Leeward Islands Adventure

From $8,418 per person

8 days

Ship: SeaDream II

A charming cobblestone street lined with colorful buildings in Old Town San Juan, Puerto Rico.
SeaDream Yacht Club logo

The British Virgin Islands and French West Indies meld into the dreamiest of island journeys, complete with the most breathtakingly diverse spots in the Caribbean. Bookended by Old Town San Juan, yacht through the Caribbean islands, unwinding on the secluded sand shores of Cruz Bay, St. John. Spend a day smitten by Jost van Dyke’s sheltered White Bay, home to our signature Champagne & Caviar Splash®. Explore Virgin Gorda’s Spanish Town and the hidden bays and water-level caves of Norman Island before overnighting in chic St. Barths, the jetsetter’s Caribbean yachting playground. Discover the awe-inspiring coral reefs and fascinating flora and fauna of Anguilla’s Sandy Ground.

Journey Summary

  • Day 1 - Dec. 7, 2025, Sun. - San Juan
  • Day 2 - Dec. 8, 2025, Mon. - Cruz Bay, St. John
  • Day 3 - Dec. 9, 2025, Tue. - White Bay, Jost van Dyke
  • Day 4 - Dec. 10, 2025, Wed. - Spanish Town, Virgin Gorda
  • Day 5 - Dec. 11, 2025, Thu. - Gustavia
  • Day 6 - Dec. 12, 2025, Fri. - Gustavia
  • Day 7 - Dec. 13, 2025, Sat. - Sandy Ground
  • Day 8 - Dec. 14, 2025, Sun. - San Juan

Detailed Itinerary

Day-by-day description of your cruise and cruise activities.

Day 1 - December 07, 2025

San Juan

San Juan, founded in the 1520’s by Spanish settlers, is both the largest city and the capital city of Puerto Rico. A territory of the Unites States, Puerto Rico is comprised of the large main island as well as five smaller islands, including the popular islands of Vieques and Culebra (both ports of call on select SeaDream voyages).

SeaDream docks in Old San Juan, the oldest part of the city. Parts of this historic port city are still surrounded by stone walls dating back to the 1500’s. Narrow cobblestone streets, small shops, and points of interest like Cathedral of San Juan Bautista make this charming city a great place to stroll. Guests sailing into or departing from San Juan will enjoy views of Castillo de San Felipe del Morro, a mid- 1700’s Spanish fortress.

San Juan Luiz Munoz Marin Airport is approximately a 30-minute drive to the port in Old San Juan. Currency in Puerto Rico is USD.

Day 2 - December 08, 2025

Cruz Bay, St. John

Two-thirds of St. John Island has been dedicated as a national park and is the most virgin of the U.S. Virgin Islands. It is blessed with many beautiful beaches and bays, fine anchorages and verdant hills. Enjoy the day with snorkeling trip to Trunk Bay with its underwater guided trail, or join our kayaking land adventure. Ask your Club Director for a guided hike to Caneel Bay stopping at beautiful Honeymoon Beach for a quiet swim. Rental Cars are available should you want to explore on your own or you could borrow a SeaDream Mountain Bike for independent exploration.

Day 3 - December 09, 2025

White Bay, Jost van Dyke

The BVI’s barefoot island and home of the "Painkiller" drink. Population depends on the month – typically 250-300. This is another SeaDream destination where you may be served Champagne & Caviar Splash® followed by a beach barbecue lunch. A hike is always offered to guests to visit the famous Foxy’s Bar at Great Harbour (hopefully, the boutique is open) or you can stroll a few meters down the beach to the Soggy Dollar Bar. Snorkeling equipment is provided as well as some of our water toys!

Day 4 - December 10, 2025

Spanish Town, Virgin Gorda

Nearly every publication written about Virgin Gorda will emphasize the need to visit “The Baths” – don’t miss it! SeaDream generally arrives early and anchors off Spanish Town to give guests an early start to view The Baths before all of the tourists arrive from the neighboring Islands. You may also consider excellent scuba diving options or an opportunity to swim with the dolphins. SeaDream navigates scenically up the coast and arrives in North Sound to anchor just off the Bitter End Yacht Club. Here we offer watersports, land adventures, hiking options with the crew and tenders to the Bitter End! Depending on the voyage, you may also visit Prickly Pear Island for another signature Champagne & Caviar Splash® option with an incredible setting.

Day 5 - December 11, 2025

Gustavia

Perhaps our most treasured destination in the Caribbean! This small island belonging to the French West Indies has so much to offer our SeaDream guests. Incredible shopping only steps away from the pier. Incredible beaches, resorts, restaurants and activities both day and night. SeaDream has created various land adventures for you to discover the island from sea or land. Ask one of the officers to take you on a hike or bike ride around the island. Another great activity here is to simply relax and watch all of the incredible yachts arriving and departing just off your SeaDream yacht.

Day 6 - December 12, 2025

Gustavia

Perhaps our most treasured destination in the Caribbean! This small island belonging to the French West Indies has so much to offer our SeaDream guests. Incredible shopping only steps away from the pier. Incredible beaches, resorts, restaurants and activities both day and night. SeaDream has created various land adventures for you to discover the island from sea or land. Ask one of the officers to take you on a hike or bike ride around the island. Another great activity here is to simply relax and watch all of the incredible yachts arriving and departing just off your SeaDream yacht.

Day 7 - December 13, 2025

Sandy Ground

This British Overseas Territory is becoming more popular due to the incredible resort options as well as world recognized beaches and amazing golf. SeaDream offers an opportunity to tee off, snorkel, or, for the energetic, bike around the island with the Club Director. Naturally, we will also offer water sports while we are anchored off Sandy Ground.

Day 8 - December 14, 2025

San Juan

San Juan, founded in the 1520’s by Spanish settlers, is both the largest city and the capital city of Puerto Rico. A territory of the Unites States, Puerto Rico is comprised of the large main island as well as five smaller islands, including the popular islands of Vieques and Culebra (both ports of call on select SeaDream voyages).

SeaDream docks in Old San Juan, the oldest part of the city. Parts of this historic port city are still surrounded by stone walls dating back to the 1500’s. Narrow cobblestone streets, small shops, and points of interest like Cathedral of San Juan Bautista make this charming city a great place to stroll. Guests sailing into or departing from San Juan will enjoy views of Castillo de San Felipe del Morro, a mid- 1700’s Spanish fortress.

San Juan Luiz Munoz Marin Airport is approximately a 30-minute drive to the port in Old San Juan. Currency in Puerto Rico is USD.

Dates and Prices

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Dec 07, 2025

Ship

Your cruise ship

SeaDream II sails gracefully on calm waters under a clear blue sky, showcasing luxury and elegance.
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consultation

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