With more sailings than any other region, the Caribbean gives you incredible flexibility to curate the exact island escape you are envisioning. From exploring the coral reefs of the Western Caribbean to swimming the deep, reliably warm waters of Aruba and Bonaire on a Southern route, enjoy a personalized approach that matches the ideal ship to your unique travel style, ensuring your vacation fits you perfectly from the start.
Your departure port dictates your island time. While cruises leaving from the Northeast require a few days at sea to reach the warm weather, departing from Florida or San Juan maximizes your time in port. The logistics of exploring are incredibly easy on these routes: in Nassau, walk just five minutes from the cruise terminal gates to the famous straw market, and in San Juan, begin your ascent to the historic El Morro fortress the moment you step off the pier.
With more sailings than any other region, the Caribbean gives you incredible flexibility to curate the exact island escape you are envisioning. From exploring the coral reefs of the Western Caribbean to swimming the deep, reliably warm waters of Aruba and Bonaire on a Southern route, enjoy a personalized approach that matches the ideal ship to your unique travel style, ensuring your vacation fits you perfectly from the start.
Your departure port dictates your island time. While cruises leaving from the Northeast require a few days at sea to reach the warm weather, departing from Florida or San Juan maximizes your time in port. The logistics of exploring are incredibly easy on these routes: in Nassau, walk just five minutes from the cruise terminal gates to the famous straw market, and in San Juan, begin your ascent to the historic El Morro fortress the moment you step off the pier.
Round-trip cruises run seven to eleven nights and depart from Miami, Fort Lauderdale, Galveston, New Orleans, and Tampa. Caribbean cruises also depart from New York, New Jersey, and Maryland. Cruises also start in San Juan, and in some seasons in Fort-de-France, Martinique. A cruise that starts in San Juan reaches those islands in seven nights without the sea days a cruise from Florida needs. A cruise starts in Fort-de-France when MSC Opera or a smaller French ship is based there for the season. Royal Caribbean, Carnival, Norwegian, Celebrity, Princess, and the rest sail these routes, ensuring the itinerary dictates the ship choice, rather than settling for a ship and hoping the route fits.
A beach day can be a quiet cove, with the water a few steps from the shade.
Cruises that depart from the Northeast have more days at sea. From New York, New Jersey, or Maryland, the ship needs extra days to reach the islands and extra days to come home. A Florida sailing of the same length spends more of those nights in port.
The reef is the reason to get in the water, whether you swim from the beach or go by boat.
A western Caribbean cruise often includes Cozumel and Grand Cayman. An eastern one often includes St. Thomas, St. Maarten, and, on a longer sailing, Antigua or Martinique. A southern routing includes Aruba, Bonaire, and Curaçao. The port page says where the ship docks, and how far the sights are from the pier.
In San Juan the walk up to El Morro starts at the pier.
A seven-night cruise that starts in Miami is usually a Bahamas cruise, a western Caribbean cruise to Cozumel and Grand Cayman, or an eastern one to St. Thomas and St. Maarten. Two or three of those nights are at sea. A seven-night cruise that starts in San Juan usually includes four or five ports, such as St. Thomas, St. Maarten, Antigua, St. Lucia, Barbados, St. Kitts, or Aruba, Bonaire, and Curaçao, and one or two nights at sea. Miami has more ships and more sailing dates, including the largest ships. The ships that start and end in San Juan are mid-size. Royal Caribbean does that year-round, on ships such as Rhapsody of the Seas and Vision of the Seas. Celebrity and Norwegian do it on some sailings. The Icon-class ships stop in San Juan. A cruise on those ships usually starts in Florida. Old San Juan is beside the dock. A taxi from the Miami terminal reaches South Beach, so a night there is a separate booking. A passport is the document to carry from either port, because several of the islands are foreign.
In Nassau the straw market is about five minutes from the cruise terminal gate.
MSC’s large ships, including World America, start in Miami. MSC Opera, about 2,600 guests, is the smaller ship in this region. From late 2026 it starts in La Romana, and later in Fort-de-France. Explora Journeys, about 900 guests, usually sails one way between San Juan and Miami. It does not start and end in the same city every week. Viking’s ocean ships, about 930 guests, sail a 10-night round trip from San Juan, and the line does not book anyone under 18. Silversea’s Silver Shadow, about 390 guests, starts and ends some cruises in San Juan and also sails one way from Miami. Drinks are in those fares. Star Clippers does not start a cruise in San Juan or Miami. The sailing ships, about 170 guests on Star Clipper and Star Flyer and about 227 on Royal Clipper, start in St. Maarten, Barbados, Antigua, Aruba, or Grenada, and they anchor off small bays. An agent requests the Explora, Silversea, Viking, and Star Clippers fares. A past-guest number, or a military discount, belongs on that request.
Royal Clipper carries about 227 guests and sails among the smaller islands.
Popular sailings
Ships dock at Cozumel, off the Yucatán. Cancún is on the mainland, and ships do not dock there
Grand Cayman — Stingray City and the reef
Nassau and Freeport
St. Thomas and St. Maarten
Costa Maya — a western Caribbean beach stop
Antigua is on an eastern Caribbean cruise. Costa Maya is on a western one. They are not stops on one seven-night sailing
Aruba, Bonaire, and Curaçao — a southern routing, usually from San Juan
Martinique, at Fort-de-France — not the small coves down the coast
Excursion ideas
Snorkel the house reef from the beach or by boat
Sunset catamaran sail with drinks in hand
Time at the beach, with loungers, snacks, and stops to swim
Zip lines and jungle ATV rides
Conch fritters in Nassau, chopped conch fried in a seasoned batter, and time at the beach
A dive with a local guide — the reef is better from underwater
In a Martinique bakery, a croissant, layered dough of flour and butter, or a pain au chocolat, that dough around a bar of chocolate
A typical island stop ends in the afternoon. Cozumel and the private islands have a beach and a swim. In Nassau, ships dock at Prince George Wharf. Walk out through Festival Place, then left onto Bay Street. The straw market is about five minutes from the gate, and Parliament Square is a couple of minutes farther. In San Juan you can walk up to El Morro. If the ship stays longer there, you have the afternoon in the old city, and an overnight leaves the evening open. Nights in Miami or Fort Lauderdale are in the city, after you leave the ship.
When to go
Ships sail the Caribbean year-round. December through April is the peak season: the steadiest weather, and the highest cruise fares. August through October is hurricane season. Named storms rarely reach a ship at sea, and the cruise fares are lower.
In port
What to expect in port
Cozumel and the private islands have beaches. In Nassau, walk out of Prince George Wharf through Festival Place and left onto Bay Street. The straw market is about five minutes from the gate. In San Juan you can walk up to El Morro, and a longer stay leaves the afternoon for the old city.
Time in port
The ship is usually in port from morning to late afternoon. On a private-island stop you use the beach at the pier.
Worth the time
Stop in Old San Juan and walk up to El Morro and the cathedral. In Martinique, stop at a bakery instead of a jewelry shop.
Travelers
This suits a first cruise, a family, or anyone who wants a short flight from the East Coast and a port on most mornings.
Also
On a short stop, the beach is not in the town. Check how far each one is from the pier before you plan both.
In port
Where the ship docks, and what you can do there
A western Caribbean cruise, an eastern one, and a southern one do not visit the same islands. This page says where the ship docks, and how far the sights are from that pier.
These are typical routings and ports. Ships, dates, and fares change.
Fort-de-France opens onto a wide bay, and some southern Caribbean cruises start here.
Western Caribbean
7 nights
Year-round. The cruise fares are lower in late summer
Round trip, departing from South Florida or the Gulf
A cruise that departs from Florida often stops at Cozumel, Grand Cayman, and Jamaica. A cruise that departs from Galveston often stops at Cozumel and Costa Maya
1From Florida: Cozumel, Grand Cayman, Jamaica
2From Galveston: Cozumel and Costa Maya
3A day at sea each way
Eastern Caribbean
7 nights, departing from San Juan. Longer if the cruise departs from Miami
December–April
A seven-night cruise departs from San Juan. A longer cruise departs from Miami
Resort or premium
1St. Thomas
2St. Maarten
3Martinique or Antigua on the longer sailings
Aruba, Bonaire, and Curaçao
7 nights, departing from San Juan. 8–11 nights if the cruise departs from Florida
Shoulder months
Round trip, departing from San Juan, or a longer loop that departs from southern Florida
A line that is actually scheduled into Aruba, Bonaire, and Curaçao
1Aruba
2Bonaire
3Curaçao
Planning Caribbean Cruises?
Send the month and the departure port. A seven-night cruise that departs from Miami has more nights at sea than a cruise of the same length that departs from San Juan, because the San Juan ship is already in the islands. A cruise of the same length that departs from New York, Baltimore, or Boston has more sea days each way. Those sea days should be on the itinerary before you choose.
