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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!
All Anguilla Small Ship Cruises

10 Best Anguilla Small Ship Cruises for 2026-2027

All Anguilla Small Ship Cruises
Soak in the sun in colorful Marigot

Cruising the Leeward Islands

8 Days from $11,070
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.
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Gustavia Harbor in St. Barths

Cruising the Leeward Islands

8 Days from $9,990
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.
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Boats Moored to the Quay at Bridgetown Harbour

Discover the Pearls of the Caribbean

15 Days from $15,980
Embark on a 15-day Caribbean cruise aboard Emerald Azzurra, exploring stunning coral reefs, granite pools, and picturesque landscapes across destinations like Anguilla and Virgin Gorda. Enjoy snorkeling, hiking, and vibrant local culture while visiting Saint Barthelemy and the British Virgin Islands.
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Explore the famous rock formations of the baths

Discover the Pearls of the Caribbean

15 Days from $21,780
Embark on a 15-day cruise aboard Emerald Azzurra from Barbados to Marigot, visiting highlights like Nelson’s Dockyard and the beaches of Iles des Saintes. Discover serene islands, snorkel vibrant reefs, and enjoy cultural experiences across the enchanting Caribbean.
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Relax on the sunny beaches of the Caribbean

Eastern Caribbean with St. Barths

8 Days from $9,990
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.
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Explore colorful Gustavia

Eastern Caribbean with St. Barths

8 Days from $7,990
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.
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Tropical waterfall and turquoise pool in lush forest of Dominica

Treasure Islands

8 Days from $1,970
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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Visit beautiful Norman Island

Vibes of the Virgin Islands

8 Days from $9,990
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.
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Relax on the white sandy beaches of the Caribbean

Treasure Islands

8 Days from $2,210
Set sail on an 8-day Caribbean cruise aboard the Star Flyer, starting and ending in Philipsburg, St. Maarten. Explore scenic spots like St. Barts, Jost Van Dyke, Virgin Gorda, and Anguilla, blending natural beauty and rich history.
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Explore beautiful Jost van Dyke

Antigua Roundtrip

8 Days from $2,010
Set sail on an 8-day round-trip cruise from St. John’s, Antigua, aboard the Star Clipper, exploring St. Barts, the British Virgin Islands, and Anguilla. Highlights include duty-free shopping, scenic hikes, and beautiful beaches before concluding in Antigua.
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All Anguilla Cruises & Tours

8 Top Anguilla Cruises & Tours for 2026-2027

All Anguilla Cruises & Tours
Umbrellas and sunbeds lined up along the White Bay Beach of Jost Van Dyke, British Virgin Islands

Treasure Islands

8 Days from $2,010
Embark on an 8-day Caribbean cruise aboard the Star Flyer, starting and ending in Philipsburg, St. Maarten. Visit Anguilla's beaches, explore the British Virgin Islands, hike Jost Van Dyke, and enjoy shopping in St. Barts while uncovering historical sites and natural beauty.
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Sunset over Philipsburg

Treasure Islands

8 Days from $2,010
Join an 8-day Caribbean cruise on the Star Flyer, starting and ending in Philipsburg, St. Maarten. Explore stunning beaches, historic sites, and vibrant islands like Anguilla, Tortola, Virgin Gorda, and St. Barts.
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Visit beautiful Norman Island

Treasure Islands

8 Days from $2,010
Embark on an 8-day roundtrip Caribbean cruise from Philipsburg, St. Maarten, aboard the Star Flyer, visiting beautiful locations like Anguilla, Tortola, and Virgin Gorda. Enjoy duty-free shopping in St. Barts and explore the colonial history of St. Kitts before returning to St. Maarten.
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Caribbean landscapes and harbors

Caribbean Sojourn

7 Days from $11,990
Embark on a 7-day Caribbean adventure aboard the Emerald Azzurra. Set sail from Barbados and explore diverse islands including Soufriere’s mud baths, Falmouth Harbor’s historic dockyard, Iles des Saintes’ picturesque beaches, Gustavia’s vibrant streets, and Marigot’s charming French town.
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Variety of boats and yachts on of Bequia's harbors in the Grenadines.

Discover Eastern Caribbean & Grenadines

15 Days from $22,140
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.
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Visit beautiful St. Vincent

Discover Eastern Caribbean & Grenadines

15 Days from $15,980
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.
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Experience laid-back Marigot

Discover Eastern Caribbean & Grenadines

15 Days from $15,980
Set sail on a 15-day Caribbean journey, where pristine beaches, vibrant coral reefs, and island-hopping adventures immerse you in diverse cultures. Experience the genuine warmth of local hospitality as you explore tropical paradises aboard the Emerald Azzurra.
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Learn about the history of the Caribbean

Eastern Caribbean with St. Barths

8 Days from $9,990
Set sail on an 8-day cruise aboard the Emerald Azzura, island-hopping through vibrant cultures and breathtaking landscapes. Discover pristine beaches, vivid coral reefs, and the genuine warmth of locals while enjoying the elegance of a luxury yacht experience.
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All Anguilla Luxury Small Ship Cruises

1 Best Anguilla Luxury Small Ship Cruises for 2026-2027

Trip Name From Days Summary
Eastern Caribbean with St. Barths $7,990 8 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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Best Small Ship Caribbean Cruises

4 Top-Rated Anguilla Small Cruise Ships for 2026-2027

Ship Name Max Passengers From Summary
Star Clipper 170 $1,000 Star Clipper is a 170-passenger vessel designed to provide a unique traveling experience unlike any other cruise vacation. Step aboard and discover a new age of sailing, where the traditions of the past are happily married to the comforts and amenities of the present day.
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Star Flyer 170 $1,710 The Star Flyer is a stylish vessel designed to accommodate 170 passengers in an intimate and comfortable atmosphere. This true clipper ship reflects its proud heritage in every inch of its polished brass and gleaming brightwork. The décor of Star Flyer is reminiscent of the grand age of sail with spacious accommodations and expansive teak decks.
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Emerald Azzurra 100 $8,390 As Emerald's first-ever ocean superyacht, the luxurious Emerald Azzurra is designed to take up to 100 passengers sailing along the Adriatic Coast, Red Sea, and the Eastern and Western Mediterranean.
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Emerald Sakara 100 $7,590 Emerald Cruises brings our award-winning reputation and service to the world's oceans and coastlines as we introduce Luxury yacht cruising on our brand new, innovative superyachts, custom-designed to allow unique access to the fascinating ports and harbors only small yachts can reach.
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All Anguilla Small Ship Cruise & Tour Deals

Top 3 Anguilla Small Ship Cruise Deals for 2026

Trip Name From Days Summary
Treasure Islands $1,970 8 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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Antigua Roundtrip $2,010 8 Set sail on an 8-day round-trip cruise from St. John’s, Antigua, aboard the Star Clipper, exploring St. Barts, the British Virgin Islands, and Anguilla. Highlights include duty-free shopping, scenic hikes, and beautiful beaches before concluding in Antigua.
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Treasure Islands $2,010 8 Join an 8-day Caribbean cruise on the Star Flyer, starting and ending in Philipsburg, St. Maarten. Explore stunning beaches, historic sites, and vibrant islands like Anguilla, Tortola, Virgin Gorda, and St. Barts.
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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

The Leeward Islands in the northeastern Caribbean are a year-round destination. December to April offers sunny weather and festivals, while May to November brings fewer tourists and lower costs. Explore these islands on small cruise ships Caribbean journeys for the best mix of culture, beaches, and local charm.
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Best Anguilla Small Ship Cruise Lines for 2026-2027
 

  • Emerald Cruises - founded in 2013 as Emerald Waterways, is an award-winning travel operator offering deluxe river cruises and luxury yacht voyages. Aboard Emerald Azzurra and Emerald Sakara, explore Anguilla’s pristine coral reefs, white-sand beaches, and natural beauty in the heart of the Caribbean.
  • 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.



 

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.

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