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Caribbean Island Hopping
Turquoise water and a new island almost every day, by cruise ship or by short hops between islands.
Few vacations are as easy or as fun as hopping from island to island in the Caribbean. Wake up in a new port, spend the day snorkeling, on a catamaran or on a beach, then head back to a ship that feels like a floating resort, with dinner, shows and your cabin waiting.
Every island has its own flavor: the curving white sand of Magens Bay on St. Thomas, the planes roaring low over Maho Beach on St. Maarten, the colorful Dutch waterfront of Willemstad on Curaçao, Aruba’s Eagle Beach, Grand Cayman’s Seven Mile Beach, Barbados’ Carlisle Bay and the clear water around Cozumel. Many itineraries add a stop in the Bahamas or at a cruise line’s private island.
I’ll help you choose the region, the ship and the stateroom that fit your group, whether it’s a couples’ getaway, a family reunion or a girls’ trip, and help you plan excursions for each port.
Rather stay put on one island? See Jamaica, Saint Lucia, Turks & Caicos, Cancun and every Sandals & Beaches resort. Sailing from Texas? See Cruising from Galveston →
Travel insurance: I highly recommend it for every trip, especially big trips paid for well in advance. I’m happy to include a quote so you can choose the coverage that’s right for you.
Let’s plan your Caribbean Island Hopping getaway.
Request a Trip QuotePrefer to talk? Call (281) 904-6411.
Caribbean Island Hopping at a Glance
Destination Highlights
St. Thomas, St. Maarten and the Bahamas.
Cozumel, Grand Cayman and Roatán, many from Galveston.
Aruba, Curaçao and Barbados.
Cruise line beach days in the Bahamas.
Choose Your Islands
Western, Eastern or Southern Caribbean?
Ports and routes change from season to season, so I’ll check current sailings for you.
Western Caribbean
Mexico and Central America, with ports such as Cozumel, Costa Maya, Roatán, Belize City and Grand Cayman. Many Western Caribbean cruises sail from Galveston, so travelers in Texas and nearby states can drive to the ship.
Eastern Caribbean
Postcard islands such as St. Thomas, St. Maarten and Puerto Rico, often with a beach day in the Bahamas or at a cruise line’s private island. Most Eastern Caribbean sailings leave from Florida.
Southern Caribbean
Farther south, with islands such as Aruba, Curaçao, Barbados, Antigua and St. Lucia. These are often longer sailings, or round trips from San Juan, which puts more islands within reach in one trip.
Choosing a Cruise Line
Lines I book in the Caribbean include Royal Caribbean, Carnival, Princess, Norwegian, Celebrity, MSC and Virgin. Several have their own private islands or beach clubs in the Bahamas, which make an easy, relaxing beach day. Not sure which line fits? Try the cruise line comparison and quiz.
Island Hopping by Land
Prefer more than a day in port? Island hopping by land means a few nights on two or three islands, linked by short flights or ferries, such as St. Thomas and St. John, Aruba and Curaçao, or a Sandals or Beaches stay split between two islands. I’ll handle the flights, transfers and resorts so the connections are smooth.
Best Time to Go
The Caribbean is warm year-round. Winter and spring are the most popular times to go, and hurricane season runs June 1 to November 30, when I’ll help you pick itineraries and protect the trip with travel insurance. Aruba, Curaçao and Bonaire lie south of the usual hurricane belt.
Photo Gallery
Picture Yourself in the Caribbean
Magens Bay, St. Thomas
Maho Beach, St. Maarten
Eagle Beach, Aruba
Willemstad, Curaçao
Seven Mile Beach, Grand Cayman
Carlisle Bay, Barbados
Palancar Beach, Cozumel
Cozumel from the lighthouseTap any photo to enlarge. Photos by Wikimedia Commons photographers under free licenses, see Photo Credits.
Tours & Excursions with Viator
Tours & Excursions in Caribbean Island Hopping
Day trips, boat tours, food tours and must-see sights. Browse and book tours, tickets and attractions through my Viator link.
