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Best Small Ship Caribbean Cruises

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19-36 of 62 Results
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Scuba diving in the reefs
$2,799
EXPLORE

Marigot to Bridgetown via Guadeloupe

8 Day Itinerary aboard SeaDream I
  • Discover St. Lucia
  • Visit the Moon Hole at Bequia
  • Relax at Mustique
  • Experience Iles des Saintes
Activities: Fishing, Helicopter Tour, Hiking, Kayaking, Scuba Diving, Small Ship Cruise, Snorkeling, Wildlife Viewing, Zip Line
Activity Level: Relaxed
This unique cruise mixes relaxation and adventure perfectly! Explore the Caribbeanwhile you enjoy incredible views of the islands on this 8-day expedition aboard the SeaDream I. VisitPort Elizabeth, well known for its reefs and long silvery stretches of beach. Among the first things you notice are …
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
Snorkel the vibrant reef system
$2,399
EXPLORE

Round-trip Barbados

7 Day Itinerary aboard SeaDream I
  • Explore St. Lucia Island
  • Visit pristine Canoaun Island
  • Snorkel & swim at Tobago Cays
  • Sail along the coast of Mustique
Activities: Fishing, Helicopter Tour, Hiking, Scuba Diving, Small Ship Cruise, Snorkeling, Wildlife Viewing
Activity Level: Relaxed
Discover the treasures of the Grenadines! Enjoy majestic volcanoes, colorful reefs, and the scent of nutmeg and vanilla on this magical 7-day sailing adventure. Scout around the snorkelers’ paradise of Tobago Cays; this horseshoe-shaped coral reef encloses four small islands that glow in rich …
Cruise Details
Vintage car in Jose Marti Square, Cienfuegos, Cuba
$4,345
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
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
A dolphin jumps out of the water
$1,999
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
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
Pink beach huts on tropical Antigua island
$1,420
EXPLORE

Windward Islands

8 Day Itinerary aboard Royal Clipper
  • Explore lush St. Lucia Island
  • Hike to Trafalgar Falls
  • Discover Falmouth Harbour, Antigua
  • Visit sophisticated Martinique
Activities: Sailing Schooner, Scuba Diving, Small Ship Cruise, Snorkeling
Activity Level: Relaxed
For connoisseurs of sail cruising, the 439-foot Royal Clipper offers the ultimate sea-going experience, balancing the grandeur, adventure and tradition of sailing with the superb service, amenities, and accommodations of the finest modern yacht. Swim and snorkel amidst the beautiful, pristine …
Cruise Details
Beautiful beache, Tobago Cays
$1,420
EXPLORE

Grenadines

8 Day Itinerary aboard Royal Clipper
  • Explore Bridgetown, Barbados
  • Take in Grenada's unique aromas
  • Snorkel in Tobago Cays
  • Admire Bequia's waterfront
Activities: Sailing Schooner, Scuba Diving, Snorkeling
Activity Level: Relaxed
Experience tropical life with a refined twist on this incredible 8-day cruise aboard the tall ship Royal Clipper. Lush mountains, rain forests, volcanic crater lakes, mangroves, beautiful beaches, and delicate coral reefs are hallmarks of this coveted destination. Enjoy a wonderful journey of …
Cruise Details
Beautiful beach in Dominica
$1,360
EXPLORE

Leeward Islands

8 Day Itinerary aboard Star Flyer
  • Visit Dominica Island
  • Snorkel at Iles des Saintes
  • Sail across Rivière Salée
  • Enjoy Gustavia's unique charm
Activities: Sailing Schooner, Scuba Diving, Small Ship Cruise, Snorkeling
Activity Level: Relaxed
With an island for every taste, the Caribbean is the ultimate place for relaxation. Explore the world-famous white sands and turquoise water throughout the Caribbean Sea. With more than 5,000 islands and cays spread across this amazing region, there’s a lot of paradise to see. Best of all, …
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
Tropical waterfall and turquoise pool in lush forest
$1,360
EXPLORE

Treasure Islands

8 Day Itinerary aboard Star Flyer
  • Visit Virgin Gorda's famous “Baths”
  • Enjoy the lifestyle of Soper's Hole
  • Walk the streets of Basseterre
  • Relax on famous St. Barts
Activities: Sailing Schooner, Scuba Diving, Small Ship Cruise, Snorkeling
Activity Level: Relaxed
Set a course for the Treasure Islands and the French Riviera of the Caribbean. Discover a treasure trove of breathtaking beaches, old forts, and seaside villages waiting for you. Starting at St Martin, makeyour way to the super-chic St Barths, historic Antigua, and lush Iles des Saintes, Dominica, …
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
Save $160-$300
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
Charlestown, Nevis
$2,799
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
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