Eastern Caribbean Cruise from San Juan

Six Islands, One Trip — Turquoise Beaches & Island Culture

Who This Eastern Caribbean Cruise Is Perfect For

Ideal for beach lovers, snorkelers, foodies, and first-time Caribbean travelers looking for a seamless tropical escape. With warm water, easy island hopping, and stunning beaches, this cruise appeals to couples, families, and solo travelers alike. Whether you’re seeking guided shore excursions, hassle-free island transfers, or a winter getaway from Canada, this San Juan departure delivers relaxation, island culture, adventure, and world-class coastal scenery — all in one unforgettable itinerary.

Signature Experiences

Sail through turquoise waters and palm-fringed islands, exploring historic ports, tropical culture, and world-class beaches in the Eastern Caribbean.

Relax on white-sand shores in Antigua, Barbados, and St. Lucia
Snorkel coral reefs, protected marine coves, and crystal-clear bays
Shop duty-free in St. Maarten and St. Thomas
Enjoy rum tastings, sunset catamaran cruises, and coastal sailing
Optional experiences: rainforest hikes, guided scenic tours, horseback riding on the beach, and historic plantation visits

The best time to cruise the Eastern Caribbean from San Juan is winter to early spring, when seas are calm, rainfall is low, and temperatures are a warm 26–29°C.

Find Your Cruise

Multiple Islands, One Trip

Hop between six islands in one week — no packing, airports, or logistics. Discover new cultures, beaches, and scenery every day.

Ideal for First-Time Caribbean Travelers

Smooth sailing, guided excursions, and tropical ports make this a stress-free way to explore.

Crystal-Clear Water & Beaches

White sand, coral reefs, and turquoise bays — perfect for snorkeling, swimming, and relaxing in the sun.

Laid-Back Culture & Cuisine

Taste local rum, enjoy island BBQs, and wander colorful markets in every port.

Why Book an Eastern Caribbean Cruise?

Perfect for Canadians wanting easy island hopping and winter cruise deals — plus access to top Eastern Caribbean ports from San Juan.

Round Trip from San Juan

San Juan, Puerto Rico
Tortola, British Virgin Islands
St. Johns, Antigua
Bridgetown, Barbados
St. Lucia
Philipsburg, St. Maarten
St. Thomas, U.S. Virgin Islands
San Juan, Puerto Rico

7 Night Eastern Caribbean

Sail San Juan, Barbados, St. Lucia, and St. Maarten on one seamless Eastern Caribbean cruise itinerary, featuring world-class beaches, vibrant island culture, and easy island-hopping — ideal for first-time Caribbean travelers.