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Best Small Ship Caribbean Cruises

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19-36 of 52 Results
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Snorkeling in the Caribbean with a starfish
$1,799
EXPLORE

St. Maarten to Antigua

7 Day Itinerary aboard Mandalay
  • Snorkel and swim from the ship
  • Enjoy morning pastries and coffee
  • Gaze at the night sky
  • Sip a rum swizzle
Activities: Sailing Schooner, Small Ship Cruise, Snorkeling
Activity Level: Relaxed
Treat yourself to a tropical paradise adventure onthis 7-day Caribbean cruise visiting various islands with warm beaches and crystal clear waters. Start your voyage in and enjoy the charming and magical Dutch island ofSt. Maarten. Afterwards navigate along Nevis, St. Kitts, St. Barths, Anguilla, …
Cruise Details
Caribbean beach bar
$1,799
EXPLORE

British Virgin Islands

7 Day Itinerary aboard Mandalay
  • Look for bird life
  • Snorkel in crystal waters
  • Gaze at the night sky
  • Relax with your favorite book
Activities: Sailing Schooner, Small Ship Cruise, Snorkeling
Activity Level: Relaxed
Board the S/V Mandalay in Tortola to St. Maarten for a 7-day Caribbean sailing adventure. Besides being one of the most scenic islands in the Caribbean, Tortola offers a decidedly cultural and historical side. Visit a selection of islands including , Anguilla, Jost Van Dyke, Norman Island, Peter …
Cruise Details
Pink beach huts on tropical Antigua island
$1,799
EXPLORE

Antigua to St. Lucia

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
Breathtaking scenery and sandy beaches are guaranteed on this spectacular 7-day once in a lifetimeCaribbean cruise. Cruising from charming Antigua to the lush and breathtaking island of St. Lucia.Hang out on the top deck looking for marine and bird life, enjoy different water sport activities on …
Cruise Details
The Pitons in St Lucia
$1,649
EXPLORE

Sail to St. Lucia

7 Day Itinerary aboard Mandalay
  • Enjoy morning coffee at sunrise
  • Snorkel & swim in Caribbean waters
  • Sip a rum swizzle
  • Relax on the top deck
Activities: Sailing Schooner, Small Ship Cruise, Snorkeling
Activity Level: Relaxed
Join the S/V Mandalay crew on this 7-day roundtrip sailing adventure starting and ending in St. Lucia, an island known for its beaches and reef-diving sites. Enjoy the winds of the Caribbean, take a turn at the helm, and partake in raising the vessel sails. Experience daily island visits for …
Cruise Details
Mountains by the ocean in St Lucia
$1,649
EXPLORE

St. Lucia & Grenada

7 Day Itinerary aboard Mandalay
  • Snorkel & swim with marinelife
  • Visit white sand beaches
  • Enjoy evening activities
  • Watch the Caribbean sunrise
Activities: Sailing Schooner, Snorkeling
Activity Level: Relaxed
White sandy beaches, turquoise water, and lush rainforests make the Caribbean an exciting and relaxing cruise experience. Starting on St. Lucia,home to the Piton Peaks and mesmerizing beauty all the way to Grenada.Admiring majestic volcanoes, colorful reefs, and the scent of nutmeg and vanilla on …
Cruise Details
Atlantic Ocean - Transatlantic Cruise
$2,350
EXPLORE

Transatlantic: St. Maarten to Lisbon

21 Day Itinerary aboard Star Flyer
  • Set sail from St. Maarten
  • Enjoy the expansive Atlantic Ocean
  • Cruise across the Caribbean
  • Discover Lisbon, Portugal
Activities: Sailing Schooner, Small Ship Cruise
Activity Level: Relaxed
Relive the golden age of cruising on this fantastic transatlantic cruise aboard the Star Flyer. Discover a haven of tranquillity as you make your way from the tropical paradise island of St. Maarten to the stunning port of Lisbon. This unique cruise isideal for people who love being on the open …
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
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
St Barts harbor view
$2,290
EXPLORE

Jamaica to Barbados

12 Day Itinerary aboard Royal Clipper
  • Enjoy Jamaican cuisine
  • Explore elegant Gustavia, St. Barts
  • Snorkel or dive at Iles des Saintes
  • Swim under stunning waterfalls
Activities: Sailing Schooner, Scuba Diving, Small Ship Cruise, Snorkeling
Activity Level: Relaxed
Enjoy a week in the Western Caribbean sailing board the Royal Clipper. Cruise through turquoise waters, watch for marine life, and relax on white-sand beaches as you escape to remote islands.Begin your island journey in Montego Bay, Jamaica, and make your way to beautiful St. Barts and Antigua …
Cruise Details
Taxi in Cuba
$5,890
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
Snorkelling the warm waters
$8,640
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
Bay of Pigs, Cuba
$4,580
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
Colorful houses in Trinidad, Cuba
$3,412
EXPLORE

Cienfuegos to Havana: People to People

8 Day Itinerary aboard Harmony V
  • 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
Snorkeling in the Caribbean with a starfish
$4,895
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
Soufrière Bay, Saint Lucia
$5,120
EXPLORE

Between Martinique and Panama

10 Day Itinerary aboard Le Champlain
  • Visit Cartagena de Indias
  • Discover the Los Roques archipelago
  • Explore Holandes Cay & San Blas
  • Learn more about the Kuna Indians
Activities: Hiking, Scuba Diving, Small Ship Cruise, Snorkeling
Activity Level: Relaxed
Start your trip by visitingFort-de-Franceand strolling through its colorful markets and lively streets. Then sail to the gorgeousisland of Saint Lucia, known for its famous Pitons, listed as aUNESCO World Heritage Site. After calling atGrenada,Le Champlainheads for the idyllicLos Roques …
Cruise Details
Promenade in Bridgetown, Barbados
$2,290
EXPLORE

Transatlantic: Barbados to Lisbon

17 Day Itinerary aboard Royal Clipper
  • Explore stunning Barbados
  • Visit Sao Miguel Island
  • Enjoy some incredible days onboard
  • Discover Lisbon's history
Activities: Sailing Schooner, Small Ship Cruise
Activity Level: Relaxed
Relish in the time-out-of-mind sensation of watching the water slip under the bow, or gaze at an infinite sea, feeling the steadying power of the sails as they capture the energy of the wind and thrust your ship through the expanse of the Atlantic Ocean. Start your adventure in the tropical …
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
An old lighthouse on Curacao
$5,120
EXPLORE

Between Panama and Martinique

10 Day Itinerary aboard Le Champlain
  • Discover the Los Roques archipelago
  • Dive & snorkel in Curacao
  • Admire the San Blas Islands
  • Encounter the Kuna Indians
Activities: Local Market, Scuba Diving, Small Ship Cruise, Snorkeling, Village Visit, Wildlife Viewing
Activity Level: Relaxed
First, succumb to the charms of the clear waters of Panama and the San Blas archipelago, composed of more than 300 islands and cays. Here, surrounded by palm trees and dugout canoes, discoverthe island of Holandes Cay, where the Kuna people live. The cities ofCartagenain Colombia andWillemstadonthe …
Cruise Details
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