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Windward Islands Beach Trips

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Choose from one of these hand-picked trips visiting the best Windward Islands beaches. Relax in the sun and sand, or enjoy beaches, cruises, snorkeling, small ship cruises, and small ship sailing as you explore Soufriere, Bequia, Bridgetown, Tobago Cays, and St. Georges. Contact one of Adventure Life's Windward Islands experts for help planning your next beach escape!
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White Sand Beach in Barbados
$1,620
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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:
Bridgetown / Bridgetown
Activities:
Small Ship Cruises, 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
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Dock going out into the crystal blue ocean
$1,620
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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
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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
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Mountains by the ocean in St Lucia
$3,840
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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:
Fort de France / Fort de France
Activities:
Scuba Diving, Small Ship Cruises, 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
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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
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Take in the sights, sounds, and colors of Barbados
$4,930
EXPLORE

Cruising the Caribbean's Windward Islands – with Smithsonian Journeys

Vieux Fort - Bridgetown - 9 Day Itinerary aboard Le Dumont-d'Urville
  • Visit UNESCO World Heritage sites
  • Discover archipelagos of Caribbean
  • Explore landscapes of Indian river
  • See Mayreau's fishes and corals
Starts / Ends:
St. Lucia / Bridgetown
Activities:
Hiking, Land & Sea Exploration, Scuba Diving, Small Ship Cruises, Snorkeling
Activity Level:
Relaxed
Call at Dominica's Portsmouth Island, which will enchant you with its pristine mountain sceneries and give you a sight of the island's fascinating flora and animals. Continue north to Les Saintes, a little archipelago off the coast of Guadeloupe that is a favorite anchorage spot with …
Cruise Details
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Tropical Caribbean Beach in Martinique
$3,620
EXPLORE

Treasured Islands & Reefs of the Western Caribbean

Fort de France-Fort de France - 9 Day Itinerary aboard Le Dumont-d'Urville
  • Swim in crystal clear waters
  • Explore the Grenadine Islands
  • Observe exceptional seabed
  • Tour Saint Lucia, a UNESCO Site
Starts / Ends:
Fort de France / Fort de France
Activities:
Hiking, Kayaking, Small Ship Cruises, Urban Exploration, Wildlife Viewing
Activity Level:
Relaxed
The easy-going Creole way of life and vast white-sand beaches await you on this 9-day Western Caribbean cruise. Sail from Fort-de-France, the capital of Martinique, to Saint Vincent and the Grenadines to Bequia Island, the "whale-hunting island," as well as its wild and pristine …
Cruise Details
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Mountains by the ocean in St Lucia
$4,755
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On the Sunny Side of Life

Philipsburg Roundtrip - 8 Day Itinerary aboard Sea Cloud
  • Visit the port town of Philipsburg
  • Experience St. Barthélemy
  • Explore the town of Terre-de-Haut
  • Tour around Dominica
Starts / Ends:
Philipsburg / Philipsburg
Activities:
Small Ship Cruises, Snorkeling
Activity Level:
Relaxed
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 hang in the air wherever you go. Admire the Caribbean's …
Cruise Details
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Enjoy the clear blue waters of the Canary Islands
$4,060
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Ocean Crossing

Malaga-Barbados - 25 Day Itinerary aboard Star Clipper
  • Visit Malaga
  • Explore Casablanca
  • Discover Canary Islands
  • Enjoy Santa Cruz
Starts / Ends:
Malaga / Bridgetown
Activities:
Small Ship Cruises
Activity Level:
Relaxed
Experience the uninhibited thrill of traversing a boundless ocean under sail, without any skills or effort required on your part. Imagine long lazy days at sea chasing the horizon, relaxing under a blanket of stars, and taking in the ocean's salty fragrance. Embarking in the city of Malaga, …
Cruise Details
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Play on the famously beautiful beaches of St. Barth's
$8,195
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Enjoy Caribbean Rhythms at the Turn of the Year

Caribbean: Round-trip Philipsb - 16 Day Itinerary aboard Sea Cloud
  • Snorkel the famed Virgin Gorda
  • See luxurious St. Barthelemy
  • Explore the culture of Grenada
  • Admire beautiful St. Lucia
Starts / Ends:
Philipsburg / Philipsburg
Activities:
Small Ship Cruises, Snorkeling
Activity Level:
Relaxed
Explore the best of the Caribbean on this round-trip cruise from Philipsburg aboard the Sea Cloud sailing ship. From the charming Dutch Colonial port town of Philipsburg, make your way to the British Virgin Islands. Snorkel the famed baths, or simply relax on the white sandy beaches before sailing …
Cruise Details
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Stroll along the beautiful beaches of the Caribbean
$6,785
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Windjammer Rendezvous in the Lesser Antilles

Philipsburg Roundtrip - 12 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 8-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
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
Gatun Lock of the Panama Canal
$3,500
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
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
Colorful harbor of Bonaire
$10,895
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
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Relax on the beaches of the Caribbean
$6,180
EXPLORE

Christmas and New Year in the Caribbean

Fort-de-France - Santo Domingo - 13 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:
Fort de France / Santo Domingo
Activities:
Small Ship Cruises, Snorkeling
Activity Level:
Relaxed
Board the luxurious Le Dumont-d'Urville to celebrate Christmas and ring in the New Year with this 13-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
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Take a leisurely stroll through beautiful Bridgetown
$4,900
EXPLORE

San Juan to Bridgetown

10 Day Itinerary aboard Silver Dawn
  • Head up to Gustavia Lighthouse
  • Visit St. Barts
  • Sail through Fort-de-France
  • Marvel around Bequia
Starts / Ends:
San Juan / Bridgetown
Activities:
Biking, Hiking, Kayaking, Scuba Diving, Small Ship Cruises, Snorkeling
Activity Level:
Relaxed
This 10-day Caribbean cruise is designed to showcase the Caribbean's vibrant sightseeing, delicious cuisine, and vibrant nightlife. Explore the sapphire waters of San Juan, a beach-blessed star of these turquoise waters, with huge fortresses, airy plazas, and absolute Caribbean splendour. No …
Cruise Details
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Enjoy the beautiful blue Caribbean
$3,840
EXPLORE

In the heart of the West Indies : Bridgetown - Vieux Fort

9 Day Itinerary aboard Le Dumont-d'Urville
  • Visit Barbados and St. Lucia
  • Tour Saint Vincent & the Grenadine
  • Discover long white-sand beaches
  • Enjoy the beach on Mayreau Island
Starts / Ends:
Les Saintes / Bridgetown
Activities:
Scuba Diving, Small Ship Cruises, Snorkeling
Activity Level:
Relaxed
This 9-day trip on Le Dumont-d'Urville combines extensive white-sand beaches with comfortable Creole living. After boarding in Bridgetown, Barbados, your cruise anchors in the Tobago Cays National Park. Amazing underwater species can be found in this rosary of islands connected by the West …
Cruise Details
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