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Top Leeward Islands Cruises & Tours in 2022

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Take a cruise to Leeward Islands in 2022 on one of our hand-selected small ships exploring the best of Philipsburg, Gustavia, Les Saintes, Fort de France, and Terre-de-Haut. The most popular activities and experiences on small ship cruises to Leeward Islands in 2022 are small ship cruises, snorkeling, small ship sailing, scuba diving, and wildlife viewing. Explore Leeward Islands's hot spots during the day and sail port-to-port on your comfortable small ship without repacking your suitcase. Savvy travelers know that small ship cruises offer an excellent balance of fewer crowds and access to small port towns, harbors, and coves that large cruise ships simply can't visit. Our cruises to Leeward Islands in 2022 range in price from $2,330 to $22,560 for expeditions of 8 to 25 days. Contact one of Adventure Life's expert Leeward Islands trip planners for help planning a seamless cruise to Leeward Islands in 2022.
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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
Pink beach huts in the Caribbean
$2,420
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
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
0
Tropical waterfall and turquoise pool in lush forest
$2,360
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
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
Beautiful beach in Dominica
$2,360
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
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
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
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Caribbean
$4,860
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
Tropical Caribbean Beach in Martinique
$2,420
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 in:
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
White Sand Beach in Barbados
$2,420
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
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Dock going out into the crystal blue ocean
$2,420
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 in:
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:
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
0
Unspoiled beaches and pristine coves in the Caribbean
$10,710
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
0
Gatun Lock of the Panama Canal
$4,300
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
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St George's Harbor - Grenada
$3,620
EXPLORE

Pearls of the Caribbean

Bridgetown Rountrip - 9 Day Itinerary aboard Le Dumont-d'Urville
  • See UNESCO World Heritage Sites
  • Visit the Grenadine Islands
  • Experience long white-sand beaches
  • Enjoy the beach on Mayreau Island
Starts/ Ends in:
Bridgetown / Bridgetown
Activities:
Scuba Diving, Small Ship Cruise, Snorkeling
Activity Level:
Relaxed
Discover a true picture-postcard of the West Indies: long white-sand beaches, colorful seabeds, and the easy Creole way of life. Board Le Dumont-d’Urville inBarbadosat the port ofBridgetown, whose UNESCO-listed historical center shows the extent of the British colonial presence, and head for …
Cruise Details
0
Colorful harbor of Bonaire
$9,615
EXPLORE

Philipsburg to Puntarenas

16 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 in:
Philipsburg / Quepos
Activities:
Sailing Schooner, Small Ship Cruise, Snorkeling, Village Visit
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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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 in:
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
0
Mountains by the ocean in St 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 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
0
Explore the beautiful Canary Islands
$3,940
EXPLORE

Transatlantic:Malaga to St.Maarten

25 Day Itinerary aboard Star Flyer
  • Admire Malaga's landmarks
  • Enjoy the expansive Atlantic Ocean
  • Cruise across the Caribbean
  • Set sail from St. Maarten
Starts/ Ends in:
Malaga / Philipsburg
Activities:
Sailing Schooner, Small Ship Cruise
Activity Level:
Relaxed
Cross the pond in style and spend your days relaxing onboard, take in the scenery, and choose an itinerary that stops off at ports you never dreamed of visiting before. Enjoy a full offshore sailing experience, from the Old to the New World. The scent of adventure still hangs in the air and much …
Cruise Details
0
Visit vibrant Las Palmas
$2,330
EXPLORE

Westbound Atlantic Ocean

Las Palmas - St. Maarten - 16 Day Itinerary aboard Star Flyer
  • Explore Caldera de Bandama
  • Visit Las Palmas
  • Enjoy La Gomera
  • Experience Garajonay National Park
Starts/ Ends in:
Las Palmas / Philipsburg
Activities:
Small Ship Cruise
Activity Level:
Relaxed
Set a course for the Atlantic Ocean.For those who value traveling in style and comfort, for romantic souls who want to experience the style and grace of the "good old days" but with all the modern conveniences, and for those who simply want to escape from the ordinary routine, nothing …
Cruise Details
0
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