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The Blog

Approachable inspiration for a stylish life. 


What You Should Know Before Traveling Solo

Kristen Berry

Venice, Italy, taken during my first international solo trip, Oct. 2015.

Venice, Italy, taken during my first international solo trip, Oct. 2015.

I first felt the urge to take a solo vacation shortly after a breakup. As I looked back on that relationship in the months that followed, what bothered me most was how much I was willing to put up with rather than being alone, rather than having to start dating again. And that’s no way to live. I had to concentrate on building a life I loved regardless of my relationship status. And I knew that such a life involved travel. A solo vacation seemed like an empowering reminder of my independence before I allowed myself to re-enter the dating scene.

And it was. Traveling alone is one of the most rewarding things I have ever experienced. I never feel more free than when I am in a new place alone, with complete control over how I spend my time, absolutely no one to answer to, and no one to consider in my plans except myself. It’s the only time when I feel it’s okay for me to be selfish. So often we prioritize the needs of others before our own. We all owe it to ourselves to concentrate on taking care of ourselves once in awhile.

These days I take solo vacations less to prove something to myself, and more because I enjoy them from time to time -- though it never hurts to remind myself just how much I can do all on my own. Having just returned from my first solo trip requiring a passport, I thought I’d share a few things I’ve learned along the way to make you feel prepared (and hopefully inspired) to take an independent excursion of your own.

Standing over Florence, Italy, Oct. 2015.

Standing over Florence, Italy, Oct. 2015.

You Should Absolutely, 100% Do It.

You might have a few doubts before you hit purchase on those plane tickets. You might wonder if it will be intimidating traveling alone. And you know what, occasionally, it will be. There may be a moment when you initially land, realize you’re alone in a foreign place, and feel overwhelmed by the idea of navigating from the airport to your Airbnb. Or you may find yourself standing in front of the ticket machine for the metro and have no idea how to operate it. Or you may wind up  sitting in a super authentic neighborhood trattoria and the only menus are hand-written and in the local language. And yes, in those moments, it will be intimidating.

But then there will the incredibly gratifying moment when you figure it out, all on your own (or with the help of a friendly local -- and believe me, they’re everywhere). You will be reminded time and time again just how strong, resourceful and capable you are, and just how kind perfect strangers can be.

Watching the hypnotic dance of the jellyfish at the Monterey Bay Aquarium, March 2015. 

Watching the hypnotic dance of the jellyfish at the Monterey Bay Aquarium, March 2015. 

Take a Mini Trip Closer to Home to Warm Up.

Traveling alone can be uncomfortable at times -- eating dinner at a restaurant by yourself, doing a group activity where everyone else is already in pairs. It’s all part of the experience. But it might be a good idea to get accustomed to it in a place where the native language is your own.

A warm up trip is a great opportunity to be a tourist near your hometown. Find somewhere worth exploring that’s within driving distance, book a hotel there for a night or two, and go explore it. Go hiking, biking, or antiquing. Take a whale watching trip. Have a spa day. Sign up for a yoga retreat. And definitely research an amazing restaurant in the area, make a dinner reservation for one (preferably somewhere with a view), and enjoy it. You’ll be surprised that no one will stare at you wondering why you’re eating alone. And on the off-chance that someone does, who really cares? You’ll never see them again. Order a decadent dessert to celebrate being awesome, savor every bite (and the memories you created that day), and wonder why you didn’t start taking these solo getaways sooner.

Just one of the views from a hike up Diamond Head crater, Oahu, Oct. 2014.

Just one of the views from a hike up Diamond Head crater, Oahu, Oct. 2014.

Be Prepared, Not Paranoid.

Yes, if you’re traveling alone, you should be extra aware of the safety of yourself and your belongings. But remember that most of the people on the train, walking down the street or touring the museum are good, honest people just like you. And, most of the things you should do to stay safe when traveling solo are things you should do when traveling with others, too.

First of all, trust your instincts. Have a bad feeling about that dark quiet street? Don’t love the way that guy is looking at you? Listen to your gut, and get outta there. To help avoid pickpocketing, make sure to carry a purse that zips securely (preferably a crossbody bag), and don’t put anything important in any external pockets. If you’re in a crowded place, keep the purse positioned in front of you and in your eyeline.

Traveling internationally? Make a copy of your passport, jot down your credit card numbers (and the phone numbers to call in case of a problem) and give it to a trusted friend, just in case they’re misplaced/stolen. I also feel better knowing that someone is aware of my general whereabouts when I’m traveling afar. I make a Google Sheet to keep track of my travel plans and overall itinerary to keep myself organized, and I share it with a few friends/loved ones so they’ll have an idea of where I am throughout the trip.

The Colosseum, Rome, Oct. 2015.

The Colosseum, Rome, Oct. 2015.

You Probably Don’t Need to be Fluent.

Now, don’t go assuming that everyone will speak English where you’re visiting. And even if English is fairly common, it’s only polite to learn how to say a few basic things in the native language. Even simple common courtesies such as “please” and “thank you” are so appreciated when spoken in the language of the land.

Duolingo is a fun, free app to begin learning a new language. I also picked up several phrases listening to “Italian For Dummies” CDs on my evening drives home from the office. I bought an adorable Italian phrasebook from Anthropologie, but I honestly didn’t use it very often. It’s not exactly practical to whip out a book during a conversation. Instead, I noted a few of the key phrases for getting around, ordering at restaurants, and checking into/out of a hotel in the notes app on my iPhone for easy reference, and it was all I needed.

Byodo-In Temple, Valley of the Temples  ,   Oahu, Oct. 2014

Byodo-In Temple, Valley of the Temples, Oahu, Oct. 2014

You Might Get Lonely Once in Awhile.

I’m a card-carrying introvert, and I relish the solitude that a solo trip provides. However, multiple days on end without a planned social interaction can make anyone feel a bit lonesome -- especially when you’re separated from friends and loved ones by thousands of miles, numerous time zones and lack of cell service.

I like booking group tours every few days of my trip. In addition to it being nice to have someone else in the driver’s seat for a change, and it being eye-opening to get a unique history of the my destination from a local, I also get an instant social circle (for at least a few hours). Oh, and if you’re leaving the country, make sure you and your peeps download WhatsApp before you leave, so you can text (and even make calls!) for free whenever you’re on wifi.

Trattoria Sostanza, the site of one of the best meals I enjoyed in Florence, Italy, Oct. 2015.

Trattoria Sostanza, the site of one of the best meals I enjoyed in Florence, Italy, Oct. 2015.

Talk to Strangers.

Chatting up locals and fellow travelers is another great way to stave off loneliness…and meet some amazing people along the way. Like the couple from LA I sat next to at dinner at a communal table in Florence who shared their incredible tips for traveling through Tuscany (and their delicious bottle of wine). Or the fellow female solo traveler on my boat tour of the Grand Canal in Venice who was in the process of (successfully) completing the same travel path I was just embarking on. Or the fantastically friendly Airbnb host in Milan who treated me to an Espresso CioccolatItaliani after check-in to talk further about the ins and outs of the city. The people you meet will be one of the most memorable aspects of your trip.

The Duomo, Santa Maria del Fiore Cathedral, Florence, Italy, Oct. 2015.

The Duomo, Santa Maria del Fiore Cathedral, Florence, Italy, Oct. 2015.

Only Pack What You Can Carry.

This is especially important if you’re planning to travel through numerous international locations, or any city where there will be trains, subways and lots of schlepping involved. I’m not the kind of person that manages to pack for a 10-day trip in a carry-on. My perfect luggage combo for my trip through Italy was a rolling suitcase just beyond carry-on size, a medium-sized duffle bag (fits easily in any overhead compartment and sits neatly atop the suitcase), and a purse large enough to hold my laptop, but small enough to slide beneath the seat in front of me on the plane. This provided me with room for everything I needed to bring with me, and enough space to bring a few new things back home.

This still required that I didn’t overpack in the first place. I filled my bags about a week in advance of the trip, and constantly reevaluated what I’d packed. Did I really need another blazer? Couldn’t I re-wear that versatile black dress? Also, double-check that you can lift your bags on your own. I had to haul my bags up and down countless metro station staircases, and onto numerous high-speed train overhead compartments in Italy. You don’t want to have to depend on the kindness of strangers throughout your trip when it comes to your baggage. And arriving at your hotel a sweaty mess from lugging your things is so not chic.

Pūpūkea Beach, North Shore, Oahu, Oct. 2014.

Pūpūkea Beach, North Shore, Oahu, Oct. 2014.

If you’re thinking about or are preparing for a solo trip, the best advice I can give you (beyond again urging you to do it), is to go into it with an open mind, a willingness to be flexible, and a firm belief in your ability to tackle any challenges that may pop up along the way.

Oh, and definitely bring a portable phone charger so you can snap as many photos as possible. This will be a trip you’ll want to remember.

- Kristen