Have questions? We're here.

Anguilla Small Ship Cruises

Travel made your way ™
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
Talk with an expert
Build your ideal Caribbean trip. Call 1.406.541.2677
Start Planning My Trip
Talk with an expert
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!
All Anguilla Small Ship Cruises

8 Best Anguilla Small Ship Cruises for 2025-2026

All Anguilla Small Ship Cruises
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.
0
Gustavia Harbor in St. Barths

Cruising the Leeward Islands

Marigot Roundtrip
8 Days from $7,590
Set sail on an 8-day Caribbean cruise with Emerald Azzurra. Start in Marigot, then visit Anguilla’s coral beaches, Virgin Gorda’s Baths, Jost Van Dyke’s Bubbly Pool, and Anegada’s sandy shores. Explore Saba’s trails and Bonaire’s marine life before ending in Gustavia. Enjoy a luxury cruise with varied landscapes and activities.
0
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!
0
Relax on the sunny beaches of the Caribbean

Eastern Caribbean with St. Barths

Bridgetown - Marigot
8 Days from $7,590
Set sail on an 8-day cruise aboard the Emerald Azzurra, exploring idyllic beaches and vibrant coral reefs—Island-hop through diverse cultures, with the warmth of the locals adding to your luxurious yacht experience.
0
Relax on the sunny beaches of the Caribbean

Eastern Caribbean with St. Barths

Marigot - Bridgetown
8 Days from $10,270
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 Harbour’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
0
Visit beautiful Norman Island

Vibes of the Virgin Islands

St Thomas Roundtrip
8 Days from $7,590
Set sail on an 8-day Caribbean cruise aboard Emerald Sakara from Saint Thomas to discover the Caribbean’s finest destinations. Explore the stunning beaches of Virgin Gorda, snorkel in Norman Island’s clear waters, and experience Anguilla’s vibrant beauty. Philipsburg’s lively port, Gustavia’s charming streets, and tranquil Saint John Island round out this cruise.
0
Panorama of Les Saintes

Caribbean Sojourn

Bridgetown - Marigot
7 Days from $7,190
Embark on a 7-day Caribbean adventure aboard the Emerald Azzurra. Set sail from Barbados and explore diverse islands including Soufrière’s mud baths, Falmouth Harbour’s historic dockyard, Îles des Saintes’ picturesque beaches, Gustavia’s vibrant streets, and Marigot’s charming French town.
0
Explore colorful Gustavia

Caribbean Enchantment

St. John's to Marigot
7 Days from $6,340
Embark on a 7-day Caribbean cruise aboard Emerald Azzurra. Start in Antigua and sail to Les Saintes, Deshaies, Virgin Gorda, and Norman Island. Explore historic sites like Fort Napoleon, snorkel in vibrant coral reefs, and relax on stunning beaches. Conclude your voyage in Marigot, Saint Martin.
0
All Anguilla Luxury Small Ship Cruises

3 Best Anguilla Luxury Small Ship Cruises for 2025-2026

Trip NameFromDaysNext DepartureSummary
Eastern Caribbean with St. Barths$102708Dec 21, 2024Embark on an 8-day Caribbean cruise aboard Emerald Sakara. Discover Anguilla’s pristine beaches, Gustavia’s vibrant streets, Nevis' historic …
0
Vibes of the Virgin Islands$75908Dec 13, 2026Set sail on an 8-day Caribbean cruise aboard Emerald Sakara from Saint Thomas to discover the Caribbean’s finest destinations. Explore the stunning …
0
Caribbean Enchantment$63407Feb 22, 2025Embark on a 7-day Caribbean cruise aboard Emerald Azzurra. Start in Antigua and sail to Les Saintes, Deshaies, Virgin Gorda, and Norman Island. …
0
Best Small Ship Caribbean Cruises

3 Top-Rated Anguilla Small Cruise Ships for 2025-2026

Ship NameMax PassengersFromSummary
Emerald Azzurra100$6340As Emerald's first-ever ocean superyacht, the luxurious Emerald Azzurra is designed to take up to 100 passengers sailing along the Adriatic Coast, …
0
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 …
0
Emerald Sakara100$7590Emerald Cruises brings our award-winning reputation and service to the world?s oceans and coastlines as we introduce Luxury yacht cruising on our …
0
All Anguilla Articles

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.
0
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.
0
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.
0
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.
0
Best Anguilla Small Ship Cruise Lines for 2025-2026
 
  • 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.


 
All Anguilla Tours

Anguilla Tour Ideas

All Anguilla Tours
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!
0

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 | 382 reviews
TrustScore 4.8 of 5
total score
Based on 382 reviews on
review score
7 hours ago
The booking was processed efficiently and quickly. We got what we wanted.
Doug Laporte
review score
8 hours ago
Great company. Good communications. Great accommodations, excursions, transport. Guide Elvira was spectacular along with transport, driver, Cesar and activities
Kathy S
review score
1 day ago
Very responsive to questions. Helpful with all arrangements
Roz
review score
2 days ago
The ship company they sent us on was perfect in every detail
lisa wegener
review score
3 days ago
I’m so glad we found AdventureLife. Jess, our planner, was such a pleasure to work with. She readily shared her extensive knowledge about Panama, she offered good suggestions and creative ideas, kept everything organized and handled the details each step of the way.
Tim King

Caribbean Travel Guide

Favorite Caribbean Caribbean All Trips

Top Caribbean Travel Destinations

Caribbean Trips by Departure Date

Top Experiences in Caribbean

Caribbean Trips by Duration

Caribbean Trips by Activity

More Reasons

Why Travel With Adventure Life

All News

Recognized By

Eric Niskanen Adventure Life employee profile
Eric N
Plan My Trip
We love travel, talk with an expert 1.800.344.6118