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 (41 Results)
Show Filter

1-18 of 41 Results
  • Length
    to
  • Price
    to
  • Start Date Range
  • Activity Level
  • Experiences
  • Activities
  • Ship
  • Destinations
    • Leeward Islands
Tropical waterfall and turquoise pool in lush forest
$1,400
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
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
St Barts harbor view
$1,400
Savings
EXPLORE

St. Maarten, St. Kitts & St. Barts

4 Day Itinerary aboard Star Flyer
  • Enjoy Gustavia's unique charm
  • Visit old plantation houses
  • Enjoy shopping in St. Maarten
Activities: Hiking, Local Market, Sailing Schooner, Small Ship Cruise
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
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
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
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
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
Famous colorful huts in Barbados
$5,805
EXPLORE

Caribbean: Antigua - Bridgetown

9 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
Pink beach huts on tropical Antigua island
$2,260
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
Dock going out into the crystal blue ocean
$2,300
EXPLORE

Antigua to Barbados

8 Day Itinerary aboard Royal Clipper
  • Enjoy Grenada's unique aromas
  • Discover Falmouth Harbour, Antigua
  • Enjoy the beach in ÎIes des Saintes
  • Explore lush St. Lucia Island
Activities: Sailing Schooner, Small Ship Cruise
Activity Level: Relaxed
Swim and snorkel amidst the beautiful, pristine waters of the Caribbean Sea on this 8-day expedition aboard Royal Clipper. Sail away from your everyday life and find tropical bliss in the islands. From the stunning drama of the spectacular Pitons at St. Luciato the captivating charm of Les Saintes, …
Cruise Details
Beautiful beach in Dominica
$1,400
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, Scuba Diving, 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
An underwater world awaits you
$5,805
EXPLORE

Caribbean: Antigua - Bridgetown via Soufrière

9 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
Immerse yourself in the spectacular charm of the Atlantic Ocean
$2,450
EXPLORE

Transatlantic: St. Maarten to Malaga

21 Day Itinerary aboard Star Flyer
  • Set sail from St. Maarten
  • Enjoy the expansive Atlantic Ocean
  • Cruise across the Caribbean
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
An underwater world awaits you
$6,565
EXPLORE

Caribbean: Barbados to Antigua

10 Day Itinerary aboard Sea Cloud
  • Admire Port Elizabeth on Bequia
  • Snorkel the Tobago Cays
  • 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
Pelicans hanging out in the ocean
$10,375
EXPLORE

Caribbean: Antigua - Bridgetown

16 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
1-18 of 41 Results

Why Travel With Adventure Life

More Reasons

Awards and Accolades

All News