Why the Caribbean Keeps Pulling Us Back
We have been to Bonaire and loved it, but the Caribbean is massive and we have barely scratched the surface. There are over thirty countries and territories spread across the region, and the variety is staggering. Dutch colonial towns in Curacao, rum distilleries in Barbados, bioluminescent bays in Puerto Rico, volcanic peaks in St Lucia. Every island has its own personality.
So we sat down and mapped out the Caribbean trips we actually want to take. Not a generic list of pretty beaches, but real itineraries based on flight availability from the US, island-hopping logistics, and what each cluster of islands offers beyond the resort fence. Here are the six trips on our list.
The ABC Islands: Curacao, Aruba, and Bonaire
We have already been to Bonaire for diving and absolutely loved it, so going back and combining it with its neighbors makes perfect sense. The idea is to base ourselves in Curacao for a few days, explore the colorful Handelskade waterfront in Willemstad, snorkel at Playa Lagun, and eat at the seafood shacks along the coast. Then hop a short flight to Aruba for the contrast: more developed, great restaurants, and the rugged north coast around Arikok National Park. Finish back in Bonaire for a few days of diving at the marine park.
The logistics here are straightforward. Divi Divi Air and EZ Air run small propeller planes between the three islands for around forty to sixty dollars each way, and the flights are only about twenty minutes. You can also fly nonstop to Aruba from most major US cities, which makes it the easiest gateway. Curacao has nonstop options from Miami and Fort Lauderdale. Bonaire has nonstop Saturday flights from Houston and Newark on United.
Best time to go is outside hurricane season, though the ABC islands sit south of the hurricane belt and rarely get hit. January through April is peak season with dry weather and prices to match. We would aim for May or early June to save money and still get good weather.
Dominican Republic, Puerto Rico, and Cuba
This is the big one. Three very different islands that happen to be close together. Start in the Dominican Republic, probably in Santo Domingo to explore the Zona Colonial, the oldest European settlement in the Americas. Spend a few days there, then head to the Samana Peninsula for whale watching if the timing is right, or the north coast around Cabarete for kitesurfing and casual beach towns.
From DR, fly to San Juan, Puerto Rico. Old San Juan is one of the most walkable historic districts in the Caribbean, and the food scene has exploded in the last few years. We would want to see the bioluminescent bay in Vieques or Fajardo, eat our way through La Placita on a Friday night, and drive out to Rincon on the west coast for surfing and sunsets.
Cuba is the wild card. Flights from the US go through specific channels and the rules change frequently, so this leg requires more planning. Havana is the obvious draw: the Malecon, classic cars, live music everywhere, and architecture that feels frozen in time. We would also want to see Vinales Valley for the tobacco farms and limestone mogotes.
Nonstop flights from the US to Santo Domingo run around five hundred dollars round trip. Puerto Rico is domestic, so flights are cheap and no passport needed. Cuba flights from Miami exist but require booking under approved travel categories.
The Windward Islands: Grenada, Barbados, and St Lucia
This cluster is pure Caribbean postcard territory but with real substance. Start in Grenada, the spice island, where you can tour nutmeg processing stations, hike to waterfalls in Grand Etang National Park, and eat some of the best local food in the Caribbean. Grand Anse Beach is stunning and far less crowded than comparable beaches elsewhere.
Hop up to St Lucia for the Pitons. These two volcanic peaks rising straight out of the ocean are one of those sights that actually lives up to the photos. Drive the winding coast road between Soufriere and Castries, soak in the volcanic mud baths, and snorkel at Anse Chastanet. St Lucia also has solid hiking if you want to climb Gros Piton.
End in Barbados for a different vibe entirely. More developed, great rum distilleries like Mount Gay and Foursquare, a proper food scene in Oistins for Friday night fish fry, and the east coast around Bathsheba for dramatic Atlantic waves crashing over rock formations.
Inter-island flights on LIAT, Caribbean Airlines, or regional charters connect these three. Barbados has the most nonstop options from the US, so it works well as a starting or ending point. Grenada has nonstop flights from Miami and New York JFK.
Puerto Rico, the US Virgin Islands, and the British Virgin Islands
This is probably the most practical trip on the list because Puerto Rico is a US territory, so no passport needed to start. Fly into San Juan, spend a few days exploring Old San Juan and the food scene, then catch a short flight or ferry to St Thomas in the US Virgin Islands.
St Thomas is the gateway to the USVI. Take the ferry to St John, which is two-thirds national park and has some of the best snorkeling in the Caribbean at Trunk Bay and Waterlemon Cay. Then head to St Croix for a completely different feel: more local, less touristy, with great diving at Buck Island and the historic town of Christiansted.
If passports are not an issue, extend to the British Virgin Islands. Tortola and Virgin Gorda are a short ferry ride from St Thomas. The Baths on Virgin Gorda, where massive granite boulders create natural pools and grottos at the shoreline, are worth the trip alone. Jost Van Dyke is tiny but famous for beach bars and a laid-back atmosphere.
Flights from San Juan to St Thomas are cheap and frequent, around a hundred dollars each way. Ferries between the USVI and BVI run regularly from Red Hook on St Thomas.
St Kitts and Nevis
This is the quieter trip on the list and that is exactly the appeal. St Kitts and Nevis are two small islands connected by a short ferry ride, and they have managed to stay relatively under the radar compared to their neighbors. St Kitts has Brimstone Hill Fortress, a UNESCO site with panoramic views, and the scenic railway that circles the island through old sugar plantations.
Nevis is even smaller and more relaxed. It is basically one volcanic peak surrounded by beaches, with a few plantation inns converted from old estates. The hiking up Nevis Peak through rainforest is supposed to be excellent, and Pinney Beach is the kind of empty Caribbean beach people imagine but rarely find.
There are nonstop flights from Miami and New York to St Kitts, typically on Saturdays, running around seven hundred dollars round trip. The inter-island ferry between St Kitts and Nevis takes about forty-five minutes and costs around twenty dollars.
Anguilla
Anguilla is the beach trip. This tiny flat island just north of St Martin has consistently been ranked as having some of the best beaches in the Caribbean, and it has stayed small and upscale without the mega-resort development you see elsewhere. Shoal Bay East, Meads Bay, and Rendezvous Bay are the headliners.
The catch is that Anguilla has no direct flights from the US. You fly into St Martin (SXM), then take a twenty-minute ferry or a short charter flight over. This keeps the crowds down but adds a layer of logistics. Hotels tend to be boutique and pricey, though there are some villa rentals that bring the per-night cost down if you are traveling in a group.
The island is small enough to drive around in a day, so the appeal is really about slowing down: beach in the morning, lunch at a beachside grill, snorkel in the afternoon, and a nice dinner. If you need constant activity, this is not the trip. If you want the best beaches in the region with very few people on them, this is it.
How We Would Prioritize
If we had to pick one trip to do next, it would be the ABC Islands because we already know we love Bonaire and want to see Curacao. The PR and Virgin Islands trip is a close second because of the easy logistics and no-passport convenience. The DR-PR-Cuba route is the most ambitious but also the most rewarding if the Cuba piece works out.
For all of these, we would be looking at using AA miles for flights since American has strong Caribbean coverage, and Hyatt or Marriott points for hotels where available. The Caribbean is generally not the cheapest region for points redemptions, but shoulder season deals pop up, especially in May and early November.
We will update this post as we actually take these trips and can report back with real details.