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Best Small Ship Caribbean Cruises

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19-36 of 60 Results
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Mandalay Caribbean Beach
$3,000
EXPLORE

British Virgin Islands

14 Day Itinerary aboard Mandalay
  • Discover the \\\"Island of Spice\\\
  • Rest on Bequia's beaches
  • Snorkel and swim at Mayreau
  • View turtles in their habitat
Activities: Sailing Schooner, Small Ship Cruise, Snorkeling, Village Visit
Activity Level: Relaxed
Sail wherever the wind takes you on this incredible trip aboard a legendary tall ship that shows you exactlywhat it was born to do, with nothing but the wind determining its course and the captain obeying its orders. This 14-day exploration of theBritish Virgin Islands includes visits to …
Cruise Details
Beautiful beach in Dominica
$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
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, Union Island, and Grenada. Discover amazing landscapes, local villages, beautiful …
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
Dock going out into the crystal blue ocean
$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
  • Learn to raise the ship's sails
Activities: Sailing Schooner, Small Ship Cruise, Snorkeling
Activity Level: Relaxed
Sail through turquoise waters, watch for marinelife, and relax on white sand beaches as you escape to these remote islands. This fabulous 14-day voyage offers you an authentic sailing experience giving you the chance to 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
The beautiful waters of the Caribbean
$1,799
EXPLORE

St. Maarten Round Trip

7 Day Itinerary aboard Mandalay
  • Watch the sunrise from the deck
  • Snorkel in crystal waters
  • Enjoy lunch ashore
  • Join in on the Mandalay Masquerade
Activities: Sailing Schooner, Small Ship Cruise, Snorkeling
Activity Level: Relaxed
Board the S/V Mandalay for a once-in-a-lifetime experience that fewothers ever see or even dream of. Partake in raising the sails, take a turn at the helm, or just enjoy the winds of the Caribbean sea filling the sails with new friends aboard. The choice is yours! Visit locations such asSt. …
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
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
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
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
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
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