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Best Small Ship Caribbean Cruises

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    • Caribbean
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
This 7-day Caribbean sailing adventure takes you from St. Lucia to Antigua. As you sail north visit a selection of islands including St. Lucia, Martinique, Iles Des Saintes, Marie-Galante, Montserrat, Nevis, Antigua, and if the wind is on your side, land on other outstanding islands as well.
Activities: Sailing Schooner, Small Ship Cruise, Snorkeling
Places: Antigua, Iles des Saintes, Marie Galante, Martinique, Montserrat, Nevis, St. Lucia
Cruise Details
The beautiful waters of the Caribbean
$1,599
EXPLORE

Grenada to St. Lucia

7 Day Itinerary aboard Mandalay
  • Snorkel & swim with marinelife
  • Visit white sand beaches
  • Enjoy evening activities
  • Watch the Caribbean sunrise
Learn how to raise the sails of the s/v Mandalay as you sail the turquoise waters of the Caribbean on this 7-day voyage. Rise early and search for marine life, learn local lore of the region, snorkel and swim from the ship, and choose from various island excursions each day on this Caribbean adventure.
Activities: Sailing Schooner, Snorkeling
Places: Caribbean, Bequia, Carriacou, Grenada, Mayreau, St. Lucia, St. Vincent des Grenadines, Tobago Cays
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
Sail the crystal waters of the Virgin Islands on this tropical 7-day cruise on the tall ship Liberty Star. Explore the ports of St. Thomas, St. John, Jost Van Dyke, and more! Leave the ship for pristine snorkeling opportunities and enjoy the company of the friendly locals as you journey through the Caribbean.
Activities: Kayaking, Small Ship Cruise, Snorkeling, Whale Watching, Wildlife Viewing
Places: Caribbean, Norman Island, St John, St. Thomas
Cruise Details
Martinique harbor
$13,980
EXPLORE

Wild Caribbean with the Grenadines

13 Day Itinerary aboard Le Ponant
  • Identify endemic bird species
  • Hike Grenada's dense forest
  • Snorkel in Tobago Cays
  • View a myriad of underwater wonders
Sail around the Eastern Caribbean aboard Le Ponant on this 14-day relaxing vacation. Each island boasts a unique history, culture, and landscape. Enjoy trips ashore each day and the opportunity to explore the ports of call.
Activities: Expedition Cruises, Hiking, Snorkeling, Wildlife Viewing
Places: Caribbean, Barbuda, Dominica, Grenada, Iles des Saintes, Martinique, Montserrat, St. Barth, St. Lucia, St. Martin, St. Vincent des Grenadines, Tobago Cays
Cruise Details
Havana Plaza Vieja
$5,590
EXPLORE

Cienfuegos to Havana: People to People

8 Day Itinerary aboard Variety Voyager
  • Engage with musicians of Cienfuegos
  • Explore historic Old Havana
  • Visit Guanahacabibes National Park
  • Tour Spanish colonial Trinidad
Embark the Variety Voyager for an 8-day Cuba people to people cruise. Explore Havana, one of the most impressive historical city centers in the Caribbean, and sail through the western part of the island that has been closed to Americans for half a century.
Activities: Local Market, Small Ship Cruise, Snorkeling, Urban Exploration
Places: Cienfuegos, Havana, Isla de la Juventud
Cruise Details
White Sand Beach in Barbados
$3,645
EXPLORE

Caribbean: Round-trip Barbados to Dominica

8 Day Itinerary aboard Sea Cloud II
  • Discover Dominica's waterfalls
  • Walk across Cabrits National Park
  • Enjoy St Barthélemy Island
  • Take a stroll on ÎIes des Saintes
Sail the beautiful blue waters of the Caribbean on this 8-day cruise. See the fascinating islands of the area, including St. Barts, Antigua, and Dominica. Swim and snorkel to your heart's content as you cruise along the archipelago.
Activities: Sailing Schooner, Snorkeling, Wildlife Viewing
Places: Bridgetown, Cabrits, Falmouth, Iles des Saintes, St. Barth
Cruise Details
Cuba!
$4,990
EXPLORE

Havana to Casilda: People to People

8 Day Itinerary aboard Panorama
  • Join a guided snorkeling experience
  • Tour the Valley of Vinales
  • Discover Old Havana
  • Explore Trinidad, a colonial city
Cruise aboard the Panorama on a people to people experience and explore the western part of the island nation and its culture. Stop at Casilda, Cienfuegos, Isla de la Juventud, Maria La Gorda, and Havana as you discover this country filled with culture, music, warm people, and art.
Activities: Local Market, Small Ship Cruise, Snorkeling, Urban Exploration
Places: Cienfuegos, Havana, Maria la Gorda
Cruise Details
Famous colorful huts in Barbados
$2,895
EXPLORE

Caribbean: Round-trip Bridgetown 2016

8 Day Itinerary aboard Sea Cloud II
  • Travel to the Argyle Waterfall
  • Snorkel & swim at Tobago Cays
  • Visit botanical gardens
  • Discover Gros and Petit Piton
Explore the crystal waters of the Caribbean on this 8-day small ship cruise. Beginning and ending in Bridgetown, Barbados, this cruise explores the pristine port cities and coves of Man-O-War Bay, St. George's, Soufriere, Port Elizabeth, and more.
Activities: Sailing Schooner, Snorkeling, Wildlife Viewing
Places: Bequia, Bridgetown, Man-O-War Bay, Soufriere, St. Georges, Tobago Cays
Cruise Details
Havana Street Performers
$2,790
EXPLORE

Cienfuegos to Havana: People to People

8 Day Itinerary aboard Panorama II
  • Immerse yourself in Old Havana
  • Visit archaeological sites
  • Snorkel in Cayo Largo
  • Engage with musicians in Cienfuegos
Board the Panorama II for an 8-day exploration of Cuba's colonial cities, verdant landscapes, crystal clear seas, and rich cultural diversity. Walk through Old Havana streets and squares, and visit marvelous locations such as Maria La Gorda, Cayo Largo, Trinidad, and Cienfuegos.
Activities: Small Ship Cruise, Snorkeling, Urban Exploration
Places: Cienfuegos, Havana, Maria la Gorda
Cruise Details
Church in Trinidad, Cuba
$5,975
EXPLORE

Caribbean: Cienfuegos to Santo Domingo

11 Day Itinerary aboard Sea Cloud II
  • Delight yourself with Cuba's music
  • Join an excursion to Trinidad
  • Walk across Santiago de Cuba
  • Discover Jamaica's natural beauty
Join the Sea Cloud ll on this amazing 11-day adventure sailing the fabulous coasts of Cuba to the paradisaical Dominican Republic. Visit Cienfuegos, Cayo Largo del Sur, Santiago de Cuba, Port Antonio, and more!
Activities: Archaeological Sites, Sailing Schooner
Places: Cienfuegos, La Romana, Port Antonio, Santiago de Cuba, Santo Domingo
Cruise Details
Iconic cars in Havana, Cuba
$7,930
EXPLORE

The Caribbean and Cuba: Havana to Santo Domingo

15 Day Itinerary aboard Sea Cloud
  • Discover the many facets of Cuba
  • Visit perfect beaches and reefs
  • Tour Trinidad, a sugar cane center
  • Dance to the spirited music of Cuba
On this 15-day adventure, experience picture-perfect beaches, breathtaking colonial architecture, lively salsa rhythms, and an endless sea. Begin your journey in Havana, exuding history and energy, and sail for the magical and serene natural settings of Jamaica before ending your small ship cruise in Santo Domingo, Dominican Republic.
Activities: Archaeological Sites, Sailing Schooner, Snorkeling
Places: Havana, Isla de la Juventud, La Romana, Port Antonio, Santiago de Cuba, Santo Domingo
Cruise Details
A snorkeler walking along a white sandy beach.
$3,775
EXPLORE

Caribbean: Barbados to Curaçao

8 Day Itinerary aboard Sea Cloud II
  • Take an excursion to Port Elizabeth
  • Visit Gotomeer Lake
  • Stroll through colonial Grenada
  • Spend two days sailing offshore
Join the Sea Cloud ll on this unique 8-day cruise exploring Caribbean hot spots. 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!
Activities: Sailing Schooner, Snorkeling, Wildlife Viewing
Places: Bequia, Bonaire, Bridgetown, Tobago Cays, Union Island, Willemstad
Cruise Details
Havana Plaza de la Catedral
$17,580
EXPLORE

Cuba Under Sail

17 Day Itinerary aboard Le Ponant
  • Immerse yourself in Cuban culture
  • Travel with ease on Le Ponant
  • Visit UNESCO World Heritage Sites
  • Snorkel or dive healthy coral reefs
  • Stroll the streets of Havana
Immerse yourself in Cuban culture as you visit friendly locals, savor traditional cuisine, and enjoy musical performances, including a visit to the Buena Vista Social Club. Travel with ease aboard the intimate, 56-guest sailing ship, Le Ponant.
Activities: History, Land & Sea, Sailing Schooner, Snorkeling, Urban Exploration, Village Visit, Wildlife Viewing
Places: Atlantic Coast, Caribbean, Cuba, North America, United States, Cienfuegos, Havana, Miami, Santiago de Cuba
Cruise Details
Havana Plaza de la Catedral
$9,500
EXPLORE

Cuba by Land and Sea: Cultural Heritage and Natural Wonders

11 Day Itinerary aboard Panorama II (LI)
  • Experience people-to-people visits
  • Explore marine habitats and reefs
  • Visit the Bay of Pigs
  • Enjoy lively music & superb cuisine
  • See Cuba's great cities
Experience Cuba People-to-People on a unique land and sea program aboard the Panorama II. Discover three of Cuba’s greatest resources: its people, colorful culture, and intact natural wonders. In Havana, meet artists, musicians, and historians who are safeguarding traditions. Explore great colonial cities and pristine marine & terrestrial habitats.
Activities: Land & Sea, Scuba Diving, Small Ship Cruise, Snorkeling, Urban Exploration, Wildlife Viewing
Places: Cienfuegos, Havana
Cruise Details
Pelicans hanging out in the ocean
$1,045
EXPLORE

Nassau to Charleston

5 Day Itinerary aboard Liberty Clipper
  • Help the crew navigate and sail
  • Enjoy the weather on deck
  • Fish for a meal in the open ocean
Join the ship in Nassau, the capital, largest city, and commercial center of the Commonwealth of the Bahamas, for this 5-day sailing adventure. This offshore passage gives you the opportunity to join the Liberty Clipper's crew and help them sail a tall ship in the open ocean as you feel like another crew member.
Activities: Sailing Schooner
Places: Nassau
Cruise Details
Sunset in ancient Mayan city of Tulum
$7,765
EXPLORE

Puerto Limón to Cienfuegos

14 Day Itinerary aboard Sea Cloud II
  • Visit Belize's Barrier Reef
  • Take the cable car at Roatán
  • Snorkel at the Great Blue Hole
  • Explore Cozumel and Belize City
Explore Central America, Mexico, and the Caribbean on this wonderful 14-day cruise aboard the Sea Cloud ll, starting at the green paradise of Costa Rica and sailing to the paradise beaches of Cuba. Visit the archipelago's hot spots including Corn Islands, Roatán, Cozumel, Belize and more!
Activities: Archaeological Sites, Sailing Schooner, Snorkeling, Wildlife Viewing
Places: Basecamp on Half Moon Caye, Belize City, Cienfuegos, Corn Islands, Puerto Limon, Roatan
Cruise Details
Blowing where the wind takes us on the Liberty Clipper
$1,045
EXPLORE

Florida to Nassau

7 Day Itinerary aboard Liberty Clipper
  • Enjoy smells of the ocean breeze
  • Sail a tall ship in the open ocean
  • Find picture-perfect sunsets at sea
  • Fish & swim in pristine waters
Join the Liberty Clipper on this 7-day cruise from Florida to the Bahamas. Sail across the Gulf Stream, a powerful, warm, and swift Atlantic Ocean current that originates in the Gulf of Mexico and stretches to the tip of Florida.
Activities: Fishing, Sailing Schooner, Snorkeling
Places: Jacksonville, Nassau
Cruise Details
19-35 of 35 Results

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