14 Cities Experts Recommend For Your First Solo Trip

Somto Ugwueze, a travel writer at SomtoSeeks.com, recommends Lisbon, Portugal for first-time travelers. “Lisbon is not only safe, but also offers tons of activities that are perfect for solo travelers,” she tells Bustle. “You can meander through the steep, narrow streets of Bairro Alto, take a tour of the Sao Jorge Castle, watch a performance of fado, ride the iconic yellow trams, and so much more.”

James Cave, the founder of Portugalist, agrees. “It’s perfect for first-timers,” he tells Bustle. He says although pickpocketing can be an issue in some parts of the city, Lisbon is the capital of the third-safest country in the world, according to the Global Peace Index — only Iceland and New Zealand are considered safer than Portugal. “Lisbon is also affordable,” he says. “A glass of wine or a beer costs $1-4, depending on where you go, and you can easily eat out for $10 per person at lunchtime (with wine).”

Lisbon also has a great social scene, Cave says, which means you’ll get to meet people on the road. “There are meetups almost every day that are advertised on Couchsurfing and Meetup.com, and many of the hostels also put on their own communal meals, nights out, and other events,” he adds. In addition, Cave says many hostels in Lisbon look more like boutique hotels and include features like a pool, free laundry service, or coworking spaces.

Jeff Peo, cofounder and CEO of sightseeing startup walkli, tells Bustle that he’d recommend Sydney, Australia for someone who’s never traveled alone before. “Sydney is far away and exotic enough to be exciting, but familiar enough not to be overwhelming.” He says it’s also quite social, so you’re unlikely to feel lonely — especially if you stay at a hostel where you’re likely to meet lots of other first-time solo travelers.

“Group activities, such as day trips to the Blue Mountains or Hunter Valley (wine country!), or surf lessons at Bondi Beach, are also great ways to make travel friends,” Peo says. “And the city itself is big and diverse enough to keep you busy exploring on your own when you feel you need time to yourself, and the great beaches and parks provide plenty of opportunities to just relax with a book.” He says the main thing to keep in mind is the cost, as airfare can be pricey and the length of the flight is long. “This means you have to commit to at least a week-long trip, and ideally longer,” he says.

Becca Siegel and Dan Gold run the travel site @halfhalftravel. They say that if someone has never traveled alone before, it pays to travel somewhere exceedingly safe. “Taipei is organized, clean, safe for women and travelers who are on their own, and it has a great variety of things to do,” they say. “For one thing, it’s a foodie heaven: There are around five to 10 ‘night markets’ of varying sizes, each featuring the best fresh eats and snacks of the city, and sometimes from different regions of Taiwan or Asia.” And on rainy days, Siegel and Gold say there are museums and creative markets to check out.

“You can also hop on a group tour for a food tour with a local expert guide, or go with a group to the nearby hiking and trekking destinations outside the city,” they say. “For a straightforward and easy trip on your own, you can take the Taipei metro to the coastal village of Tamsui for some local culture and seafood by the water.” Plus, Taipei is also an ideal jumping-off point for seeing the rest of Taiwan, they add.

Marissa Pedersen, a travel writer at Postcards to Seattle, recommends Krakow, Poland. “The city is inexpensive for Americans, so you can easily visit on a budget and still have delicious meals,” she says. “Transportation is also affordable, so you can take the train to other cities in Poland for a quick day trip.” She says you’ll also find many other solo travelers visiting and staying in hostels that you can hang out with.

Mark Whitman, who runs the blog Mountain IQ, tells Bustle that while Cape Town has a reputation as being unsafe, it is an amazing place for solo travel. “During the peak tourist season, which runs over the summer months from November to February, the city sees a huge influx of tourists, many of which are solo backpackers,” he says. “This means there is no shortage of people in a similar position, making the process of meeting fellow travelers easy and fun.” He says the city itself is jam-packed with tourist activities, from amazing outdoor hikes up the famous Table Mountain or Lion’s Head to cultural tours, like visiting Robben Island, where Nelson Mandela was imprisoned.

“After a few days exploring the city sites, make sure to get some downtime chillaxing on the pearly white-sand beaches of Clifton or Camps Bay,” he says. And he notes that if food and wine are your thing, then you’ll find the world-famous Cape Winelands just 30 minutes outside of Cape Town. “Think Northern California at a quarter of the price,” he adds.

“The first place I traveled alone, and the one that I recommend to everyone, is Southeast Asia,” Kristin Addis, CEO of BeMyTravelMuse.com, says. “Chiang Mai in Thailand is perfect because it’s not too big, it is full of expats, and it’s very easy to travel in.” She adds that thanks to the tourism industry, English is very commonly spoken. “There’s so much to do, like ethical elephant encounters and exploring beautiful temples, and there are tons of hostels, which makes it easy to meet people,” she says. “Plus, it’s easy on the wallet — $1 curry? Yes please!”

One destination that may come to mind sooner is London, England. Apart from English being the primary language spoken, London is a massive melting pot of languages, cultures, and history. "London provides the best of so many worlds," Brie Shelly, a therapist and host of the Real Talk Travels podcast, tells Bustle. “Thanks to London being the capital of a country full of history of both current and past political dominance, it continues to be a cultural hotspot for fine cuisine, entertainment, sports, fashion, academics, and more." With several free museums and many centuries’ worth of history to absorb, there is not shortage of history lessons and experiences, she adds. “Plus, London's location makes it a great warm-up for those seeking to jump to another destination while on their solo journey, too,” Shelly says.

Cherise V. Stewart, owner and chief travel officer at Irgo Travel, agrees. “It’s a great cosmopolitan city with so many things to do and explore: restaurants, arts, entertainment, shopping, and nightlife,” she tells Bustle. “Plus, you don’t need a partner to pay for the hop-on, hop-off bus, museum tours, or a ride on the London Eye — other cities I’ve visited require a minimum of two passengers before you can book certain excursions, which isn’t too cool when you’re solo.”

Sara Graham, author of How to Make Big Moves: Relocate Without Losing Your Mind, recommends Prague in the spring, she tells Bustle. “The ‘Paris of the East’ has a bit of everything and at a fraction of the price of other popular European capitals.” She says it’s also easy to navigate on both foot and via the transit system. “Museums offer loads of history, but personally I loved taking art walks to take in all the quirky street sculptures,” she says. “Beer tours are a fun way to meet people, as would be staying at high-end hostels, like MeetMe23.” Graham says the city is stunning day and night and that some of the best views are from the Vltava River. “Grab some new friends and snacks and rent a pedal boat,” she says. “Cruising the area around Prague Castle is a trip back in time, and the gorgeous gardens behind the castle are not to be skipped.” She adds that there are fun street festivals throughout the year, too, including many that put a focus on food, like Prague's International Food Festival in the fall.

Courtnie Nichols, founder and CEO of TravelBash, a boutique travel company that specializes in curated trips, tells Bustle that she’d recommend a few solo-friendly cities in Costa Rica: Tamarindo, La Fortuna, or Puerto Viejo. “Costa Rica is a destination that’s easy to make new friends [in], as well as meet other travelers exploring, too,” she says. “Many also love it because of its natural beauty and because there is so much to see and do.” She says whether you want to hit reset and try out one of the world-class thermal spas or hot springs, zipline through the jungle, or hit up some afternoon waves for your first surf lesson, you will have plenty of options to choose from. “Costa Rica has waterfalls, volcanoes, beaches, and hosts tons of wellness and yoga retreats that draw in a lot of solo travelers every year,” Nichols says.

Joanna Lin, who started the travel and video blog ReadySetJo.com after a solo trip spanning 20 cities and nine countries in three months, tells Bustle that Tokyo is a great initial solo destination. “There’s nowhere like it anywhere else,” she says. “Besides being one of the safest cities in the world, there’s a lot in Tokyo that will stir your curiosity — from its incredible food and drink scene to their etiquette, culture, and sub-culture.” Although there may be a language barrier, a lot of things (like menus) are illustrated or have an English version, she says. “And Google Maps makes navigation a breeze — you almost want to get lost in Tokyo,” she adds. “Plus, the city is so efficient and clean with such a rich history — you’ll be so fascinated by it all, and probably not think about your qualms of solo travel.”

Gabby Beckford, digital content creator and travel blogger at PacksLight.com, recommends Dubai. “I can tell you there are an infinite number of activities for any solo traveler on any sort of trip,” she says. “You can easily meet people at a famous Friday Dubai Brunch, on group dune bashing tours in the Dubai Desert, or at one of the many hosted events you can find throughout the city.” She adds that if you’re really looking to emphasize the solo in solo travel, you can relax on any of Dubai’s stunning beaches or take an easy day trip to Abu Dhabi and wander around any of their stunning museums, including the Louvre Abu Dhabi.

“Dubai also has an amazing infrastructure: public transportation is extremely straightforward and cheap, cellphone service is strong, and there is free WiFi almost everywhere,” Beckford says. She adds that, in her experience living there solo for a year, many people speak English and the city is very friendly to women traveling alone.

According to Vincent Sim, senior destination manager at GetYourGuide, Bali offers a first-time solo traveler everything in one place: beaches, underwater worlds, volcanoes, waterfalls, rainforests, local culture, history, wellness, nightlife, cuisine, and more. “The people strongly preserve their culture and nature, making sure Bali is always a safe place for everyone to travel, including first-time solo travelers.” He says that it’s relatively cheap and that there are housing options for everyone from backpackers to high-end travelers.

Namita Kulkarni is a yoga teacher and traveler who blogs at Radically Ever After. She tells Bustle that Hội An, Vietnam is perfect for someone’s first solo trip. “It offers the right mix of being tourist-friendly yet retaining its soul and unique character,” she says. “It has a rich historical dimension — like walking through the living museum that is Hội An Ancient Town — yet is contemporary in its attitudes and everyday life.” She says it’s safe and that creature comforts are within reach at reasonable prices, too. “Hội An offers you the right mix of adventure and novelty on one hand, and ease and convenience on the other hand,” she says.

Megan Walters, manager of Selvista Guesthouses, tells Bustle she’d suggest Queenstown, New Zealand, as someone’s first solo travel destination. “It was my first city abroad as a solo traveler and is known as the adventure capital of the world — you can bungee jump, skydive, parasail, and much more,” she says. Plus, travelers under 30 or 35 (depending on what country they are from) can apply for a working visa and stay longer. “People are super friendly, open, helpful, welcoming, and speak English,” she adds. “And the country is super safe and multi-cultural with progressive attitudes, governments, and policies.” She also says that the center of town is really compact and it’s easy to get around. “It has lots of bars and restaurants in just four blocks and is very walkable,” she says.

Like everything else in life, no one destination is going to be perfect for everyone. Laura Freeman, owner of The Trip Trotter, a travel planning agency, tells Bustle that the city that’s best for a first solo trip is a destination that’s high on your bucket list. “A trusted adviser can help to plan your trip so it’s safe for a solo traveler,” she says. “And the excitement of traveling to a place that you’re passionate about visiting helps to take away from any jitters.” She also says you can prepare for solo travel by doing new activities, like taking yourself out to dinner or going to a show, alone while in your own city. “This way, you can start to get a feel for doing things alone while still having the comfort of your home turf,” she says.

Lena Papadopoulos, an intercultural consultant, says the best destination for your first solo trip largely depends on you as an individual and suggests asking yourself: How do you typically deal with change, unfamiliarity, and the unexpected?

At the end of the day, there are several destinations that would make for an ideal first-solo-trip location — it all depends on what you want to achieve on your trip. And if you run out of time to do everything, you get a destination you know and love to go back to.