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Caribbean Small Ship Cruise Tours

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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
Green sea turtle swimming
$3,399
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
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. Explorethe capital of …
Cruise Details
Unspoiled beaches and pristine coves in the Caribbean
$2,999
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
Deep blue waters await you on your Caribbean cruise
$3,299
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
Relax on the beaches of the Caribbean
$7,275
Savings
EXPLORE

Caribbean: Round-trip Philipsburg

11 Day Itinerary aboard Sea Cloud
  • Snorkel the British Virgin Islands
  • See luxurious St. Barths
  • Watch stunning sunsets
  • Explore charming Soufriere
Starts/ Ends in:
Philipsburg / Gustavia
Activities:
Small Ship Cruise, Snorkeling
Activity Level:
Relaxed
Experience the blue waters of the wonderful Caribbean on this 11-day round-trip cruise from Philipsburg in St. Maarten. As you sail, visit the charming port cities and remote coves of Gustavia, Virgin Gorda and more. The Caribbean is a vibrant, lively region of colorful islands and friendly locals. …
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
Savings
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
Savings
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
Mountains by the ocean in St Lucia
$3,199
EXPLORE

Castries to San Juan

8 Day Itinerary aboard SeaDream I
  • Relax on beautiful beaches
  • Bike around Gustavia
  • Experience Iles des Saintes
  • Enjoy Saint Lucia
Starts/ Ends in:
Bequia / San Juan
Activities:
Small Ship Cruise, Snorkeling
Activity Level:
Relaxed
On this once-in-a-lifetime Caribbean adventure, join SeaDream on an 8-day exploration.Enjoy an incredible hike as well as an exciting water sport in different islands. Many beautiful places are waiting for you to visit, explore and to discover!
Cruise Details
Jost Van Dyke, British Virgin Islands
$3,199
EXPLORE

Castries, St. Lucia to San Juan

8 Day Itinerary aboard SeaDream I
  • Dive along the coast of St. Barts
  • Enjoy a unique dolphin encounter
  • Enjoy the sulfur springs at Soufrie
  • Visit the Spanish fortress
Starts/ Ends in:
Bequia / San Juan
Activities:
Scuba Diving, Small Ship Cruise, Snorkeling
Activity Level:
Relaxed
Sail the beautiful blue waters of the Virgin Islands on this 8-day Caribbean cruise. See the fascinating islands of the area, including Castries St. Lucia, Port Elizabeth, Bequia, Soufriere Bay and and many more.Swim and snorkel in one of the most incredible landscapes in the world or dive to your …
Cruise Details
Explore the colorful streets of Marigot
$3,199
EXPLORE

Marigot to Castries St. Lucia

8 Day Itinerary aboard SeaDream I
  • Enjoy the scenic Saba Island
  • Bike around Gustavia
  • Relax on beautiful beaches
  • Experience Iles des Saintes
Starts/ Ends in:
Marigot / Mayreau
Activities:
Small Ship Cruise, Snorkeling
Activity Level:
Relaxed
Embark SeaDream I for a spectacular 8-day journey across the Caribbean. Explore the beautiful town ofMarigot, where itscolonial houses stand beside cafés and bistros, pastry shops and luxury boutiques. Enjoy an incredible hike to a scenic overview of Saba Island. Many beautiful places are …
Cruise Details
Beautiful beach, Tobago Cays
$3,399
EXPLORE

Marigot to Bridgetown

8 Day Itinerary aboard SeaDream II
  • Visit Union Island
  • Discover Mayreau
  • Swim and snorkel at Tobago Cays
  • Explore Bridgetown's beaches
Starts/ Ends in:
Marigot / Bridgetown
Activities:
Hiking, Small Ship Cruise
Activity Level:
Relaxed
SeaDream II anchors off in different places and offers an exciting adventure.Discover beautiful and magnificent beaches in the Caribbean. Embark the ship in the four streets wide city of Marigot and take time to go around it. One of these days, you will visit Tobago Cays and the Tobago Cays Marine …
Cruise Details
Peaceful seclusion in the Caribbean
$3,099
EXPLORE

Marigot to Marigot

8 Day Itinerary aboard SeaDream I
  • Relax on beautiful beaches
  • Hike or bike around the islands
  • Discover the town of Marigot
  • Visit Gustavia
Starts/ Ends in:
Marigot / Marigot
Activities:
Small Ship Cruise
Activity Level:
Relaxed
Explore the Caribbean on this incredible journey full of land adventures for you to discover the islands from sea or land. Embark and disembark in Marigot,the main town and capital on the French side of Saint Martin, an area well known for its elegant stores with the latest in European designer …
Cruise Details
Charlestown, Nevis
$2,999
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
Starts/ Ends in:
Charlotte Amalie / San Juan
Activities:
Biking, Hiking, Kayaking, Scuba Diving, Small Ship Cruise, Snorkeling
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
$8,355
Savings
EXPLORE

Philipsburg Round Trip

11 Day Itinerary aboard Sea Cloud Spirit
  • Spend two days at Nature Isle
  • Visit charming Terre-de-Haut
  • Enjoy touring Moskito Island
  • Explore St. Barthélemy
Starts/ Ends in:
Philipsburg / Philipsburg
Activities:
Sailing Schooner, Small Ship Cruise, Snorkeling
Activity Level:
Relaxed
Join the Sea Cloud Spirit on this 11-day experience-of-a-lifetime Caribbean cruise. This voyage which starts at Philipsburg, St. Maarten will take you to exquisite places. Visit the charming main town of Terre-de-Haut, explore the unspoiled beauty of the Winward Islands -Dominica, immerse in the …
Cruise Details
Take the time to explore St. Lucia
$3,800
EXPLORE

Bridgetown to Fort Lauderdale (Florida)

11 Day Itinerary aboard Silver Whisper
  • Visit Scarborough's botanic gardens
  • Ride Basseterre's scenic train
  • Explore Jost Van Dyke
  • Enjoy shopping and dining
Starts/ Ends in:
Bridgetown / Fort Lauderdale
Activities:
Biking, Hiking, Kayaking, Scuba Diving, Small Ship Cruise, Snorkeling
Activity Level:
Relaxed
Be amazed by the Caribbean’s distinctive charms as you travel everywhere from the “Nature Island” to the “Isle of Spice.” The landscapes you’ll see are sure you leave you in breathless appreciation—beautiful waterfalls, towering mountains, fertile green …
Cruise Details
37-54 of 76 Results

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