A Cruise Companion guide

Caribbean Cruises

The Caribbean is the world’s most popular cruise region — and the easiest way to sample a dozen sun‑drenched islands in a single week. Ships sail year‑round from Florida and beyond, and itineraries split three ways: Eastern (beaches and duty‑free shopping), Western (Maya ruins, reefs and Mexico), and Southern (the deep, less‑crowded islands).

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Book a Caribbean sailing

Live fares, dates and cabins on Trip.com, the Guild’s booking partner. The Guild is credited when you book, at no extra cost to you.

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Would rather not fly to Florida? The Panama Canal and Mexican Riviera sail from the West Coast instead. See the West Coast guide ›

Ports of Call

The stops that make up a typical Caribbean sailing — tap any to browse places to stay in port.

San Juan, Puerto Rico

Old San Juan’s blue cobblestones and the El Morro fortress — a favorite Eastern turnaround port.

Hotels in San Juan on Trip.com ›

St. Thomas, USVI

Duty‑free shopping in Charlotte Amalie and the postcard sand of Magens Bay.

Hotels in Charlotte Amalie on Trip.com ›

St. Maarten

Two nations, one island — French cafes to the north, Dutch beaches and Maho’s jet‑spotting to the south.

Hotels in Philipsburg on Trip.com ›

Cozumel, Mexico

The Western Caribbean’s reef capital — world‑class diving plus a hop to the Tulum ruins.

📖 Read our Cozumel port guide ›Hotels in Cozumel on Trip.com ›

Grand Cayman

Stingray City sandbars and Seven Mile Beach; tender in to George Town.

Hotels in Grand Cayman on Trip.com ›

Ocho Rios, Jamaica

Dunn’s River Falls, bamboo rafting and jerk on the beach.

Hotels in Ocho Rios on Trip.com ›

Aruba

Southern‑Caribbean sun outside the hurricane belt — Eagle Beach and desert‑island calm.

📖 Read our Aruba port guide ›Hotels in Aruba on Trip.com ›

Nassau, Bahamas

A frequent first stop — Paradise Island, forts, and quick beach breaks.

📖 Read our Bahamas cruise guide ›Hotels in Nassau on Trip.com ›

Best time to cruise

The sweet spot is December through April — warm, dry and calm. Hurricane season runs June through November; sailings still go (and prices drop), but pack flexibility with the weather. Cruise lines shift ships south in winter, so that’s when choice is widest.

Who sails here

Major lines cruising Caribbean:

Royal CaribbeanCarnivalNorwegianPrincessCelebrityMSCDisney
See Caribbean fares & book →

Trip.com carries Carnival, Disney, Norwegian, Princess, Holland America, Celebrity, Cunard, MSC and Costa — but not Royal Caribbean, so book that line with your travel agent or direct. Fares are per person and include port fees.

Common questions

Eastern, Western or Southern Caribbean — what is the difference?Eastern sailings run to San Juan, St Thomas, St Maarten and the nearer islands; they are beach-and-shopping cruises with short sea days. Western sailings go to Cozumel, Grand Cayman, Jamaica and Roatan, and lean towards ruins, reefs and cave tubing. Southern sailings reach Aruba, Curacao, Barbados and the Grenadines — the furthest, the driest, usually the longest at ten nights or more, and generally the ones seasoned cruisers rate highest.

When is hurricane season, and should I avoid it?1 June to 30 November, with mid-August through October the busiest stretch. Most sailings in those months go exactly as planned, and fares are noticeably lower. What changes is certainty: a captain will re-route around a storm with a day's notice, and you may see different islands than the ones you booked. If that would spoil the trip for you, sail between December and May. If it would not, the low season is good value — but buy travel insurance.

Do I need a passport?For any flight to or from the Caribbean, yes. On a closed-loop cruise that starts and ends at the same U.S. port, U.S. citizens may be allowed to board with a birth certificate and photo ID, but several islands — Aruba among them — want a passport regardless, and you cannot fly home without one if you miss the ship. Carry the passport.

Should I book shore excursions through the ship or independently?The ship's excursions cost more, and the ship waits for them if they run late. Independent operators are usually cheaper and often better, but if their van breaks down the ship sails without you. The Guild's rule of thumb: book through the ship in ports where you are going a long way from the pier, and go independent when you are staying close to town. Trip.com does not sell shore excursions for these ports, so we do not put a button here — book with your line or a licensed operator at the pier.

Which island has the best beach?The honest answer is that it depends on the day you get. Eagle Beach in Aruba and Seven Mile Beach on Grand Cayman are the two that most consistently earn the reputation, and both are an easy taxi ride from the pier. Ocho Rios and St Thomas are prettier from the water than the cruise dock suggests. Whatever the brochure says, you have six hours ashore — pick one beach and enjoy it rather than chasing three.

Is there a Mexican tax on cruise passengers?Yes, if your sailing calls in Mexico — which most Western Caribbean itineraries do, at Cozumel or Costa Maya. Mexico charges foreign cruise passengers a non-resident duty: $5 a head from July 2025, $10 since 1 August 2026, and it is scheduled to rise to $15 in July 2027 and $21 in August 2028. It is charged once for the whole itinerary rather than once for each Mexican port, and the cruise lines collect it — most fold it into the taxes, fees and port expenses line of your invoice instead of naming it, so you may never see it itemised. Ten dollars a person will not change anyone's plans; we mention it so the figure on your final invoice is not a surprise. Eastern and Southern sailings that never call in Mexico do not pay it. The rate has already been revised more than once, so confirm the current amount with your line before you sail.

Is there a Bahamian tax on cruise passengers?Yes, if your sailing calls in the Bahamas — and many Eastern and short itineraries do, at Nassau or at a cruise line's private island. The Bahamas charges a departing cruise passenger $23 for leaving by sea from any Bahamian harbour, plus a $5 tourism sustainability levy and a $2 tourism enhancement levy: $30 a person. A higher $25 rate, which makes $32, applies only to a passenger leaving from a private island on a sailing that calls at no other port in The Bahamas — so an itinerary that takes in Nassau as well pays the $30. The charge is for leaving the country rather than for each stop, so it is paid once. The $23 and $25 rates took effect on 1 July 2023 and the $2 enhancement levy on 1 January 2024. Your line collects it and usually folds it into the taxes, fees and port expenses line of your invoice, so you may never see it itemised. Sailings that never call in the Bahamas do not pay it. Our Bahamas Cruises guide carries the full picture.

📖 Part of The Cruise Companion — a book in the Guild Travel Library. Curated by our Explorers, kept current, and free to use.

Curated by Our Guild Explorers · Updated September 2026

Destinations Guild is an independent travel company and a proud partner of Trip.com. Book through our links and you pay the same price while the Guild earns a small commission that keeps our guides free. Hotel prices are shown live on Trip.com. Cruise sailings are booked with your travel agent or the cruise line.