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

Lesser Antilles Cruises & Travel

Travel made your way
Talk with an expert
Customize any aspect of your Caribbean trip. 1.800.344.6118
Help Me Plan My Trip
Talk with an expert
Filter & Sort (43 Results)
Show Filter

19-36 of 43 Results
  • Length
    to
  • Price
    to
  • Start Date Range
  • Activity Level
  • Experiences
  • Activities
  • Ship
  • Destination
    • Lesser Antilles
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
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
Activities: Sailing Schooner, Small Ship Cruise, Snorkeling
Activity Level: Relaxed
This 7-day adventure aboard the S/V Mandalay takes you from St. Maarten to St. Lucia for a memorable vacation in paradise. Swim, snorkel, and relax on golden beaches bathed in crystal-clear Caribbean waters. Visit a selection of islands including St. Maarten, Nevis, St. Kitts, Anguilla, Dominica, …
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
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
Activities: Sailing Schooner, Small Ship Cruise, Snorkeling
Activity Level: Relaxed
Board the S/V Mandalay in St. Maarten or Tortola for a 7-day Caribbean sailing adventure. Visit a selection of islands including St. Maarten, Anguilla, Jost Van Dyke, Norman Island, Peter Island, Virgin Gorda, Tortola, and based on wind conditions, many more locations! Hang out on the top deck …
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
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
Grenada at night - Mandalay
$1,599
EXPLORE

Sailing the Grenadines

7 Day Itinerary aboard Mandalay
  • Snorkel in crystal-clear waters
  • Enjoy Bloody Marys at sunrise
  • Partake in nightly activities
  • Rise early & search for marine life
Activities: Sailing Schooner, Snorkeling
Activity Level: Relaxed
Enjoy a week in the Southern Caribbean sailing the Grenadines on board the Mandalay. Cruise 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 …
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
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
Promenade in Bridgetown, Barbados
$7,695
EXPLORE

Caribbean: Round-trip Bridgetown

15 Day Itinerary aboard Sea Cloud
  • Visit Cabrits National Park
  • Enjoy the magical Argyle Waterfall
  • Discover Bequia's turtle sanctuary
  • Snorkel at Tobago Cays
Activities: Hiking, Sailing Schooner, Snorkeling, Wildlife Viewing
Activity Level: Relaxed
Experience the blue waters of the wonderful Caribbean on this 15-day round-trip cruise from Barbados. As you sail, visit the charming port cities and remote coves of Tobago Cays, Soufriere, Cabrits, and more. The Caribbean is a vibrant, lively region of colorful buildings and friendly locals. Fall …
Cruise Details
Green sea turtle swimming
$5,400
EXPLORE

Charlotte Amalie to San Juan via St. Barts

8 Day Itinerary aboard SeaDream II
  • Visit beautiful St. John Island
  • Enjoy scenic Saba Island
  • Discover Soper's Hole, Tortola
  • Hike & snorkel at Norman Island
Activities: Hiking, Scuba Diving, Small Ship Cruise, Snorkeling, Wildlife Viewing
Activity Level: Relaxed
Fall in love with the crystal waters and islands of the Caribbean on this 8-day Virgin Islands and Puerto Rico cruise. Begin in Charlotte Amalie and make your way for the sheltered coves and small towns of Cruz Bay, North Sound, Gustavia, and more. As you explore the island paradise of the …
Cruise Details
Snorkelling the warm waters
$8,640
Save 5%
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
Activities: Sailing Schooner, Small Ship Cruise, Snorkeling, Wildlife Viewing
Activity Level: Relaxed
Stand on deck as Sea Cloud’s 30 white sails fill with wind, and measure the passage of time by a distant island’s approach on the horizon.Join thisextraordinary and historic yacht for an 8-day voyage that brings you into lesser-known ports of the "Old Caribbean" and offers the …
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
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
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
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
Snorkeling in the Caribbean with a starfish
$4,595
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
A view off the beautiful coast of Madeira.
$5,400
EXPLORE

Bridgetown to Lisbon

13 Day Itinerary aboard SeaDream I
  • Sit back and relax on board
  • Discover the tranquility offshore
  • Sample wine at Funchal, Madeira
  • Enjoy perfect views of Lisbon
Activities: Small Ship Cruise, Urban Exploration, Wine Tasting
Activity Level: Relaxed
Crossing the Atlantic in a small ship is an experience that leaves a lasting impression. For 13 days sail across the Atlantic Ocean, making your way from Barbados to the enchanting city of Lisbon. Sit back and relax, surrounded by vast horizons and perfect tropical weather conditions as you leave …
Cruise Details
San Juan, Puerto Rico
$6,900
EXPLORE

San Juan to San Juan

8 Day Itinerary aboard SeaDream II
  • Snorkel at Norman Island
  • Dive & explore Saba Island
  • Discover diverse marine life
  • Explore Tortola Island's canopy
Activities: Biking, Hiking, Scuba Diving, Small Ship Cruise, Snorkeling, Wildlife Viewing
Activity Level: Relaxed
Discover the Caribbean on this exclusive 8-day cruise aboard the SeaDream ll. Explore paradisical island beaches as you enjoy the perfect tropical weather this region offers. Wear your swim suit, bring a towel, water, and plenty of sun protection, and get ready to enjoy your days in this beautiful, …
Cruise Details
Tranquil shores on your Virgin Islands cruise
$4,795
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
Activities: Archaeological Sites, Sailing Schooner, Snorkeling
Activity Level: Relaxed
Sail across the Caribbean waters on this 8-day bucketlist cruise. Start your journey in Santo Domingo,the capital and largest city in the Dominican Republic, and sail to the exclusive and famous St John's, Antigua. Explore around St Barts, an elegant island that offers a distinctly …
Cruise Details
19-36 of 43 Results

Why Travel With Adventure Life

More Reasons

Awards and Accolades

All News