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Best Small Ship Caribbean Cruises

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55-72 of 121 Results
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Pelicans hanging out in the ocean
$8,990
Savings
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
Green sea turtle swimming
$3,199
EXPLORE

Charlotte Amalie to San Juan

8 Day Itinerary aboard SeaDream I
  • Visit beautiful St. John Island
  • Enjoy scenic Saba Island
  • Discover Soper's Hole, Tortola
  • Hike & snorkel at Norman Island
Starts/ Ends in:
Charlotte Amalie / San Juan
Activities:
Scuba Diving, Small Ship Cruise, Snorkeling
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
Caribbean
$4,545
EXPLORE

Philipsburg Round Trip

8 Day Itinerary aboard Sea Cloud Spirit
  • Visit the port town of Philipsburg
  • Visit the birthplace of Sanjuaneros
  • Explore the famous ‘Love City’ Cruz
  • Discover the stunning White Bay
Starts/ Ends in:
Philipsburg / Philipsburg
Activities:
Kayaking, Sailing Schooner, Small Ship Cruise, Snorkeling
Activity Level:
Relaxed
Board the Sea Cloud Spirit and start your exciting adventure from the beautiful city of Philipsburg, St. Maarten. Voyage along the idyllic and warm waters of the Caribbean and explore the beauty of each destination. Visit San Juan, Isla Culberita, and Esperanza in Puerto Rico. Explore the beautiful …
Cruise Details
The Southeast Peninsula of Saint Kitts with Nevis in the Background
$3,299
EXPLORE

San Juan to Charlotte Amalie via Antilles

8 Day Itinerary aboard SeaDream II
  • Enjoy the canopy at Tortola Island
  • Dive along the coast of St. Barths
  • Explore Tortola Island
  • Visit the beaches of St. Thomas
Starts/ Ends in:
San Juan / Charlotte Amalie
Activities:
Scuba Diving, Small Ship Cruise
Activity Level:
Relaxed
Sail through the Caribbean on this 8-day cruise beginning in Puerto Rico and ends in 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 …
Cruise Details
Bridgetown, Barbados
$3,299
EXPLORE

Bridgetown to Marigot

8 Day Itinerary aboard SeaDream I
  • Discover Mayreau
  • Enjoy a horseback ride on Nevis
  • Snorkel at St. Barts
  • Hike the lush island Nevis
Starts/ Ends in:
Bridgetown / Marigot
Activities:
Hiking, Small Ship Cruise, Snorkeling
Activity Level:
Relaxed
Explore the Caribbean Sea on this 8-day voyage starting in Bridgetown, aUNESCO Heritage Sites itself. You will be given time to visit spectacular places like Charlestown where you can enjoy a thrilling but comfortable horseback ride through the rolling countryside passing many natural and …
Cruise Details
Islands of the Caribbean
$2,999
EXPLORE

Bridgetown to Marigot: Wine Voyage

8 Day Itinerary aboard SeaDream I
  • Enjoy a horseback ride on Nevis
  • Snorkel at St. Barts
  • Hike the lush island Nevis
  • Discover Bridgetown's beaches
Starts/ Ends in:
Bridgetown / Marigot
Activities:
Hiking, Small Ship Cruise, Snorkeling
Activity Level:
Relaxed
Designed to enhance both your culinary and yachting experience, explore the flavors and history from some of the world's most renowned wineries while relaxing aboard the luxurious SeaDream I. Join exclusive wine tastings and a dinner consisting of a specially curated menu complemented with top …
Cruise Details
Soak in the sun in colorful Marigot
$2,999
EXPLORE

Marigot to Bridgetown

8 Day Itinerary aboard SeaDream I
  • Discover the underwater world
  • Enjoy the stunning St. Lucia
  • Fish at Marigot
  • Enjoy the glamour of St. Barts
Starts/ Ends in:
Marigot / Bridgetown
Activities:
Biking, Hiking, Small Ship Cruise, Snorkeling
Activity Level:
Relaxed
Enjoy a little bit of everything on this amazing 8-day cruise, starting at Saint Martin and sailing to beautiful Barbados. Visit the famous jet-set island of St.Barts, well known for its charming streets, glamorous cafes and restaurants, and luxurious white sand beaches. Explore the capital of …
Cruise Details
Relax on the sunny beaches of the Caribbean
$3,699
EXPLORE

San Juan to Charlotte Amalie via Anguilla

8 Day Itinerary aboard SeaDream II
  • Enjoy sun bathing in Colombier Bay
  • Dive along the coast of St. Barts
  • Swim in the Caribbean
  • Visit the beaches of St. Thomas
Starts/ Ends in:
San Juan / Charlotte Amalie
Activities:
Small Ship Cruise, Snorkeling, Wine Tasting
Activity Level:
Relaxed
Sail the beautiful blue waters of the Virgin Islands on this 8-day Caribbean cruise. Explore the fascinating islands of the area, including St. Barths, St. Kitts & Nevis, and Anguilla.Swim and snorkel in some of the most incredible seascapes in the world! Join optional excursions such as an …
Cruise Details
Unspoiled beaches and pristine coves in the Caribbean
$3,599
EXPLORE

Round-trip San Juan

8 Day Itinerary aboard SeaDream II
  • Visit the Puerto Rican capital
  • Snorkel at Trunk Bay
  • Explore Tortola by land rover
  • Zip line at South Friar's Bay
Starts/ Ends in:
San Juan / San Juan
Activities:
Hiking, Small Ship Cruise, Snorkeling
Activity Level:
Relaxed
Relish in the beauty and culture of the Caribbean on this 8-day voyage aboard the SeaDream II. Depart from San Juan, Puerto Rico, and set sail for St. John Island, the "most virgin" of the U.S. Virgin Islands. Visit the Caribbean paradise of Saba and the treasured destination of St. …
Cruise Details
The Southeast Peninsula of Saint Kitts with Nevis in the Background
$3,399
EXPLORE

San Juan to Marigot

8 Day Itinerary aboard SeaDream I
  • Visit Prickly Pear Island
  • Explore many of the local sights
  • Relax on beautiful beaches
  • Hike and bike islands
Starts/ Ends in:
San Juan / Marigot
Activities:
Biking, Hiking, Small Ship Cruise, Snorkeling
Activity Level:
Relaxed
Depart from San Juan, the largest city and the capital city of Puerto Rico to start this 8-day adventure. SeaDream I continues to sails tosome of the most wonderful and best places in the Caribbean like in Saba, where you can enjoybeautiful natural surroundings while hikingalong the Crispeen Track. …
Cruise Details
Skyline of Old Havana Cuba
$3,394
EXPLORE

Cuban Panorama: Cienfuegos to Havana

8 Day Itinerary aboard Panorama
  • Visit a tobacco plantation
  • Enjoy Guanahacabibes National Park
  • Discover Spanish colonial Trinidad
  • Explore historic Old Havana
Starts/ Ends in:
Cienfuegos / Havana
Activities:
Archaeological Sites, Small Ship Cruise, Snorkeling, Urban Exploration
Activity Level:
Relaxed
Go back in time to a place rooted in culture and history, where the people are as warm and welcoming as the climate. Discover Cuba's land and people on this breathtaking 8-day cruise, including vibrant Havana and its amazing Old Town, Cienfuegos with its neoclassical French architecture, …
Cruise Details
Deep blue waters await you on your Caribbean cruise
$3,199
EXPLORE

Charlotte Amalie to San Juan via St. Barts

7 Day Itinerary aboard SeaDream I
  • Visit beautiful St. John Island
  • Enjoy scenic Saba Island
  • Discover Soper's Hole, Tortola
  • Hike & snorkel at Norman Island
Starts/ Ends in:
Charlotte Amalie / San Juan
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 7-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
Enjoy a blissful snorkeling trip.
$2,999
EXPLORE

San Juan to Charlotte Amalie via Vieques

6 Day Itinerary aboard SeaDream I
  • 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 6-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
Take in the sights, sounds, and colors of Barbados
$4,900
EXPLORE

Bridgetown to Bridgetown

11 Day Itinerary aboard Silver Whisper
  • Enjoy unspoiled Bequia Island
  • Admire the slopes of St. Kitts
  • Explore white sandy shores
  • Discover bustling Port of Spain
Starts/ Ends in:
Bridgetown / Bridgetown
Activities:
Hiking, Scuba Diving, Small Ship Cruise, Snorkeling
Activity Level:
Relaxed
When Bing Crosby sang "White Christmas," perhaps he meant the powdery sand of the Caribbean! Swap eggnog for rum punch, roast turkey for freshly grilled lobster and cold snowy days for long, sunny ones … but there’s no need to completely forget the holiday season: with the …
Cruise Details
Pink beach huts in the Caribbean
$3,960
EXPLORE

Bridgetown to Fort Lauderdale (Florida)

10 Day Itinerary aboard Silver Whisper
  • Relax on Jost Van Dyke's beaches
  • Visit Les Saintes
  • Tour Port Elizabeth on Bequia
  • Admire Mayreau Island
Starts/ Ends in:
Bridgetown / Fort Lauderdale
Activities:
Biking, Kayaking, Small Ship Cruise, Snorkeling
Activity Level:
Relaxed
Discover the Caribbean on this 10-day sailing adventure from Bridgetown to Fort Lauderdale, Florida. Visit the colorful small cities and the exceptional beaches this archipelago is famous for as you sit back and relax while sailing through one of the most exclusive regions in the world aboard the …
Cruise Details
Explore the small island of Virgin Gorda as you sail the Caribbean
$7,515
EXPLORE

Philipsburg Round Trip

10 Day Itinerary aboard Sea Cloud Spirit
  • Visit the charming Virgin Islands
  • Explore stunning White Bay
  • Discover magnificent Isla Culebrita
  • Tour Cruz Bay known as ‘Love City’
Starts/ Ends in:
Philipsburg / Philipsburg
Activities:
Sailing Schooner, Small Ship Cruise, Snorkeling, Village Visit
Activity Level:
Relaxed
Sea Cloud Spirit takes you to the seas for a stunning adventure packed with incredible experiences starting at the charming port town of Philipsburg, St. Maarten. As you sail, visit the British Virgin Islands with heavenly bays, gorgeous beaches, idyllic anchoring spots, smart yacht clubs, and …
Cruise Details
Explore the famous rock formations of the baths
$4,099
EXPLORE

San Juan to San Juan

10 Day Itinerary aboard SeaDream II
  • Stroll in the city of San Juan
  • Swim with dolpins at Sandy Ground
  • Relax at White Bay
  • Enjoy the canopy at Tortola Island
Starts/ Ends in:
San Juan / San Juan
Activities:
Small Ship Cruise, Snorkeling
Activity Level:
Relaxed
The Caribbean is known for its opportunities to relax beside crystal blue waters and pristine sands, but there are also exciting activities to enjoy on this 10-day cruise. Embark on the SeaDream II in San Juan, the largest city and the capital of Puerto Rico, where you can see the Castillo de …
Cruise Details
St Barth Island, Caribbean
$4,199
EXPLORE

Philipsburg to Marigot

9 Day Itinerary aboard SeaDream I
  • Experience shopping in Philipsburg
  • Relax on Antigua's beaches
  • Explore Gustavia by hike or bike
  • Visit the famous Foxy’s Bar
Starts/ Ends in:
Philipsburg / Marigot
Activities:
Small Ship Cruise, Snorkeling
Activity Level:
Relaxed
Explore the Caribbean on this incredible9-day cruise through the islands of Saint Martin, Montserrat, Antigua and Barbuda, Anguilla, St. Barths, Jost van Dyke, and Virgin Gorda. Enjoy water sports, leisurely tours, land adventures and hiking options to make the most of your Caribbean adventure.
Cruise Details
55-72 of 121 Results

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