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Sailing Trips in Caribbean

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Choose from one of these 23 Caribbean sailing cruises in 2023. Sailing with the sails full and the sun shining is an unforgettable experience that Adventure Life's Caribbean sailing cruise experts can help you plan to perfection. Contact one of our Caribbean sailing cruise experts for help planning your next trip.
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Dock going out into the crystal blue ocean
$1,620
EXPLORE

Classic Yachtsman Caribbean

Antigua to Barbados - 8 Day Itinerary aboard Royal Clipper
  • Enjoy Grenada's unique aromas
  • Discover Falmouth Harbour, Antigua
  • Enjoy the beach in ÎIes des Saintes
  • Explore lush St. Lucia Island
Starts / Ends:
St. John's / Bridgetown
Activities:
Small Ship Cruises, Small Ship Sailing
Activity Level:
Relaxed
Swim and snorkel amidst the beautiful, pristine waters of the Caribbean Sea on this 8-day expedition aboard Royal Clipper. Sail away from your everyday life and find tropical bliss in the islands. From the stunning drama of the spectacular Pitons at St. Luciato the captivating charm of Les Saintes, …
Cruise Details
0
Pelicans hanging out in the ocean
$10,880
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:
Small Ship Cruises, Small Ship Sailing, 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
0
Stroll along the beautiful beaches of the Caribbean
$6,785
EXPLORE

Windjammer Rendezvous in the Lesser Antilles

Phillipsburg Roundtrip - 11 Day Itinerary aboard Sea Cloud
  • Visit the port town of Philipsburg
  • Discover the stunning White Bay
  • Explore Cruz Bay in St. John
  • Experience St. Barthélemy
Starts / Ends:
Philipsburg / Philipsburg
Activities:
Small Ship Sailing, Snorkeling
Activity Level:
Relaxed
Fall in love with the Caribbean region's sun, sand, and culture during this incredible 11-day cruise aboard Sea Cloud. 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 …
Cruise Details
0
Gatun Lock of the Panama Canal
$3,570
EXPLORE

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:
Small Ship Cruises, Small Ship Sailing, 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
$1,620
EXPLORE

Windward Islands

8 Day Itinerary aboard Royal Clipper
  • Explore beaches in Barbados
  • See lush island of St. Lucia
  • Discover Falmouth Harbour, Antigua
  • Visit sophisticated Martinique
Starts / Ends:
Bridgetown / Bridgetown
Activities:
Small Ship Cruises, Small Ship Sailing, 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
0
Tropical Caribbean Beach in Martinique
$1,620
EXPLORE

Windward Islands Christmas Cruise

8 Day Itinerary aboard Royal Clipper
  • Discover lush St. Lucia Island
  • Enjoy Trafalgar Falls
  • Visit Falmouth Harbour, Antigua
  • View sophisticated Martinique
Starts / Ends:
Bridgetown / Bridgetown
Activities:
Small Ship Cruises, Small Ship Sailing, Snorkeling
Activity Level:
Relaxed
The 439-foot Royal Clipper is the ultimate sea-going experience for sail cruising enthusiasts, combining the grandeur, adventure, and tradition of sailing with the superior service, amenities, and accommodations of the finest modern yacht. Swim and snorkel in the Caribbean Sea's pristine …
Cruise Details
0
Tropical waterfall and turquoise pool in lush forest
$1,560
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:
Philipsburg / Philipsburg
Activities:
Small Ship Cruises, Small Ship Sailing, 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
Beautiful beach in Dominica
$1,560
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:
Philipsburg / Philipsburg
Activities:
Small Ship Cruises, Small Ship Sailing, 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
0
Colorful harbor of Bonaire
$11,655
EXPLORE

Island Flair and Colorful Colonial Towns

Philipsburg to Puntarenas - 18 Day Itinerary aboard Sea Cloud Spirit
  • View a tropical paradise Grenada
  • Immerse in traditions and culture
  • Transit the famous Panama Canal
  • Explore spectacular Costa Rica
Starts / Ends:
Philipsburg / Panama City
Activities:
Small Ship Cruises, Small Ship Sailing, Snorkeling, Village Visits
Activity Level:
Relaxed
Fall in love with the crystal waters of the Caribbean, Panama and Costa Rica on this 16-day cruise aboard the Sea Cloud Spirit. Begin your exciting journey in Philipsburg, St. Maarten. Enjoy the tropical scenery of the best diving and snorkeling spots in the Carribean. Explore the colonial center …
Cruise Details
0
Enjoy a ride around the islands.
$1,499
EXPLORE

Bahamas Sailing Adventure

7 Day Itinerary aboard Liberty Clipper
  • Explore the Out Islands
  • Learn how to sail and steer
  • Encounter unique wildlife
  • Kayak, snorkel, or paddle board
Starts / Ends:
Nassau / Nassau
Activities:
Kayaking, Small Ship Sailing, Snorkeling, Stand Up Paddle Boarding, Wildlife Viewing
Activity Level:
Relaxed
Set sail for new horizons on a barefoot 7-day cruise in the Bahamas. On the 125-foot schooner, the tall ship Liberty Clipper, explore the Out Islands of the Bahamas from this majestic windjammer. Be welcomed aboard by expert crew who are there for your safety and enjoyment. From qualified Captains …
Cruise Details
0
Boats Moored to the Quay at Bridgetown Harbour
$6,655
EXPLORE

Sailing Together with the Sea Cloud

Caribbean: Bridgetown - Philip - 12 Day Itinerary aboard Sea Cloud II
  • Enjoy ÎIes des Saintes
  • Snorkel along the Union Island
  • Admire volcanic sulphur springs
  • Hike the Morne Gazo trail
Starts / Ends:
Philipsburg / Bridgetown
Activities:
Scuba Diving, Small Ship Sailing, Snorkeling
Activity Level:
Relaxed
Join the Sea Cloud II on this fascinating 12-day cruise around the Caribbean. 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. Barthelemy, a top holiday destination for the rich and famous from …
Cruise Details
0
Explore colorful Gustavia
$4,655
EXPLORE

Sailing on the Warm Trade Wind

8 Day Itinerary aboard Sea Cloud II
  • Drift and relax in the Caribbean
  • Live a laid-back lifestyle
  • Enjoy Îles des Saintes' French vibe
  • Enjoy breathtaking sunsets
Starts / Ends:
Philipsburg / Santo Domingo
Activities:
Small Ship Sailing
Activity Level:
Relaxed
Set sail on Sea Cloud II's Caribbean island-hopping cruise for an unforgettable experience of total relaxation!Îles des Saintes offers a taste of French flair. Experience the laid-back barefoot lifestyle of the BVI boat owners.Sundowner offers views of palm trees, volcanoes, and the …
Cruise Details
0
White Sand Beach in Barbados
$4,495
EXPLORE

Pirate Islands, Sailors' Haunts and Dream Beaches

9 Day Itinerary aboard Sea Cloud II
  • Explore dream beaches
  • Swim and snorkel on clear waters
  • Enjoy the Caribbean's trade winds
  • Relax on holiday heaven St. Barths
Starts / Ends:
Philipsburg / Dominican Republic
Activities:
Scuba Diving, Small Ship Cruises, Small Ship Sailing, Snorkeling
Activity Level:
Relaxed
Join the Sea Cloud II on this fantastic nine-day cruise around the Caribbean. Exchange the winter blues for the pastels of the Caribbean, sailing into the sun along famous pirate routes. Visit Gustavia, located on the well-known St. Barths, a top holiday destination for the rich and famous from …
Cruise Details
0
Cuban musician playing the trumpet in Havana, Cuba
$9,995
EXPLORE

Experience Firsthand the Festive Days in Cuba

15 Day Itinerary aboard Sea Cloud II
  • Stroll down the Malecon
  • Snorkel and swim at Maria La Gorda
  • Visit banana farms in Jamaica
  • Marvel at historic Santo Domingo
  • Appreciate Cuban music culture
Starts / Ends:
Santo Domingo / Havana
Activities:
Archaeological Site Visits, Small Ship Cruises, Small Ship Sailing, Snorkeling
Activity Level:
Relaxed
Warm hospitality, eventful history, and lively musical tradition make Cuba and Jamaica two dream destinations in the Caribbean. As different as the two islands are, culture, beach, and nature go perfectly hand in hand and fit under one hat. Board Sea Cloud II for this 15-day cruise from Havana to …
Cruise Details
0
Boats Moored to the Quay at Bridgetown Harbour
$3,570
EXPLORE

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:
Bridgetown / Balboa
Activities:
Small Ship Cruises, Small Ship Sailing, 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
The sun sets off the Canary Islands
$14,245
EXPLORE

Dream of A Lifetime: Transatlantic Crossing

18 Day Itinerary aboard Sea Cloud
  • Follow Columbus's course
  • Sail across the Atlantic Ocean
  • Enjoy an offshore sailing adventure
  • Observe incredible sunsets
Activities:
Small Ship Cruises, Small Ship Sailing
Activity Level:
Relaxed
Follow the route Columbus took across the Atlantic as you set sail for new horizons on a voyage of discovery. Discover this 17-day pure sailing adventure where for two whole weeks, the expansive ocean is the home of Sea Cloud. Water currents and trade winds are all that propel the yacht forwards. …
Cruise Details
0
Stroll along the beautiful beaches of the Caribbean
$5,255
EXPLORE

The Sunny Side of the Lesser Antilles

Roundtrip St. Philipsburg - 10 Day Itinerary aboard Sea Cloud
  • Visit the port town of Philipsburg
  • Discover the stunning White Bay
  • Stroll around Terre-de-Haut
  • Experience St. Barthélemy
Starts / Ends:
Philipsburg / Philipsburg
Activities:
Small Ship Sailing, Snorkeling
Activity Level:
Relaxed
During this stunning 8-day voyage aboard Sea Cloud, fall in love with the region's sun, beach, and culture.Admire the Caribbean's vibrant, lively region of colorful scenery and friendly people. Delight yourself with deep volcanic lakes, dense rainforests, waterfalls, and small river courses …
Cruise Details
0
The stunning blue coastline of the Canary Islands
$2,410
EXPLORE

Transatlantic: Las Palmas to Barbados

16 Day Itinerary aboard Star Clipper
  • Visit Las Palmas, Gran Canaria
  • Take in the fresh ocean breeze
  • Explore San Sebastian, La Gomera
  • Relax on paradise beaches
Activities:
Small Ship Cruises, Small Ship Sailing
Activity Level:
Relaxed
Crossing the mighty Atlantic Ocean provides the time to truly appreciate the pure pleasure of the sea. Imagine sailing the Atlantic in the footsteps of legendary explorers, enjoying the Old World family charm and the wonders of the New World. Admire Gran Canaria's exotic vegetation and magical …
Cruise Details
0
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