The Art Of The Solo Trip.

Foreword by Brandi.

Welcome to a new blog series! In this series, we have invited guests on the blog to talk about different topics and inspire us all in new ways! Our second edition of The Art of, features Rilee Smith, who has taken TikTok by storm with her travels and packing tips. When she posted her NYC Solo trip last Fall, I was so inspired! A dreamy itinerary, the fearlessness to travel NYC solo, and solitude to recharge her soul in a way a group trip cannot. With that, I am thrilled to introduce the second blog in this series, The Art of the Solo Trip. So, get cozy & enjoy!

XO ,

Brandi

Hi, I’m Rilee, and my favorite way to see the world is…without a plus one!

Now, don’t get me wrong—I love my friends and family to pieces, and we’ve been on some amazing and unforgettable journeys together! But some of my favorite trips and adventures I’ve ever had were solo vacations!

As someone who is introverted, I’ve always struggled with group trips, even when they’re spent with the best of friends. I’m someone who recharges my battery in moments of quiet and solitude, which is hard to do when you’re sharing a hotel room or walking around trying to find a restaurant that will appeal to six different appetites!

(Anyone else feel me? 🙋‍♀️)

So, when I started planning a bucket-list Christmas trip to Quebec City back in 2018 and none of my friends could join, I thought, “Why not just go solo?” So, I did! And it was one of the most magical trips I’ve ever taken. Picture this: snowy streets, cozy cafes, twinkling lights—pure Christmas snowglobe vibes. And it was all mine to enjoy at my own pace.  

It was on that trip that I realized just how much you can learn about yourself when you travel solo. It’s both reflective and invigorating, empowering and relaxing—and I’ve been hooked ever since!

The Perks of Solo Travel

One of my favorite parts of traveling on my own is the sense of freedom that it offers. Imagine waking up and deciding your plan for the day based on your mood and nothing else. Want to spend hours reading in a cozy bookstore? Do it. Want to explore every attraction in town inspired by your favorite movie or musical artist? Carpe diem! (Yes, this is foreshadowing a Taylor Swift-inspired trip coming later in this blog.)

There’s also so much less pressure when you’re traveling solo. I’m a people pleaser by nature, so I’m always a little bit anxious on group trips, making sure everyone is enjoying themselves and is happy with the plan. All of that pressure melts away on a solo trip, because you’re only focused on your needs. That’s a liberating feeling! You can be as spontaneous or as planned as you like.

And finally, you learn so much about yourself when you travel solo. It’s like dating yourself. You get to try new things, adapt to new situations, and discover hidden strengths. It’s like, "Oh hey, I didn’t know I could do that!" in the most empowering and unexpected way. When you take yourself out of your comfort zone, you get to nurture new parts of yourself.

How to Plan a Solo Trip

Planning a solo trip can feel overwhelming or intimidating the first time you do it, but I promise, it’s easier and more enjoyable than you think:

1. Plan a trip that’s tailored to you. You’re the main character in this Eat Pray Love experience, so choose a destination that is so you. Maybe it’s a weekend hiding away in a cozy cabin with a stack of books, or maybe it’s museum-hopping in a romantic city. Whatever it is, make sure it speaks to your soul.

2.  Create an itinerary of must-do activities but leave room for spontaneity. Make reservations for things you don’t want to miss, like the restaurant you saved on Instagram or a popular guided tour, and pencil in the rest. Cushion each activity with plenty of time to get lost, explore, or sit and read in the park.

3. If you’re new to solo travel, start small. Get comfortable with the idea in a nearby city or local destination, just to get your toes wet and make sure you like the experience. From there, try an international city where the language barrier isn’t so big, like London or Dublin. Once you’ve got the hang of it, go big.

Travel planning tip: My favorite trip planning app is Wanderlog. It’s perfect for organizing all your travel details, ideas, reservations, travel maps, and more. Plus, you can share your itinerary with family and friends back home for peace of mind.

Solo Trip Inspo: NYC Edition

This past winter, I found myself in New York City for work and decided to extend the trip a few days to do NYC my way. See, I had been to the city a couple of times before, but always on a jam-packed schedule of top destinations—Times Square, Statue of Liberty, the whole shebang. This time, I wanted to see the city through a more relaxed lens, sprinkled with places and references I had heard about from some of my favorite New Yorkers.

The result? A three-day trip filled with cozy bookshops, a mac and cheese tasting platter, and a self-guided Taylor Swift tour. (I’ve included some reference links for all my non-Swifties.) Here’s my itinerary for inspo.

Day 1: Eats & Reads

• Get checked into your hotel (I stayed in the Flatiron District because it was right in the middle of everything I wanted to do!)

• Walk over to the East Village, stopping at cute shops along the way.

• Get lunch at S’MAC East Village and order the S’MAC Sampler - a platter of eight different kinds of Mac & Cheese. Yes, for one person. (Just do it.)

• Walk over to Book Club, a cozy bookstore with a bar that makes delicious handcrafted drinks. Find a cozy spot and lose the rest of your afternoon!

• Grab dinner at Hotel Chelsea and listen to The Tortured Poets Department on your way home
  

Day 2: Shopping Through Soho

• Grab brunch at Serra Rooftop for great food and great vibes.

• Walk to Partea NYC for a #throwback afternoon of claw machine fun (with Bubble Tea!)

• Spend the afternoon shopping your way through Soho, hitting up cute stores like The Alchemist's Kitchen.

• Stop into Housing Works Bookstore Cafe for some reading, thrift shopping, and listening to All Too Well on repeat.

• Enjoy pizza amid romantic candlelit vibes at Gemma, the restaurant inside The Bowery Hotel.

Day 3: Village Eats & Streets

• Start your day at Maman in the West Village where you can grab a coffee and Oprah’s favorite cookie.

• Stop by the famous Friends Apartment Building for a selfie.

• Venture around the cute shops in the West Village and Greenwich Village (keep an eye out for Cornelia Street).

• Eat a late lunch in a ski chalet at The Lavaux while enjoying some Swiss wine and fondue.

• Finish off your evening at Bathhouse Flatiron, a thermal spa and recovery experience, to cap off the perfect solo trip!

I hope this dive into the art of solo travel has helped inspire you to embrace the adventure! If you’ve been thinking about taking your first ever solo vacation, this is your sign to just book it.  Solo travel is one of the most empowering, inspiring, and comforting adventures you can have!

Thanks for joining me on this journey, and a huge shoutout to Brandi for letting me contribute to "The Art Of..." blog series. For more tips and inspiration, feel free to follow me on social media @rileejsmith. Happy Travels!