[Pilot]

Everyone dreams of a Caribbean holiday. With those perfect beaches, crystal clear blue waters and weather so toasty you could spread marmalade on it – these paradise islands really are dreamboats. Although there are over 7,000 islands in the Caribbean, at least 30 of those are island nations, which means you’ve got a bumper crop when it comes to choosing where you want to go. But which Caribbean island is right for you? Will it be the verdant mountains of Jamaica, the azure waters of Barbados or the postcard views of St Lucia. Our quiz below will solve that in a jiffy.

[ehaileyyatesn]

Happy with the result? Share the quiz with your family, friends to see how they measure up. But in the meantime, if you’re new to the world of Oliver’s Travels, let us point you in the right direction. We specialise in luxury villas in Europe and the Caribbean and with over 2000 villas in our portfolio, our concierge team are sure to find you the perfect holiday home. here

[helen123]

here

[painge]

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[1kewlchicu2]

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[Foam]

[chariottrading]

Best For: Foodies, Beach Lovers, Couples, and Luxury Travel
Accessibility from US and Canada: Moderate with ferries departing from St. Martin
Price Range: $$ [links]

[cdwebbtech]

Whether you're an adventure seeker looking to hike the mountains and dive with the stingrays, or you're researching where you can indulge and relax near the beach on some luxury Caribbean vacations, this Caribbean Island Guide will help you decide where to go based on your style, travel schedule, and budget. Browse the islands below, grab your sunnies and bathing suit, and get ready to book your ticket!

[jondavis468]

Best For: Luxury Travelers, Foodies, Couples, and Beach Lovers
Accessibility from US and Canada: Will most likely have to connect on a flight from a nearby island, like Puerto Rico or Antigua
Price Range: $$

[SmokeTooMuch]

If you’re looking to relax near some of the most beautiful beaches in the world, then Turks and Caicos is your place. The islands are surrounded by crystal clear waters and beautiful coral reefs to explore. Turks and Caicos is also wonderful destination for visitors looking to be pampered and treated by some of the best health and wellness retreats and resorts in the Caribbean. here

[DSuttonsls]

The island of Barbados is perfect for people who are looking to explore outdoor activities at a lower cost than some of its neighboring islands. Some of the beaches offer perfect waves for surfing or windsurfing. Golfers can also come and indulge here as Barbados offers some really exquisite golf courses (it was actually the destination for Tiger Woods’ wedding).

[cheggers]

Some of the best travel destinations for seniors include more than just leisure. A program called Road Scholars offers educational and cultural trips of one to four weeks to exciting international and U.S. travel destinations. One of their most popular excursions is a week-long adventure in New Mexico learning about the artwork of Georgia O’Keefe and Native American cultures. here

[Poorboy]

Hawaii is one of the few US travel destinations where you can get a taste of the Caribbean without leaving the country. You can even take a Hawaiian cruise if you want to see more of the islands without moving from hotel to hotel. more

[aurelian]

Among US travel destinations, Williamsburg shines for its wide variety of activities to suit any senior—golf, museums, shopping, even historic reenactments. To keep costs low, look for hotels that offer kitchenettes and take a few meals in your room. You’ll get the best rates during the off seasons, usually spring and fall, and avoid the crowds of the summer peak season. more

[FatherMcGruder]

If you have Medicare Supplement (Medigap) Plan C, D, E, F, G, H, I, J, M or N, your plan may cover foreign travel emergency care if it begins during the first 60 days of your trip, and if Medicare doesn’t otherwise cover the care. Medicare Supplement generally pays 80% of the billed charges for medically necessary treatment you receive on an emergency basis, after you meet at $250 deductible. Your foreign travel benefits are capped at $50,000 over your lifetime. [links]

[Comatus]

Becoming eligible for Medicare can be daunting. But don't worry, we're here to help you understand Medicare in 15 minutes or less.

[nickwit]

Lush rainforests, hot springs, and botanical gardens are everywhere. It’s no wonder this is the top destination for honeymooners.

[Anthonyse]

Forgot to renew your passport or did you apply too late? It doesn’t matter when you go to these Caribbean locations.

[Dark_Ghost]

You don’t have to return home wondering how you will survive without groceries. Beauty, relaxation, and a good time can be had at these affordable places. here

[kavindave26]

With a closed-loop cruise, you can enjoy the ABC island of Curacao, an amazing mix of Creole, Asian, French, and of course, Dutch cultures.

[Verybest23]

It may be a British territory, but it is passport-protected if your cruise starts and ends in the U.S. Then a birth certificate and government-issued ID is all you need to enjoy Bermuda on a closed-loop cruise getaway.

[kat]

From small, isolated islands and underwater caves to a huge party scene, it can never be overstated that the Caribbean has something for everyone.