Caribbean & Bahamas Vacations, Planned Free
Stacey Vacations plans Caribbean and Bahamas vacations at no fee — resorts, honeymoons, and island-hopping across more than a dozen islands. I'm Stacey Haines, a Florida-based travel agent with Castle Dreams Travel; the resorts and suppliers pay my commission, so expert planning costs you nothing extra.
Which island is right for you? It depends what you're flying in for: the shortest flights, the best diving, French food, a wedding venue, or a resort that handles everything. Here's my honest one-minute take on each island I book.
Dominican Republic
The Caribbean's all-inclusive capital. Punta Cana delivers the most resort for the money in the region, Puerto Plata adds colonial charm and quieter sands, and Santo Domingo's Zona Colonial is the oldest European city in the Americas.
Jamaica
Reggae, jerk chicken, Dunn's River Falls, and Seven Mile Beach — Jamaica has the strongest personality in the Caribbean and the deepest all-inclusive bench, including seven Sandals resorts and Beaches Negril. First-timers and honeymooners are equally easy to place here.
Puerto Rico
No passport needed for U.S. citizens — that alone makes Puerto Rico the easiest big Caribbean trip. Old San Juan's blue cobblestones, the El Yunque rainforest, and kayaking a glowing bioluminescent bay will fill a week fast.
St. Martin
One island, two countries. The French side brings beaches like Orient Bay and some of the best food in the Caribbean around Marigot; the Dutch side answers with Philipsburg's duty-free shopping and the famous low-flying jets over Maho Beach.
St. Kitts and Nevis
A quiet two-island nation for travelers who've already done the big names. Brimstone Hill Fortress and rainforest hikes fill St. Kitts; little Nevis next door moves at plantation-inn pace beneath its cloud-capped peak.
Barbados
Calm Caribbean water on the west coast, surf on the wild east coast, and the birthplace of rum in between — plus Crop Over, the island's exuberant summer carnival. Barbados is also home to two side-by-side Sandals resorts in the St. Lawrence Gap.
St. Lucia
The Pitons give St. Lucia the most dramatic backdrop in the Caribbean, which is why it leads my honeymoon shortlist. Add three Sandals resorts, a drive-in volcano with mud baths, and rainforest running to the horizon.
Martinique
France in the tropics: a French overseas territory where boulangeries share streets with rum distilleries. Hike Mount Pelée, swim at Les Salines, and eat Creole cooking that rewards travelers who plan around meals.
Aruba
Dry, breezy, and sitting outside the main hurricane belt, Aruba is the safe bet when your dates can't move. Eagle Beach and Palm Beach are the postcard; the cactus-and-cave desert of Arikok National Park is the surprise.
Curaçao
Willemstad's pastel Dutch waterfront is a UNESCO World Heritage site, and the diving ranks with the southern Caribbean's best. Sandals Royal Curaçao gives couples an all-inclusive base here, with beaches like Playa Kenepa a drive away.
Bonaire
The B in the ABC islands is a diver's island, full stop — a protected marine park rings the coast, and most sites are shore dives you can reach with a rental pickup. Flamingos, salt flats, and Washington Slagbaai National Park fill the surface days.
Turks and Caicos
Grace Bay on Providenciales regularly tops world's-best-beach lists, and one of the largest coral reef systems on earth sits just offshore. It's also home to Beaches Turks & Caicos — my go-to recommendation for big family trips.
Trinidad
Trinidad is culture over beaches: Carnival is the hemisphere's biggest party, the street food — doubles, roti, callaloo — is reason enough to fly, and thousands of scarlet ibis roost in the Caroni Swamp at dusk.
Azores
A geography asterisk on this page — the Azores are Portuguese islands in the mid-Atlantic, not the Caribbean — but these nine volcanic islands earn their spot: crater lakes, hot springs, whale watching, and direct flights from the U.S. East Coast.
Belize
Technically Central America, practically Caribbean. The Belize Barrier Reef — the second-largest on the planet — anchors the snorkeling and diving, while Mayan ruins like Xunantunich and Caracol, plus Garifuna drumming and cuisine, anchor the land days.
Which Island Should You Book?
Tell me your travel month, your budget, and who's coming, and I'll narrow this list to two or three real options with quotes. The planning is free, I work with travelers nationwide from my Florida base, and the islands stop looking interchangeable the moment someone who books them walks you through the differences.
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