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Best Small Ship Caribbean Cruises

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19-36 of 69 Results
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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
Barbados Island, Caribbean
$6,900
EXPLORE

Marigot to Bridgetown via Dominica

8 Day Itinerary aboard SeaDream I
  • Discover Iles des Saintes
  • Enjoy a tubing trip on Layou River
  • Visit the Sapphire Waterfall
  • Explore St. Barts
Activities: Biking, Fishing, Helicopter Tour, Hiking, Kayaking, Small Ship Cruise, Snorkeling, Wildlife Viewing, Zip Line
Activity Level: Relaxed
Explore the Caribbean on this exclusive 8-day voyage starting at Marigot,the main town and capital on the French side of Saint Martin, and ending onthehistorical island ofBarbados.Experience the real St. Lucia; depart at Rodney Bay Marina for a drive through the town of Castries up to the Morne …
Cruise Details
The charming streets of Colonial Caribbean
$6,900
EXPLORE

Round-trip Charlotte Amalie via St. Barts

8 Day Itinerary aboard SeaDream II
  • Discover Tortola Island
  • Visit the beaches of St. Thomas
  • Observe St. Bart's marine life
  • Enjoy the ambience of White Bay
Activities: Hiking, Kayaking, Small Ship Cruise, Snorkeling, Wildlife Viewing
Activity Level: Relaxed
This 8-day exploration of the Caribbean Islands includes visits to magnificent bays and inhabited islands surrounded by the most beautifulblue waters. Enjoy snorkeling opportunities andsoak up the sun on charming sandy beaches. Relax and take in the sea winds as you navigate through the Virgin …
Cruise Details
$6,900
EXPLORE

Bridgetown to Marigot via Bequia

8 Day Itinerary aboard SeaDream I
  • Discover Amerindian history
  • Explore diverse Chevalier Islet
  • Visit Coconut Grove beach
  • Relax on a catamaran at Mustique
Activities: Fishing, Hiking, Kayaking, Small Ship Cruise, Snorkeling, Wildlife Viewing, Zip Line
Activity Level: Relaxed
Fall in love with the glittering island jewels of the Caribbean on this 8-day small ship cruise. Beginning in cultural Bridgetown, this cruise rounds the islands of the archipelago and stops at Bequia, St. Lucia, Martinique and more. As you sail, admire the blue waters of the region and disembark …
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
Sea turtle
$5,400
EXPLORE

Round-trip Bridgetown via St. Lucia

8 Day Itinerary aboard SeaDream I
  • Helicopter ride across St Lucia
  • Enjoy a catamaran ride to Mustique
  • Discover the Southern Grenadines
  • Kayak at Grande Anse
Activities: Fishing, Helicopter Tour, Hiking, Kayaking, Scuba Diving, Small Ship Cruise, Snorkeling, Wildlife Viewing
Activity Level: Relaxed
Sun and sand are yours on this exceptional 8-day round-trip Barbados cruise. Begin your island journey in Bridgetown and make your way to the beautiful Rodney and Soufriere Bays, Port Elizabeth, and the stunning Canouan and Union Islands. Disembark daily to explore colorful markets and snorkel, …
Cruise Details
Bridgetown, Barbados
$6,900
EXPLORE

Bridgetown to Marigot via Mayreau

8 Day Itinerary aboard SeaDream I
  • Join the America's Cup
  • Discover the underwater world
  • Hike the lush island Nevis
  • Enjoy stunning St. Lucia
Activities: Helicopter Tour, Hiking, Horseback Riding, Kayaking, Scuba Diving, Small Ship Cruise, Snorkeling, Wildlife Viewing, Zip Line
Activity Level: Relaxed
Sail across the Caribbean on this once-in-a-lifetime 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; in …
Cruise Details
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
Snorkelling the warm waters
$8,640
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
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
Explore the small island of Virgin Gorda as you sail the Caribbean
$7,125
EXPLORE

Caribbean: Santo Domingo to Antigua

11 Day Itinerary aboard Sea Cloud
  • Discover the Maravillas Caves
  • See “The Baths” granite formations
  • Sail Sir Francis Drake Channel
  • Visit Cabrits National Park
Activities: Hiking, Sailing Schooner, Wildlife Viewing
Activity Level: Relaxed
Join the Sea Cloud on this wonderful11-day cruise from Santo Domingo to Antigua. Sit back andenjoy thisbeautiful sailing destination, with itswhite-sand beaches, coral reefs, and friendly beach bars.Visit the“Cave of Wonders”, a magic spot with stunning lighting and echoes of cathedral …
Cruise Details
Anses d'Arlet village, Martinique, West Indies
$5,400
EXPLORE

Marigot to Bridgetown

8 Day Itinerary aboard SeaDream I
  • Enjoy incredible ocean views
  • Observe the process of cocoa making
  • Fish at St. Martin
  • Swim and snorkel at Tobago Keys
Activities: Fishing, Helicopter Tour, Hiking, Kayaking, Scuba Diving, Small Ship Cruise, Snorkeling, Wildlife Viewing, Zip Line
Activity Level: Relaxed
Sit back and relax while you enjoy incredible views of the Caribbean on this 8-day expedition aboard the SeaDream I. VisitMarigot, an incredible place once named the capital during the reign of King Louis XVI, who built Fort St. Louis on a hill near Marigot Bay. Today, that building is the most …
Cruise Details
Promenade in Bridgetown, Barbados
$4,400
EXPLORE

Bridgetown to Bridgetown

5 Day Itinerary aboard SeaDream I
  • Enjoy the fresh breeze on deck
  • Discover Clifton Bay's local crafts
  • Explore \\"The Moon Hole”
Activities: Fishing, Hiking, Snorkeling
Activity Level: Relaxed
Spend some time exploring the Caribbean on this 5-day sailing adventure. Enjoy a slow panoramic ride alongBequia'scoast while a knowledgeable guide points out where the luxurious houses of the rich and famous can be seen including Ralph Lauren and Sir Paul McCartney. Discover an intimate …
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
The Pitons of St. Lucia
$4,295
EXPLORE

Caribbean: Round-trip Bridgetown 2017

8 Day Itinerary aboard Sea Cloud II
  • Explore the Argyle Waterfall
  • Discover Grenada Island
  • Swim in the Tobago Cays
  • Visit Old Hegg Turtle Sanctuary
Activities: Sailing Schooner, Snorkeling, Wildlife Viewing
Activity Level: Relaxed
Start off the New Year in the laid-back Caribbean and discover the pearls of the Lesser Antilles and the Grenadines. Start your adventure atBridgetown, Barbados and srtoll down its historic center, with colonial architecture surrounding Trafalgar Square. VisitGrenada, a paradisiacal spotblessed …
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
19-36 of 69 Results

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