Eastern Caribbean itineraries head southeast from Florida, the Northeast or San Juan toward the islands at the top of the Lesser Antilles chain. The classic week includes St. Thomas, St. Maarten and often San Juan or the Dominican Republic, with a private island or a sea day or two along the way.
This is the beach-and-water side of the Caribbean. St. Thomas has Magens Bay and quick ferries to St. John, where most of the island is national park. St. Maarten offers two countries on one island, Tortola is the jumping-off point for the boulders and pools of The Baths on Virgin Gorda, and Old San Juan gives you 500 years of history within walking distance of the pier.
From Florida, a 7-night Eastern Caribbean cruise usually spends more time at sea than a Western one because the islands are farther away. From San Juan you skip the long crossing entirely and can fit in five or six islands in a week. Sailings from New York, New Jersey and Baltimore also reach these islands, typically on 8 to 12 night trips.
- January: Best time, average high 84 degrees F
- February: Best time, average high 84 degrees F
- March: Best time, average high 85 degrees F
- April: Best time, average high 86 degrees F
- May: Shoulder season, average high 87 degrees F
- June: Cruises run, average high 89 degrees F
- July: Cruises run, average high 90 degrees F
- August: Cruises run, average high 90 degrees F
- September: Cruises run, average high 89 degrees F
- October: Cruises run, average high 88 degrees F
- November: Shoulder season, average high 87 degrees F
- December: Best time, average high 85 degrees F
- Best time
- Shoulder season
- Cruises run
- Few or none
Temperatures in Fahrenheit, long-term averages. Climate source.
Sailings run year-round. December to April is the dry season and peak demand. The islands sit in the main Atlantic hurricane track, so June through November, and especially mid-August to mid-October, carries the highest chance of itinerary changes.
Weather to plan around: The Atlantic hurricane season runs June 1 to November 30, and the Virgin Islands and Leeward Islands lie in the path of many storms that form off Africa in late summer. Most activity falls between mid-August and mid-October. Expect possible port swaps in those months. Winter trade winds can make sea days a little bumpy on the open-ocean leg from Florida.
Ports you'll likely visit
- Charlotte Amalie, St. Thomas, US Virgin Islands
Magens Bay, duty-free shopping, the Skyride viewpoint and ferries to St. John's national park beaches. - Philipsburg, St. Maarten, Sint Maarten
Beach right off the boardwalk, plus quick trips to the French side, Orient Bay and Maho Beach. - San Juan, Puerto Rico (US)
Old San Juan's forts and colorful streets are a short walk from the pier, and evening departures leave time for dinner ashore. - Road Town, Tortola, British Virgin Islands
Boat trips to The Baths on Virgin Gorda and to some of the best sailing waters in the Caribbean. - Basseterre, St. Kitts, St. Kitts and Nevis
Brimstone Hill Fortress (a UNESCO World Heritage Site), a scenic railway and a short boat ride to Nevis. - St. John's, Antigua, Antigua and Barbuda
Many beaches close to port and the restored Nelson's Dockyard at English Harbour. - Puerto Plata (Amber Cove or Taino Bay), Dominican Republic
Purpose-built cruise centers with pools, plus excursions to waterfalls, beaches and the city cable car.
Highlights
Postcard beaches
Magens Bay, Trunk Bay on St. John and Orient Bay are within easy reach of the ship.
The Virgin Islands
US and British Virgin Islands on one trip, with calm, clear water for snorkeling and sailing.
Old San Juan
Spanish colonial forts and streets right next to the cruise piers.
Two countries, one island
St. Maarten and Saint-Martin share an island, with Dutch-side shopping and French-side beaches and food.
How long, and what documents
7 nights is standard from Florida and San Juan. Sailings from New York, New Jersey and Baltimore usually run 8-12 nights because of the extra distance.
Cruises that begin and end at the same US port are "closed-loop" sailings. U.S. Customs and Border Protection says US citizens on a closed-loop cruise can re-enter the United States with a birth certificate plus a government-issued photo ID, and children under 16 need only proof of citizenship such as a birth certificate (most lines want an original or certified copy, not a photocopy). CBP also warns that the countries your ship visits may still ask for a passport, and cruise lines can set stricter rules than the government does. We recommend a passport book anyway: if you miss the ship or have to fly home early from a foreign port, you cannot board an international flight without one, and a passport card works only for land and sea crossings. Non-US citizens, including green card holders, have different rules. Check current requirements with your cruise line and the State Department before you sail. St. Thomas, St. John and Puerto Rico are US territories, but your other stops are foreign countries with their own entry rules.
Specialist tips
- If you want more island time and fewer sea days, look at round trips from San Juan.
- St. Thomas is a US territory, so US cell plans and the dollar work there, and US citizens get a higher duty-free allowance on purchases made in the USVI.
- Ferries from St. Thomas to St. John take time; book a ship excursion or leave a wide margin if you go on your own.
- Charlotte Amalie has two cruise piers (Havensight and Crown Bay); check which one your ship uses before planning transport.
