Americas

Caribbean

Turquoise water, private island beach days, and laid-back island-hopping.

Overview

Sailing the Caribbean

The Caribbean is the most flexible region I book. Short long-weekend sailings out of Florida, or full week-plus itineraries through the Eastern, Western, or Southern islands, with easy departures from multiple Florida ports practically year-round. Warm water and reliable weather make it an easy, low-stress choice, especially for first-timers and families.

Best time to sail: December – April

Where to Sail

The routes within the Caribbean

Same sea, three different trips. Here’s how Western, Eastern, and Southern compare.

Western Caribbean

The classic short getaway: Mayan ruins, reef diving, and easy 4–7 night sailings out of Florida, Texas, or Louisiana.

Cozumel, MexicoCosta Maya, MexicoGrand CaymanRoatán, HondurasFalmouth, Jamaica

Eastern Caribbean

The most-sailed route and the easiest first cruise: postcard beaches, duty-free shopping, and a private cruise-line island almost every itinerary includes.

Nassau, BahamasSan Juan, Puerto RicoSt. Thomas, USVITortola, BVIPerfect Day at CocoCay

Southern Caribbean

Fewer crowds and more variety. Dutch, French, and British colonial towns, plus some of the region’s best diving. Usually a longer 10–14 night sailing.

ArubaCuraçaoBonaireBarbadosSt. LuciaGrenada

Did You Know

Why the Caribbean is worth it

1The Caribbean Sea holds more than 7,000 islands, islets, reefs, and cays. Most itineraries touch a handful, which means there's almost always somewhere new to add to your next trip.

2At Grand Cayman's Stingray City, you wade waist-deep in open water and hand-feed wild stingrays that have gathered on the same sandbar for generations.

3Trunk Bay in St. John has an underwater snorkeling trail marked right on the seafloor, so you can follow it past real coral and reef fish without a guide.

4Puerto Rico is home to one of the brightest bioluminescent bays on Earth. Paddle it on a moonless night and the water glows blue every time your oar touches it.

5Aruba, Bonaire, and Curaçao sit just south of the main hurricane belt, so they stay reliably dry and sunny nearly year-round while the rest of the region has a storm season.

6In Ocho Rios, Jamaica, you can climb Dunn's River Falls hand-in-hand as a group, one of the only waterfalls in the world you're actually allowed to climb from the beach to the top.

A Closer Look

What the Caribbean actually looks like

Trunk Bay, St. John
Often called one of the most photographed beaches in the world, and it's a short taxi and ferry from where ships dock in St. Thomas.

The Pitons, Soufrière
You don't have to hike them to enjoy them. It's a popular shore excursion from Castries, where Southern Caribbean ships actually dock in St. Lucia.

Eagle Beach, Aruba
Consistently ranked among the best beaches in the Caribbean, and since Aruba sits outside the hurricane belt, it's a safe bet even in shoulder season.

Grand Anse Beach, Grenada
A two-mile stretch of sand that stays quiet even with a ship in port, one reason Southern Caribbean itineraries feel less crowded.

Reef life off Bonaire
The reefs start just steps from shore here, no boat needed, which is why Bonaire is one of the world's top shore-diving spots.

The east coast of Cozumel
The wilder, undeveloped side of the island, a short cab ride from the cruise pier and the crowds on the west coast.

Photos: Prayitno, Wikimedia Commons, CC BY 2.0 · Wikimedia Commons, public domain · DDJJ, Wikimedia Commons, CC BY-SA 4.0 · Varun Kapoor, Wikimedia Commons, CC BY 3.0 · Chris Coccaro/NOAA, Wikimedia Commons, public domain · Bernard Dupont, Wikimedia Commons, CC BY-SA 2.0

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