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 (99 Results)
Show Filter

1-18 of 99 Results
  • Start Date
    OR, More specific start
  • Length
    to
  • Price
    to
  • Activity Level
  • Experiences
  • Activities
  • Ship
  • Destinations
    • Leeward Islands
Clear water in the bay
$3,730
EXPLORE

Jewels of the Caribbean

9 Day Itinerary aboard Le Champlain
  • Visit Brimstone Hill Fortress
  • Admire stunning white-sand beaches
  • Discover Dominica Island
  • Swim across the Caribbean waters
Starts/ Ends in:
Fort de France / Fort de France
Activities:
Scuba Diving, Small Ship Cruise, Snorkeling
Activity Level:
Relaxed
Sail toSt. Kitts, a volcanic island with fine sandy beaches and rich colonial heritage. DiscoverSaint-Martin, a small cosmopolitan island that is half-French, half-Dutch. Further west, between the Lesser Antilles and the Greater Antilles,the British Virgin Islandswill offer you idyllic …
Cruise Details
Explore colorful St. Kitts
$8,199
EXPLORE

Charlotte Amalie to Marigot via St. John

8 Day Itinerary aboard SeaDream II
  • Relax on St. Thomas' beaches
  • Scuba dive the waters of Nevis
  • Swim with dolphins at Anguilla
  • Explore the town of Marigot
Starts/ Ends in:
Charlotte Amalie / Marigot
Activities:
Scuba Diving, Small Ship Cruise, Snorkeling
Activity Level:
Relaxed
Explore the Caribbean on this incredible journey full of opportunities for you to discover these beautiful islands by sea or land exploration. Shop in the luxury boutiques of Marigot,the main town and capital on the French side of Saint Martin. Snorkel the crystal clear waters of the famed Baths of …
Cruise Details
A snorkeler walking along a white sandy beach.
$3,499
EXPLORE

Round-trip Charlotte Amalie via St. John

8 Day Itinerary aboard SeaDream I
  • Enjoy scenic views at St. Thomas
  • Hike and snorkel at Norman Island
  • Visit glamorous St. Barths
  • Enjoy incredible food on board
Starts/ Ends in:
Charlotte Amalie / Charlotte Amalie
Activities:
Biking, Hiking, Small Ship Cruise, Snorkeling, Wildlife Viewing
Activity Level:
Relaxed
Explore the Caribbean on this wonderful 8-day cruise that mixes adventure and relaxation perfectly, giving you the opportunity to join some unique land excursions. Enjoy an epic trip to The Baths, anddiscover thisintriguing group of sea caves and unusual rock formations spectacularly set on an …
Cruise Details
Snorkel in the Baths of the Virgin Islands
$3,299
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 l 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
$2,999
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
Starts/ Ends in:
Marigot / Marigot
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
Deep blue waters await you on your Caribbean cruise
$3,299
EXPLORE

Marigot to Marigot via Anguilla

6 Day Itinerary aboard SeaDream II
  • Swim with dolpins at Sandy Ground
  • Visit the famous St. Barts
  • Enjoy Antigua's beaches
  • Discover St. Martin
Starts/ Ends in:
Marigot / Marigot
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. Relax on the glamorous white sand beaches of St. Barts or participate in custom designed land adventures including snorkeling, scuba diving, land rover safari, and zip-lining. For guests …
Cruise Details
Snorkel in the Baths of the Virgin Islands
$3,199
EXPLORE

Charlotte Amalie to San Juan

7 Day Itinerary aboard SeaDream II
  • Visit the beaches of St. Thomas
  • Hike & enjoy Saba's natural beauty
  • Snorkel at Jost van Dyke
  • Hike & snorkel at Norman Island
Starts/ Ends in:
Charlotte Amalie / San Juan
Activities:
Scuba Diving, Small Ship Cruise, Snorkeling
Activity Level:
Relaxed
Join the Sea Dream II on this 7-day cruise. Depart from charming Charlotte Amalie to sail across the Caribbean, enjoying the natural and cultural treasures of this region. Snorkel around the Virgin Islands, hike the Dutch Antilles, or simply relax on the beaches of the French West Indies. With …
Cruise Details
Relax on the shores of the Caribbean
$2,999
EXPLORE

Round-trip Charlotte Amalie

6 Day Itinerary aboard SeaDream II
  • Visit the beaches of St. Thomas
  • Hike Saba's Crispeen Track
  • Visit glamorous St. Barths
  • Enjoy the ambiance of White Bay
Starts/ Ends in:
Charlotte Amalie / Charlotte Amalie
Activities:
Small Ship Cruise, Snorkeling
Activity Level:
Relaxed
Bask in the romantic Caribbean on this 6-day round-trip St. Thomas adventure. Begin in Charlotte Amalie and make your way for the shelteredcoves and small towns of Cruz Bay, Saba, Gustavia, and more. As you explore the island paradise of the Caribbean, disembark daily to bike, hike, snorkel, or …
Cruise Details
Tropical waterfall and turquoise pool in lush forest
$2,240
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, 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
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
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
Starts/ Ends in:
St. Martin / Tortola
Activities:
Sailing Schooner, Small Ship Cruise, Snorkeling
Activity Level:
Relaxed
Board the S/V Mandalay in St. Maartenand make your way to Tortola 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 …
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
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
St George's Harbor - Grenada
$1,599
EXPLORE

Grenada Round Trip

7 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
Starts/ Ends in:
Grenada / Grenada
Activities:
Sailing Schooner, Small Ship Cruise, Snorkeling
Activity Level:
Relaxed
Sail through turquoise waters, watch for marine life, and relax on white sand beaches as you escape to these remote islands. This fabulous 7-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
Peaceful seclusion in the Caribbean
$5,699
EXPLORE

San Juan to Charlotte Amalie via Anguilla

9 Day Itinerary aboard SeaDream I
  • Zip-Line on St. Martin
  • Snorkel at Treasure Island
  • Dive along the coast of St. Barts
  • Explore Tortola Island
Starts/ Ends in:
San Juan / Charlotte Amalie
Activities:
Hiking, Small Ship Cruise, Snorkeling
Activity Level:
Relaxed
Sail the Caribbean on this 9-day cruise beginning in Puerto Rico en route to Virgin Gorda. As you cruise the blue waters, admire the vast horizon and shallow reef system, disembarking almost daily to explore the most charming coastal villages. Learn about the fascinating history of the region and …
Cruise Details
Beautiful beach in Dominica
$1,640
EXPLORE

Leeward Islands

8 Day Itinerary aboard Star Flyer
  • Visit Dominica Island
  • Snorkel at Iles des Saintes
  • Sail across Rivière Salée
  • Enjoy Gustavia's unique charm
Activities:
Sailing Schooner, Small Ship Cruise, Snorkeling
Activity Level:
Relaxed
With an island for every taste, the Caribbean is the ultimate place for relaxation. Explore the world-famous white sands and turquoise water throughout the Caribbean Sea. With more than 5,000 islands and cays spread across this amazing region, there’s a lot of paradise to see. Best of all, …
Cruise Details
St Barts harbor view
$2,999
EXPLORE

Charlotte Amalie, St. Thomas to San Juan

8 Day Itinerary aboard SeaDream II
  • Visit the beaches of St. Thomas
  • Enjoy a unique dolphin encounter
  • Dive along the coast of St. Barts
  • Visit the island of St. Thomas
Starts/ Ends in:
Charlotte Amalie / San Juan
Activities:
Hiking, Scuba Diving, Small Ship Cruise, Snorkeling
Activity Level:
Relaxed
Sail the beautiful blue waters of the Virgin Islands on this 8-day Caribbean cruise. See the fascinating islands of the area, including St. Thomas, Tortola, and Anguilla.Swim and snorkel in one of the most incredible landscapes in the world! Join optional excursions such as an exclusive horseback …
Cruise Details
1-18 of 99 Results

Why Travel With Adventure Life

More Reasons

Awards and Accolades

All News