5 Amazing Trips to Take On Your Own

This old-school New England island is a haven of peace and privacy. Go in February or March to catch up on paperbacks and take coastal hikes while staying at one of the many adorable bed-and-breakfasts. Our favorite, the Hob Knob Inn, serves fresh lemonade and just-baked scones on the porch at all times. The island is also blissfully cheap and quiet in the winter (to put it into perspective: The summer population of 100,000 dwindles to a mere 15,000 after Labor Day.)

Inns on Martha's Vineyard don’t stay open 'til all hours. Find out when your B&B locks up for the night so you don’t end up sleeping in your car.

Sip homemade ginger beer at legendary mixology bar La Factoría and world-famous coffee at Caficultura (one of the first artisan coffee shops in the city). Stroll along miles of unpopulated coastline. And take in a whole lotta natural beauty on an afternoon trip to the El Yunque rain forest. Best of all, friendly locals are everywhere.

Check your guidebooks and transportation schedules before leaving the hotel, train or tourist office. A single lady poring over maps is an open invitation for unwanted attention. Also, plan to arrive during the day. This way, if you have to wait for a taxi, you can get your bearings and ask some locals for directions.

If a tropical vacation isn’t your thing but you still want beaches, check out Ireland. With plenty of hiking and a fascinating history, you’ll get a solo-traveler-friendly vacation without the barriers of a foreign language or major culture shock. And of course, the Guinness Storehouse in Dublin is a must. It’s like Disneyland for beer lovers. It’s impossible not to make friends.

Chat up your waiter. Restaurant staff is always in the know about secret local gems. It’s how we discovered St. Tola, a life-changing goat cheese, at Sheridan’s Cheesemongers.

The biodiverse South American country (ooh, deserts and snowcapped mountains!) has become a huge destination for single backpackers who want to take in the local culture and gape at Machu Picchu. Several tour groups offer affordable trips, and they love when solo travelers join. Bonus: You don’t need a ton of cash to cross things off your bucket list. With prices starting at $389, View Peru Tours offers an all-inclusive five-day hike that’s pretty tough to beat.

Learn conversation basics in non-English-speaking countries (at the very least, you’ll want to know how to order lomo saltado, Peruvian meat and potatoes, and ask for directions). Sign up for Fluent City classes or get high-tech with Jibbigo, an app that can restate your words in more than 20 languages.

This small island nation is as safe as it is cosmopolitan. Check out the jaw-dropping shopping (the futuristic Ion Orchard mall spans eight retail floors, has 333 stores and cost a whopping $2 billion to build), well-preserved cultural districts like Kampong Glam and dreamy seaside escapes like Telunas, a private island resort that’s a gorgeous, two-hour ferry ride from the city center, there’s more than enough to keep you entertained.

Your carry-on bag is your best friend. Being able to handle your stuff on your own means less money spent on taxis and more money spent on Singapore Slings. We love the old adage “When preparing to travel, lay out all of your clothes and all of your money. Then take half the clothes and twice the money.” Truer words were never spoken.