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Best Small Ship Caribbean Cruises

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19-36 of 54 Results
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    • Caribbean
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
Mayreau Island, St Vincent and Grenadines
$6,900
EXPLORE

Bridgetown to Bridgetown via Bequia

8 Day Itinerary aboard SeaDream I
  • Explore unspoiled Canouan Island
  • Visit Union Island
  • Snorkel at Tobago Cays
  • Discover Mayreau
Activities: Biking, Helicopter Tour, Hiking, Scuba Diving, Small Ship Cruise, Snorkeling, Wildlife Viewing
Activity Level: Relaxed
Enjoy some water sports, relax on one of the most beautiful beachesin the world, or hike through magical landscapes on this 8-day adventure sailing across the Caribbean. Visit Pigeon Island National Park, witness the ruins of military buildings, and discover the signature Caviar Splash and Beach …
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
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
Anses d'Arlet village, Martinique, West Indies
$9,595
EXPLORE

Caribbean: Round-trip Bridgetown 2017

15 Day Itinerary aboard Sea Cloud II
  • Enjoy luxurious St. Barts
  • Discover the ÎIes des Saintes
  • Snorkel the Tobago Cays
  • Visit Grenada, the island of spice
Activities: Sailing Schooner, Snorkeling
Activity Level: Relaxed
Spend the holidays on thisunforgettable 15-day cruise exploring Caribbean hotspots. Enjoy stunning volcanic sceneries and island hideaways on the sunny side of the Lesser Antilles and the Grenadines. Discover the unique charm of this exclusive region - with more than 60 islands and reefs (of which …
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
$7,125
EXPLORE

Caribbean: Antigua to Barbados

11 Day Itinerary aboard Sea Cloud
  • Explore Virgin Gorda
  • Snorkel and swim at Tobago Cays
  • Discover Port Elizabeth, Bequia
  • Enjoy sophisticated St Barthélemy
Activities: Sailing Schooner, 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
The charming streets of Colonial Caribbean
$4,995
EXPLORE

Caribbean: Bridgetown to Bridgetown

8 Day Itinerary aboard Sea Cloud
  • Visit the famous Argyle Waterfall
  • Hike to the top of Morne Gazo
  • Snorkel & swim at Tobago Cays
  • Discover St Lucia Island
Activities: Hiking, Sailing Schooner, Snorkeling, Wildlife Viewing
Activity Level: Relaxed
Discover the treasures of the Grenadines! Enjoy majestic volcanoes, colorful reefs, and the scent of nutmeg and vanilla on this exclusive 8-day sailing adventure. VisitGrenada, the island of spice, and explore its deep volcanic lakes, dense rainforests, waterfalls, sugar cane fields, and spice …
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
Mandalay Caribbean Beach
$3,000
EXPLORE

British Virgin Islands

14 Day Itinerary aboard Mandalay
  • Discover the "Island of Spice"
  • Rest on Bequia's beaches
  • Snorkel and swim at Mayreau
  • View turtles in their habitat
Activities: Sailing Schooner, Small Ship Cruise, Snorkeling, Village Visit
Activity Level: Relaxed
This 14-day exploration of theBritish Virgin Islands includes visits to magnificent bays,inhabited islands, and crystal clear waters. Enjoy snorkeling opportunities andsoak up the sun on beautiful Caribbean sandy beaches. Take part in raising the sails or just enjoy the sea winds as you navigate …
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
Mandalay Raising the Sails
$1,799
EXPLORE

Antigua to St. Maarten

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
Experience this 7-day Caribbean adventure visiting a selection of islands with warm beaches and crystal clear waters. Start your voyage in Antigua, an island also known as Waladi or Wadadli by the native population. Afterwards navigate along Nevis, St. Kitts, St. Barths, Anguilla, St. Maarten, and …
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
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
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
19-36 of 54 Results

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