Once the holiday festivities have passed, winter starts to sound a lot less appealing. For many Canadians, that means it’s time to start planning a warm winter getaway to the Caribbean. However, choosing a Caribbean destination, finding the perfect accommodations and planning what you’ll do when you arrive can be overwhelming.
These eight simple tips will help you plan an unforgettable Caribbean getaway, so you can get a taste of summer during winter’s coldest months.
The Caribbean is an area that encourages travelers to visit more than one destination in each visit. Decide whether you want to island hop (cruises make this easy) or if you’d like to stay put and soak in the sun in one destination. Making this critical decision will also help you decide which destinations you’ll visit.
Choosing a destination (or multiple destinations) in the Caribbean can seem like an impossible task. Options range from Puerto Rico and the Dominican Republic to the U.S. Virgin Islands, the British Virgin Islands, Cuba, Jamaica, and tiny island paradises like Aruba and Curacao. It helps to turn to guides, like Lonely Planet’s Caribbean Islands travel guide, to choose a destination that suits your travel wants and needs. Friends and family who have traveled to Caribbean destinations can also offer helpful first-hand advice.
A key part of understanding how much money you’ll need for your getaway is knowing how long you will be traveling. Set your travel dates, so you can start determining your travel budget and shopping for affordable flights. Always make sure your anticipated travel dates don’t interfere with work or other obligations.
Booking your flight is the most important part of planning your getaway. Once you have a ticket in hand, your Caribbean getaway is set in stone. Booking a flight can be stressful, but using online travel agencies, like FlightNetwork.com or Expedia.com, can help ensure that you’re getting the best deal. Sites that offer price drop protection give travelers the peace of mind that if ticket prices drop, they’ll be refunded the difference in fares.
Reading reviews is a relatively new step in the travel planning process, and it’s also one of the most helpful. Reading hotel and resort reviews on sites like TripAdvisor can help you determine if the accommodations will be a good fit for you. Always read a wide selection of reviews to get a broad view of the hotel or resort. Many reviewers may not have the same expectations or standards as you.
After booking your flight, booking your accommodations is the next most important step. Once your accommodations are booked, you can really start anticipating your upcoming escape. Reserve your accommodations well ahead of time to guarantee you get the room and amenities you want.
Keep in mind that there is no international standard in terms of hotel ratings, so what may be a four-star hotel in one part of the world may not be the same in another. Be sure you’re confident in where you want to stay before you book, and thoroughly read the booking and cancellation policies before solidifying your plans.
Many travelers expect their winter getaway to continue from start to finish without a glitch. However, mishaps are common while traveling. Delayed flights happen, reservations get mixed up, and rainy days occur. Don’t let small, unfortunate circumstances ruin your time away from home. Enter the vacation without any expectations, and you’ll be pleasantly surprised with an unforgettable Caribbean experience.
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Where: Iceland
Outdoor activities are king in Iceland. Base yourself in the capital for easy day trips to virtually any corner of the country, beauty spot, or adventurous activity. Iceland frequently tops solo travelers’ lists of most user-friendly destinations. In Reykjavik, hang out at The Laundromat Café, a social meeting hub where travelers and locals casually dine, wash laundry, drink coffee, read books, and share travel tips.
Insider Tip: If you’re daunted by the thought of eating alone, The Laundromat Café also makes for an ideal dining spot. Head there for a late lunch and chances are you’ll meet others and end up staying until dinner, or perhaps even traveling together afterwards.
Plan Your Trip: Visit Fodor’s Reykjavik Guide
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Where: France
With an extraordinary array of bistros and cafés, Paris is a city where you can while away hours poring over a café au lait, chocolate chaud, and sumptuous patisseries while observing French culture through the fenêtres (windows) on the Champs-Élysées. Solo travelers gravitate towards Café de Flore and Deux Magots, which serve as meeting places for solo travelers to join up to explore the city. Also of note: Paris is a relatively safe European city for women traveling alone.
Insider Tip: Check out the hugely popular Franglish, a speed-dating-type event minus the dating, where you rotate tables with French-speakers to improve your language skills and make friends.
Plan Your Trip: Visit Fodor’s Paris Guide
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Where: Indonesia
Yoga, spirituality, spas, massages, beaches, organic eateries and markets— are you sold, yet? With such diversity, Bali is a staple for solo travelers from across the globe. People drift into its ease of life and wealth of fellow traveler-settlers. It helps that food is delicious and cheap, as is the cost of living in general.
Insider Tip: Begin a trip at Family Guesthouse in Ubud, which provides budget-friendly accommodation in a central location. Attracting repeat visitors, this is a popular base for meeting and mingling with other travelers over sumptuous communal breakfasts in a lush tropical property.
Plan Your Trip: Visit Fodor’s Bali Guide
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Where: Thailand
Solo travel and Bangkok have a long and convoluted history. It’s often said that you’d be lucky to meet a Thai in some parts of Bangkok. Luckily, other parts retain deep-rooted authenticity, which still attracts even the worldliest travelers. Temples, floating markets, cheap shopping, and nightlife galore keep the most active visitors busy traversing the city thanks to its excellent infrastructure.
Insider Tip: If you’re happy to meet backpackers by the dozen, head to Khao San Road: a hub of hostels, bars and youngsters living it up. Otherwise, any spot of particular personal interest to you is a likely way to meet others with similar interests. Bangkok is notorious for creating easy friendships.
Plan Your Trip: Visit Fodor’s Bangkok Guide
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Where: Spain
The capital of Andalusia reflects all the romantic notions of Spain, as it plays home to Moorish architecture, bullfighting, and flamenco. Easily navigable on foot, Seville offers colorful ceramics, cobbled alleyways and mouth-watering markets. The city is a photographer’s dream with inexhaustible charm, luring enthusiasts to stay a while.
Insider Tip: Seville blissfully blends the best of food and socializing. Drenched in warm climes, locals congregate outside tapas bars, which are the foundation of community spirit. One favorite is Casa Morales, where the reputation for authenticity precedes itself. Chat with friendly locals over shrimp and chunks of garlic cooked in terra-cotta dishes.
Plan Your Trip: Visit Fodor’s Seville Guide
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Where: Croatia
With an infrastructure geared for tourists, solo travel is straightforward in “The Pearl of the Adriatic,” as christened by Lord Byron. Shoulder season is warm and not yet overcrowded. Take day trips to Montenegro or Bosnia and Herzegovina. If adventure gets you going, take a hiking or rock climbing tour with Croatia Traveller, where you’ll meet others with the same interest or relax on an island cruise with others while sipping sundowners along the dramatic Dalmatian coastline.
Insider Tip: Stay in lodgings near the city center with communal lounges for socializing, such as Stari Grad or Jinx Jinxy.
Plan Your Trip: Visit Fodor’s Dubrovnik Guide
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Where: Ireland
Anyone anywhere could make friends over a pint of Guinness, and Irish hospitality is world-famed for warmth and friendliness, especially in Dublin. Head to a traditional Irish pub, havens of chatter, to converse with locals who are completely used to tourists, even in the most remote countryside spots. Join walking tours exploring the literary greats, from Oscar Wilde to George Bernard Shaw, earning Dublin its UNESCO City of Literature status.
Insider Tip: For a reasonably priced and elegant stay, try Kilronan House. An 8-minute stroll from major attractions, owner Terry Masterton goes all out to help with itineraries, sightseeing, and introducing guests to others.
Plan Your Trip: Visit Fodor’s Dublin Guide
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Where: New Zealand
The adventure capital of New Zealand’s South Island can leave you exasperated trying to fit it all in. From bungee jumping to zorbing to horseback riding, Queenstown is a mecca for adventure travellers. There’s also superb gastronomy and nightlife, too. Travelers often end up staying longer than planned, so consider yourself warned. It’s easy to rent a car or join a group trip; the latter is a sure-fire way to meet others traveling through a country known for its safety.
Insider Tip: A great starting point is the BBH Budget Backpacker Hostels. Even non-backpackers will find connections and tips on the website alone. Time2Go provides invaluable meet-and-greet orientation tours, by locals, on arrival.
Plan Your Trip: Visit Fodor’s Queenstown Guide
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© Peter Guttman
Where: Chile
Consistently raved about by travelers for its advanced transportation networks, excellent restaurants, and beautiful public spaces, Santiago is a sophisticated and accessible yet authentic South American city. Head straight for Bellavista, a trendy bohemian quarter with bars, quirky buildings, and artistic graffiti. Within easy reach from Santiago are colorfulValparaiso and glitzy Vina del Mar.
Insider Tip: Drink a michelada at Bar Don Rodrigo (Victoria Subercaseaux 355, Santiago), a time warp to the past. Perch on a bar stool and chat with friendly barman Don Santiago, who’ll look after you and even introduce you to the locals. It’s probable you’ll find yourself going native with invitations to family asdos (barbecues), as the locals are very inviting.
Plan Your Trip: Visit Fodor’s Santiago Guide
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Where: Kenya
Nature has a way of bringing people together. In the Masai Mara’s vast Big 5 terrain, a safari plunges visitors deep into the grasslands. Independent travelers are joined up with others on Jeep safaris, providing an instant set of friends. June to October is best to witness the Great Migration, a movement of millions of wildebeests. But during low season, many lodges waive single supplements.
Insider Tip: Stay in a setting designed to meet others. Naibor Camp is intimate, with few eco-luxury tents where guests can interact over communal dining with the friendly and entertaining managing couple, Ken and Michelle. Dinner is preceded by drinks around the campfire under immense starlight.
Plan Your Trip: Visit Fodor’s Masai Mara Guide
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Where: Canada
Summer is kicking in the bohemian and laid-back city of Vancouver. Live music festivals, such as Osheaga, are a big draw here. Non-stop summer sunshine guarantees plenty of outdoor fun, allowing you to bask in the rays in the signature, relaxed ambiance for which Vancouver has become known.
Insider Tip: Over the summer, students rent out their rooms on the rental section of website Couchsurfing, which has a huge global following. Many travelers use the site to make local friends before even stepping foot in the city. It’s always fun to head to gigs and events with people.
Plan Your Trip: Visit Fodor’s Vancouver Guide
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Where: Belize
The coolest Central American destination right now has to be Belize. Ambergris Caye lives up to the hype, and there are bars, beaches, and natural beauty in huge quantities. Interspersed with Mayan ruins, a spectacular barrier reef, and rainforest, this English-speaking nation appeals to expats and solo travelers alike.
Insider Tip: Stay at Victoria House for an expansive private beach and friendly staff very willing to show you safely around town. The Phoenix is a sassy, stylish spot with fully loaded apartments, including a mobile phone and the best concierge in town for handy hangout tips.
Plan Your Trip: Visit Fodor’s Ambergris Caye Guide
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Where: Japan
You’ll need 3–4 days in Tokyo at the very least. Indulge in the cuisine with sushi, ramen, and tempura that’s better than you’ve ever tasted. If you’re keen to meet English speakers, head to Pink Cow bar in Roppongi, known for its expat following. The Hub is a chain of pubs, popular with younger crowds, where it’s easy to meet people organically.
Insider Tip: The buzzy name on the traveler scene is Asakusa Smile hostel, a popular spot for meeting fellow travellers. Traditional ryokan guesthouses also offer plenty local interaction. The Friends section of Japanguide.com is great for meeting locals online before heading out. The site has a good track record.
Plan Your Trip: Visit Fodor’s Tokyo Guide
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Where: Southwest USA
This beautiful, vast Grand Circle spans five states loaded with national parks and monuments, interwoven by designated scenic byways. It’s an attractive route to Grand Canyon, Bryce Canyon, Zion National Park, and more.
Insider Tip: Hire a tour guide, rent a car, and meet fellow solo travelers on the way. Grand Circle’s website has tour guides and connects travelers online. Otherwise, meet people in lodges en route, like Far View Lodge. Guided tours and ferry trips, such as Burr Ferry, are always teeming with visitors from across the globe who are often happy to meet others on the journey.
Plan Your Trip: Visit Grand Circle’s Website
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Where: USA
Whale watching, dog-sledding, horseback riding through the mountains, and eating fresh salmon are just a few of the highlights onboard an Alaska cruise.
Insider Tip: An Alaska cruise offers a happy medium for independent travelers, with an instant set of friends with whom to dine and enjoy activities. The safety net of tour guides appeals to solo travelers, who can take excursions together yet retain personal space back on the ship. For a small boutique service, try Un-Cruise Adventures, which offers exciting itineraries for those who aren’t typical cruise-goers.
Plan Your Trip: Visit Fodor’s Alaska Guide
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