Leeward Islands Discovery

Leeward Islands Discovery

San Juan to San Juan

Jan 9, 2027 to Jan 16, 2027

7 Days

SeaDream I

12703

The trade winds of the Leeward Islands beckon with a new island experience each day, paused by an overnight in chic St. Barths, the jetsetter’s Caribbean playground radiating the ambiance of the South of France with a distinct island flair. Bookended by Old Town San Juan, your yachting journey takes you from St. John’s beautiful Cruz Bay through the secluded French West Indies and British Virgin Islands. Take in the awe-inspiring coral reefs and private beaches of Anguilla’s Sandy Ground. Discover the hidden bays and water-level caves of Norman Island. Relax on the barefoot beaches of Jost van Dyke and its sheltered White Bay, home to our signature Champagne & Caviar Splash®. Explore Spanish Town, your gateway to The Baths, Virgin Gorda’s geologic wonder made of awe-inspiring boulders that form sheltered sea pools on the beach’s edge, and Leverick Bay, kissing Virgin Gorda’s northern coast.

Date Ports of Call Arrive Depart
Jan 09, 2027 San Juan,
Puerto Rico
2 PM - 4 PM
(Embarkation)
Evening
Jan 10, 2027 Cruz Bay, St. John,
U.S.V.I.
Morning Evening
Jan 11, 2027 Sandy Ground,
Anguilla,B.W.I.
Morning Afternoon
Jan 11, 2027 Gustavia,
St. Barths, F.W.I.
Evening Overnight
Jan 12, 2027 Gustavia,
St. Barths, F.W.I.
Evening
Jan 13, 2027 Norman Island,
B. V. I.
Morning Evening
Jan 14, 2027 White Bay, Jost van Dyke,
B. V. I.
Morning Late Evening
Jan 15, 2027 Spanish Town, Virgin Gorda,
B. V. I.
Early Morning Morning
Jan 15, 2027 Leverick Bay, Virgin Gorda,
B. V. I.
Morning Evening
Jan 16, 2027 San Juan,
Puerto Rico
Morning 8 AM - 10 AM
(Disembarkation)

Ports

  • San Juan
    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.

  • Cruz Bay, St. John
    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.

  • Sandy Ground
    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.

  • Gustavia
    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.

  • Norman Island
    Norman Island

    Norman Island is located at the southern tip of the British Virgin Islands. It could very well be the very same island reputed to be the inspiration for Robert Louis Stevenson's pirate novel Treasure Island. It is said that the island was named after a pirate who purchased it at some point during the early 18th century. The island is uninhabited and privately owned by Dr Henry Jarecki. Its area is about 600 acres (2.4 km²), and it is about 2.5 miles (4 km) long. A large harbor is known as "The Bight" offers one of the most protected anchorages in the area. Guests will enjoy some great hiking opportunities as well as snorkeling and scuba diving. Another attractive option may be to check out the Willie T that is generally anchored in the harbor or simply have a beverage at the Pirates Bight Bar.

  • White Bay, Jost van Dyke
    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!

  • Spanish Town, Virgin Gorda
    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.

  • Leverick Bay, Virgin Gorda
    Leverick Bay, Virgin Gorda

    Enjoy the welcoming Caribbean breeze and the famous Baths located nearby. Other attractions include the Coppermine Ruins and Gorda Peak National Park. Of course, snorkeling is popular as are the sandy white beaches.


Suites & Staterooms

*Single Supplement for this voyage is 175% for Yacht Club Deck 2, 3 and 4. For Commodore, Admiral and Owners Suite, a 200% single supplement rate applies.


Government, Port, Document Issuance, Handling & Service fees: $420 per guest (included)


Please Note: Fares are capacity controlled and may change without notice. The fares are per person based on double occupancy. Single and third person rates are also available. SeaDream Yacht Club strongly recommends that all guests purchase travel insurance.


Yachting Land Adventures & Activities

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Testimonials

We've had a lovely time. My husband's request for his 70th birthday was to be on SeaDream in the Caribbean, and we've really enjoyed it. SeaDream is by far, the best cruise line in the Caribbean. Catherine B.Great Britain
This was the best small ship cruise we have undertaken and thoroughly enjoyed the experience. We would certainly recommend Seadream and intend [to] return in the future. Mr. & Mrs. CowieEngland