Choosing the Right Caribbean Island to Visit

All of us have dreamt of a Caribbean escape at some point, especially after a particularly long week at work or a difficult project. When you’re ready for a vacation but a trip across the world isn’t feasible, head to the Caribbean for a dose of culture and excitement. It’s close to the U.S. and because there are nearly thirty separate countries consisting of thousands of different islands, everyone will find a spot they love. We’ve broken down the region into four categories to help you plan.

Affordable Picks 

Source: Arnob Alam

Puerto Rico

This U.S. territory is relatively close to the continental U.S. and frequent daily flights make it a great option for those looking for a Caribbean vacation on a budget. Fly into San Juan and start off by visiting Old San Juan, a historic part of the city made up of cobblestone streets and colorful buildings that just ooze charm. Nearby, the Bioluminescent Bay is a must visit; we recommend renting a kayak to see it up close. Round out your vacation with trip to Vieques, an island off the coast that’s home to beautiful secluded beaches, wild horses, and great snorkeling.

When to go: Late spring (any time between April through June) is a great time to go, but for the best savings, head there in the fall.

Dominican Republic

This island is another one that’s easily accessible from the U.S. and you can often find good flight deals, which make it an affordable vacation spot. There are a few beaches to choose from, but Punta Cana is typically a great option—especially if you want to stick to a budget without scrimping on amenities. There are several high end, all-inclusive resorts as well as a few smaller, budget options. During low season, you’ll be surprised at how far your dollar will go, and you may very well be able to snag a luxury property at a very deep discount. La Romana is yet another option that’s home to several resorts, beautiful beaches, and a plethora of water activities.

When to go: The Dominican Republic is relatively affordable all year, but March through August is a good bet. Just be cautious when traveling during hurricane season.

Best Beaches

Source: Roman Leinwather


Antigua is known for having 365 days worth of beaches (as in a beach for every day of the year) so there’s bound to be a beach here for just about anyone to enjoy. You’ll find that classic Caribbean beach you imagine in your head: Sands are soft and white, the water is crystal blue, and the vibe is relaxed and quiet. Hotels and resorts are abundant with beach chairs and umbrellas lining the sand waiting for you to relax. You can also rest easy while taking in the rays or reading a book, as almost all beachside areas will serve you cocktails and snacks directly on the beach.

When to go: Go during off-season (May through November) to avoid crowds. The weather will still be amazing, and you’ll have the beach to yourself.


Many laud it as one of the most beautiful islands in the Caribbean, and it’s easy to see why once you catch a glimpse of its beaches. While other parts of the Caribbean have faced overdevelopment, Anguilla manages to retain its island charm. Be sure to spend some time at Shoal Bay East, a beautiful stretch of sand that offers restaurants and bars looking out to crystal blue waters. For a slightly more secluded adventure, head around the corner to Upper Shoal Bay to experience what is arguably the whitest powdery sand in the entire region.

When to go: May through August right after the high season is the best time to go. Fall is another option if you’re looking for a deal, but many properties do close down during this time.

Foodie Paradise

Source: Telegraph


For food overflowing with flavor and locals eager to share their food traditions with you, head to Jamaica. You’ve probably had jerk chicken or pork (the national dish), but there is a whole lot more to discover here. As you might suspect, the local seafood is excellent and incredibly fresh. If you haven’t had the pleasure of feasting on curried goat or oxtail stew, take a chance and try some of the most flavorful dishes often served with a side of Jamaican rice and peas.

When to go: Head here towards the end of the year anytime from October through early December for good weather without the threat of a hurricane. If you’re okay with risking it, you can get great deals during the summertime beacuse of hurricane season (try to get traveler’s insurance if you go this route).

St. Martin/Sint Maarten

The island is split into two sides: French and Dutch, and both offer a plethora of excellent dining options sure to make any foodie happy. Traditional French cooking techniques (as well as other international cuisine) are infused with quintessential Caribbean style and flavors. Think delectable lobster bisque to start, roasted local fish for the main course, and flambéd pineapple or coconut ice cream for dessert. If you aren’t looking for a fancy meal, you can’t go wrong with the many roadside barbecues serving up local flavor.

When to go: Many spots here close down during hurricane season so it’s best to visit from May through June or from November through December to get a good price. Avoid the height of winter as prices typically go up significantly.

Scuba and Snorkeling

Source: Carlos Villoch via

Cayman Islands

Often celebrated for having some of the most crystal clear waters in the world, the Cayman Islands should be your first choice for underwater activities. They offer no shortage of choices when it comes to picking the best underwater company to snorkel or dive among. Off the shores of Grand Cayman lies the famous “Stingray City” where visitors head to pet and interact with rays in a shallow part of Grand Cayman’s North Sound. You can also head out on a catamaran for a day of snorkeling in the nearby reefs.

When to go: Go during May through July for warm weather and discounted hotel rates.


The tiny island of Bonaire in the southern Caribbean is heaven for scuba divers. The coast is lined with reefs, making for a perfect destination for both serious divers and more casual snorkelers. The reefs are gorgeous and well preserved, and harbor more than 350 different species of fish. Almost every hotel and resort has an on-site dive shop, and those that don’t usually partner with one very close by.

When to go: October through November is the best time to visit if you can swing it. The weather will still be quite warm, and prices will be discounted.

Tell us! Have you visited the Caribbean? How was it?