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Caribbean Small Ship Cruises

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Caribbean
  • 37 Cruises + Land Tours
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Clear waters of the Caribbean sea
Anguilla
  • 2 Cruises
Snorkeling in the Caribbean with a starfish
Antigua
  • 6 Cruises
Lush green forests and clear blue waters of the Caribbean
Aruba
  • 3 Cruises
Relax on the shores of the Caribbean
Barbados
  • 10 Cruises
Take a leisurely stroll through beautiful Bridgetown
Dominica
  • 8 Cruises
Encounter tropical wildlife while you sail on the Aranui
Greater Antilles
  • 14 Cruises + Land Tours
Picturesque Cuba
Lesser Antilles
  • 28 Cruises
Wander the white-sand beaches of St. Johns on your Virgin Islands cruise
Grenada
  • 11 Cruises
Snorkel the clear, tropical waters
Puerto Rico
  • 2 Cruises
Discover incredible history and culture in Puerto Rico
St. Barth
  • 9 Cruises
Play on the famously beautiful beaches of St. Barth's
St. Martin
  • 9 Cruises
Pelicans hanging out in the ocean
Virgin Islands
  • 20 Cruises
Relax on the beaches of the Caribbean
Union Island
  • 2 Cruises
Uwe Moser
Bright blue waters of the Caribbean
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Stroll along the white sandy beaches of St. Barth's
$9,265
EXPLORE

Caribbean: Round-trip Philipsburg

15 Day Itinerary aboard Sea Cloud
  • See St Barths' luxurious lifestyle
  • Visit beautiful islands
  • Discover The Baths at Virgin Gorda
  • Observe incredible sunsets
Starts/ Ends in:
Philipsburg / Philipsburg
Activities:
Small Ship Cruise, Snorkeling
Activity Level:
Relaxed
Fall in love with the region's sun, sand, and culture. Delight yourself with deep volcanic lakes, dense rainforests, waterfalls, and small river courses that form the primordial backdrop of the island’s sugar cane fields and spice plantations. The scent of cloves, cinnamon, and nutmeg …
Cruise Details
0
White Sand Beach in Barbados
$1,580
EXPLORE

Grenadine Islands

8 Day Itinerary aboard Royal Clipper
  • Visit one island in Grenadines
  • Smell the aroma of Grenada
  • Walk and swim at Marigot Bay
  • Taste the spicy Creole cooking
Starts/ Ends in:
Bridgetown / Bridgetown
Activities:
Small Ship Cruise, Snorkeling
Activity Level:
Relaxed
Join the Royal Clipper on this 8-day cruise through theGrenadine Islands. Embark on an interesting adventure, visiting towns full of contrasts,Bridgetown, Barbados. Then, call on one of the islands of Grenadine, for a blissful, laid-back beach day.From the horseshoe-shaped Carenage at St. …
Cruise Details
0
Relax in the sunny squares of historic Savannah
$5,599
EXPLORE

Boston, MA to Nassau, Bahamas

16 Day Itinerary aboard Ocean Voyager
  • Learn Boston's history
  • Wander through historic Baltimore
  • Experience Southern hospitality
  • Explore Charleston's architecture
Starts/ Ends in:
Boston / Nassau
Activities:
Archaeological Sites, Small Ship Cruise, Urban Exploration, Village Visit
Activity Level:
Relaxed
Sail on this 16-day itinerary cruising the seaboard from bustling Boston to beachy Nassau aboard Ocean Voyager. With stops in Baltimore, Charleston, West Palm Beach, and more, this journey has been handcrafted to sample the Eastern cities of the United States as you head to your final destination …
Cruise Details
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Pelicans hanging out in the ocean
$9,870
EXPLORE

Sailing the Caribbean

8 Day Itinerary aboard Sea Cloud
  • 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
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Beautiful beach in Dominica
$1,520
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
Starts/ Ends in:
Philipsburg / Philipsburg
Activities:
Sailing Schooner, 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
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Gatun Lock of the Panama Canal
$4,300
EXPLORE

Panama Canal: Panama to Antigua

15 Day Itinerary aboard Royal Clipper
  • Transit the historic Panama Canal
  • Enjoy Grenada's unique aromas
  • Discover Dutch colonial Curacao
  • Swim in paradise in Bonaire
Activities:
Sailing Schooner, Small Ship Cruise, Snorkeling, Wildlife Viewing
Activity Level:
Relaxed
Royal Clipper takes you to the seas for a stunning adventure packed with incredible experiences starting at the charming port town of Bridgetown, Barbados. Scour the streets of the UNESCO-listed cities of Cartagena de Indias, Colombia, and Willemstad, Curaçao. Swim in the protected, …
Cruise Details
0
Pink beach huts in the Caribbean
$1,580
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
Starts/ Ends in:
Bridgetown / Bridgetown
Activities:
Sailing Schooner, 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
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Tropical waterfall and turquoise pool in lush forest
$1,520
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
Starts/ Ends in:
Philipsburg / Philipsburg
Activities:
Sailing Schooner, 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
0
Relax on the beaches of the Caribbean
$6,180
EXPLORE

Christmas and New Year in the Caribbean

Fort-de-France - Santo Domingo - 14 Day Itinerary aboard Le Dumont-d'Urville
  • Explore gardens and parks
  • See UNESCO World Heritage Sites
  • Swim in crystal clear waters
  • Learn the history of the region
Starts/ Ends in:
Fort de France / Santo Domingo
Activities:
Small Ship Cruise, Snorkeling
Activity Level:
Relaxed
Board the luxurious Le Dumont-d'Urville to celebrate Christmas and ring in the New Year with this 14-day cruise. Set sail from Fort-de-France and cruise to some of the finest islands in the Caribbean. From the lush rainforest and mountainous terrain of Dominica, to the warm, clear waters of …
Cruise Details
0
Caribbean
$5,295
EXPLORE

Philipsburg Round Trip

8 Day Itinerary aboard Sea Cloud Spirit
  • Visit the port town of Philipsburg
  • Visit the birthplace of Sanjuaneros
  • Explore the famous ‘Love City’ Cruz
  • Discover the stunning White Bay
Starts/ Ends in:
Philipsburg / Philipsburg
Activities:
Kayaking, Sailing Schooner, Small Ship Cruise, Snorkeling
Activity Level:
Relaxed
Board the Sea Cloud Spirit and start your exciting adventure from the beautiful city of Philipsburg, St. Maarten. Voyage along the idyllic and warm waters of the Caribbean and explore the beauty of each destination. Visit San Juan, Isla Culberita, and Esperanza in Puerto Rico. Explore the beautiful …
Cruise Details
0
Soufrière Bay, Saint Lucia
$3,620
EXPLORE

Pearls of the Caribbean

Roundtrip Fort-de-France - 9 Day Itinerary aboard Le Dumont-d'Urville
  • See UNESCO World Heritage Sites
  • Visit the Grenadine Islands
  • Observe marine animals
  • Enjoy the beach on Mayreau Island
Starts/ Ends in:
Fort de France / Fort de France
Activities:
Scuba Diving, Small Ship Cruise, Snorkeling
Activity Level:
Relaxed
Take this opportunity to explore the enchanting islands in the Caribbean Sea. Join Le Dumont-d'Urville on this 9-day cruise combining long, white-sand beaches and the laid-back Creole way of life. Discover the UNESCO-listed sites in Saint Lucia and the historic center of Bridgetown and its …
Cruise Details
0
Relax on the sunny beaches of the Bahamas
$4,140
EXPLORE

Bridgetown to Fort Lauderdale

9 Day Itinerary aboard Silver Wind
  • See Conception Island's wildlife
  • Visit Devil’s Bay National Park
  • Marvel at Barbuda's frigatebirds
  • Dip in the hot springs of Roseau
Starts/ Ends in:
Bridgetown / Fort Lauderdale
Activities:
Small Ship Cruise, Snorkeling, Wildlife Viewing
Activity Level:
Relaxed
Experience the Caribbean as never before during this 9-day cruise from Bridgetown to Fort Lauderdale. Spend time relaxing on white sandy beaches and enjoying coral reefs and the warm, clear waters of islands such as Dominica, St. Vincent and Antigua. But the Caribbean is so much more: tiny, off the …
Cruise Details
0
St Barth Island, Caribbean
$1,999
EXPLORE

San Juan to Charlotte Amalie

5 Day Itinerary aboard SeaDream II
  • Visit the Virgin Islands
  • Dive along the coast of St. Barths
  • See the island of St. Thomas
  • Explore San Juan, Puerto Rico
Starts/ Ends in:
San Juan / Charlotte Amalie
Activities:
Small Ship Cruise
Activity Level:
Relaxed
Board the SeaDream II on this exclusive 5-day adventure sailing across the Caribbean and discover all the picture-perfect views that make this region famous. Stop at pristine beaches for swimming in crystal-clear warm waters and relaxation under the sun. Bring your camera and sunscreen and prepare …
Cruise Details
0
Relax on the sunny beaches of the Bahamas
$5,590
EXPLORE

Exploring the Bahamas’ Out Islands: Natural Wonders & Hidden History

Great Exuma, Bahamas Roundtrip - 8 Day Itinerary aboard National Geographic Sea Lion
  • Explore remote islands
  • Visit Conception National Park
  • Learn Bahamian history and culture
  • Kayak between mangroves
Starts/ Ends in:
George Town,The Exumas / George Town,The Exumas
Activities:
Kayaking, Small Ship Cruise, Snorkeling, Stand Up Paddle Board, Wildlife Viewing
Activity Level:
Relaxed
Discover the Bahamas’ wild side on a voyage to some of its most far-flung islands and hearan intriguing history of pirates, pilgrims,lost civilizations,and the slave trade.Snorkel with abundant sea life inwarm turquoise waters, explore waterways by kayak, and get introduced to the …
Cruise Details
0
Stroll along the beautiful beaches of the Caribbean
$5,760
EXPLORE

The Essential of the Caribbean

Fort-de-France Roundtrip - 13 Day Itinerary aboard Le Champlain
  • Cruise in West Indies
  • Visit heritage sites
  • Discover British Virgin Islands
  • Explore Dominica
Starts/ Ends in:
Fort de France / Fort de France
Activities:
Scuba Diving, Skiing, Small Ship Cruise, Snorkeling, Stand Up Paddle Board
Activity Level:
Relaxed
You begin your voyage in St. Kitts, a volcanic island known for its excellent sandy beaches and rich colonial history. Your cruise then docks in Anguilla before continuing west to the British Virgin Islands, which have gorgeous landscapes. Then, sail to Saint Barthelemy and the enchanted setting of …
Cruise Details
0
Boats Moored to the Quay at Bridgetown Harbour
$3,500
EXPLORE

Panama Canal: Barbados to Panama

15 Day Itinerary aboard Royal Clipper
  • Explore Bridgetown, Barbados
  • Enjoy Grenada's unique aromas
  • Discover Dutch colonial Curacao
  • Transit the historic Panama Canal
Starts/ Ends in:
Bridgetown / Balboa
Activities:
Sailing Schooner, Small Ship Cruise, Snorkeling, Wildlife Viewing
Activity Level:
Relaxed
Royal Clipper takes you to the seas for a stunning adventure packed with incredible experiences starting at the charming port town of Bridgetown, Barbados. Scour the streets of the UNESCO-listed cities of Cartagena de Indias, Colombia, and Willemstad, Curaçao. Swim in the protected, …
Cruise Details
0
Spot monkeys in the rainforest canopy
$13,680
EXPLORE

Fortaleza to Bridgetown

22 Day Itinerary aboard Silver Wind
  • Visit the Forte do Castelo in Belem
  • Marvel at Giant Water Lilies
  • Tour the city of Georgetown
  • Observe wildlife
Starts/ Ends in:
Fortaleza / Bridgetown
Activities:
Local Market, Small Ship Cruise, Urban Exploration, Wildlife Viewing
Activity Level:
Relaxed
Travel north from Fortaleza all the way to the Caribbean, taking in some spectacular sights – and sites – along the way. Everything you could possibly want from Brazil is on this voyage – Zodiac expeditions into the mighty Amazon jungle, gastronomic excellence, unprecedented …
Cruise Details
0
Unspoiled beaches and pristine coves in the Caribbean
$11,635
EXPLORE

Transatlantic: Las Palmas to St Maarten

18 Day Itinerary aboard Sea Cloud
  • Enjoy a full sailing experience
  • Follow Columbus’s course
  • Sit back and relax on deck
  • Obeserve magnificent sunsets
Starts/ Ends in:
Las Palmas / Philipsburg
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
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1-18 of 29 Results

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