurants. If you are approached by strangers (particularly creepy men), they can step in and help shoo them away if needed.
  • Experiencing moments of loneliness when traveling solo is normal. This happens to me from time to time for sure, especially when I am traveling on my own for more than three or four days. The key to getting past it is understanding that it is a temporary state that can probably be easily resolved. Things that I do to resolve it include:
    • Going for a walk outside, preferable along the beach if I am in a location with a beach nearby
    • Finding a bar or a restaurant with a bar in it and having a drink or some food. Food is a social event and sitting at a bar can be an easy way to find folks to talk to
    • Calling/FaceTiming my mom and dad or sister
    • Watching a show or listening to music that has fond memories associated with it

The moderator finished the panel part of the evening by asking the panelists what benefits they get out of traveling solo. I discussed the benefits from my perspective in a previous post but I liked some of their answers so I thought I would share some of them as well.

Benefits of Traveling Solo

  • Traveling solo highlights your strengths and it can also strengthen your weaknesses. Often when we travel in groups, we fall into roles – the navigator, the planner, the driver, the foodie who picks where everyone eats. When traveling solo, you have to assume all of those roles, even if you are not very good at them. It is a great way to practice and improve those skills.
  • Solo travel increases your confidence and you gain a sense of empowerment. This is one I also mentioned in my previous post about the benefits of traveling solo but I think it the most important benefit so I am mentioning it here too. I love knowing that I can analyze and think my way out of unplanned or difficult situations. I know I can make good decisions alone, even when under pressure.
  • Anxiety is common before leaving for a trip (this is a big issue for me) but once you get to your location, it all seems to fall away. There are sights to be seen, food to be eaten and people to meet. There is no time for anxiety to hold you back!
  • There are no apologies necessary. You have no one else to please or think about. You can choose to get a local experience or you can do all of the touristy stuff. Both are good options and you don’t have to worry about what anyone else wants or thinks.

As you can see, I learned several good tips for women traveling solo at this event. It was worth my time and I hope to attend more like it soon! Maybe someday, I can even be a panelist at one! If you travel solo (for work or leisure), what would be one tip you would give for women traveling solo? Tell me in the comments below!

Note 1: If you don’t know about Away bags, they are a great brand of suitcases. The suitcases come in lots of fun colors (see the photo below). I have the bigger carry on with the removable battery in violet and I love it! I know there is some confusion about these batteries on planes. I have to remove the battery from the suitcase before boarding. I put it in my backpack that goes under the seat in front of me and have not had any issues.

Away bags for tips for women traveling solo event

Note 2: I was recently featured in a post about female solo travelers on the blog A Not So Young Woman Abroad. You can find the post here! The article features other solo female travelers that you should check out as well!

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I’m Looking for a Bit of Inspiration

Millennium Park in Chicago

Do you have those days when you are looking for a bit of inspiration?

I was at a get together with some people I mostly didn’t know a few nights ago and I was telling a fellow attendee about a trip I’m taking in September. I’m going on the trip with a tour instead of going solo. It’s been a while since I’ve done that but I’m looking forward to it.

After I finished my comment, the fellow attendee said to me “So you’re not comfortable being alone then?”

I’m not going to lie – I was a little taken aback by that reply. His question didn’t make any sense to me. My response back to him was “I’ve lived alone for almost 15 years. I’m by myself many hours each day and I travel solo quite often as well. Trust me, I’m comfortable being alone.”

I can’t help but wonder why I can’t stop thinking about that comment and worse, why I’m letting it bother me? But before we judge, the guy was actually very nice and friendly. He and his wife are lovely. I think he just said something I wasn’t expecting.

Of course I WISH I wasn’t alone so much. If you had asked me 20 years ago what my life would be like right now, my current situation wouldn’t have been my answer.

However, it is what it is.

Overall, I’m doing pretty well. I have a job that’s steady and pays the bills. I’m blessed with amazing friends all over the world and I’m close to my family. I live in a great city and bought a small but perfect-for-me townhome a couple of years ago. I’ve managed to keep my dog alive for almost eight years now. I also get to do lots of fun things and travel often too.

But I know what’s missing, or at least what people think I’m missing. The truth is – I’m really bad at dating. I get bored or frustrated and lose interest really quickly. I end things so I don’t “waste my time.” And honestly, it’s been a while since I’ve met a guy who has a good job and is motivated with some hobbies who doesn’t live at home with his parents. True story.

My sister used to tell me all the time that I’m “too picky” but I’ve been privy to enough bad relationships to know I don’t want one of those. I also don’t want to have a baby on my own. So in the meantime, I’m just doing the solo life thing and trying to make the most of my alone time. Some days, I enjoy it more than others.

While I was home alone most of this past weekend, I worked on a blog post about Hawaii that I was going to publish today. It’s a decent post but it’s uninspiring to me right now, which is something I’ve struggled with a lot when it comes to this blog recently.

So I’ve decided to turn to you, my amazing readers. I am looking for a bit of inspiration. What kinds of things would you like me to write about? It can be anything – not just travel. What about me or my life intrigues you that you’d like to learn more about? Don’t be shy, anything is on the table. Leave a comment below or send me a message. I’d love to hear from you.

Subjects I’ve considered include…

  • Single life in the city and maybe even dating stories.
  • My never ending quest to find non toxic sunscreen that works well and skincare products that are gentle but effective (especially for my rosacea)
  • Tips for hosting and cooking for a party (many of which are from my mom who really is the hostess with the mostest)
  • What it’s like to be on the board of a nonprofit
  • How to find nonprofits that match your passions
  • Stories from my book club and/or cookbook club – and why you should have these in your life too!
  • My favorite books
  • What it was like to grow up on a farm

Of course I’ll still post lots of travel things too. I love telling those stories and hopefully, inspiring you to get out and travel on your own.

In the meantime, tell me what you want to read and know! Also, for all of you who are wondering, I’m heading to Croatia and Slovenia with Trafalgar in September. While most of the trip will be pretty structured with not a lot of free time, I’d love to hear your suggestions if you’ve been there and have them. I’d love to have excuses to sneak away and be comfortable on my own when I can.

Finally, while I haven’t been posting a lot lately, I am having a great summer. Check out a few of the highlights in the photos below.

My brother and his family (including the little cutie above) came to visit a couple of weeks ago. It was the first time they’ve brought their kids to Chicago and we had a great time going to the Shedd Aquarium and the beach!!

Stella has taken a lot of uncomfortable looking naps this summer.

I had my eyebrows colored. I thought they were too dark and that I looked like a freak as a result. But my friends disagreed so I kept them…and yes I know I’m about 20 years behind on this one. I should have been having them done all along.

I went to a really fun concert at Millennium Park. The Grant Park Orchestra did their “Envelope, Please” show that night.

I spent Memorial Day with a friend and this beauty and her husband at their lake house outside of Houston. We had a great time!

Want to read more? Check out my posts from my trip to Greece here and here.

Things to do in Chicago in the Summer

Summer in Chicago.

Three of my favorite words. If you haven’t had the opportunity to visit Chicago during the summer, you are missing out!

Chicago is my favorite city and I will argue until I’m blue in the face that it’s one of the best cities in the world, especially during the summer months.

There are so many things to do in Chicago during the summer and there’s such a vibrant energy all around. I love being a part of it.

So what are some of those things that you can do when visiting? Here is a list so you can start planning a trip:

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Summertime in Chicago

  • Book an architectural boat tour with the Chicago Architecture Foundation (or Wendella or Shoreline. They’re all good). Rumor has it the architectural boat tours in Chicago are the second most popular tour in the world (after the Vatican).
  • Visit the Bean (formally named Cloudgate) in Millennium Park. It is nicknamed “the Bean” due to its shape. Go early in morning to avoid the big crowds. If you have kids, I also encourage you to check out Maggie Daly Park and its playground nearby.

Cloudgate, aka “the Bean”

  • Go to a concert, movie or show at Millennium Park. Pack a picnic and grab a blanket and hang out in the pavilion area for some free entertainment. The NPR podcast “Wait, Wait Don’t Tell Me” is one of my favorite shows to catch there during the summer along with concerts showcasing the Broadway shows currently showing or coming soon.

Jay Pritzker Pavilion during a taping of the NPR podcast “Wait, Wait Don’t Tell Me.”

  • Head to Cindy’s Rooftop for great views of Millennium Park and Lake Michigan. You can enjoy the views while having some apps and cocktails.

The view of Millennium Park from the terrace at Cindy’s Rooftop

  • Explore the Lincoln Park Zoo. This is the free zoo on the north side of the city. It’s not as big as the zoo out in Brookfield but for the price, you can’t beat it. Check out my favorites, the zebras and polar bears while you’re there!
  • Catch the fireworks at Navy Pier. They have fireworks shows on Wednesday and Saturday nights. It’s definitely worth checking out if you’re downtown around 9:30 on those evenings.
  • Go to a baseball game at Wrigley Field. Ignore what you’re told. Skip the bleachers and sit in the stands where it’s shaded (important for a fair gal like me) and cooler when the lake breeze is blowing. Don’t forget to have a beer and hot dog.

Beautiful Wrigley Field. Go Cubs Go!

  • Hang out along Lake Michigan. One of the most popular destinations for locals and tourists alike during the summer months is the lakefront. There are beaches. There are beach bars scattered about where you can enjoy some drinks while enjoying the views. There’s also a lot of grassy park space for picnics or relaxing on a blanket while reading a good book (pup pictured below not included).

The view of Lake Michigan Stella and I often enjoy

  • Go for a walk or bike ride along the 606. The 606 goes through neighborhoods west of the city, such as Wicker Park. It’s a great walking and bike path that allows you to explore different areas of the city. There are also lots of great restaurants and bars in Wicker Park and Bucktown if you decide to stop along the way. Tip: Don’t have a bike? Look for the blue Divvy bike stations located all over the city where you can easily rent a bike.
  • Have a meal on the patio at the many places available around the city. El fresco dining is definitely one of my favorite summer activities in Chicago and there are hundreds of restaurants that have great patios. If you want a list to choose from, check out Shelley from @chicagoismyboyfriend’s story highlights on Instagram. She lists lots of amazing Chicago patio and rooftop options in that reel.
  • Walk around the city and enjoy all the art and murals along with the beautiful flowers the city plants and maintains. These are the things that I think make Chicago so unique. There is so much care put into the plantings and the art. I try to remember to stop and appreciate it often and encourage you to do the same.

Possibly my favorite mural in the city. It’s 4,000-square-feet and located at the intersection of Lincoln, Ashland and Belmont in the Lakeview neighborhood.

The bright red 53-foot-tall steel stabile “Flamingo” in Federal Plaza in downtown Chicago

So there is my list. If you have visited during the summer and think I missed something, let me know in the comments below.

Looking for more ideas for things to do in Chicago? Check out some of my other Chicago posts here and here.

How to Spend a Girls Weekend in Chicago

With its amazing architecture, good food and wonderful people, a girls weekend in Chicago is the perfect way to spend three days, especially during the summer. I was looking back through previous blog posts recently and I realized that I don’t blog about my favorite city often. I suppose since I live here, I get caught up in the day to day grind and forget how much fun it can be.

So I made a decision – from here forward, I am going to make a conscious effort to post about all of the great things there are to see, do and eat in Chicago. I hope it inspires you to visit and that once you’re here, you will love it as much as I do!

I recently had an opportunity to be a tourist in my own city when my cousin Brittany came to visit. Brittany had been to Chicago before but only briefly so I figured this would be a great chance for me to put my plan into action.



How to Spend a Girls Weekend in Chicago

Friday evening

No girls weekend in Chicago can be complete without checking out some of its amazing restaurants.

On Friday night, we headed to a restaurant I hadn’t been to in a long but really like. We went to Mia Francesca’s, a small Italian restaurant on the north side of the city. The restaurant is usually packed so I recommend getting a reservation if you don’t like long waits. We were able to get right in with our reservation and really enjoyed our meal. One of my favorite parts about Mia Francesca’s is that they don’t rush their diners. We were allowed to relax and catch up while finish our wine over dinner.

Saturday morning

On Saturday morning, we boarded the Red line (the Chicago transit system is known as the CTA and the trains are referred to as the “El”) and headed downtown to the River North neighborhood. I highly recommend taking public transportation when visiting Chicago. Traffic is bad and parking is expensive. The easiest and more economical way to get around town is by taking the train or a bus. The regular fare for the train is $2.50 while the fare for a bus ride is $2.25. They also have bulk passes that you can buy as well. You can find out more here.


Our first stop was to find some food. We chose to have brunch at Beatrix. I had been wanting to Beatrix for a while because I had heard lots of good things. I had the steak and eggs with chimichurri sauce…yum!

Architectural Boat Tour

After filling our bellies, we set out for one of my favorite “touristy” things to do in Chicago – an Architectural Boat Tour. This is a great activity for a girls’ weekend in Chicago as well as for a family weekend or a solo trip.

The architecture in Chicago is world class and there is no better way to see it and learn about it than aboard a boat. There are several companies that do these tours. I recommend going with the Chicago Architecture Foundation or Wendella. Go on a tour that goes up and down the river as well as out onto the lake. It takes a bit of time to get through the locks between the river and lake but on the lake is where you will get great skyline views of the city.

Girls Weekend in Chicago
The beautiful Chicago skyline.

Girls Weekend in Chicago
Brittany, me and the Chicago skyline

Admire the Amazing Views

After the architectural boat tour, we stopped by Cindy’s Rooftop to admire the views of Michigan Avenue and Millennium Park….and maybe to get a drink and bathroom break too!

Cindy’s is located on Michigan Avenue across from Millennium Park. The bar is on the 13th floor and has an outdoor patio with amazing views of the park and Lake Michigan. I have been to Cindy’s several times and can attest that the views are spectacular in both the daytime and at night.

There tends to be a line so if you can plan ahead and snag a reservation, I highly recommend it. There was a line when we arrived without a reservation but it went pretty quickly.  The good thing about the line and the crowd control was that the restaurant and patio were not overly crowded. We could stand along the patio railing and admire the views without be shoved or feeling pressured to move on so someone else could take our place.

A view of Millennium Park and "the Bean" from Cindy's Rooftop in downtown Chicago.
A view of Millennium Park and “the Bean” from Cindy’s Rooftop in downtown Chicago.

A Walk in the Park

A quick stop in Millennium Park was next on our agenda. Millennium Park is located along Michigan Avenue on the east side of the loop downtown. It opened in 2004 and covers 24.5 acres. It is the most popular tourist destination in the Midwest USA!

Millennium Park is home to the famous Cloud Gate sculpture (also known as “The Bean”) and the fountains with the faces on it. It also features the Pritzker Pavilion, which hosts free concerts and events throughout the summer (I highly recommend!).

In the winter, the park is home to a couple of ice skating rinks so you can skate while admiring the beautiful city views.

As I expected, the park was VERY crowded but we were able to weave our way through the crowds, see what we wanted to see and snap some photos.

Visit a Museum

To escape the heat and the crowds, we decided to finish our time downtown by exploring the Art Institute of Chicago. The Art Institute of Chicago located just south of Millennium park. It was founded in 1879 and is one of the oldest and largest art museums in the United States. The museum hosts approximately 1.5 million people annually. Its permanent collection has nearly 300,000 works of art and is augmented by more than 30 special exhibitions yearly. In layman terms, it is huge!

We only had an hour and a half or so to explore it before it closed so we only saw a few wings of the museum. We saw lots of interesting and famous art while concurrently enjoying the air conditioning and benches that allowed us to rest our feet when needed (my feet were barking pretty loud by this point in the day!).

Girls Weekend in Chicago
Seen at the Art Institute – Yellow Hickory Leaves with Daisy by Georgia O’Keeffe. This is one of my favorite paintings of the ones we saw. It is so bright and colorful.


After dinner on Saturday evening, we went to one of my favorite ice cream parlors in Chicago, Lickity Split. There are two locations – one of the far north side of the city and one on the northwest side of the city. They have great ice cream and lots of candy and sweet treats to choose from. The Tasty Turtle sundae is my favorite thing on their menu.


On Sunday, we grabbed a quick breakfast at home and then decided to give our feet a break and spend the day hanging out by Lake Michigan. We walked to one of the beaches on the north side, set up some chairs and spend the rest of the morning and early afternoon enjoying the company, breeze and people watching.

There are beaches all along the lake in Chicago. You can check out the list of them here. The ones closest to downtown, particularly Oak Street Beach and North Avenue Beach, tend to be really crowded, particularly on the weekends. If you are looking for the “scene”, this is where you should go. If you want something quieter, head further north or south from downtown.

And with that, our girls weekend in Chicago came to an end

After spending a few hours at the lake and dipping our toes into the water, our girls weekend in Chicago was over. I had so much fun and was sad to see Brittany go. I hope she had fun too and that she comes back to visit us soon!

You can check out more of my Chicago adventures here.

Girls’ Weekend in Chicago featuring Jimmy Buffett

Fun. So much laughter. Lots of good food and drinks. Girl talk….

All of these can be used to describe the weekend I had with my sister and our friend Meagan over the past couple of days. I was so excited for them to come visit!

They got in on Friday afternoon and we headed out for dinner that night at Cafe BaBa Reeba. If you’ve followed my blog, you know this is one of my favorite restaurants and my go-to when friends visit. It’s a tapas (small plates) restaurant near Halsted and Armitage in Lincoln Park. It never disappoints and didn’t this time either.

We followed Cafe BaBa Reeba with some drinks at Merkles. Merkles is a Hawkeye bar on N Clark St in Wrigleyville. The sign behind us in the photo below says “This is Hawkeye country.” I agree but Meagan may not since she is a Cyclone.

Brunch at Tuco and Blondie (on the corner of Southport and Roscoe in Lakeview) is quickly becoming one of my favorite weekend activities. I had been to Tuco and Blondie once before and really enjoyed it so I decided to take Meagan and Amber there on Saturday morning. I’m glad I did because was a hit! I had to laugh when we first got there at 10am because I opened the drink menu and Amber commented “You’re going to have a margarita at 10am with breakfast?” Yes, I was, and I did. And they did too. Apparenty, I previously failed to convey proper brunch etiquette to Amber. ????

I had the passion fruit margarita, Amber had strawberry and Meagan had the regular margarita. All were great and not too sweet (which can sometimes happen with flavored margaritas).

I had the gringo omelette and their famous potatoes. Their potatoes are more like a crispy on the outside but creamy on the inside potato casserole. Delicious!

Amber had the breakfast burrito

We finished brunch with the obligatory photo in front of the mural on the outside of the restaurant. Amber and Meagan coordinated their colors to the mural very well!

Next up, the Jimmy Buffet concert! This is one day I look forward to each summer. I have been to a Jimmy Buffett concert almost every year with my friend Joe since I first moved to Chicago in 2002. I would say that this was probably my 15th concert of his then. Does that make me an official parrothead? ???? It was Amber’s second Buffett concert and Meagan’s first. I was so excited to go with them!

We started the evening with a Buffett preparty drink at Sports Corner. (Nice photobomb by the gentleman behind us. He was very proud of himself for it).

Fins Up!

After a quick stop at the Sports Corner, we headed over to Brickhouse to meet my friends Joe and Chris. Brickhouse is a new bar that opened as part of the Park at Wrigley just west of the stadium (Clark and Waveland for street reference). I was skeptical as we were walking over but I ended up really enjoying the bar and our time there. The music was great! The wait staff was friendly and attentive. The food was good. The drinks were tasty. And it was steps to the entrance of the stadium. Wins all around!

Quick selfie in front of the marquee on our way to Brickhouse

Brickhouse is two stories. We were on the second floor patio pictured here. I highly recommend it if you’re heading to a game or concert or even just in the neighborhood not going to Wrigley.

I love this hula girls headband. (I should have left my sunglasses on for this photo).

Chris and me

My favorite Parrotheads, Joe and Chris

Quick photo with Ronny Woo Woo and my friend, Laura, at Brickhouse.

Time for the concert!

Tuco and Blondie gave away beach balls to its brunch patrons heading to the concert. Pretty neat marketing idea!

Joe and Chris opted for rooftop tickets to listen to the concert rather than be inside the stadium. As luck would have it, they are in the rooftop directly behind us. How funny!

Pretty sunset behind Wrigley

Cool coloring of the crowd during the show

It was such a great weekend. I miss Amber and Meagan already. I’m so glad we had the opportunity to spend the weekend together and have a ton of fun! I hope they come back soon!