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Nothing feels more like paradise than the turquoise waters and tranquil island cultures of the Caribbean. While many of the most well known cruises are the mammoth floating hotels, the smaller vessels offer the best way to navigate the Caribbean Islands. You will have exclusive access to the hidden coves, vibrant reefs, & small port cities that the bigger ships simply can't reach. Just because you're on a smaller boat doesn't mean you have to sacrifice luxury, especially on ships like the Ponant or the Voyager. Many actually prefer the intimate environment. If you want a truly unique and relaxing experience, consider booking your trip on a small sailboat like the Liberty Clipper, the Mandalay, or the Panorama. Adventure Life's team of Caribbean specialists can answer any of your questions about your Caribbean vacation.
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Enjoy a ride around the islands.
$1,299
EXPLORE

Bahamas Sailing Adventure

7 Day Itinerary aboard Liberty Clipper
  • Explore the Out Islands
  • Learn how to sail and steer
  • Encounter unique wildlife
  • Kayak, snorkel, or paddle board
Activities:
Kayaking, Sailing Schooner, Snorkeling, Stand Up Paddle Board, Wildlife Viewing
Activity Level:
Relaxed
Set sail for new horizons on a barefoot 7-day cruise in the Bahamas. On the 125-foot schooner, the tall ship Liberty Clipper, explore the Out Islands of the Bahamas from this majestic windjammer. Be welcomed aboard by expert crew who are there for your safety and enjoyment. From qualified Captains …
Cruise Details
Unspoiled beaches and pristine coves in the Caribbean
$10,905
EXPLORE

Caribbean: Santo Domingo - Bridgetown

16 Day Itinerary aboard Sea Cloud
  • Observe incredible sunsets
  • Follow Columbus's course
  • Snorkel at Tobago Cays
  • Explore Virgin Gorda
Activities:
Sailing Schooner, Small Ship Cruise, Snorkeling
Activity Level:
Relaxed
Experience the blue waters of the wonderful Caribbean on this 16-day cruise from Santo Domingo to Barbados. As you sail, visit the charming port cities and remote coves of Tobago Cays, Soufriere, Cabrits, and more.Heavenly bays, gorgeous beaches, idyllic anchoring spots, smart yacht clubs and …
Cruise Details
San Juan, Puerto Rico
$4,899
EXPLORE

San Juan to San Juan

8 Day Itinerary aboard SeaDream II
  • Discover diverse marine life
  • Dive & explore Saba Island
  • Explore Tortola Island's canopy
Starts/ Ends in:
San Juan / San Juan
Activities:
Biking, Hiking, Scuba Diving, Small Ship Cruise, Snorkeling, Wildlife Viewing
Activity Level:
Relaxed
Discover the Caribbean on this exclusive 8-day cruise aboard the SeaDream ll. Explore paradisical island beaches as you enjoy the perfect tropical weather this region offers. Wear your swim suit, bring a towel, water, and plenty of sun protection, and get ready to enjoy your days in this beautiful, …
Cruise Details
Skyline of Old Havana Cuba
$4,599
EXPLORE

Havana to Cienfuegos

8 Day Itinerary aboard SeaDream I
  • Admire Havana's heritage
  • Swim across the Caribbean waters
  • Visit Trinidad, a colonial city
  • Discover Cienfuegos' architecture
Starts/ Ends in:
Havana / Cienfuegos
Activities:
Small Ship Cruise, Snorkeling
Activity Level:
Relaxed
Experience a harmonious balance between conventional cruising and private yachting, along with an exciting voyage of discovery, unraveling the wonders of Cubaawaiting to be discovered. This incredible 8-day voyage allows you to discover charming ports, hidden coves with crystal blue waters to cool …
Cruise Details
$5,699
EXPLORE

San Juan to Charlotte Amalie via Anguilla

9 Day Itinerary aboard SeaDream I
  • Zip-Line on St. Martin
  • Snorkel at Treasure Island
  • Dive along the coast of St. Barts
  • Explore Tortola Island
Starts/ Ends in:
San Juan / Charlotte Amalie
Activities:
Hiking, Small Ship Cruise, Snorkeling
Activity Level:
Relaxed
Sail the Caribbean on this 9-day cruise beginning in Puerto Rico en route to Virgin Gorda. 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 …
Cruise Details
Parque Marti in Cienfuegos, Cuba
$4,599
EXPLORE

Cienfuegos to Havana

8 Day Itinerary aboard SeaDream I
  • Admire Cienfuegos heritage
  • Visit the captiving Trinidad
  • Enjoy Cayo Largo's beaches
  • Explore Isla de Juventud
Starts/ Ends in:
Cienfuegos / Havana
Activities:
Small Ship Cruise, Snorkeling
Activity Level:
Relaxed
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, Trinidad's baroque mansions, and Isla de Juventud. Admire the breathtakingPunta Frances Marine National Park, which is …
Cruise Details
St George's Harbor - Grenada
$3,400
EXPLORE

Pearls of the Caribbean

8 Day Itinerary aboard Le Champlain
  • See UNESCO World Heritage Sites
  • Discover the Grenadine Islands
  • Observe marine animals
  • Enjoy the beach on Mayreau Island
Activities:
Scuba Diving, Small Ship Cruise, Snorkeling, Whale Watching, Wildlife Viewing
Activity Level:
Relaxed
Take this opportunity to explore the enchanting islands in the Caribbean Sea. Join Le Champlain on its 8-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
Snorkel in the Baths of the Virgin Islands
$3,299
EXPLORE

Charlotte Amalie to Charlotte Amalie

8 Day Itinerary aboard SeaDream II
  • Ride a jet above St. Thomas
  • Visit The Baths at Virgin Gorda
  • Enjoy the ambience of White Bay
  • Hike Saba's Crispeen Track
Activities:
Biking, Hiking, Kayaking, Scuba Diving, Small Ship Cruise, Snorkeling, Wildlife Viewing
Activity Level:
Relaxed
Join the SeaDream l on the journey of a lifetime across the Caribbean, starting and ending at the incredible island of St.Thomas and exploring this wonderful archipelago. Ecologically and culturally recognized for its pure beauty, this magical destination is among the world’s most …
Cruise Details
Green sea turtle swimming
$3,199
EXPLORE

Charlotte Amalie to San Juan via St. Barts

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
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
Mayreau Island, St Vincent and Grenadines
$3,099
EXPLORE

Bridgetown to Bridgetown via Bequia

8 Day Itinerary aboard SeaDream I
  • Explore unspoiled Canouan Island
  • Visit Union Island
  • Snorkel at Tobago Cays
  • Discover Mayreau
Starts/ Ends in:
Bridgetown / Bridgetown
Activities:
Biking, Helicopter Tour, Hiking, Scuba Diving, Small Ship Cruise, Snorkeling, Wildlife Viewing
Activity Level:
Relaxed
Enjoy some water sports, relax on one of the most beautiful beachesin the world, or hike through magical landscapes on this 8-day adventure sailing across the Caribbean. Visit Pigeon Island National Park, witness the ruins of military buildings, and discover the signature Caviar Splash and Beach …
Cruise Details
Portsmouth, Dominica
$2,999
EXPLORE

Marigot to Bridgetown via Antigua

9 Day Itinerary aboard SeaDream I
  • Hike to Saltwhistle Bay, St Vincent
  • Fish at St. Martin
  • Discover spectacular natural beauty
  • Enjoy Saint Lucia
Starts/ Ends in:
Marigot / Bridgetown
Activities:
Biking, Fishing, Helicopter Tour, Hiking, Kayaking, Scuba Diving, Small Ship Cruise, Snorkeling, Wildlife Viewing, Zip Line
Activity Level:
Relaxed
On this once-in-a-lifetime Caribbean adventure, navigate across the Indian River, explore Cabrits National Park, enjoy the quiet village ofFalmouth, and discoverthe beauty and versatility of this exclusive landscape well known for its colonial houses, cafés and bistros, pastry shops, and …
Cruise Details
A dolphin jumps out of the water
$2,999
EXPLORE

Marigot to Marigot

6 Day Itinerary aboard SeaDream I
  • Relax on beautiful beaches
  • Dive in pristine Caribbean waters
  • Hike or bike around the islands
  • Join exciting optional excursions
Starts/ Ends in:
Marigot / Marigot
Activities:
Biking, Hiking, Scuba Diving, Small Ship Cruise, Snorkeling, Zip Line
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 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 fashions and fine …
Cruise Details
St. Martin, Caribbean
$2,999
EXPLORE

Marigot to Marigot

8 Day Itinerary aboard SeaDream I
  • Visit Coconut Grove beach
  • Hike along the Crispeen Track
  • Explore the waters of Les Saintes
  • Dive in St. Bart's waters
Starts/ Ends in:
Marigot / Marigot
Activities:
Biking, Hiking, Kayaking, Scuba Diving, Small Ship Cruise, Snorkeling, Zip Line
Activity Level:
Relaxed
Explore the Caribbean on this incredible journey full of land adventures for you to discover the islands from sea or land. Shop at 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 fashions and fine …
Cruise Details
Deep blue waters await you on your Caribbean cruise
$3,299
EXPLORE

Marigot to Marigot via Anguilla

6 Day Itinerary aboard SeaDream II
  • Swim with dolpins at Sandy Ground
  • Visit the famous St. Barts
  • Enjoy Antigua's beaches
  • Discover St. Martin
Starts/ Ends in:
Marigot / Marigot
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. Relax on the glamorous white sand beaches of St. Barts or participate in custom designed land adventures including snorkeling, scuba diving, land rover safari, and zip-lining. For guests …
Cruise Details
The Pitons of St. Lucia
$3,920
EXPLORE

Caribbean: Bridgetown - Bridgetown

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
Visit the laid-back Caribbean and discover the pearls of the Lesser Antilles and the Grenadines. Start your adventure atBridgetown, Barbados and stroll down its historic center, with colonial architecture surrounding Trafalgar Square. VisitGrenada, a paradisiacal spotblessed with around 45 …
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
Iconic vintage car on a street in Havana
$3,396
EXPLORE

Sights and Sounds of Cuba: Havana to Cienfuegos

8 Day Itinerary aboard Variety Voyager
  • Enjoy charming Havana
  • Listen and dance to salsa music
  • Visit Guanahacabibes National Park
  • Explore Presidio Modelo
Activities:
Archaeological Sites, Small Ship Cruise, Snorkeling, Urban Exploration
Activity Level:
Relaxed
Imagine going back to other times - the culture, music, art, and people of Cuba await! Enjoy lively beats, picture-perfect beaches, and narrow city streets with colonial charm on this incredible 8-day cruise. Witness a mixture of beautiful old baroque and neo-classical monuments, arcades and …
Cruise Details
Picturesque Cuba
$3,575
EXPLORE

Sights and Sounds of Cuba: Cienfuegos to Havana

8 Day Itinerary aboard Variety Voyager
  • Explore enchancting Cienfuegos
  • Visit the colonial city of Trinidad
  • Enjoy sightseeing in Nueva Gerona
  • Snorkel at Maria La Gorda
Activities:
Archaeological Sites, Small Ship Cruise, Snorkeling, Urban Exploration
Activity Level:
Relaxed
Start your "bucket list" cruise in the enchanting and French-styled city of Cienfuegos, declared a UNESCO World Heritage site. Visit the graphic arts workshop and attend a local musical performance. Discover Trinidad'srich architecture, cobblestone streets, palaces and plazas - it is …
Cruise Details
1-18 of 59 Results

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