The Definitive Guide to Holland America Caribbean Cruises

The Caribbean is a vast tapestry of islands, each uniquely beautiful with its own history and cultures. Island-hopping by cruise is one of the best ways to explore — one day, you could be unwinding on a serene, white-sand beach and the next, you could be ambling through the sun-washed streets of a historic town.

This guide explains how to choose the best Caribbean cruise for your travel desires, how to find longer port calls, and what to expect on our private island, RelaxAway, Half Moon Cay™.

While it’s teeth-chattering cold in many places, the Caribbean always shines. Visitors are treated to swaying palms, warm waters, and excellent visibility for snorkeling excursions.

Holland America’s Caribbean favorites include Eastern routes (San Juan, St. Thomas), Western routes (Key West, Cozumel), and Southern routes (Aruba, Bonaire, Curaçao). For planning tips and port highlights, see our in-depth Caribbean regions travel guide: Cruising the Caribbean: Travel Guide.

Caribbean cruise regions at a glance:

• Eastern Caribbean (San Juan, St. Thomas)
  • Highlights: Historic forts, beautiful harbors, and shopping; trade-winds, moderate temperatures
  • When to go: Late January for lighter crowds; March for longer daylight.
• Western Caribbean (Key West, Cozumel, Grand Cayman)
  • Highlights: Reefs, turquoise cenotes, and Mayan history; sheltered seas can be gentle in mid-winter
  • When to go: January–April for drier conditions on the Yucatán.
• Southern Caribbean (Aruba, Bonaire, Curaçao)
  • Highlights: Outside the main hurricane belt; striking Dutch-influenced waterfronts, and superb snorkeling
  • When to go: November–March for consistently warm, dry weather.
• Panama Canal Discovery cruises
  • Highlights: Bucket-list canal experience plus Caribbean calls; dry season typically December–March
  • Holiday sailings: Thanksgiving, Christmas, and New Year’s cruises often feature festive menus, holiday programming, and celebratory parties under a canopy of stars

A late-night or evening stay means we remain docked for a longer period of time so you can experience more of the Caribbean’s dining scene and postcard-worthy sunsets.

Tip: Look for a crescent-moon icon next to a port name on the itinerary map to spot extended stays. Many sailings also feature full-day calls in ports such as San Juan, St. Kitts, Curaçao, Key West, and Puerto Limón.

After you’ve booked, the Navigator app lets you reserve shore excursions and dining as soon as they open — so you can secure the most popular times.

• San Juan, Puerto Rico: Sunset tours of historic forts and relaxed evening beach time
• Willemstad, Curaçao: After-dusk strolls along Handelskade and visits to the floating market
• Kralendijk, Bonaire: Sunset cruises with mojitos and tapas
• Key West, Florida: Live music on Duval Street and sunset celebrations at Mallory Square
• Puerto Limón, Costa Rica: Full-day eco-adventures, including sloth sanctuaries and canal wildlife tours

A multi-island itinerary calls on three or more distinct Caribbean nations or territories, maximizing variety in a single trip. Holland America’s 7–14-day sailings typically visit four to seven islands, while 14–20-day Collectors’ Voyages combine back-to-back routes for even broader exploration.

Our 7-day roundtrip Caribbean cruises are perfect for those who are new to island hopping. Most of our Caribbean itineraries sail roundtrip from Fort Lauderdale’s Port Everglades which simplifies flights, transfers, and embarkation. Some cruises depart from Miami. On board, our award-winning service and Navigator® app make it easy to settle in quickly.

For travel confidence and cruise know-how, explore our concise first-time Caribbean cruise guide.

• Clothing essentials: Lightweight, breathable layers (linen or cotton), moisture-wicking tees, swimsuit(s), coverup, a UPF rash guard or sun shirt, and a packable rain jacket for passing showers
• Footwear: Comfortable walking shoes or sandals with tread, water shoes, and one dressier pair for evenings
• Sun & swim kit: Reef-safe SPF 30+ sunscreen, lip balm with SPF, polarized UV-blocking sunglasses, wide-brim hat, and after-sun aloe
• Day ashore gear: Small backpack or crossbody, dry bag or waterproof phone case, reusable water bottle, lightweight towel, casual outfits, a light sweater or wrap for air-conditioned venues, and one dressier ensemble
• Evenings on board: Smart-casual outfits, a light sweater or wrap for air-conditioned venues, elevated wear for Dressy Nights, and your brightest, whackiest Orange Party ensemble(s)
• Health & comfort: Prescription meds (in original containers), basic first-aid items, motion-comfort remedies, and insect repellent.
• Tech & docs: Key identification documents, travel insurance details, credit card(s), compact USB charger, and charging cables
• Nice-to-have extras: A beach read, underwater camera, magnetic hooks for cabin organization, small laundry kit (travel detergent and stain stick), fold-flat tote for souvenirs, and pocket binoculars for coastal views

• Before you book: Consider the Caribbean regions you’d most like to visit and your preferred balance of port and sea days
• 60–30 days out: Upload travel documents and payment method
• 45–21 days out: Reserve shore excursions and specialty dining
• 14 days out: Coordinate embarkation arrival time; review transfer options
• 7 days out: Reconfirm passports/visas, flight times, and travel insurance

Instead of flying from island to island, traveling by sea means unpacking once, unwinding on your way from port to port. Our 7- to 14-day sailings often visit four to seven islands, while our Collectors’ Voyages (14–20 days) link back-to-back itineraries into one voyage for a more immersive exploration.

Nearly all of our 2026-2027 Caribbean cruises visit RelaxAway, Half Moon Cay™, our Bahamas paradise, voted the #1 private island 20 years in a row. Everything you need to have the ultimate beach day awaits, from fresh flavors to sun-and-surf supplies.

• Enhanced beach facilities, shopping venues, and new pickleball courts, soft beaches, clear lagoon, and protected wildlife habitats, Roaming Aperol Spritz Tricycles and Bacardi Beach Buggies.
• Powdery white sand, crystal-clear water, protected wildlife habitats
• Reef snorkeling, horseback riding in the surf, and guided nature walks
• Upgraded cabanas and villas, plus canopy loungers for two
• Casual island eats and bars along sandy beaches

Plan your perfect beach day with our curated list of top things to do on RelaxAway, Halfmoon Cay™.

Fort Lauderdale–Hollywood International Airport (FLL) is about a 10-minute transfer; Miami International Airport (MIA) is about 35–60 minutes depending on traffic. Ride shares, private cars, and Holland America transfers are all available.

Most sailings are 7–14 nights roundtrip from Fort Lauderdale, visiting ports such as RelaxAway, Half Moon Cay™; San Juan; St. Thomas; Aruba; Curaçao; and Cozumel. Some depart from Miami.

Reserve as early as possible — ideally right after booking — using Manage My Cruise and the Navigator® app for the best selection of times and experiences.

You’ll find accessible staterooms on board, food allergy accommodations, and other accessibility options; it’s important to make requests well in advance to the Guest Accessibility Department so we can assist during your cruise.

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