"The Caribbean" sounds like one place, but on a cruise it's really three: the Eastern, Western and Southern Caribbean. Each has its own personality, its own ports and its own kind of perfect day. Lucky for us Floridians, our home ports are the gateway to all three. Here's how to pick yours.
Eastern Caribbean: Beaches, Duty-Free Shopping and Easy Island Hopping
Typical ports: St. Thomas (U.S. Virgin Islands), St. Maarten/St. Martin, San Juan (Puerto Rico), Tortola (British Virgin Islands), Grand Turk, the Dominican Republic, plus Bahamas stops like Nassau and cruise-line private islands.
What it's known for: Postcard white-sand beaches (hello, Magens Bay on St. Thomas!), some of the best duty-free shopping in the Caribbean, historic Old San Juan with its centuries-old forts and cobblestone streets, and a relaxed, "no worries" vibe. Snorkeling, sailing and beach days are the stars here.
Typical length from Florida: Usually about a week (7 nights), since the islands are farther east of Florida than the Western ports.
Florida homeports: Port Canaveral, PortMiami and Port Everglades (Fort Lauderdale).
Best for: Beach lovers, shoppers, first-time cruisers and anyone who wants a laid-back, easy-going island week.
Western Caribbean: Mayan Ruins, Reefs and Adventure
Typical ports: Cozumel, Costa Maya and Progreso (Mexico), Belize City, Roatán (Honduras), Grand Cayman, Jamaica (Falmouth, Ocho Rios, Montego Bay) and sometimes Key West or a cruise-line private island.
What it's known for: Adventure! Think ancient Mayan ruins on the Yucatán, world-class snorkeling and diving on the Mesoamerican Reef, swimming with stingrays at Grand Cayman's Stingray City, climbing Dunn's River Falls in Jamaica, zip-lining through the rainforest in Belize and Roatán, and plenty of tacos and Caribbean flavors along the way.
Typical length from Florida: The most flexible region. You'll find short 4- and 5-night getaways as well as full 7-night sailings.
Florida homeports: PortMiami, Port Everglades, Port Canaveral and Tampa (it's also popular from Gulf ports like Galveston and New Orleans).
Best for: Adventurers, families, history buffs, divers and snorkelers, and anyone short on vacation days.
Southern Caribbean: The Bucket-List Islands (More Sea Days, Yay!)
The ABC Islands: the heart of a Southern Caribbean cruise
Most Southern Caribbean itineraries are built around the "ABC" islands: Aruba, Bonaire and Curaçao. They sit just off the coast of South America and are part of the Kingdom of the Netherlands, so you get Dutch charm with Caribbean sunshine.
Aruba: Dreamy white-sand beaches like Eagle Beach and Palm Beach, and a sunny, dry climate.
Bonaire: A diver's and snorkeler's paradise, famous for easy shore diving in its protected marine park.
Curaçao: The colorful Dutch waterfront of Willemstad and its floating Queen Emma Bridge, plus hidden-cove beaches.
Add-on ports on some itineraries: Barbados, St. Lucia (home of the dramatic twin Pitons), Antigua, Grenada (the "Spice Isle"), Dominica's rainforests, St. Kitts and Martinique. Their mix of Dutch, French, British and Caribbean heritage makes every port feel different, and many of these islands are less crowded than their northern neighbors.
Getting there: here's the part we love
The Southern Caribbean islands sit a long way from Florida, so you'll get there one of two ways:
Sail round-trip from Florida on a longer cruise. Southern Caribbean sailings from Florida typically run 10 nights or more, which means more sea days. Yay! 🎉 Sea days are pure vacation: sleep in, lounge by the pool, book that spa treatment, catch a show, try a new restaurant onboard, or just watch the ocean go by with a cocktail in hand. On a longer cruise, getting there really is half the fun.
Fly to San Juan, Puerto Rico (or another southern homeport like Barbados) and cruise from there. Starting in San Juan puts you right next door to the southern islands, so you spend your week (or longer) hopping between ports instead of crossing open ocean. Some cruises are one-way, like San Juan to Barbados or San Juan back to Miami, so you may fly home from a different city.
Good to know about San Juan: Puerto Rico is a U.S. territory, so U.S. citizens don't need a passport to fly between the mainland and Puerto Rico. Just bring a REAL ID-compliant ID (or your passport). That said, your cruise will visit foreign islands, so we strongly recommend that every traveler carry a valid passport for the cruise itself. It makes things much easier if you ever need to fly home from a foreign port. Starting in San Juan? Plan to arrive the day before. We're happy to set up your flights and a pre-cruise hotel so you can enjoy Old San Juan without stressing about sailing day.
Florida homeports: Mainly Port Everglades and PortMiami (often on longer sailings), plus San Juan and Barbados as fly-to homeports.
Best for: Experienced cruisers who've "done" the Eastern and Western Caribbean, sea-day lovers, culture seekers and divers.
Quick Comparison
| Eastern | Western | Southern | |
|---|---|---|---|
| Signature ports | St. Thomas, St. Maarten, San Juan, Bahamas | Cozumel, Costa Maya, Roatán, Belize, Grand Cayman, Jamaica | ABC islands (Aruba, Bonaire, Curaçao), plus add-ons like Barbados, St. Lucia, Antigua, Grenada |
| Known for | Beaches, duty-free shopping, Old San Juan | Mayan ruins, reefs, adventure excursions | Dramatic scenery, culture, diving, fewer crowds |
| Typical length | ~7 nights | 4–7 nights | 10+ nights from Florida, or ~7 from San Juan |
| Florida homeports | Canaveral, Miami, Fort Lauderdale | Miami, Fort Lauderdale, Canaveral, Tampa | Fort Lauderdale, Miami (longer sailings); fly to San Juan or Barbados |
| Best for | First-timers, beach lovers, shoppers | Adventurers, families, short getaways | Repeat cruisers, sea-day lovers, culture seekers |
Weather and Hurricane Season Tips
The Atlantic hurricane season runs June 1 to November 30, with peak activity from mid-August through mid-October. Cruising during that time is still very common (and often a great value). Ships simply reroute around storms, so an itinerary might change. Travel insurance is a smart idea any time of year, and especially in hurricane season.
Aruba, Bonaire and Curaçao sit at the southern edge of the region, below the main hurricane belt, which makes them a popular late-summer and fall pick. December through April brings the driest, most comfortable weather across the Caribbean, and it's also the busiest time, so book early.
So… Which One Is Right for You?
First cruise or just want to relax on the beach? Go East.
Short on time or craving adventure? Go West.
Been there, done that, and love a sea day? Go South to the ABC islands!
Still can't decide? That's what we're here for. Contact Jerry and Kara at Bucket Lets Go Travel and we'll match you with the right region, ship and sailing, and handle the flights and hotels before or after your cruise too. Let's go! 🌴🚢
Follow us on Instagram: @bucketletsgotravel
Photo credits
Magens Bay, St. Thomas, USVI, by dbking, CC BY 2.0, via Wikimedia Commons
Tulum, God of the Winds Temple, by Martin Falbisoner, CC BY-SA 4.0, via Wikimedia Commons
Queen Emma Bridge and Handelskade, Willemstad, Curaçao, by Martin Falbisoner, CC BY-SA 4.0, via Wikimedia Commons