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Leeward Islands Cruises & Travel

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    • Leeward Islands
An underwater world awaits you
$3,000
EXPLORE

Antigua to Grenada

14 Day Itinerary aboard Mandalay
  • Discover Bequia's landscapes
  • Explore local bars and restaurants
  • Visit St. Lucia's beaches and reefs
  • Snorkel and swim from the boat
Board the S/V Mandalay for a 14-day true vessel experience discovering the Caribbean islands. Sail through exceptional landscapes and stunning islands with beautiful sandy beaches including Nevis, Isle Des Saintes, Dominica, St. Lucia, St. Vincent, Bequia, Canouan, Tobago Cays, Mayreau, and Union Island.
Activities: Sailing Schooner, Small Ship Cruise, Snorkeling
Places: Antigua, Bequia, Canouan Island, Carriacou, Dominica, Grenada, Iles des Saintes, Mayreau, Nevis, St. Lucia, St. Vincent des Grenadines, Tobago Cays, Union Island
Cruise Details
Snorkel the clear, tropical waters
$3,000
EXPLORE

Grenada to St. Maarten

14 Day Itinerary aboard Mandalay
  • Enjoy tours through local villages
  • Visit the small island of Mayreau
  • Snorkel with sea turtles
  • Partake in raising the sails
Discover the charm of the Caribbean islands on this 14-day sailing adventure on the S/V Mandalay. Visit local islands and stunning sandy beaches with breathtaking views as you cruise through Grenada, Carriacou, Union Island, Mayreau, Tobago Cays, Canouan, Bequia, and St. Maarten.
Activities: Sailing Schooner, Small Ship Cruise, Snorkeling, Village Visit
Places: Anguilla, Bequia, Canouan Island, Carriacou, Grenada, Mayreau, Nevis, St. Barth, St. Kitts, St. Lucia, St. Martin, St. Vincent des Grenadines, Tobago Cays, Union Island
Cruise Details
Mandalay Caribbean Beach
$3,000
EXPLORE

British Virgin Islands

14 Day Itinerary aboard Mandalay
  • Discover the "Island of Spice"
  • Rest on Bequia's beaches
  • Snorkel and swim at Mayreau
  • View turtles in their habitat
Board the S/V Mandalay in St. Maarten or Tortola and disembark in Tortola or St. Maarten. Discover exceptional views, golden sand beaches, and enjoy water sports opportunities as you navigate through Anguilla, Union Island, Mayreau, Bequia, Carriacou, Tobago Cays and Grenada.
Activities: Sailing Schooner, Small Ship Cruise, Snorkeling, Village Visit
Places: Anguilla, Bequia, Carriacou, Grenada, Jost Van Dyke, Mayreau, Nevis, Peter Island, St. Kitts, St. Martin, Tobago Cays, Tortola, Union Island, Virgin Gorda
Cruise Details
The s/v Mandalay
$2,800
EXPLORE

Grenada Round Trip

14 Day Itinerary aboard Mandalay
  • Rise early & search for marine life
  • Snorkel in crystal-clear waters
  • Enjoy views of the night sky
  • Learn to raise the ship's sails
On the S/V Mandalay, experience a Caribbean few others ever see. Partake in raising the sails, take a turn at the helm, or just enjoy the winds of the Caribbean sea filling the sails with new-found friends aboard. The choice is yours!
Activities: Sailing Schooner, Small Ship Cruise, Snorkeling
Places: Caribbean, Bequia, Canouan Island, Carriacou, Grenada, Mayreau, St. Lucia, St. Vincent des Grenadines, Tobago Cays, Union Island
Cruise Details
Snorkeling Mandalay
$1,799
EXPLORE

St. Maarten Round Trip

7 Day Itinerary aboard Mandalay
  • Watch the sunrise from the deck
  • Snorkel in crystal waters
  • Enjoy lunch ashore
  • Join in on the Mandalay Masquerade
Join this 7-day Caribbean cruise for a unique round-trip sailing adventure from/to St. Maarten. Visit a selection of islands including St. Maarten, St. Barths, Nevis, St. Kitts, Anguilla, Tintamarre, and possibly some other stops along the way!
Activities: Sailing Schooner, Small Ship Cruise, Snorkeling
Places: Anguilla, St. Barth, St. Kitts, St. Martin
Cruise Details
Diving off the side of the s/v Mandalay
$1,799
EXPLORE

St. Lucia to Antigua

7 Day Itinerary aboard Mandalay
  • Taste early morning delights
  • Snorkel and swim in rich waters
  • Enjoy lunch ashore on the beach
  • Join in on the Mandalay Masquerade
This 7-day Caribbean sailing adventure takes you from St. Lucia to Antigua. As you sail north visit a selection of islands including St. Lucia, Martinique, Iles Des Saintes, Marie-Galante, Montserrat, Nevis, Antigua, and if the wind is on your side, land on other outstanding islands as well.
Activities: Sailing Schooner, Small Ship Cruise, Snorkeling
Places: Antigua, Iles des Saintes, Marie Galante, Martinique, Montserrat, Nevis, St. Lucia
Cruise Details
Top Deck
$1,799
EXPLORE

Sail to St. Lucia

7 Day Itinerary aboard Mandalay
  • Enjoy morning coffee at sunrise
  • Snorkel & swim in Caribbean waters
  • Sip a rum swizzle
  • Relax on the top deck
Board the S/V Mandalay in St. Lucia for a round-trip 7-day Caribbean cruise. Go where the wind takes you and be prepared to visit a selection of islands like St. Lucia, Martinique, Dominica, Iles Des Saintes, Marie-Galante and possibly some more!
Activities: Sailing Schooner, Small Ship Cruise, Snorkeling
Places: Dominica, Iles des Saintes, Marie Galante, Martinique, St. Lucia
Cruise Details
Mandalay Raising the Sails
$1,799
EXPLORE

Antigua to St. Maarten

7 Day Itinerary aboard Mandalay
  • Snorkel and swim from the ship
  • Enjoy morning pastries and coffee
  • Gaze at the night sky
  • Sip a rum swizzle
This 7-day sailing voyage from Antigua to St. Maarten explores the highlights of the Caribbean islands, including Nevis, St. Kitts, St. Barths, Anguilla, and St. Maarten. Enjoy on board delights, relax on the top deck looking for wildlife, and participate in water activities such as swimming and snorkeling at the most outstanding islands.
Activities: Sailing Schooner, Small Ship Cruise, Snorkeling
Places: Anguilla, Antigua, Nevis, St. Barth, St. Kitts, St. Martin
Cruise Details
Sunset of Mandalay Caribbean
$1,799
EXPLORE

British Virgin Islands

7 Day Itinerary aboard Mandalay
  • Look for bird life
  • Snorkel in crystal waters
  • Gaze at the night sky
  • Relax with your favorite book
Experience a 7-day Caribbean cruise aboard the S/V Mandalay boarding in St. Maarten or Tortola and disembarking in Tortola or St. Maarten. Make new friends aboard as you partake in raising the sails, swimming from the ship, or snorkeling in crystal clear waters.
Activities: Sailing Schooner, Small Ship Cruise, Snorkeling
Places: Anguilla, Jost Van Dyke, Norman Island, Peter Island, Tortola, Virgin Gorda
Cruise Details
The beautiful Caribbean
$1,799
EXPLORE

St. Maarten to St. Lucia

7 Day Itinerary aboard Mandalay
  • View marine life and birds
  • Listen to local lore
  • Relax on Caribbean beaches
  • Taste local seafood
Join this 7-day cruise expedition through the Caribbean waters on the S/V Mandalay, a historic sailing vessel. Start your voyage in St. Maarten and explore a selection of islands including Nevis, St. Kitts, Anguilla, Dominica, and St. Lucia, the final spot of your sailing adventure.
Activities: Sailing Schooner, Small Ship Cruise, Snorkeling
Places: Anguilla, Dominica, Nevis, St. Kitts, St. Lucia, St. Martin
Cruise Details
The beautiful waters of the Caribbean
$1,599
EXPLORE

Grenada to St. Lucia

7 Day Itinerary aboard Mandalay
  • Snorkel & swim with marinelife
  • Visit white sand beaches
  • Enjoy evening activities
  • Watch the Caribbean sunrise
Learn how to raise the sails of the s/v Mandalay as you sail the turquoise waters of the Caribbean on this 7-day voyage. Rise early and search for marine life, learn local lore of the region, snorkel and swim from the ship, and choose from various island excursions each day on this Caribbean adventure.
Activities: Sailing Schooner, Snorkeling
Places: Caribbean, Bequia, Carriacou, Grenada, Mayreau, St. Lucia, St. Vincent des Grenadines, Tobago Cays
Cruise Details
Snorkel in the Baths of the Virgin Islands
$1,450
EXPLORE

Sailing the Virgin Islands

7 Day Itinerary aboard Liberty Star
  • Island-hop the Virgin Islands
  • Experience vibrant ports and towns
  • Walk along pink-sand beaches
  • Hike ruins and historical sites
Sail the crystal waters of the Virgin Islands on this tropical 7-day cruise on the tall ship Liberty Star. Explore the ports of St. Thomas, St. John, Jost Van Dyke, and more! Leave the ship for pristine snorkeling opportunities and enjoy the company of the friendly locals as you journey through the Caribbean.
Activities: Kayaking, Small Ship Cruise, Snorkeling, Whale Watching, Wildlife Viewing
Places: Caribbean, Norman Island, St John, St. Thomas
Cruise Details
Martinique harbor
$13,980
EXPLORE

Wild Caribbean with the Grenadines

13 Day Itinerary aboard Le Ponant
  • Identify endemic bird species
  • Hike Grenada's dense forest
  • Snorkel in Tobago Cays
  • View a myriad of underwater wonders
Sail around the Eastern Caribbean aboard Le Ponant on this 14-day relaxing vacation. Each island boasts a unique history, culture, and landscape. Enjoy trips ashore each day and the opportunity to explore the ports of call.
Activities: Expedition Cruises, Hiking, Snorkeling, Wildlife Viewing
Places: Caribbean, Barbuda, Dominica, Grenada, Iles des Saintes, Martinique, Montserrat, St. Barth, St. Lucia, St. Martin, St. Vincent des Grenadines, Tobago Cays
Cruise Details
A green heron found in the Caribbean
$6,255
EXPLORE

Caribbean: Antigua to Barbados

11 Day Itinerary aboard Sea Cloud
  • Explore Virgin Gorda
  • Snorkel and swim at Tobago Cays
  • Discover Port Elizabeth, Bequia
  • Enjoy sophisticated St Barthélemy
Follow famous pirate trails and sail along the trade winds to the Lesser Antilles and the British Virgin Islands on this amazing 11-day cruise. Sail from Antigua all the way to Barbados aboard the Sea Cloud.
Activities: Sailing Schooner, Snorkeling
Places: Antigua, Bequia, Bridgetown, Gustavia, Iles des Saintes, Jost Van Dyke, Soufriere, Tobago Cays, Union Island, Virgin Gorda
Cruise Details
Explore the small island of Virgin Gorda as you sail the Caribbean
$6,255
EXPLORE

Caribbean: Santo Domingo to Antigua

11 Day Itinerary aboard Sea Cloud
  • Discover the Maravillas Caves
  • See “The Baths” granite formations
  • Sail Sir Francis Drake Channel
  • Visit Cabrits National Park
Explore the natural beauty of the Caribbean on this 11-day cruise sailing from Santo Domingo, Dominican Republic to St. John's, Antigua aboard the Sea Cloud.
Activities: Hiking, Sailing Schooner, Wildlife Viewing
Places: Antigua, Cabrits, Gustavia, Iles des Saintes, Jost Van Dyke, La Romana, Santo Domingo, Virgin Gorda
Cruise Details
Snorkelling the warm waters
$8,640
EXPLORE

Sailing the Caribbean

8 Day Itinerary aboard Sea Cloud (LI)
  • Experience a 4-masted, 30-sail ship
  • Sail into lesser-known ports
  • Explore wildlife, culture, and sea
  • Enjoy the relaxed Caribbean pace
While there are many ways to experience the Caribbean, exploring aboard an authentic square-rigger tall ship offers an unrivaled experience and guarantees you an in-depth encounter with all its wonders.
Activities: Sailing Schooner, Small Ship Cruise, Snorkeling, Wildlife Viewing
Places: Antigua, Bequia, Dominica, Grenadines, Iles des Saintes, St. Lucia
Cruise Details
Tranquil shores on your Virgin Islands cruise
$4,170
EXPLORE

Caribbean: Santo Domingo to Antigua

8 Day Itinerary aboard Sea Cloud II
  • Discover Taino cave paintings
  • Take an excursion to The Baths
  • Sail Sir Francis Drake Channel
  • Enjoy luxurious St Barts
Discover the Lesser Antilles and the British Virgin Islands on this amazing 8-day cruise aboard the Sea Cloud ll. Enjoy the exclusive Caribbean waters as you make your way from hidden pirate bays to a famous jet set island.
Activities: Archaeological Sites, Sailing Schooner, Snorkeling
Places: Antigua, Gustavia, Jost Van Dyke, La Romana, Santo Domingo, Virgin Gorda
Cruise Details
White Sand Beach in Barbados
$3,645
EXPLORE

Caribbean: Round-trip Barbados to Dominica

8 Day Itinerary aboard Sea Cloud II
  • Discover Dominica's waterfalls
  • Walk across Cabrits National Park
  • Enjoy St Barthélemy Island
  • Take a stroll on ÎIes des Saintes
Sail the beautiful blue waters of the Caribbean on this 8-day cruise. See the fascinating islands of the area, including St. Barts, Antigua, and Dominica. Swim and snorkel to your heart's content as you cruise along the archipelago.
Activities: Sailing Schooner, Snorkeling, Wildlife Viewing
Places: Bridgetown, Cabrits, Falmouth, Iles des Saintes, St. Barth
Cruise Details
1-18 of 19 Results

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