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Caribbean Travel Deals

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Below we have selected the best deals on only the best small ships that cruise the Caribbean. It's common to see deals on Caribbean cruises, but most deals you'll run across are for huge cruise ships that carry thousands of passengers. On one of Adventure Life's hand-picked small ship cruises, you'll have exclusive access to smaller port towns, and coves and get to know the Caribbean and the Caribbean people intimately, in ways that are impossible on a huge cruise ship. See a sampling of small ship cruise deals below, and contact us with the dates you wish to travel, and our team of Caribbean cruise experts can help you find a deal on a boat that matches your budget, schedule and interests. Contact us for more details.
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    • Caribbean
An old lighthouse on Curacao
$9,455
Save $730
EXPLORE

Transatlantic: Gran Canaria to Curaçao

18 Day Itinerary aboard Sea Cloud II
  • Enjoy a full sailing experience
  • Follow Columbus’s course
  • Sit back and relax on deck
  • Obeserve magnificent sunsets
Activities: Sailing Schooner, Small Ship Cruise
Activity Level: Relaxed
Crossing the Atlantic in a traditional tall ship is an experience that leaves a lasting impression. For 18 days your exact course is determined only by the elements. When the crew sets the sails at dizzying heights, and the wind is caught in the sailcloth and the ropes creak as they are stretched …
Cruise Details
The sun sets off the Canary Islands
$10,595
Save $690
EXPLORE

Transatlantic: Las Palmas to Bridgetown

17 Day Itinerary aboard Sea Cloud
  • Follow Columbus's course
  • Sail across the Atlantic Ocean
  • Enjoy an offshore sailing adventure
  • Observe incredible sunsets
Activities: Sailing Schooner, Small Ship Cruise
Activity Level: Relaxed
Follow the route Columbus took across the Atlantic as you set sail for new horizons on a voyage of discovery. Discover this 17-day pure sailing adventure where for two whole weeks, the expansive ocean is the home of Sea Cloud. Water currents and trade winds are all that propel the yacht forwards. …
Cruise Details
Promenade in Bridgetown, Barbados
$7,695
Save $600
EXPLORE

Caribbean: Round-trip Bridgetown

15 Day Itinerary aboard Sea Cloud
  • Visit Cabrits National Park
  • Enjoy the magical Argyle Waterfall
  • Discover Bequia's turtle sanctuary
  • Snorkel at Tobago Cays
Activities: Hiking, Sailing Schooner, Snorkeling, Wildlife Viewing
Activity Level: Relaxed
Experience the blue waters of the wonderful Caribbean on this 15-day round-trip cruise from Barbados. As you sail, visit the charming port cities and remote coves of Tobago Cays, Soufriere, Cabrits, and more. The Caribbean is a vibrant, lively region of colorful buildings and friendly locals. Fall …
Cruise Details
Famous colorful huts in Barbados
$9,555
Save $560
EXPLORE

Caribbean: Jamaica to Barbados

14 Day Itinerary aboard Sea Cloud
  • Admire Santo Domingo's old town
  • Visit a rum and cigar factory
  • Discover The Baths at Virgin Gorda
  • Explore glamorous St Bart's
Activities: Sailing Schooner, Small Ship Cruise
Activity Level: Relaxed
Voyage through a tropical paradise from Jamaica to the archipelago of the Lesser Antilles on an exceptional 14-day sailing expedition. Enjoy some ofthe most beautiful sceneries in the world; with its perfect beaches, lush tropical vegetation, and countless caves, rivers, and waterfalls, the …
Cruise Details
Vintage car in Jose Marti Square, Cienfuegos, Cuba
$4,345
Save $500
EXPLORE

Cienfuegos to Havana: People to People

8 Day Itinerary aboard M/Y Callisto
  • Engage with musicians of Cienfuegos
  • Visit Guanahacabibes National Park
  • Tour Spanish colonial Trinidad
  • Explore historic Old Havana
Activities: Archaeological Sites, Small Ship Cruise, Snorkeling, Urban Exploration
Activity Level: Relaxed
It has never been so easy to 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 8-day cruise, including vibrant Havana and its amazing Old Town, Cienfuegos with its neoclassical French …
Cruise Details
Parque Marti in Cienfuegos, Cuba
$4,345
Save $500
EXPLORE

Havana to Cienfuegos: People to People

8 Day Itinerary aboard M/Y Callisto
  • 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
Cycling through the revolutionary landscape of Cuba
$4,669
Save $500
EXPLORE

Cienfuegos to Havana: People to People

8 Day Itinerary aboard Panorama
  • Visit a tobacco plantation
  • Enjoy Guanahacabibes National Park
  • Discover Spanish colonial Trinidad
  • Explore historic Old 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
Iconic vintage car on a street in Havana
$5,242
Save $500
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
$5,242
Save $500
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
Caribbean
$6,895
Save $470
EXPLORE

Caribbean: Barbados to Antigua

12 Day Itinerary aboard Sea Cloud II
  • Visit a turtle sanctuary on Bequia
  • Snorkel along the Tobago Cays
  • Admire volcanic sulphur springs
  • Discover the famous Baths
Activities: Hiking, Sailing Schooner, Small Ship Cruise, Snorkeling
Activity Level: Relaxed
Exchange the winter blues for the pastels of the Caribbean, sailing into the sun along famous pirate routes. Visit Gustavia, located on well-known St Barthélemy, a top holiday destination for the rich and famous from around the world. Its red roof houses nestled into the green hills look …
Cruise Details
A green heron found in the Caribbean
$6,995
Save $430
EXPLORE

Caribbean: St. John's to Bridgetown

11 Day Itinerary aboard Sea Cloud II
  • Explore Virgin Gorda
  • Enjoy sophisticated St. Barthélemy
  • Discover Port Elizabeth, Bequia
  • Visit charming Dominica
Activities: Sailing Schooner, Small Ship Cruise, Snorkeling
Activity Level: Relaxed
Join this exclusive 11-day adventure, admire the blue waters of the region, and disembark daily to discover small towns with cobbled streets and amazing European style - the Caribbean Islands are a real dream destination. People from all over the world dream of their perfect tropically warm waters …
Cruise Details
Snorkel in the Baths of the Virgin Islands
$6,995
Save $430
EXPLORE

Caribbean: Antigua to Barbados

11 Day Itinerary aboard Sea Cloud II
  • Explore Brimstone Hill Fortress
  • Visit a botanical garden
  • Snorkel along the Tobago Cays
  • Hike the Morne Gazo trail
Activities: Sailing Schooner, Small Ship Cruise, Snorkeling
Activity Level: Relaxed
Join the Sea Cloud II on this 11-day cruise discovering Caribbean hot spots. Enjoy exclusive picture-perfect beaches, deep volcanic lakes, dense rainforests, amazing waterfalls, and small river courses that form the primordial backdrop of the island’s sugar cane fields and spice plantations. …
Cruise Details
The Pitons of St. Lucia
$6,595
Save $390
EXPLORE

Caribbean: Round-trip Barbados

10 Day Itinerary aboard Sea Cloud
  • Discover the Argyle waterfall
  • Hike the Morne Gazo trail
  • Snorkel the Tobago Cays
  • Visit volcanic sulphur springs
Activities: Hiking, Sailing Schooner, Small Ship Cruise, Snorkeling
Activity Level: Relaxed
This wonderful 10-day cruise has everything you're looking for to make your Caribbean experience unforgettable, offering picture-perfect beaches,deep volcanic lakes, dense rainforests, and waterfalls. Visit snorkelers’ paradise in the Tobago Cays, where its famous Horseshoe Reef encloses …
Cruise Details
Snorkeling in the Caribbean with a starfish
$4,895
Save $300
EXPLORE

Caribbean: Roundtrip Antigua via Jost van Dyke

8 Day Itinerary aboard Sea Cloud II
  • Discover The Baths at Virgin Gorda
  • Enjoy glamorous St. Barths
  • Sail through famous landscapes
  • Visit the Brimstone Hill Fortress
Activities: Sailing Schooner, Small Ship Cruise, Snorkeling
Activity Level: Relaxed
The wind in the sails, the feet in the sand – set course for dream islands with colonial flair and nature’s magic. Admire the wonders of the Caribbeanwith their white sandy beaches, coral reefs, and friendly beach bars, one of the most desired destinations on Earth. Discover “The …
Cruise Details
A snorkeler walking along a white sandy beach.
$4,895
Save $300
EXPLORE

Caribbean: Round-trip Antigua

8 Day Itinerary aboard Sea Cloud II
  • Visit a turtle sanctuary
  • Snorkel the Tobago Cays
  • Explore Cabrits National Park
  • Enjoy ÎIes des Saintes
Activities: Sailing Schooner, Small Ship Cruise, Snorkeling
Activity Level: Relaxed
Caribbean joie de vivre, nature in all its glory, and French holiday flair. For many, life under water is a fascinating world – one that becomes even more magical the closer you get. The Tobago Cays’ Horseshoe Reef is such a place. This horseshoe-shaped coral reef encloses four small …
Cruise Details
Sunset over Cartagena
$3,895
Save $300
EXPLORE

Costa Rica & Panama Canal: Curaçao to Panama

8 Day Itinerary aboard Sea Cloud II
  • Visit the ABC islands
  • Enjoy incredible weather
  • Explore beautiful Cartagena
  • Discover Colon, Panama
Activities: Sailing Schooner, Small Ship Cruise
Activity Level: Relaxed
Sail from Curaçao to Cartagena, Colombia, and disembark in Panama City, experiencing Caribbean summer winds and the Latin-American zest for life. ExploreAruba, Bonaire and Curaçao – the ABC islands are considered the “Netherlands of the Caribbean”, and their Dutch …
Cruise Details
1-16 of 16 Results

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