Have questions? We're here.
Relax on the beaches of the Caribbean

Top Leeward Islands Trips & Tours in December 2022

Travel made your way
Talk with an expert
Build your ideal Caribbean trip. Call 1.406.541.2677
Start Planning My Trip
Discover Leeward Islands in December 2022 on one of these 12 tours hand-selected by the travel experts at Adventure Life. Explore the best of Terre-de-Haut, Gustavia, Virgin Gorda, Philipsburg, and Fort de France during December 2022 as you enjoy cruises, small ship cruises, snorkeling, beaches, and small ship sailing. Prices for trips in December 2022 range from $1,560 to $21,395 for a vacation of 8 to 17 days. Choose any of the below 12 amazing itineraries in December 2022 and customize it to make it your own with the help of one of Adventure Life's expert Leeward Islands trip planners.
Filter (12 Results)
  • Start Date
    OR, More specific start
  • Length
    to
  • Price
    to
  • Activity Level
  • Experiences
  • Activities
  • Ship
  • Destinations
    • Leeward Islands
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
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 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
Relax on the beaches of the Caribbean
$8,430
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
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
White Sand Beach in Barbados
$1,620
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:
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
0
Dock going out into the crystal blue ocean
$1,660
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
Stroll along the white sandy beaches of St. Barth's
$10,185
EXPLORE

Relaxed Festive Days Under Palms

Round-trip Philipsburg - 17 Day Itinerary aboard Sea Cloud
  • See St Barths' luxurious lifestyle
  • Visit beautiful islands
  • Discover volcanoes
  • Observe incredible sunsets
Starts / Ends:
Philipsburg / Philipsburg
Activities:
Small Ship Cruises, 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
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
Clear water in the bay
$7,040
EXPLORE

The Essential of the Caribbean

13 Day Itinerary aboard Le Dumont-d'Urville
  • Cruise in West Indies
  • Visit heritage sites
  • Discover British Virgin Islands
  • Explore Dominica
Starts / Ends:
Fort de France / Fort de France
Activities:
Small Ship Cruises, Snorkeling
Activity Level:
Relaxed
Sail the idyllic waters of theCaribbean Seato discover stunning islands, as well as historical and architectural landmarks. Visit St.Kitts, a volcanic island with sandy beaches and a colonial past. Stop at Anguilla before reaching the British Virgin Islands, which offer gorgeous landscapes. …
Cruise Details
0
Tropical Caribbean Beach in Martinique
$3,840
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
0
1-12 of 12 Results

Caribbean Travel Guide

Favorite Caribbean All Trips

Top Leeward Islands Travel Destinations

Leeward Islands Trips by Departure Date

Top Experiences in Leeward Islands

Leeward Islands Trips by Duration

Leeward Islands Trips by Activity

More Reasons

Why Travel With Adventure Life

All News

Recognized By