Eastern Caribbean Cruises

San Juan is full of vibrant colors, from its candy-colored homes and 17th-century architecture to its shimmering lagoons and lush rain forests. Taste your way through the city’s extraordinary culinary scene or immerse yourself in its history.

Ocho Rios is known for its stunning white-sand beaches, crystal-clear waters, and lush tropical landscapes. The town offers a perfect blend of relaxation and adventure, with opportunities to explore natural wonders like Dunn's River Falls and indulge in local cuisine and cultural experiences. 

With a mix of modern amenities, duty-free shopping, and a stunning waterfront, George Town offers a unique blend of Caribbean charm and international sophistication. George Town is also a melting pot of culinary offerings, making it one of the best places to eat in the Caribbean.

An Eastern Caribbean cruise to St. Thomas is full of surprises. Though the island is known for luxury shopping and dining, it has pristine beaches, some of the area’s highest viewpoints, and excellent snorkeling opportunities.

Get the VIP beach experience. Relax on padded lounge beds, sip specialty cocktails, and indulge in a four-course lunch as you enjoy your serene surroundings.

Embark on a day of unforgettable adventures in St. Thomas. Take in stunning scenery as you kayak through a lagoon, hike a mangrove forest, and snorkel past colorful marine life. 

Take in the sights and flavors of beautiful Grand Cayman. Cruise past several famous landmarks on your way to the Seven Fathoms Rum Distillery, where you can sample the island’s award-winning rum. 

Kayak through enchanting waters at Laguna Grande of Fajardo. The bay is filled with bio-luminescent organisms that light up as you paddle, producing a glow-in-the-dark effect that’s truly magical. 

Island hop the Caribbean. Snorkel Turks and Caicos’ vivid reefs, gondola to St. Thomas’ breathtaking Paradise Point, and dip into RelaxAway, Half Moon Cay’s™ Bonefish Lagoon.

Leave your cares behind on a sun-soaked Eastern Caribbean cruise. Dive reefs off Grand Turk, meander the cobblestoned Old San Juan, and ride horses into the sea on RelaxAway, Half Moon Cay™.

Set sail on this spectacular 18-day roundtrip cruise and explore the rainbow reefs off Grand Turk, the blue cobblestones of Old San Juan, and the emerald peaks of St. Thomas.

Find out the best time of year to cruise the Caribbean, whether you want to avoid crowds, save money, or enjoy the sunniest days possible.

Arrive prepared for all your Caribbean adventures with our complete guide on what to bring. 

RelaxAway, Half Moon Cay™ is your private island playground. From relaxing activities to unique thrills, here are the top ways to spend your day on the island.

Satisfy your every craving with our exquisite on-board dining experiences. Embark on a mouthwatering journey of fine dining, award-winning cocktails, and local flavors.

Extend your tropical getaway. Add a resort package to your Western Caribbean cruise and indulge in an unforgettable overnight before or after your cruise.

Book flights that depart and arrive in time for Caribbean cruises with Holland America Line Flight Ease®. Find low prices, loads of options, and enjoy flexibility and support should plans change.