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Anguilla Small Ship Cruises

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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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10 Best Anguilla Small Ship Cruises for 2025-2026

All Anguilla Small Ship Cruises
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4 Top Anguilla Cruises & Tours for 2025-2026

Best Small Ship Caribbean Cruises

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

Ship Name Max Passengers From Summary
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 $7,990 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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Top 10 Anguilla Small Ship Cruise Deals for 2026

Trip Name From Days Summary
Eastern Caribbean with St. Barths $9,990 8 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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Cruising the Leeward Islands $10,990 8 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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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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Vibes of the Virgin Islands $9,990 8 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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Cruising the Leeward Islands $9,990 8 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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Caribbean Sojourn $11,990 7 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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Eastern Caribbean with St. Barths $9,990 8 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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Eastern Caribbean with St. Barths $7,990 8 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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Discover Eastern Caribbean & Grenadines $15,980 15 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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Discover Eastern Caribbean & Grenadines $21,340 15 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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Anguilla Travel Guide

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.

Best Anguilla Small Ship Cruise Lines for 2025-2026
 

  • 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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