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Caribbean Small Ship Cruise Tours

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Beautiful beach in Dominica
$3,199
EXPLORE

Charlotte Amalie to Bridgetown

8 Day Itinerary aboard SeaDream II
  • Explore highlights of St. Thomas
  • Shop at Charlotte Amalie
  • Hike to Saltwhistle Bay in Mayreau
  • Discover Bridgetown's beaches
Starts/ Ends in:
Charlotte Amalie / Bridgetown
Activities:
Small Ship Cruise, Snorkeling
Activity Level:
Relaxed
Join the Sea Dream on this incredible 8-day cruise. Sail across the Caribbean enjoying all the treasures of this magical region. Visit the U.S. Virgin Islands, blessed with many beautiful beaches and bays, fine anchorages, and verdant hills. Sail to St Martin and visit the city of Marigot. Explore …
Cruise Details
Snorkel in the Baths of the Virgin Islands
$3,199
EXPLORE

Charlotte Amalie to San Juan

7 Day Itinerary aboard SeaDream II
  • Visit the beaches of St. Thomas
  • Hike & enjoy Saba's natural beauty
  • Snorkel at Jost van Dyke
  • Hike & snorkel at Norman Island
Starts/ Ends in:
Charlotte Amalie / San Juan
Activities:
Scuba Diving, Small Ship Cruise, Snorkeling
Activity Level:
Relaxed
Join the Sea Dream II on this 7-day cruise. Depart from charming Charlotte Amalie to sail across the Caribbean, enjoying the natural and cultural treasures of this region. Snorkel around the Virgin Islands, hike the Dutch Antilles, or simply relax on the beaches of the French West Indies. With …
Cruise Details
Take the time to explore St. Lucia
$3,399
EXPLORE

Bridgetown to Charlotte Amalie

7 Day Itinerary aboard SeaDream II
  • Explore Bridgetown
  • Sit back and relax on board
  • Take an off road adventures
  • Hike or bike in Gustavia
Starts/ Ends in:
Bridgetown / Charlotte Amalie
Activities:
Small Ship Cruise
Activity Level:
Relaxed
Fall in love with the crystal waters and colorful islands of the Caribbean on this 7-day adventure with SeaDream II.Begin your journey in Bridgetown and sail to the islands of Saint Lucia,Guadeloupe, St. Barthsand more! As you explore the island paradise of the Caribbean, disembark daily to bike, …
Cruise Details
Sea turtle
$3,899
EXPLORE

Round-trip Bridgetown via St. Lucia

9 Day Itinerary aboard SeaDream I
  • Helicopter ride across St Lucia
  • Enjoy a catamaran ride to Mustique
  • Discover the Southern Grenadines
  • Kayak at the Caribbean
Starts/ Ends in:
Bridgetown / Bridgetown
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 9-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
Relax on the shores of the Caribbean
$2,999
EXPLORE

Round-trip Charlotte Amalie

6 Day Itinerary aboard SeaDream II
  • Visit the beaches of St. Thomas
  • Hike Saba's Crispeen Track
  • Visit glamorous St. Barths
  • Enjoy the ambiance of White Bay
Starts/ Ends in:
Charlotte Amalie / Charlotte Amalie
Activities:
Small Ship Cruise, Snorkeling
Activity Level:
Relaxed
Bask in the romantic Caribbean on this 6-day round-trip St. Thomas adventure. Begin in Charlotte Amalie and make your way for the shelteredcoves and small towns of Cruz Bay, Saba, Gustavia, and more. As you explore the island paradise of the Caribbean, disembark daily to bike, hike, snorkel, or …
Cruise Details
Cuba el Morro the fortress in Havana
$3,394
EXPLORE

Cuban Panorama: Havana to Cienfuegos

8 Day Itinerary aboard Panorama
  • Explore old Havana
  • Visit Trinidad, a colonial city
  • Snorkel at Maria La Gorda
  • Journey through Cienfuegos
Activities:
Archaeological Sites, Local Market, Small Ship Cruise, Snorkeling, Urban Exploration
Activity Level:
Relaxed
Explore the western part of the island nation famous for its culture, music, warm people, and art on this 8-day people to people cruise.Go back in time to a place rooted in culture and history, where the people are as warm and welcoming as the climate, and visit Havana, Maria La Gorda, Isla …
Cruise Details
Tropical waterfall and turquoise pool in lush forest
$1,440
EXPLORE

Treasure Islands

8 Day Itinerary aboard Star Flyer
  • Visit Virgin Gorda's famous “Baths”
  • Enjoy the lifestyle of Soper's Hole
  • Walk the streets of Basseterre
  • Relax on famous St. Barts
Activities:
Sailing Schooner, Scuba Diving, Small Ship Cruise, Snorkeling
Activity Level:
Relaxed
Set a course for the Treasure Islands and the French Riviera of the Caribbean. Discover a treasure trove of breathtaking beaches, old forts, and seaside villages waiting for you. Starting at St Martin, makeyour way to the super-chic St Barths, historic Antigua, and lush Iles des Saintes, Dominica, …
Cruise Details
St George's Harbor - Grenada
$1,599
EXPLORE

Grenada Round Trip

7 Day Itinerary aboard Mandalay
  • Rise early & search for marine life
  • Snorkel in crystal-clear waters
  • Enjoy views of the night
  • Learn to raise the ship's sails
Starts/ Ends in:
Grenada / Grenada
Activities:
Sailing Schooner, Small Ship Cruise, Snorkeling
Activity Level:
Relaxed
Sail through turquoise waters, watch for marine life, and relax on white sand beaches as you escape to these remote islands. This fabulous 7-day voyage offers you an authentic sailing experience giving you the chance to learn how to raise the sails, take a turn at the helm, or just relax on deck! …
Cruise Details
Bright blue waters of the Caribbean
$8,295
EXPLORE

Sail the Caribbean - from St. Maarten to Bridgetown

12 Day Itinerary aboard Sea Cloud II
  • Enjoy fine sand in Foxy Island
  • Discover Virgin Gorda
  • Stroll through Gustavia
  • Sunbathe on the Plage de Pompierre
Starts/ Ends in:
Philipsburg / Bridgetown
Activities:
Small Ship Cruise, Snorkeling
Activity Level:
Relaxed
This 12-day cruise will explore the Caribbean from St. Maarten to Bridgetown. Sailacross the sunny heart of the Caribbean between Cuba and the Lesser Antilles.
Cruise Details
A view off the beautiful coast of Madeira.
$1,999
EXPLORE

Bridgetown to Lisbon

10 Day Itinerary aboard SeaDream II
  • Sit back and relax on board
  • Discover the tranquility offshore
  • Enjoy perfect views of Lisbon
Starts/ Ends in:
Bridgetown / 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 10 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
The Pitons in St Lucia
$3,730
EXPLORE

Pearls of the Caribbean 2021

9 Day Itinerary aboard Le Champlain
  • See UNESCO World Heritage Sites
  • Visit the Grenadine Islands
  • Observe marine animals
  • Enjoy the beach on Mayreau Island
Starts/ Ends in:
Fort de France / Fort de France
Activities:
Scuba Diving, Small Ship Cruise, Snorkeling
Activity Level:
Relaxed
Take this opportunity to explore the enchanting islands in the Caribbean Sea. Join Le Champlain on its 9-day cruise combining long, white-sand beaches and the easy Creole way of life. Discover the UNESCO-listed sites in Saint Lucia and the historic center of Bridgetown and its garrison. Visit …
Cruise Details
Take in the sights, sounds, and colors of Barbados
$3,799
EXPLORE

Marigot to Bridgetown via Montserrat

9 Day Itinerary aboard SeaDream I
  • Snorkel at St. Barts
  • Fish at St. Martin
  • Discover spectacular natural beauty
  • Swim and snorkel at Tobago Cays
Starts/ Ends in:
Marigot / Bridgetown
Activities:
Scuba Diving, Small Ship Cruise, Snorkeling
Activity Level:
Relaxed
Join this Caribbean voyage aboard the SeaDream I. Explore the French-influenced town of Marigot before setting sail to enjoy other lush islands across the Caribbean sea. Call at the famously beautiful St. Barths and snorkel in its clear waters, learn the story of Montserrat, explore National Parks …
Cruise Details
Admire the locals on your Virgin Islands cruise
$3,499
EXPLORE

Bridgetown to Bridgetown

9 Day Itinerary aboard SeaDream I
  • Explore unspoiled Canouan Island
  • Visit Union Island
  • Snorkel at Tobago Cays
  • Discover Mayreau
Starts/ Ends in:
Bridgetown / Bridgetown
Activities:
Kayaking, Scuba Diving, Small Ship Cruise, Snorkeling
Activity Level:
Relaxed
Discover the many facets of the Caribbean on this exclusive 9-day expedition. Observe reefs, fish, coral, and other aquatic life. Board a lovely catamaran that takes you on an exclusive sail-away to the beautiful Tobago Keys for a morning of swimming, snorkeling, and sunning.Discover an intimate …
Cruise Details
White Sand Beach in Barbados
$5,099
EXPLORE

Bridgetown to Bridgetown

9 Day Itinerary aboard SeaDream I
  • Explore Bridgetown
  • Relax and enjoy luxurious amenities
  • Snorkel at Tobago Cays
  • Delight yourself with a Champagne a
Starts/ Ends in:
Bridgetown / Bridgetown
Activities:
Small Ship Cruise
Activity Level:
Relaxed
Be a part of this incredible 9-day sailing adventure aboard the SeaDream I.Visit Pigeon Island National Park, witness the ruins of military buildings, and discover the signature Caviar Splash.Enjoy playing from the water sports marina as the ship anchors off on different ports.
Cruise Details
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
37-54 of 113 Results

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