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Leeward Islands Cruises & Travel

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    • Leeward Islands
Snorkel in the Baths of the Virgin Islands
$4,699
EXPLORE

Charlotte Amalie to Charlotte Amalie

8 Day Itinerary aboard SeaDream II
  • Ride a jet above St. Thomas
  • Visit The Baths at Virgin Gorda
  • Enjoy the ambience of White Bay
  • Hike Saba's Crispeen Track
Activities: Biking, Hiking, Kayaking, Scuba Diving, Small Ship Cruise, Snorkeling, Wildlife Viewing
Activity Level: Relaxed
Join the SeaDream ll on the journey of a lifetime across the Caribbean, starting and ending at the incredible island of St.Thomas and exploring this wonderful archipelago. Ecologically and culturally recognized for its pure beauty, this magical destination is among the world’s most …
Cruise Details
A dolphin jumps out of the water
$1,999
EXPLORE

Marigot to Marigot

6 Day Itinerary aboard SeaDream I
  • Relax on beautiful beaches
  • Dive in pristine Caribbean waters
  • Hike or bike around the islands
  • Join exciting optional excursions
Activities: Biking, Hiking, Scuba Diving, Small Ship Cruise, Snorkeling, Zip Line
Activity Level: Relaxed
Explore the Caribbean on this incredible journey full of land adventures for you to discover the islands from sea or land. Embark in Marigot,the main town and capital on the French side of Saint Martin, an area well known for its elegant stores with the latest in European designer fashions and fine …
Cruise Details
Beautiful beach in Dominica
$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
Activities: Sailing Schooner, Small Ship Cruise, Snorkeling
Activity Level: Relaxed
Board the S/V Mandalay in Antigua and disembark in Grenada. As the wind marks the navigation course visit islands like Nevis, Isle Des Saintes, Dominica, St. Lucia, St. Vincent, Bequia, Canouan, Tobago Cays, Mayreau, Union Island, and Grenada. Discover amazing landscapes, local villages, beautiful …
Cruise Details
The Southeast Peninsula of Saint Kitts with Nevis in the Background
$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
Activities: Sailing Schooner, Small Ship Cruise, Snorkeling, Village Visit
Activity Level: Relaxed
This 14-day adventure takes you from Grenada to St. Maarten aboard the S/V Mandalay, a true sailing vessel that currently navigates through the Windward and Leeward islands. Begin your sailing adventure in Grenada, known as the "Island of Spice" because of the abundance of locally grown …
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
Activities: Sailing Schooner, Small Ship Cruise, Snorkeling, Village Visit
Activity Level: Relaxed
Sail wherever the wind takes you on this incredible trip aboard a legendary tall ship that shows you exactlywhat it was born to do, with nothing but the wind determining its course and the captain obeying its orders. This 14-day exploration of theBritish Virgin Islands includes visits to …
Cruise Details
Dock going out into the crystal blue ocean
$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
  • Learn to raise the ship's sails
Activities: Sailing Schooner, Small Ship Cruise, Snorkeling
Activity Level: Relaxed
Sail through turquoise waters, watch for marinelife, and relax on white sand beaches as you escape to these remote islands. This fabulous 14-day voyage offers you an authentic sailing experience giving you the chance to learn how to raise the sails, take a turn at the helm, or just relax on deck! …
Cruise Details
Tropical waterfall and turquoise pool in lush forest
$1,360
EXPLORE

Treasure Islands

8 Day Itinerary aboard Star Flyer
  • Visit Virgin Gorda's famous “Baths”
  • Enjoy the lifestyle of Soper's Hole
  • Walk the streets of Basseterre
  • Relax on famous St. Barts
Activities: Sailing Schooner, Scuba Diving, Small Ship Cruise, Snorkeling
Activity Level: Relaxed
Set a course for the Treasure Islands and the French Riviera of the Caribbean. Discover a treasure trove of breathtaking beaches, old forts, and seaside villages waiting for you. Starting at St Martin, makeyour way to the super-chic St Barths, historic Antigua, and lush Iles des Saintes, Dominica, …
Cruise Details
The beautiful waters of the Caribbean
$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
Activities: Sailing Schooner, Small Ship Cruise, Snorkeling
Activity Level: Relaxed
Board the S/V Mandalay for a once-in-a-lifetime experience that fewothers ever see or even dream of. 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 friends aboard. The choice is yours! Visit locations such asSt. …
Cruise Details
Pink beach huts on tropical Antigua island
$1,799
EXPLORE

Antigua to St. Lucia

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
Activities: Sailing Schooner, Small Ship Cruise, Snorkeling
Activity Level: Relaxed
Breathtaking scenery and sandy beaches are guaranteed on this spectacular 7-day once in a lifetimeCaribbean cruise. Cruising from charming Antigua to the lush and breathtaking island of St. Lucia.Hang out on the top deck looking for marine and bird life, enjoy different water sport activities on …
Cruise Details
Snorkeling in the Caribbean with a starfish
$1,799
EXPLORE

St. Maarten to Antigua

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
Activities: Sailing Schooner, Small Ship Cruise, Snorkeling
Activity Level: Relaxed
Treat yourself to a tropical paradise adventure onthis 7-day Caribbean cruise visiting various islands with warm beaches and crystal clear waters. Start your voyage in and enjoy the charming and magical Dutch island ofSt. Maarten. Afterwards navigate along Nevis, St. Kitts, St. Barths, Anguilla, …
Cruise Details
Caribbean beach bar
$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
Activities: Sailing Schooner, Small Ship Cruise, Snorkeling
Activity Level: Relaxed
Board the S/V Mandalay in Tortola to St. Maarten for a 7-day Caribbean sailing adventure. Besides being one of the most scenic islands in the Caribbean, Tortola offers a decidedly cultural and historical side. Visit a selection of islands including , Anguilla, Jost Van Dyke, Norman Island, Peter …
Cruise Details
Mountains by the ocean in St Lucia
$1,649
EXPLORE

St. Lucia & Grenada

7 Day Itinerary aboard Mandalay
  • Snorkel & swim with marinelife
  • Visit white sand beaches
  • Enjoy evening activities
  • Watch the Caribbean sunrise
Activities: Sailing Schooner, Snorkeling
Activity Level: Relaxed
White sandy beaches, turquoise water, and lush rainforests make the Caribbean an exciting and relaxing cruise experience. Starting on St. Lucia,home to the Piton Peaks and mesmerizing beauty all the way to Grenada.Admiring majestic volcanoes, colorful reefs, and the scent of nutmeg and vanilla on …
Cruise Details
The Pitons in St Lucia
$1,649
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
Activities: Sailing Schooner, Small Ship Cruise, Snorkeling
Activity Level: Relaxed
Join the S/V Mandalay crew on this 7-day roundtrip sailing adventure starting and ending in St. Lucia, an island known for its beaches and reef-diving sites. Enjoy the winds of the Caribbean, take a turn at the helm, and partake in raising the vessel sails. Experience daily island visits for …
Cruise Details
Atlantic Ocean - Transatlantic Cruise
$2,350
EXPLORE

Transatlantic: St. Maarten to Lisbon

21 Day Itinerary aboard Star Flyer
  • Set sail from St. Maarten
  • Enjoy the expansive Atlantic Ocean
  • Cruise across the Caribbean
  • Discover Lisbon, Portugal
Activities: Sailing Schooner, Small Ship Cruise
Activity Level: Relaxed
Relive the golden age of cruising on this fantastic transatlantic cruise aboard the Star Flyer. Discover a haven of tranquillity as you make your way from the tropical paradise island of St. Maarten to the stunning port of Lisbon. This unique cruise isideal for people who love being on the open …
Cruise Details
The Pitons of St. Lucia
$12,980
EXPLORE

Hidden Gems of the Caribbean

12 Day Itinerary aboard Le Ponant (ZE)
  • Visit little-explored Grenadines
  • Seek out a variety of endemic birds
  • Snorkel or dive to discover reefs
  • Learn the history of the islands
Activities: Hiking, Scuba Diving, Snorkeling, Village Visit, Wildlife Viewing
Activity Level: Relaxed
Explore the lesser-known island gems of the eastern Caribbean on an itinerary exclusively designed to take you far from the standard cruise ship routes. Join Le Ponant on this 12-day journey, discovering several of the idyllic islands thatcomprise the little-explored Grenadines, an island chain in …
Cruise Details
A green heron found in the Caribbean
$6,995
EXPLORE

Caribbean: St. John's to Bridgetown

11 Day Itinerary aboard Sea Cloud II
  • Explore Virgin Gorda
  • Enjoy sophisticated St. Barthélemy
  • Discover Port Elizabeth, Bequia
  • Visit charming Dominica
Activities: Sailing Schooner, Small Ship Cruise, Snorkeling
Activity Level: Relaxed
Join this exclusive 11-day adventure, admire the blue waters of the region, and disembark daily to discover small towns with cobbled streets and amazing European style - the Caribbean Islands are a real dream destination. People from all over the world dream of their perfect tropically warm waters …
Cruise Details
Snorkel in the shallows of the Caribbean as you sail its tropical waters
$4,699
EXPLORE

Marigot to Bridgetown via Anguilla

8 Day Itinerary aboard SeaDream I
  • Explore St. Lucia by helicopter
  • Zip-line across St. Martin
  • Discover the Southern Grenadines
  • Snorkel at St. Barts
Activities: Fishing, Helicopter Tour, Hiking, Kayaking, Scuba Diving, Snorkeling, Wildlife Viewing, Zip Line
Activity Level: Relaxed
Explore Caribbean hotspots on this unique 8-day adventure cruising between Marigot to Bridgetown. Visit St. Martin and spend your day finding the perfect fishing spot forblue marlin, tuna, swordfish, mahi-mahi, white marlin, sailfish, wahoo, barracuda, and more! Discover the benefits of paddling a …
Cruise Details
Pink beach huts on tropical Antigua island
$1,420
EXPLORE

Windward Islands

8 Day Itinerary aboard Royal Clipper
  • Explore lush St. Lucia Island
  • Hike to Trafalgar Falls
  • Discover Falmouth Harbour, Antigua
  • Visit sophisticated Martinique
Activities: Sailing Schooner, Scuba Diving, Small Ship Cruise, Snorkeling
Activity Level: Relaxed
For connoisseurs of sail cruising, the 439-foot Royal Clipper offers the ultimate sea-going experience, balancing the grandeur, adventure and tradition of sailing with the superb service, amenities, and accommodations of the finest modern yacht. Swim and snorkel amidst the beautiful, pristine …
Cruise Details
1-18 of 40 Results

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