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Best Small Ship Caribbean Cruises

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19-36 of 42 Results
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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
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
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
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
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
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
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
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
Enjoy a blissful snorkeling trip.
$6,900
EXPLORE

San Juan to Charlotte Amalie via Vieques

7 Day Itinerary aboard SeaDream II
  • Enjoy St. Thomas Island highlights
  • Relax at White Bay
  • Visit Culebrita Island
  • Hike the Crispeen Track
Activities: Hiking, Scuba Diving, Small Ship Cruise, Wildlife Viewing
Activity Level: Relaxed
Sail the Caribbean on this 7-day cruise beginning in Puerto Rico en route to St.Thomas. 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 fall …
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
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
Havana Plaza de la Catedral
$9,500
Save 5%
EXPLORE

Cuba by Land and Sea: Cultural Heritage and Natural Wonders

11 Day Itinerary aboard Panorama II (LI)
  • Experience people-to-people visits
  • Explore marine habitats and reefs
  • Visit the Bay of Pigs
  • Enjoy lively music & superb cuisine
  • See Cuba's great cities
Activities: Land & Sea, Scuba Diving, Small Ship Cruise, Snorkeling, Urban Exploration, Wildlife Viewing
Activity Level: Relaxed
The world’s fascination with Cuba has lasted for many generations, and for good reason. Cuba is a cultural hub, with a mix of descendants of indigenous people, European immigrants, and slaves, and its music and art draw on these diverse influences. Cuba has also exerted an outsize influence …
Cruise Details
Admire the locals on your Virgin Islands cruise
$5,400
EXPLORE

San Juan to Malaga

14 Day Itinerary aboard SeaDream II
  • Enjoy the relaxing fresh air at sea
  • Take a cable car trip up to Monte
  • Observe marvelous sunsets on board
  • Discover Malaga's old town
Activities: Small Ship Cruise, Urban Exploration, Wine Tasting
Activity Level: Relaxed
Leave the picture-perfect Caribbean Islands behind as you make your way to the historical city of Lisbon, Portugal and on to Malaga, Spain. Experience 14 days of pure sailing adventure where for two whole weeks, the expansive ocean is the home of SeaDream ll. Enjoy the opportunity to sit back and …
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
Havana Plaza de la Catedral
$17,380
EXPLORE

Cuba Under Sail

17 Day Itinerary aboard Le Ponant (ZE)
  • Immerse yourself in Cuban culture
  • Travel with ease on Le Ponant
  • Visit UNESCO World Heritage Sites
  • Snorkel or dive healthy coral reefs
  • Stroll the streets of Havana
Activities: Archaeological Sites, Land & Sea, Sailing Schooner, Snorkeling, Urban Exploration, Village Visit, Wildlife Viewing
Activity Level: Relaxed
Gain a rare and valuable perspective into the daily lives of Cuba’s citizens on this 17-day tour.The 56-guest ship, Le Ponant, providesthe perfect way to see the sights and enjoy the exquisite coastal scenery. Tour the Arte Corte interactive museum and enjoy musical performances, including a …
Cruise Details
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