Have questions? We're here.
Famous colorful huts in Barbados

Leeward Islands Cruises & Travel

Travel made your way
Talk with an expert
Customize any aspect of your Caribbean trip. 1.406.541.2677
Help Me Plan My Trip
Talk with an expert Ask a Question
Filter & Sort (31 Results)
Show Filter

1-18 of 31 Results
  • Length
    to
  • Price
    to
  • Start Date Range
  • Activity Level
  • Experiences
  • Activities
  • Ship
  • Destination
    • Leeward Islands
Snorkel in the Baths of the Virgin Islands
$7,400
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 green heron found in the Caribbean
$6,900
EXPLORE

Round-trip Charlotte Amalie via Anguilla

8 Day Itinerary aboard SeaDream II
  • Visit the island of St. Thomas
  • Discover Tortola Island
  • Dive and explore Saba Island
  • Observe St. Bart's marine life
Activities: Biking, Hiking, Horseback Riding, Scuba Diving, Small Ship Cruise, Snorkeling, Wildlife Viewing
Activity Level: Relaxed
Discover what freedom tastes like as you sail across the pristine turquoise Caribbean waters in the comfort of a luxury yacht on this 8-day adventure aboard the SeaDream ll. Explore and shop in the colorful markets of St. Thomas, and enjoy swimming and snorkeling around the clear waters of Norman …
Cruise Details
Deep blue waters await you on your Caribbean cruise
$6,900
EXPLORE

Marigot to Marigot via Anguilla

8 Day Itinerary aboard SeaDream I
  • Swim with dolpins at Sandy Ground
  • Snorkel at Norman Island
  • Explore Tortola Island by jeep
  • Discover St. Kitts' zip-line trails
Activities: Biking, Fishing, Hiking, Horseback Riding, Scuba Diving, Small Ship Cruise, Snorkeling, Wildlife Viewing, Zip Line
Activity Level: Relaxed
Explore the Caribbean and enjoy the opportunity to tee off, swim with dolphins, or bike around the islands. Visit wonderful landscapes, such as South Friar's Bay and Soper's Hole. Relax on the glamorous white sand beaches of St. Barts or participate in custom designed land adventures …
Cruise Details
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
Activities: Sailing Schooner, Small Ship Cruise, Snorkeling
Activity Level: Relaxed
This 14-day cruise offers the best opoortunirty for a true sailing vessel journey. 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, …
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
Activities: Sailing Schooner, Small Ship Cruise, Snorkeling
Activity Level: Relaxed
Enjoy two weeks in the Southern Caribbean sailing on board the Mandalay. Sail through turquoise waters, watch for marinelife, and relax on white sand beaches as you escape to these remote islands. While onboard learn how to raise the sails, take a turn at the helm, or just relax on deck!
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
Activities: Sailing Schooner, Small Ship Cruise, Snorkeling
Activity Level: Relaxed
Experience a memorable Caribbean sailing adventure on this 7-day cruise fromSt. Lucia to Antigua.Hang out on the top deck looking for marine and bird life, enjoy different water sport activities on paradisiac islands, and choose from various Island excursions each day. Partake in raising the sails, …
Cruise Details
Snorkel in the Baths of the Virgin Islands
$1,550
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
Activities: Kayaking, Small Ship Cruise, Snorkeling, Whale Watching, Wildlife Viewing
Activity Level: Relaxed
Board the Liberty Star for this 7-day cruise between the US and British Virgin Islands. The Liberty Star never follows a fixed itinerary, enabling the Captain to chart a course that results in the best wind and weather. Wake up each morning on a different island and seize the opportunity to …
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
Save $430
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
Unspoiled beaches and pristine coves in the Caribbean
$7,400
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
The looming fort walls of San Juan
$6,900
EXPLORE

Round-trip San Juan

5 Day Itinerary aboard SeaDream II
  • Relax on beautiful beaches
  • Enjoy the glamour of St. Barts
  • Snorkel at Jost van Dyke
Activities: Small Ship Cruise, Snorkeling, Wildlife Viewing
Activity Level: Relaxed
Discover the Caribbean on this exclusive 5-day cruise aboard the SeaDream ll. Explore the paradisical island beaches as you enjoy the perfect tropical weather this region offers. Wear your swimsuit, bring a towel, water and plenty of sun protection, and get ready to enjoy your days in this …
Cruise Details
Charlestown, Nevis
$6,900
EXPLORE

Charlotte Amalie to San Juan via St. John

8 Day Itinerary aboard SeaDream II
  • Relax on St. Thomas' beaches
  • Enjoy incredible food on board
  • Scuba dive the waters of Nevis
  • Swim with dolphins at Anguilla
Activities: Biking, Hiking, Horseback Riding, Scuba Diving, Small Ship Cruise, Snorkeling, Wildlife Viewing, Zip Line
Activity Level: Relaxed
Delight yourself with all the European charm of the Caribbean on this wonderful 8-day cruise that mixes adventure and relaxation perfectly. From your small ship, the SeaDream II, you have the opportunity to join some incredible land excursions and practice different water sports to let out the …
Cruise Details
Scuba diving in the reefs
$6,900
EXPLORE

Marigot to Bridgetown via Guadeloupe

8 Day Itinerary aboard SeaDream I
  • Discover St. Lucia
  • Visit the Moon Hole at Bequia
  • Relax at Mustique
  • Experience Iles des Saintes
Activities: Fishing, Helicopter Tour, Hiking, Kayaking, Scuba Diving, Small Ship Cruise, Snorkeling, Wildlife Viewing, Zip Line
Activity Level: Relaxed
This unique cruise mixes relaxation and adventure perfectly! Explore the Caribbeanwhile you enjoy incredible views of the islands on this 8-day expedition aboard the SeaDream I. VisitPort Elizabeth, well known for its reefs and long silvery stretches of beach. Among the first things you notice are …
Cruise Details
Snorkeling in the Caribbean with a starfish
$4,895
Save $300
EXPLORE

Caribbean: Roundtrip Antigua via Jost van Dyke

8 Day Itinerary aboard Sea Cloud II
  • Discover The Baths at Virgin Gorda
  • Enjoy glamorous St. Barths
  • Sail through famous landscapes
  • Visit the Brimstone Hill Fortress
Activities: Sailing Schooner, Small Ship Cruise, Snorkeling
Activity Level: Relaxed
The wind in the sails, the feet in the sand – set course for dream islands with colonial flair and nature’s magic. Admire the wonders of the Caribbeanwith their white sandy beaches, coral reefs, and friendly beach bars, one of the most desired destinations on Earth. Discover “The …
Cruise Details
Famous colorful huts in Barbados
$10,900
EXPLORE

Bridgetown to Marigot

10 Day Itinerary aboard SeaDream I
  • Hike through beautiful Saba
  • Participate in the America's Cup
  • Enjoy an extreme Marigot zip-line
  • Kayak and discover Les Saintes
Activities: Fishing, Helicopter Tour, Hiking, Kayaking, Scuba Diving, Small Ship Cruise, Snorkeling, Wildlife Viewing, Zip Line
Activity Level: Relaxed
Enjoy the Caribbean's famous and perfect tropical weather on this incredible 10-day cruise from Bridgetown to Marigot. Visit picturesque Palm Island, and discover its small town delights whilst doing some shopping for local crafts, souvenirs, or tropical fruits, jams, jellies or preserves. …
Cruise Details
Le Marin, Martinique
$6,900
EXPLORE

Bridgetown to Marigot

6 Day Itinerary aboard SeaDream I
  • Hike at Chevalier Islet
  • Explore Les Saintes by kayak
  • Enjoy a horseback ride on Nevis
  • Snorkel among colorful marine life
Activities: Fishing, Hiking, Horseback Riding, Kayaking, Scuba Diving, Small Ship Cruise, Snorkeling, Wildlife Viewing, Zip Line
Activity Level: Relaxed
Sail across the Caribbean on this exclusive 6-day adventure. Indulge yourself with paradisical beaches full of history and tropical warm temperatures. Stroll along picturesque streets full of colonial houses standing beside smart cafés and bistros, pastry shops and luxury boutiques at St. …
Cruise Details
Enjoy a blissful snorkeling trip.
$8,095
EXPLORE

Caribbean: Barbados to Antigua

12 Day Itinerary aboard Sea Cloud
  • Admire Port Elizabeth on Bequia
  • Snorkel the Tobago Cays
  • Explore the Brimstone Hill Fortress
  • Enjoy ÎIes des Saintes
Activities: Sailing Schooner, Small Ship Cruise
Activity Level: Relaxed
Enjoy the spectacular pastels of the Caribbean while sailing into the sun along famous pirate routes. When the Sea Cloud meets the Sea Cloud II against an exquisite Caribbean backdrop and they sail together, there is a real sense of joy at the reunion of these two ships. One moment, the windjammers …
Cruise Details
Anguilla, British Virgin Islands
$7,400
EXPLORE

Bridgetown to Marigot via St. Barts

8 Day Itinerary aboard SeaDream I
  • Visit Sandy Ground, Anguilla
  • Enjoy the glamour of St. Barts
  • Join the St.Martin 12-meter Regatta
  • Hike the lush island of Nevis
Activities: Fishing, Hiking, Horseback Riding, Scuba Diving, Small Ship Cruise, Snorkeling, Wildlife Viewing, Zip Line
Activity Level: Relaxed
Discover the Caribbean's magic on this amazing 8-day cruise sailing across enchanting and unique islands. Explore St. Barts, a beautiful island full of incredible beaches, resorts, restaurants, and activities both day and night. Enjoy a fun and exclusive Champagne and Caviar Splash at …
Cruise Details
1-18 of 31 Results

Why Travel With Adventure Life

More Reasons

Awards and Accolades

All News