Solo travel.

It’s something we get asked about, alot.

But because we’ve spent the last 10 years almost exclusively traveling together, we didn’t have much to say about one the most popular forms of traveling.

Until now.

Solo Travel Graphic

When Hilton approached us about doing a solo travel challenge – each one of us would travel alone to a US city we had never been to and experience it the way WE wanted – we jumped at the chance.

While I was going to a Cubs’ games, eating pan pizza, and staying at the newly opened LondonHouse in Chicago, Heather would be laying on the beach, indulging herself at the spa, and enjoying the Conrad Miami.

And we’d each learn a thing (or two…or three) about the solo travel experience.

What were some of the biggest advantages of traveling solo?

Trav:  The first advantage is a pretty obvious one – you get to do whatever you want, whenever you want!

No asking someone else what they want to do, how they feel, or worrying about their opinions.

For someone who usually travels with at least one other person, this “selfish” mindset was pretty liberating – and fun.

There was also one major logistical advantage – getting in to restaurants and bars!

On my first night, I tried to get a reservation at one of Chicago’s most popular restaurants, Girl and the Goat.

They were already fully booked for the night, but told me I could try to walk in.  When I arrived, I was told there was a 2 hour wait, but….

…since I was there as just a single person, they stuck me on the end of another table immediately.

I had already eaten a fantastic meal and paid by the time people who came before me were just sitting down.

Score one for solo travel!

Heather: Being able to do whatever you want without regard to anyone else! :)

What were some of the biggest disadvantages of solo travel?

Trav: The major disadvantage was not getting to share the experience with someone else.

Since we constantly travel together, I never gave it much thought that when we come home from a trip and reminisce, the other person shares those memories.

This time, after coming home, I was happy to hear about Heather’s great time in Miami, but I couldn’t “feel” her experience or picture it the same as if I had been there.

Sharing the travel highs, lows, and everything in between with someone else is something I take for granted, since it always happens, but is something I can appreciate much more now that I’ve had a solo travel experience.

Heather: After four days of being basically alone I was definitely ready to see my loved ones and not eat dinner alone.

But other than that, I would say there weren’t any disadvantages. Oh… except not having my personal photographer husband. I had to take more selfies! You can check out my attempts on Instagram.

What Are a few things you did that you wouldn’t have done if the other person was there?

Trav:  BIKING!

It’s no secret that I absolutely love biking, especially around cities.  While Heather will sometimes humor me and bike around a bit, she’d never make it her main means of transportation.

In Chicago, which I found to be one of the most bike friendly big cities in America, I took advantage of this and biked everywhere.

The first day, I used their bikeshare program, Divvy, to get around.  But I wanted to be able to go wherever I wanted, whenever I wanted (back to that selfish attitude again!) and so for the last two days, I rented my own personal road bike.

40 miles later, I had gone up and down the lakefront a few times, visited almost every neighborhood north and west of the Loop, and had the time of my life!

Another thing I did was take a lot of public transportation.

Much like biking, my affinity for public transportation is unmatched by Heather.

And since LondonHouse was in a perfect spot, centrally located right in the Loop district and near every train line, when I wasn’t taking my bike, I was riding the “El”.

Biking and public transportation – Heather would have hated it, but I couldn’t have been happier!

Heather: When we stay at nice hotels, Trav NEVER wants to eat at their restaurants!

He is always in search of small local places, which is fun, but…

…sometimes hotel restaurants have amazing food!

So I indulged fully while staying at the Conrad Miami.

The first night I ate at their restaurant, Atrio, which is on the 25th floor with amazing views of the city and it was also the best meal I had the entire time!

I also ordered room service (usually another hard NO from Trav).

It felt incredibly luxurious and indulgent to order room service and something I would never typically do with Trav.

key lime tart at Conrad Miami

Every time we stay at a hotel, I longingly look at the spa brochures but unless we are in Thailand (where massages cost less than $10) I regretfully ignore them and move on.

Since we were solo traveling I decided to check out the spa at the Conrad Miami – and it was awesome!

They had a very large spa complete with any sort of treatment you can imagine.

Getting a relaxing facial and then laying by the pool in the Miami sunshine is basically my ideal way to spend a morning!


View from the rooftop pool at the sleek Conrad Miami.

What things didn’t you do because you were by yourself that you would have done if you were together?

Trav:  Drink wine!  Just kidding.

A few things I didn’t do that typically Heather and I would do if were together was go to coffee shops (no use going if I don’t like coffee) and museums.

I certainly don’t mind going to museums and galleries, but I’d never choose it over other activities like going to sporting events and other outdoor activities.

I actually biked by the Art Institute of Chicago and thought:

“That looks pretty cool, I bet we’d be in there if Heather was here.

Then I took off biking down to check out Soldier Field (where the Bears play).

Heather: Trav and I usually check out cool bars or breweries when we travel but being on my own I didn’t have much motivation to go out at night.

I didn’t mind going out to dinner alone, but going to bars alone in Miami didn’t seem that enticing to me.

Instead, I opted for chilling in my hotel room – which had amazing views of Biscayne Bay – and read a few books.

Also, when we travel together we usually set a rapid pace to fit in every activity, restaurant and brewery into our schedule.

Being alone in Miami allowed me to be as relaxed as I wanted to be – including spending an entire day at the Bentley Beach Club at the Hilton in Miami Beach.

Even when the clouds rolled in I continued to lounge in my chair and enjoy the beautiful views.


What was the biggest surprise of solo travel?

Trav:  How much I take having someone to talk to for granted.

Even though I found it really easy to talk to people as a solo traveler, there were plenty of moments where I was sitting alone – at a restaurant, brewery, on a boat tour, at the beach – and had no one to talk to.

Most of the time, it was enjoyable to have some time alone, but it was still a big surprise when I realized just how much time I usually spent talking with someone else.

Heather: I didn’t really miss Trav a lot.

Not to sound callous or insensitive, especially because I don’t think he missed me either – but we travel so frequently together that it was a nice chance to just have alone time.

Did you find people talked to you more or less as a solo traveler?

Trav:  I definitely felt that more people talked to me as a solo traveler.  Granted, I like to talk to people, so that does play a part in it.

However, most of the time it was the other person who started the conversation, usually by asking something like

“so, what are you doing in Chicago?”

As a solo traveler, you’re much more approachable, and I also think that generally people are interested in why someone is there alone since it’s less common than being with someone else or in a group.

One of the places I felt most at ease was at my hotel, LondonHouse.

I’ve never encountered a more genuinely friendly, nice, and kind staff.

From Corey the doorman remembering that I went to the Cubs game and asking me about it the next day to the awesome staff at LH on 22, their incredible rooftop bar, I felt totally at home during my three days there, which really helped, especially as a solo traveler.


What’s really great is that I felt the same friendliness from the staff at a totally different type of establishment, The Drake.

While the LH on 22 rooftop bar is the newest hot spot in Chicago, The Drake is a place to go to experience “real Chicago” and has one of the oldest bars in the city, Coq d’Or.

A cozy bar, stiff drinks, steak dinners, and live lounge singers and piano players – The Drake is definitely your grandfather’s Chicago!

Two totally different places with two totally different vibes – but the same friendly service, which had me feeling comfortable as a solo traveler.

Heather: I did not think this was the case. People didn’t really talk to me at all as a solo traveler.

The only place people were especially friendly to me was at my hotel. I also spent a lot of time there – eating or hanging out and all of the staff were attentive and even chatty, which was nice!

Was it more stressful to travel alone?

Trav:  Aside from losing my wallet within half an hour of landing in Chicago (woohoo, another travel mishap story!), I found that after getting over the initial apprehension and awkward feeling of traveling solo, that it was actually less stressful.

Even though Heather is more than capable of taking care of herself – and in fact, probably more capable than I am (case in point, I lost my wallet immediately after landing) – I still find myself worrying about her when we travel together.

Also, when traveling with someone else, I generally ask a lot of questions and overthink scenarios.

Oddly enough, when it’s just me, I just do it – probably because there is no one to ask about it!

Heather: I didn’t think it was more stressful to travel alone. 

However, It was a short trip and also a domestic flight so we didn’t have to deal with any situations that were difficult or stressful.

Did you feel uncomfortable going out by yourself?

Trav:  At first, yeah, it felt a bit awkward, especially going to a sit down restaurant like Girl and the Goat.

Usually, that awkwardness dissipated pretty quickly after I started chatting someone up, especially if it was somewhere less formal like a brewery.

But it definitely was a new feeling, and one that took some getting used to.

Heather: It was the opposite for me.

I didn’t feel uncomfortable at first. But after the 3rd meal eating out alone, I felt conspicuous and also just a little lonely.

How did you feel about night life as a solo traveler?


Trav:  There were a few times when I was out at night that I felt a bit awkward being alone, especially because every other person was with someone else.

It was still fun, especially doing activities like the Second City Comedy Club, but the “night life” component was certainly when I felt the most self conscious about being a solo traveler.

Heather: Miami has quite the reputation as a party city, but I didn’t venture out too much at night – clubbing isn’t really my thing and especially not solo!

I would go out for dinner, but I was basically back in my room by 9 or 10 – which felt kind of lame but I really enjoyed relaxing in my room and watching whatever I wanted or reading without interruption.

Plus the views from the floor to ceiling windows were stunning and nice to look out at night.

What were 3 things you learned from solo travel?


 1. Embrace the silence

As mentioned above, one of the biggest surprises was just how little time I spend in silence and not having someone else around.

I learned to embrace and enjoy it, and it made my trip much more enjoyable.

2. Just do it

If you want to do something, do it.

Want to rent a bike and cruise around the city?  Do it!

Want to go to a sporting event in the middle of the day?  Do it.

Fancy heading to a brewery to taste a delicious brew before noon?  Go for it!

One of the best things about solo travel is getting to do whatever you want, whenever you want – and not having to worry about anyone else’s opinions!

3. Some things will suck…and that’s ok

I had a ton of amazing experiences and met some great people while I was traveling solo…

…but that doesn’t mean each time I went out and did something it was amazing.

I went on a hour and a half boat tour and didn’t talk to a single person the whole time.

I went to a brewery before the Cubs game, tried to chat with some of the staff there (it was 11 am, so I was the only customer) and basically got a few grunts back.

Not everything will be great and not everyone will want to talk to you.

Take it for what it is and move on without worrying about it too much.


1. It’s ok to do whatever you want.

If I didn’t feel the desire to go out and explore the city I could just sit by the pool instead – guilt free.

2. It’s ok to be alone and to dine alone.

It takes a certain level of confidence to eat alone and feel comfortable. 

If there were moments I lacked the confidence I could always hide behind my iPhone or book.

Which brings me to #3…

3. Bring something to entertain yourself. 

I always had my kindle with me so that if no one was being especially chatty I could pull out my book or my phone.

I would try not to do this right away so that I wouldn’t dissuade people from talking to me and missing out on an experience, but it was always my backup!

Do you have any tips for meeting people when traveling solo?

Trav: You can certainly do some things to give yourself a much better chance of meeting people when traveling solo.

First, head to places where other interesting people might be hanging.

You could go to the hotel’s lobby bar, take a free walking tour, join a group tour, etc.

You could also join a Facebook group for the area you’re going to or check if there is a Couchsurfing group in that area and go to one of their meetups.

Heather: I’m not sure – I probably could have used some tips before this trip! The only thing I can think of is to join a group tour or group activity of some sort. That way you can easily interact with other people.

Were there any times you felt unsafe as a solo traveler?

Trav: No.

Granted, being a male it’s a bit different, and I was staying in a really nice area by the LondonHouse and doing activities that certainly weren’t dangerous, but I never once felt unsafe.

Heather: No, not really. But I also wasn’t out late at night.

What tips would you give a first time solo traveler?

Trav: Be selfish – go out and experience the things YOU want to experience.

Don’t be afraid to take a trip alone.

Embrace the quiet times.

And if you want to meet others, put yourself in situations to do it, and it’ll happen.

Heather: Be open to try new things or to feel uncomfortable.

For me especially, eating out alone is somewhat outside my comfort zone – especially every meal for four days.

But I didn’t let that stop me from researching and finding the best restaurants in Miami.

Also, depending on your situation and length of trip, take time to spoil yourself…often!

I think that solo travel is a great time to indulge because you can literally do whatever you want to do.

In my case, I lounged by the beach for an entire day, went to the spa at my hotel and ordered room service – indulgences I wouldn’t normally do with Trav.

What were the 3 best experiences you had during this trip?



1. Going to Wrigley Field for a Cub’s Day Game 

There are very few things I love more than going to sporting events, and Wrigley Field is the holy grail.

It lived up to the hype and then some – and it didn’t hurt that the Cubs won!

2.  The Chicago “Triathlon”

On Saturday, I pulled off the Chicago triathlon – a bike ride up Lakefront Trail, a swim in Lake Michigan, and a deep dish pizza.

And as great as Pequod’s pizza was, nothing beats the first two “legs” of the triathlon.

Biking up the lake followed by a swim are must-do’s if you’re in Chicago in the summer.


3.  The Rooftop Bar at LondonHouse, LH on 22

There’s a reason that this is the newest hotspot in Chicago and that every single person I talked to asked me if I had been to the rooftop at LondonHouse.

It’s that awesome!

The highest rooftop bar in the city, the best views, and some killer cocktails makes it an awesome place to spend an afternoon…and an evening…and a late night!


1.The Conrad Miami

Honestly, I had the most enjoyable times when I was at the Conrad Miami.

The amenities and the employees there made my solo travel feel much more friendly and comfortable – from getting great suggestions at the concierge to enjoying a meal with amazing views. 

I even ventured out to the exclusive and trendy Soho House for happy hour at their restaurant and the juxtaposition between the two hotels was astounding!

The bar tender was not friendly at all  – a complete 180 from the staff at the Conrad Miami.

2. Spending the day at the Bentley Beach Club.

Reading a book while gazing at the ocean is my little piece of heaven.

3. The Perez Art Museum and Wynwood District

The last day of my trip I went to the Perez Art Museum and then wandered around the eclectic Wynwood District.

The Perez is filled with very interesting modern art concepts, but I have to say the part I enjoyed the most was finding the entrance through a jungle-like maze.


The Wynwood District of Miami is filled with cool galleries, shops and walls covered in art.

It is definitely a hip area to explore and I thoroughly enjoyed my iced nitro latte from Panther Coffee.


Want to Follow in Our Footsteps?

Because it’s one of the biggest hotel chains in the world, one of the best things about Hilton is that they have a variety of properties around the globe that stretch across every budget.

In Chicago alone, they have over 20 different hotels just in downtown, including the LondonHouse where I stayed, and in Miami, they’ve got 25 different hotels.

If you’re looking to take a summer solo travel trip, you can take advantage of the Hilton World Sale, which is running through September 6. If you’re a Hilton HHonors member, you can get up to 30 percent off your room, which is an awesome value.

And of course, you can always use your Hilton HHonors points to book a free night (or two, or three) and experience Chicago and Miami just like we did!

Final Word(s)

Both of us loved our solo travel experience and are glad that we finally got to “try out” a huge part of the travel landscape that we previously hadn’t really known.

Inherently, we knew it would be different, but were shocked at just how different the solo travel experience actually was from traveling with another person or a group.

And while it was great to do whatever we wanted, whenever we wanted, we certainly aren’t going to only solo travel from now.

We will still be traveling together most of the time, but we do plan on mixing in some solo travel adventures going forward so that we can both continue to experience cities and places in a way that just isn’t possible when you’re with someone else.

Have you been a solo traveler before?  What are the biggest differences you experienced between solo travel and traveling with someone else?  And what are your favorite solo travel destination (we want to try them out!)?

Let us know in the comments below!

Our “solo travel challenge” was sponsored by Hilton. All the opinions expressed are solely our own and are based on our actual experiences.

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