It’s your trip, your way!

Where to? Well that all depends entirely on you (huzzah!) and your heart’s innermost travel desires. And the key to choosing the right destination for your first solo trip is balancing the passion (your hankerings for French pastries, zip-lining between two mountains, touring vineyards) with the practical (how easy is it to get around, speak the local language, is it safe?). With that in mind, here are a few of the best places to visit on your first solo adventure.


Request Now

New York City

It’s called the city that never sleeps for good reason, and that’s a bonus for solo travellers. Things are open late, if not 24-7, and that means you have more activity options to keep you busy, and there are always people on the streets (#safetyFTW). Getting across the city is relatively easy, there’s the subway, Uber, ferries (sightseeing and transport!) or you can easily (and with the right footwear) trek around on foot. Some highlights: the Chelsea Highline walkway, the Brooklyn Bridge, the Metropolitan Museum of Art, the MoMA, Central Park, shopping in Greenwich Village, taking in a show on Broadway—you can’t possibly fit it all in, but it’s really fun to try. (View our photographers in New York City.)


Small, charming, walkable Florence is totally safe and easy to navigate. Everything is either north or south of the Arno River, which works as such a great reference point, even in a city where a lot of the ancient yellow buildings can look the same. Hit up the designer shops on the Via Tornabuoni, compare the Gucci Garden to the Boboli Gardens, take selfies on the iconic Ponte Vecchio bridge (early bird gets the selfie worm), wander through the local markets, gape at tiny shoes at the Salvatore Ferragamo Museum, or just eat and drink your way through the wine bars and pizza joints. (View photographers in Florence.)


Even the vandalism is art, people! Street-art beautiful Lisbon isn’t tiny, but its central areas are so easy to navigate, the people are so very friendly (and also speak English, Spanish and French typically, because of their tourist economy), and the food is so beyond superlatives you won’t even believe it. Take a free walking tour to get the lay of the land and learn about Portugal’s wild and storied history, then visit the Time Out Market, Tower of Belem, the Old Town Alfama, stop in at any tapas bar, try the cod four ways, try any breakfast pastry, and wash it all down with some Douro Valley wine or Porto port. (View photographers in Lisbon.)


Nice English-speaking Canadians, nice mountains, fabulous transit. You can get around all of the small-ish downtown peninsula on $3 (buses, skytrains, Canada Line) or walk or rent a bike from one of the many city bike parking lots throughout Vancouver. Walking/cycling the Seawall around Stanley Park or visiting historic cobblestone Gastown are big draws, but don’t be afraid to cross over into boutique-y, Portland hipster-esque “East Van.” Main Street in East Vancouver is a particular delight (from about 7th Ave. up to 28th Ave.) and is packed with oodles of craft breweries, boutique shops and restaurants. (View photographers in Vancouver)


This Netherland gem is always at the top of everyone’s solo travel lists because it is safe, walkable and cute as all get out. Forget the weed and the Red Light District stigmas, this is a place for cultured adults! Go check out a museum (where you get to go at your own pace) like the Van Gogh Museum, Rijkismuseum (Dutch National Museum, i.e. art, history) or the Stedelijk Museum (modern art central). Walk the gorgeous bike-lined city canals, see the Brouwerijhe t’ ij brewery that’s next to a windmill, visit/smell your way through a floating barge flower market on the Singel Canal, or wander around the cobblestone web of Nine Streets (De Negen Straatjes) to check out independent boutiques and vintage shops. (View photographers in Amsterdam.)

Costa Rica (the Group Trip)

Group trips or tours (e.g. Contiki, G Adventures) are probably the best way to ease into solo travel because everything is planned for you (accommodation, transport, local activities) and set up in advance. This takes the stress out of travelling (it doesn’t matter if your train is late, if you don’t know where you are, can’t find your hotel, can’t read a sign, it’s all good!) and can be a fantastic way to see countries that are less touristy. Costa Rica is one of the friendliest, safest countries in Central America, but the beauty is visiting more than one city, and to do so you have to take tourist vans through mountainous rocky roads. Group trips take you all over, from surfing lessons and sea kayaking in Tamarindo to jungle zip-lining and canyoneering near Monteverde. Your local tour guide will give you insight into the people and the traditions—plus you get to meet new people (your trip companions) and try new experiences without any fear. Other great group trip destinations: Belize, Vietnam, Thailand, Malaysia and New Zealand.


Request Now