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Best Small Ship Caribbean Cruises

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19-36 of 52 Results
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    • Caribbean
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
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
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
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
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
Cuba el Morro the fortress in Havana
$4,669
EXPLORE

Havana to Cienfuegos: People to People

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
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
An underwater world awaits you
$3,000
EXPLORE

Antigua to Grenada

14 Day Itinerary aboard Mandalay
  • Discover Bequia's landscapes
  • Explore local bars and restaurants
  • Visit St. Lucia's beaches and reefs
  • Snorkel and swim from the boat
Activities: Sailing Schooner, Small Ship Cruise, Snorkeling
Activity Level: Relaxed
This 14-day cruise offers the best opoortunirty for a true sailing vessel journey. Board the S/V Mandalay in Antigua and disembark in Grenada. As the wind marks the navigation course visit islands like Nevis, Isle Des Saintes, Dominica, St. Lucia, St. Vincent, Bequia, Canouan, Tobago Cays, Mayreau, …
Cruise Details
The s/v Mandalay
$2,800
EXPLORE

Grenada Round Trip

14 Day Itinerary aboard Mandalay
  • Rise early & search for marine life
  • Snorkel in crystal-clear waters
  • Enjoy views of the night sky
  • Learn to raise the ship's sails
Activities: Sailing Schooner, Small Ship Cruise, Snorkeling
Activity Level: Relaxed
Enjoy two weeks in the Southern Caribbean sailing on board the Mandalay. Sail through turquoise waters, watch for marinelife, and relax on white sand beaches as you escape to these remote islands. While onboard learn how to raise the sails, take a turn at the helm, or just relax on deck!
Cruise Details
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
Activities: Sailing Schooner, Small Ship Cruise, Snorkeling
Activity Level: Relaxed
Experience a memorable Caribbean sailing adventure on this 7-day cruise fromSt. Lucia to Antigua.Hang out on the top deck looking for marine and bird life, enjoy different water sport activities on paradisiac islands, and choose from various Island excursions each day. Partake in raising the sails, …
Cruise Details
Snorkel in the Baths of the Virgin Islands
$1,550
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
Activities: Kayaking, Small Ship Cruise, Snorkeling, Whale Watching, Wildlife Viewing
Activity Level: Relaxed
Board the Liberty Star for this 7-day cruise between the US and British Virgin Islands. The Liberty Star never follows a fixed itinerary, enabling the Captain to chart a course that results in the best wind and weather. Wake up each morning on a different island and seize the opportunity to …
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
$7,590
EXPLORE

Cuba: Cultural Experience

9 Day Itinerary aboard Le Ponant
  • Snorkel at Punta Frances
  • Discover enticing Cayo Largo
  • Experience the Bay of Pigs
  • Admire Trinidad's charm
Activities: Small Ship Cruise, Snorkeling
Activity Level: Relaxed
Explore the eye-catching wonders of the stunning island of Cuba on a remarkable 9-day sailing expedition aboard Le Ponant. In addition to all that you can learn from encounters with Cubans from various walks of life, be privileged to travel in the company of the expert Franklin Knight, who speaks …
Cruise Details
Charlestown, Nevis
$6,900
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
Activities: Biking, Hiking, Horseback Riding, Scuba Diving, Small Ship Cruise, Snorkeling, Wildlife Viewing, Zip Line
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
Snorkelling the warm waters
$8,640
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
Bay of Pigs, Cuba
$6,690
EXPLORE

Cuba: History, Culture & Contemporary Life

8 Day Itinerary aboard Le Ponant
  • Enjoy Havana's main attractions
  • Visit Punta Frances beach
  • Explore Palacio de Valle
  • Discover colonial Trinidad
Activities: Small Ship Cruise, Snorkeling
Activity Level: Relaxed
Admire the dazzling landscapes and vibrant culture of the enchanting island of Cuba on this spectacular cruise. Swim and snorkel the crystal-clear waters of the Caribbean. Visit the beach of Parque Nacional Marino de Punta Frances Punta Pedernales, a marine conservation area established in 1978. …
Cruise Details
19-36 of 52 Results

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