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Top Anguilla Trips & Tours in December 2025

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Discover Anguilla in December 2025 on one of these 6 tours hand-selected by the travel experts at Adventure Life. Explore the best of during December 2025 as you enjoy Archaeological Site Visits, Snorkeling, Village Visits, Local Market Visits, and Kayaking. Prices for trips in December 2025 range from $1,970 to $62,480 for a vacation of 8 to 15 days. Choose any of the below 6 itineraries in December 2025 and customize it when you contact one of Adventure Life's expert Anguilla trip planners.
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    • Anguilla
Soak in the sun in colorful Marigot
from $10,990
OBC
EXPLORE

Cruising the Leeward Islands

Marigot Roundtrip - 8 Day Itinerary aboard Emerald Sakara
  • Explore Virgin Gorda’s iconic Baths
  • Swim Norman Island coves
  • Unwind Jost van Dyke beach
  • Stroll Anegada’s quiet beaches
Starts / Ends
Marigot / Marigot
Activity Level
Variable
Set sail on an 8-day cruise from Marigot, Saint Martin, aboard the Emerald Sakara, visiting stunning destinations like Anguilla and Virgin Gorda. Enjoy snorkeling, exploring grottoes, and embracing the relaxed island lifestyle amidst breathtaking coastal views.
Cruise Details
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Explore colorful Gustavia
from $10,670
OBC
EXPLORE

Eastern Caribbean with St. Barths

Bridgetown - Marigot - 8 Day Itinerary aboard Emerald Sakara
  • Explore Soufriere coral reefs
  • Visit Iles des Saintes towns
  • Discover Falmouth Harbor dockyard
  • Experience Charlestown’s Nevis
Starts / Ends
Bridgetown / Marigot
Activity Level
Variable
Set sail on an 8-day cruise aboard the Emerald Sakara, exploring idyllic beaches and vibrant coral reefs—Island-hop through diverse cultures, with the warmth of the locals adding to your luxurious yacht experience.
Cruise Details
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Tropical waterfall and turquoise pool in lush forest of Dominica
from $1,970
EXPLORE

Treasure Islands

St. Maarten Roundtrip - 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 Sailing
Activity Level
Variable
Don't miss the opportunity to relax on one of the beaches and enjoy the tropical sun's warmth. Soak up the sun in one of the world's most gorgeous locations, the Caribbean. Visit St. Maarten, Anguilla, Jost Van Dyke, St. Kitts, and St. Barts on this 8-day small ship trip!
Cruise Details
0
Variety of boats and yachts on of Bequia's harbors in the Grenadines.
from $22,140
OBC
EXPLORE

Discover Eastern Caribbean & Grenadines

Marigot - Bridgetown - 15 Day Itinerary aboard Emerald Sakara
  • Explore Anguilla’s turquoise waters
  • Stroll through Gustavia
  • Admire Nevis’ tranquil shores
  • Visit Antigua’s Falmouth Bay
Starts / Ends
Marigot / Bridgetown
Activity Level
Variable
Set sail on a 15-day cruise to explore unspoiled beaches, vibrant coral reefs, and captivating island cultures. Experience the genuine warmth of the locals as you hop between tropical paradises, creating unforgettable memories aboard the Emerald Sakara.
Cruise Details
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Visit beautiful St. Vincent
from $21,340
OBC
EXPLORE

Discover Eastern Caribbean & Grenadines

Bridgetown - Marigot - 15 Day Itinerary aboard Emerald Sakara
  • Explore Bridgetown’s capital
  • Wander Speightstown’s streets
  • Discover Kingstown’s gardens
  • Unwind on Bequia Island
Starts / Ends
Bridgetown / Marigot
Activities
Snorkeling, Local Market Visits, Village Visits, Archaeological Site Visits, Kayaking
Activity Level
Variable
Set sail on a 15-day cruise to explore unspoiled beaches, vibrant coral reefs, and captivating island cultures. Experience the genuine warmth of the locals as you hop between tropical paradises, creating unforgettable memories aboard the Emerald Sakara.
Cruise Details
0
Relax on the beaches of the Caribbean
from $7,990
OBC
EXPLORE

Eastern Caribbean with St. Barths

Marigot - Bridgetown - 8 Day Itinerary aboard Emerald Sakara
  • Discover Anguilla’s coral coast
  • Explore Gustavia’s boutiques
  • Wander Nevis seaside buildings
  • Visit Antigua’s English Harbor
Starts / Ends
Marigot / Bridgetown
Activity Level
Variable
Embark on an 8-day Caribbean cruise aboard Emerald Sakara. Discover Anguilla’s pristine beaches, Gustavia’s vibrant streets, Nevis' historic charm, Saint Kitts’ stunning nature, Falmouth Harbor’s historical docks, Îles des Saintes’ picturesque islands, and Barbados’ lively culture. Experience crystal-clear waters, vibrant local culture, and luxurious amenities throughout your cruise
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