Leeward & Windward Islands Explorer

Leeward & Windward Islands Explorer

San Juan to Bridgetown, Barbados

Feb 12, 2028 to Feb 23, 2028

11 Days

SeaDream II

22808

Volcanic silhouettes, secluded palm-lined beaches, and unassuming island charm define your yachting journey through the British Virgin Islands, French West Indies, Guadeloupe, and the Grenadines. Sailing from Old Town San Juan, call on St. John’s sheltered Cruz Bay, for snorkeling and diving spots off perfectly manicured beaches. Discover 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. Explore the hidden bays and water-level caves of Norman Island. Overnight in chic St. Barths, the jetsetter’s Caribbean playground, radiating the ambiance of the South of France with a distinct island flair. Stroll bustling Philipsburg, the capital of Sint Maarten. See the isle of St. Kitts through the eyes of South Friars Bay, stretching along the isthmus coast of the island’s southeast peninsula. Explore Îles des Saintes, a small archipelago of eight incredible islands off the southern coast of Guadeloupe. Overnight in Bequia, a tiny island of quiet lagoons, reefs, and silvery stretches of beach, often referred to as “the best-kept secret” of the Caribbean. Unwind in secluded Mayreau, just east of the Tobago Cays, where the azure waters of Salt Whistle Bay meet the aroma of savory lobster.

Date Ports of Call Arrive Depart
Feb 12, 2028 San Juan,
Puerto Rico
2 PM - 4 PM
(Embarkation)
Evening
Feb 13, 2028 Cruz Bay, St. John,
U.S.V.I.
Morning Late Evening
Feb 14, 2028 Spanish Town, Virgin Gorda,
B. V. I.
Morning Afternoon
Feb 14, 2028 Norman Island,
B. V. I.
Afternoon Evening
Feb 15, 2028 Gustavia,
St. Barths, F.W.I.
Morning Overnight
Feb 16, 2028 Gustavia,
St. Barths, F.W.I.
Late Evening
Feb 17, 2028 South Friars Bay,
St. Kitts & Nevis
Afternoon Late Evening
Feb 18, 2028 Terre De Haut, Îles des Saintes,
Guadeloupe, F.W.I.
Morning Evening
Feb 19, 2028 Port Elizabeth, Bequia,
St. Vincent and the Grenadines
Afternoon Overnight
Feb 20, 2028 Port Elizabeth, Bequia,
St. Vincent and the Grenadines
Evening
Feb 21, 2028 Tobago Cays,
St. Vincent and the Grenadines
Morning Evening
Feb 22, 2028 Mayreau,
St. Vincent and the Grenadines
Morning Evening
Feb 23, 2028 Bridgetown, Barbados,
Barbados
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. From Cruz Bay, we offer several Yachting Land Adventures specially created for SeaDream guests, including an exclusive experience at the Lovango Resort & Beach Club, tucked away on a private island just off St. John.

  • 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.

  • 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.

  • 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.

  • South Friars Bay
    South Friars Bay

    South Friar's Bay offers SeaDream guests a new way to explore the island of St. Kitts. Rather than docking at the capital, the yacht will be anchored in the bay. This particular bay is one of the two bays stretching along the coast of the isthmus connecting the Southeast Peninsula, with the rest of the island of Saint Kitts. From swimming and snorkeling on the south side to body surfing on the north, Friar's Bay offers guests several options. Many locals consider the southern beach the best on the island. If you are thirsty, no worries as there are multiple beach bars, offering various food and beverage options. The island itself offers several land adventure options including the Unesco Awarded Brimstone Fortress, Zip Lines, off road adventures and golf at the Royal St. Kitts.

  • Terre De Haut, Îles des Saintes
    Terre De Haut, Îles des Saintes

    If you’re looking for a small part of France in the heart of Guadeloupe, Terre de Haut is your go-to. Being the largest of the eight small islands that make up Les Saintes, Terre de Haut is a charming and scenic village rich with red-roofed houses and accompanying gardens of flourishing Hibiscus. Known for its robust reefs and great underwater visibility, Terre de Haut has also become a favorite among divers.

  • Port Elizabeth, Bequia
    Port Elizabeth, Bequia

    Bequia is the northernmost and largest of the Grenadines, just seven square miles of quiet lagoons, reefs, and long silvery stretches of beach. Among the first things you will notice are the colorful model boats set up on stands around the tiny harbor, representing the island's maritime history. If you are lucky enough to have a late call, don’t miss Mac’s Lobster Pizza.

  • Tobago Cays
    Tobago Cays

    Imagine an intimate cluster of five uninhabited islands, heavenly lagoons full of green turtles, coral reefs, colorful fish and crystal clear waters. This is the setting when SeaDream anchors off the Tobago Cays. Zodiacs will whisk guests from the marina to the beautiful beach. There may be some locals selling crafts so remember to bring some dollars. This is an idyllic yachting anchorage, a dream for scuba divers, a paradise for beachcombers, and a film location for the Pirates of the Caribbean, the Tobago Cays and the Tobago Cays Marine Park is one of the world’s most awe inspiring island destinations.

  • Mayreau
    Mayreau

    Accessible only by yacht and small sailboats, Mayreau is the smallest public island of the Grenadines, with an area of about .46 square miles and a population of less than 300, centered in an unnamed village on a hilltop in the southwest of the island—its highest point and a nice hike from Saline Beach, where SeaDream anchors. Surrounded by magnificent coral reefs and gorgeous beaches, Mayreau and its surrounding Tobago Cays waters sit in a nationally protected area that has experienced a resurgence of marine life, including turtles that swim and feed while you mingle with and observe them. Take in the flora and fauna and don’t miss some of the best snorkeling in the world. Perhaps the ideal spot to anchor, Saline Bay provides easy access to Saline Bay Beach and Salt Whistle Bay Beach, a rare double-sided beach.

  • Bridgetown, Barbados
    Bridgetown, Barbados

    SeaDream uses the port of Bridgetown as the hub for their Southern Caribbean voyages as well as some voyages that cross the Atlantic. The Island itself includes UNESCO Heritage Sites, excellent beaches and history dating back to 1628. The climate is tropical with constant warm temperatures during the year cooled by light trade winds.


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: $660 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

    Please check back soon for updates.


Testimonials

...We had a great time-best ever, and will be coming back...Charlie and I feel like we've been yachting with our "best friends". Hard to believe we didn't know anyone on the yacht 8 days ago-now we've met new traveling friends for the years to come. Mr & Mrs HoganWashington
Excellent Chef – nice choices & variety. Mr & Mrs HoaglandBelgium