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Anguilla Small Ship Cruises

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Anguilla
Snorkeling in the Caribbean with a starfish
Antigua
Lush green forests and clear blue waters of the Caribbean
Aruba
Relax on the shores of the Caribbean
Barbados
Take a leisurely stroll through beautiful Bridgetown
British Virgin Islands
Relax on the beaches of the Caribbean
Grenada
Snorkel the clear, tropical waters
Greater Antilles
Picturesque Cuba
Lesser Antilles
Wander the white-sand beaches of St. Johns on your Virgin Islands cruise
Dominica
Encounter tropical wildlife while you sail on the Aranui
Netherlands Antilles
Enjoy a blissful snorkeling trip.
Puerto Rico
Discover incredible history and culture in Puerto Rico
St. Barth
Play on the famously beautiful beaches of St. Barth's
St. Kitts
Stroll along the beautiful beaches of the Caribbean
St. Martin
Pelicans hanging out in the ocean
St. Vincent des Grenadines
Visit beautiful St. Vincent
Union Island
Uwe Moser
Bright blue waters of the Caribbean
British Virgin Islands
Relax on the beaches of the Caribbean
Virgin Islands
Relax on the beaches of the Caribbean
U.S. Virigin Islands
View gorgeous sunsets over the Virgin Islands
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Explore the long-time British territory and paradise in the Caribbean: Anguilla. Join Adventure Life for an exceptional cruise to Anguilla, any amount of Caribbean islands, or even combine your trip to Anguilla with a trip to Portugal! In Anguilla, you'll get tons of opportunities to relax, swim, snorkel, sail, or participate in a large variety of water sports. Visit Meads Bay, Rendezvous Bay, Sandy Ground, Prickly Pear Cays, Dune Preserve, or Shoal Bay East. If you're interested in a trip to Anguilla, contact Adventure Life's Caribbean travel experts now to begin planning a personalized trip!
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2 Best Anguilla Small Ship Cruises for 2024-2025

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Soak in the sun in colorful Marigot

Cruising the Leeward Islands

Marigot Roundtrip
8 Days from $10,270
Embark on an 8-day Cruising the Leeward Islands aboard Emerald Sakara from Marigot roundtrip. Explore Anguilla, Virgin Gorda, and other stunning destinations, immersing yourself in picturesque landscapes, vibrant cities, and unique natural wonders.
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Tropical waterfall and turquoise pool in lush forest

Treasure Islands

Philipsburg to Philipsburg
8 Days from $1,640
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!
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Best Small Ship Caribbean Cruises

2 Top-Rated Anguilla Small Cruise Ships for 2024-2025

Ship NameMax PassengersFromSummary
Star Flyer170$1640The Star Flyer is a stylish vessel designed to accommodate 170 passengers in an intimate and comfortable atmosphere. This true clipper ship reflects …
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Emerald Sakara100$10270Emerald Cruises brings our award-winning reputation and service to the world?s oceans and coastlines as we introduce Luxury yacht cruising on our …
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Top 1 Anguilla Small Ship Cruise Deals for 2024

Trip NameSaveFromDaysNext DepartureSummary
Treasure IslandsSavings$16408Dec 7, 2024Don'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 …
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Anguilla Travel Guide

Fresh produce at a market

Leeward Islands Cuisine

The varied cuisines that travelers enjoy while cruising the Leeward Islands reflect the diverse cultures from which they come, featuring a broad palate of seafood dishes drawing from local Caribbean and African, French, Dutch, British and Asian influences.
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Best Time to Visit Anguilla

Anguilla is a fantastic place to visit year round- outside of hurricane season which runs between June 1 - November 30.

Between December and April is usually considered the best time to visit Anguilla. This is the high tourism season so there will be large crowds and hotels will be more expensive when compared to other months but the weather is ideal and there's infrequent rain. Additionally, the island will be in full swing in terms of activities, restaurants, shopping, and service.

Between May and August is a good time to visit Anguilla. This is the off season going in to the beginning of the hurricane season so there may be a bit of rainfall but it won't be extreme and hurricanes are extremely unlikely to hit Anguilla during these beginning months of hurricane season. Additionally, the hotel prices will drop by as much as 50% and flight prices are likely to drop as well.

Between September and November is the worst time to visit Anguilla. You'll be able to find amazing hotel deals during this time - for good reason. It's possible that a hurricane will hit Anguilla during these months, many hotels and restaurants will be closed, and although the temperature is warm still there's a ton of rain that hits the island during these months.
Enjoy the natural beauty of the Caribbean

Leeward Islands Geography

Along with the Windward Islands, the small Leeward Islands form the Lesser Antilles on the eastern border of the Caribbean Sea. The geography of the Leeward Islands is comprised primarily by coral and volcanic islands. The soil on the coral islands is not well suited to agriculture, making these countries' primary economic engine tourism.
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Explore charming Charlotte Amalie

Leeward Islands Politics

The Leeward Islands, a geographical grouping with an essentially shared history, have developed over time into six separate nations. They have a common interest in tourism, and in economic and cultural advancement for their ethnically diverse but essentially harmonious populations.
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Stroll along the white sandy beaches of St. Barth's

Leeward Islands Weather

As long as you avoid the hurricane season during the latter half of the year, you'll enjoy pleasant tropical temperatures between 81°F and 95°F (27°C and 35°C) and bright sunny days that never seem to end.
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Best Anguilla Small Ship Cruise Lines for 2024-2025
 
  • Ponant - founded in 1988, has established the standard for a new era of luxury cruises. Le Champlain cruises to Anguilla's beautiful sandy beaches, creeks, caves, prehistoric petroglyphs, former colonial mansions, natural reserves, and Greg Norman's famous golf course. Golf enthusiasts can tee off in breathtaking Caribbean golf cruises to Cuisinart Golf Club Anguilla.
  • Star Clippers Americas - For more than three decades, the recognized expert in sailing cruises has shared a lifelong passion for the sea with thousands of passengers from all over the world. Its tall ship, the Star Flyer, anchors off Anguilla's most beautiful sandy beaches, accentuating the turquoise waters of the Caribbean.


 
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Anguilla Tour Ideas

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Tropical waterfall and turquoise pool in lush forest

Treasure Islands

Philipsburg to Philipsburg
8 Days from $1,640
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!
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Anguilla FAQ Section

Is Anguilla safe for tourists?
Like many British territories, Anguilla is extremely safe for tourists, it's one of the safest islands in the Caribbean.

How do I get to Anguilla?
Flights can be expensive but they're relatively easy to find with light research. The other option is to contact Adventure Life's travel experts and we'll help you either find an inexpensive flight or assist you in finding an Adventure Life cruise that goes from your destination to Anguilla.

What is Anguilla known for?
Anguilla is known for it's pristine beaches, important coral reefs, and variety of water sports.

Do I need a visa, vaccinations, or a passport for Anguilla?
You do not need any vaccinations for Anguilla but you will need a passport and may have to prove when your departure from Anguilla will be. There are also no visa requirements other than to prove when your departure will be.

What language do they speak in Anguilla?
Being a British territory, they speak UK English with a Caribbean twist. The other language many people from Anguilla speak is Creole. 

Is Anguilla a tax haven?
For many wealthy British citizens Anguilla is used as a tax haven because they don't have income tax, property taxes, or capital gain taxes.

Should I purchase travel insurance for my visit to Anguilla?
You should definitely purchase travel insurance, especially if you plan on traveling during the off-season/hurricane season. Adventure Life makes it easy through our partner, TravelGuard, on our Once You've Booked page.
TrustScore 4.8 | 208 reviews
TrustScore 4.8 of 5
total score
Based on 208 reviews on
review score
6 hours ago
They answered every question and concern that I had and put me at ease. Very excited for this once in a life-time trip.
Customer Tim
review score
1 day ago
I am a returning client to Adventure Life and am very pleased with their commitment to put together a great trip. Clara replied and clarified to any and all questions we had.
Claire Palmer
review score
3 days ago
Jessica was very responsive to my questions and never balked when I asked her to go back and find more options. She really worked hard to find the right cruise for us.
Amy Siegel
review score
3 days ago
Friendly, accommodating, knowledgeable, timely. They have made us feel very comfortable for our trip!
Gregg Chamberlain
review score
3 days ago
Adventure Life took care of a lot of details for me because I flew separately and met up with the group at the start of the trip. On the return they dropped me off in Cantania and flew back to the UK as one group. I was the only American on the Exodus trip which was not a problem. Communication between the two companies was good.
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