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Cruises to Anguilla

Anguilla (Photo: Kristopher Kettner/Shutterstock)

About Anguilla

A spindly spoke in the archipelago surrounding St. Maarten/St. Martin, Anguilla is a beach-lover's dream. Mile after mile of loamy, cream-white sand fringes this supine island, with tony resorts and high-end restaurants dotting the coastline. A relative newcomer on the cruise circuit, Anguilla is a terrific destination for beach- and resort-focused travelers, but cruise visitors looking for shopping, ziplines and jeep excursions might be left wanting.

If it all sounds a bit like nearby St. Barts, that's because Anguilla sparked to life in the years following the French island's emergence on the celebrity scene. They share a notable trait: Both islands are rocky and were unsuited for farming, which made for a hardscrabble existence, mostly devoid of the plantations that cropped up through most of the region. Like the British Virgin Islands, Anguilla remains a British overseas territory, but it probably owes a bit of its success to that Gallic neighbor, which provided inspiration for what a polished, swank beach destination could be. Because Anguilla took shape well after the initial arrival of tourists to the region, it escaped the mass development that coursed through most of the Caribbean in the 1960s and after.

Anguilla is a tender port and, for now, attracts only smaller ships (under 500 passengers). The island covers just 35 square miles but the population is less than 15,000, so you won't find yourself following in the footsteps of a bazillion other cruise visitors, much less fighting for your own patch of sand with the easygoing, exceedingly friendly Anguillians.


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  • 7 Night
    Cruise to Anguilla

    Leaving:
    St. Thomas
    Visiting:
    Virgin Gorda, Jost Van Dyke ... see more
    Cruise Line:
    SeaDream Yacht Club
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    Itinerary

    Cruise Itinerary

    7 Night Cruise to Anguilla Route (SeaDream Yacht Club)
    • Day 1
      St. Thomas
    • Day 2
      Virgin Gorda
    • Day 3
      Virgin Gorda
    • Day 3
      Jost Van Dyke
    • Day 4
      Anguilla
    • Day 4
      St. Barts
    • Day 5
      St. Barts
    • Day 6
      Nevis
    • Day 7
      Nevis
    • Day 7
      South Friars Beach
    • Day 8
      St. Martin
    Ship Details

    SeaDream II - SeaDream Yacht Club

    Pros

    All-inclusive, ultra-small ship with amazing food and service

    Cons

    Limited onboard entertainment, especially if you don't like to socialize over drinks

    Bottom Line

    Closest most people will get to a vacation on a private yacht

    Reviews

    SeaDream II Reviews

    Cruise Critic Editor Ratings
    Overall
    5.0/5
    Cabins5.0
    Dining5.0
    Service5.0
    Value4.5

    "It's yachting, not cruising" has been SeaDream's tagline since the company launched in 2001, but ...

    Cruise Critic Member Ratings
    HHB fun
    Sail Date Oct 2018
    Fabulous Caribbean Holiday
    Read More
    Perhedegaard
    Sail Date Mar 2018
    18 paying passengers - yet poor service and zero flexibility.
    Read More
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  • 7 Night
    Cruise to Anguilla

    Leaving:
    Barbados
    Visiting:
    Iles des Saintes, Montserrat ... see more
    Cruise Line:
    SeaDream Yacht Club
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    Itinerary

    Cruise Itinerary

    7 Night Cruise to Anguilla Route (SeaDream Yacht Club)
    • Day 1
      Barbados
    • Day 2
      Iles des Saintes
    • Day 3
      Montserrat
    • Day 4
      St. Barts
    • Day 5
      St. Barts
    • Day 6
      St. Barts
    • Day 6
      Anguilla
    • Day 7
      Jost Van Dyke
    • Day 8
      St. Thomas
    Ship Details

    SeaDream I - SeaDream Yacht Club

    Intimate ship with casual, social atmosphere

    Outstanding cuisine always served in open seating

    Water sports platform: jet ski from the ship

    Reviews

    SeaDream I Reviews

    Cruise Critic Editor Ratings
    Overall
    5.0/5
    Cabins5.0
    Dining5.0
    Service5.0
    Value5.0

    With SeaDream I (and sister SeaDream II), SeaDream Yacht Club has managed to carve out a unique...

    Cruise Critic Member Ratings
    ATAJanie
    Sail Date Jan 2020
    Only 100 passengers, First Class Casual Luxury, Extremely Personalized, and FUN!
    Read More
    cpbw
    Sail Date Nov 2019
    Seadreaming - Epicurean Delights & Casual Perfection
    Read More
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  • 7 Night
    Cruise to Anguilla

    Leaving:
    San Juan
    Visiting:
    St. John (U.S.V.I.), Virgin Gorda ... see more
    Cruise Line:
    SeaDream Yacht Club
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    Itinerary

    Cruise Itinerary

    7 Night Cruise to Anguilla Route (SeaDream Yacht Club)
    • Day 1
      San Juan
    • Day 2
      St. John (U.S.V.I.)
    • Day 3
      Virgin Gorda
    • Day 4
      Norman Island
    • Day 5
      Anguilla
    • Day 5
      St. Barts
    • Day 6
      St. Barts
    • Day 7
      Jost Van Dyke
    • Day 8
      San Juan
    Ship Details

    SeaDream I - SeaDream Yacht Club

    Intimate ship with casual, social atmosphere

    Outstanding cuisine always served in open seating

    Water sports platform: jet ski from the ship

    Reviews

    SeaDream I Reviews

    Cruise Critic Editor Ratings
    Overall
    5.0/5
    Cabins5.0
    Dining5.0
    Service5.0
    Value5.0

    With SeaDream I (and sister SeaDream II), SeaDream Yacht Club has managed to carve out a unique...

    Cruise Critic Member Ratings
    Paul Jenks
    Sail Date May 2019
    Disappointing Luxury Cruise.
    Read More
    Sarasavoy
    Sail Date Mar 2019
    THE BEST CRUISE LINE EVER!!!! I will never go back to a big ship!
    Read More
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  • 7 Night
    Cruise to Anguilla

    Leaving:
    St. Thomas
    Visiting:
    Sopers Hole, Norman Island ... see more
    Cruise Line:
    SeaDream Yacht Club
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    Itinerary

    Cruise Itinerary

    7 Night Cruise to Anguilla Route (SeaDream Yacht Club)
    • Day 1
      St. Thomas
    • Day 2
      Sopers Hole
    • Day 2
      Norman Island
    • Day 3
      Virgin Gorda
    • Day 3
      Prickly Pear Island
    • Day 4
      Anguilla
    • Day 4
      St. Barts
    • Day 5
      St. Barts
    • Day 6
      Guadeloupe
    • Day 7
      Dominica
    • Day 8
      St. Lucia
    Ship Details

    SeaDream II - SeaDream Yacht Club

    Pros

    All-inclusive, ultra-small ship with amazing food and service

    Cons

    Limited onboard entertainment, especially if you don't like to socialize over drinks

    Bottom Line

    Closest most people will get to a vacation on a private yacht

    Reviews

    SeaDream II Reviews

    Cruise Critic Editor Ratings
    Overall
    5.0/5
    Cabins5.0
    Dining5.0
    Service5.0
    Value4.5

    "It's yachting, not cruising" has been SeaDream's tagline since the company launched in 2001, but ...

    Cruise Critic Member Ratings
    gwennw
    Sail Date Jun 2018
    Best cruise we ever took
    Read More
    BDMCruiser
    Sail Date Feb 2018
    5-Star Cruise, but Could Have Been Better
    Read More
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  • 7 Night
    Cruise to Anguilla

    Leaving:
    St. Maarten
    Visiting:
    Sopers Hole, Jost Van Dyke ... see more
    Cruise Line:
    Windstar Cruises
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    • Fare Includes
    Itinerary

    Cruise Itinerary

    7 Night Cruise to Anguilla Route (Windstar Cruises)
    • Day 1
      St. Maarten
    • Day 2
      Sopers Hole
    • Day 2
      Jost Van Dyke
    • Day 3
      Jost Van Dyke
    • Day 3
      Virgin Gorda
    • Day 4
      Virgin Gorda
    • Day 5
      St. Barts
    • Day 6
      Anguilla
    • Day 7
      Antigua
    • Day 8
      St. Maarten
    Ship Details

    Wind Surf - Windstar Cruises

    Pros

    Laid-back yacht feel; unique watersports platform; fantastic deck barbecue; friendly crew

    Cons

    No balcony cabins; food and service hit and miss; stairwells and passageways feel tired

    Bottom Line

    Intimate seven-sail ship with low-key entertainment; needs improvements to dining options

    Reviews

    Wind Surf Reviews

    Cruise Critic Editor Ratings
    Overall
    4.0/5
    Cabins4.0
    Dining4.0
    Service3.5
    Value4.0

    The stunning five-mast, seven-sail Wind Surf takes the prize of largest vessel in the Windstar ...

    Cruise Critic Member Ratings
    Misty Morning
    Sail Date Mar 2020
    Great Yachtsman’s Caribbean Cruise
    Read More
    Sgjacobson
    Sail Date Nov 2019
    Repairs galore
    Read More
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    Fare Includes

    What’s included in My Cruise Fare?

    • Cabin
      Room with bed and private bathroom
    • Port Taxes & Fees
    • Service Gratuities
    • Most Onboard Entertainment
    • Kids Club
    • Shore Excursions
    • Wi-Fi
    • Spa Services
    • Select Dining
      Main dining room and/or buffet
    • Specialty Alternative Dining
    • Room Service
    • Butler Service
    • Basic Drinks
      Still water, coffee, and tea
    • Soft Drinks
      Soda and Juice
    • Alcohol
      Beer, wine, and spirits
    • Specialty Coffee Drinks
      Including smoothies and blended drinks
    • Specialty Fitness Classes

    ** inclusions in your cruise fare are based on Cruise Critic’s editorial expertise and not provided by the individual cruise lines. When you book with one of our cruise partners, please be sure to check their site for a full disclosure of all applicable fees. Cruise Critic does not guarantee any specific rates, prices, or amenities included in the fare. Inclusion items in the fare may change at any time and fees may apply for additional items.

  • 7 Night
    Cruise to Anguilla

    Leaving:
    San Juan
    Visiting:
    Virgin Gorda, Nevis ... see more
    Cruise Line:
    SeaDream Yacht Club
    View Deal
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    Itinerary

    Cruise Itinerary

    7 Night Cruise to Anguilla Route (SeaDream Yacht Club)
    • Day 1
      San Juan
    • Day 2
      Virgin Gorda
    • Day 3
      Nevis
    • Day 4
      South Friars Beach
    • Day 5
      Anguilla
    • Day 5
      St. Barts
    • Day 6
      St. Barts
    • Day 7
      Jost Van Dyke
    • Day 8
      St. Thomas
    Ship Details

    SeaDream II - SeaDream Yacht Club

    Pros

    All-inclusive, ultra-small ship with amazing food and service

    Cons

    Limited onboard entertainment, especially if you don't like to socialize over drinks

    Bottom Line

    Closest most people will get to a vacation on a private yacht

    Reviews

    SeaDream II Reviews

    Cruise Critic Editor Ratings
    Overall
    5.0/5
    Cabins5.0
    Dining5.0
    Service5.0
    Value4.5

    "It's yachting, not cruising" has been SeaDream's tagline since the company launched in 2001, but ...

    Cruise Critic Member Ratings
    Vicky2
    Sail Date Feb 2018
    A cruise is more than food and excellent service
    Read More
    jam48
    Sail Date Jan 2018
    SeaDream II - Relaxing, small-ship, luxury cruise
    Read More
    Cabin Comparison

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  • 7 Night
    Cruise to Anguilla

    Leaving:
    St. Lucia
    Visiting:
    St. Vincent, St. Lucia ... see more
    Cruise Line:
    SeaDream Yacht Club
    View Deal
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    Itinerary

    Cruise Itinerary

    7 Night Cruise to Anguilla Route (SeaDream Yacht Club)
    • Day 1
      St. Lucia
    • Day 2
      St. Vincent
    • Day 3
      St. Lucia
    • Day 4
      Iles des Saintes
    • Day 5
      Anguilla
    • Day 5
      St. Barts
    • Day 6
      St. Barts
    • Day 7
      Jost Van Dyke
    • Day 8
      San Juan
    Ship Details

    SeaDream I - SeaDream Yacht Club

    Intimate ship with casual, social atmosphere

    Outstanding cuisine always served in open seating

    Water sports platform: jet ski from the ship

    Reviews

    SeaDream I Reviews

    Cruise Critic Editor Ratings
    Overall
    5.0/5
    Cabins5.0
    Dining5.0
    Service5.0
    Value5.0

    With SeaDream I (and sister SeaDream II), SeaDream Yacht Club has managed to carve out a unique...

    Cruise Critic Member Ratings
    Hansmallorca
    Sail Date Oct 2017
    ABSOLUTELY SUPERB - Again!
    Read More
    AWHW
    Sail Date Sep 2017
    Memorable Cruise
    Read More
    Cabin Comparison

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  • 7 Night
    Cruise to Anguilla

    Leaving:
    St. Thomas
    Visiting:
    South Friars Beach, St. Barts ... see more
    Cruise Line:
    SeaDream Yacht Club
    View Deal
    View Cruise Info
    Hide Cruise Info
    • Itinerary
    • Ship Details
    • Reviews
    • Cabin Comparison
    • View All Prices
    Itinerary

    Cruise Itinerary

    7 Night Cruise to Anguilla Route (SeaDream Yacht Club)
    • Day 1
      St. Thomas
    • Day 2
      South Friars Beach
    • Day 2
      St. Barts
    • Day 3
      St. Barts
    • Day 4
      Anguilla
    • Day 5
      Virgin Gorda
    • Day 6
      Norman Island
    • Day 6
      Beef Island
    • Day 7
      Beef Island
    • Day 7
      Jost Van Dyke
    • Day 8
      San Juan
    Ship Details

    SeaDream II - SeaDream Yacht Club

    Pros

    All-inclusive, ultra-small ship with amazing food and service

    Cons

    Limited onboard entertainment, especially if you don't like to socialize over drinks

    Bottom Line

    Closest most people will get to a vacation on a private yacht

    Reviews

    SeaDream II Reviews

    Cruise Critic Editor Ratings
    Overall
    5.0/5
    Cabins5.0
    Dining5.0
    Service5.0
    Value4.5

    "It's yachting, not cruising" has been SeaDream's tagline since the company launched in 2001, but ...

    Cruise Critic Member Ratings
    Msdenny
    Sail Date Jan 2018
    The most amazing yacht cruise from beginning to end!
    Read More
    LnG4Crusing
    Sail Date Jul 2017
    Amazing ! We are already booked for 2 more trips !
    Read More
    Cabin Comparison

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  • 7 Night
    Cruise to Anguilla

    Leaving:
    St. Thomas
    Visiting:
    St. John (U.S.V.I.), Virgin Gorda ... see more
    Cruise Line:
    SeaDream Yacht Club
    View Deal
    View Cruise Info
    Hide Cruise Info
    • Itinerary
    • Ship Details
    • Reviews
    • Cabin Comparison
    • View All Prices
    Itinerary

    Cruise Itinerary

    7 Night Cruise to Anguilla Route (SeaDream Yacht Club)
    • Day 1
      St. Thomas
    • Day 1
      St. John (U.S.V.I.)
    • Day 2
      St. John (U.S.V.I.)
    • Day 3
      Virgin Gorda
    • Day 4
      Virgin Gorda
    • Day 4
      Prickly Pear Island
    • Day 5
      Norman Island