Anguilla Cruises: Sailings, Embarkations & Ports of Call
18 ships from 10 cruise lines
Anguilla cruises at a glance
Waterways Cruise lists 77 upcoming sailings on 18 ships from 10 cruise lines visiting Anguilla, calling at 1 place. Cruises visit Anguilla as a port of call and do not start or end here. More Caribbean cruises.
Reviewed and fact-checked by J. Richard · About this page · About us
Compare Anguilla cruise lines
See every Anguilla cruise line by ocean and river and by ultra-luxury, luxury, premium and contemporary style, with fares, cruise lengths, ships and ports.
About Anguilla
Anguilla is the unflashy antidote to the Caribbean's busy cruise ports: a low-lying British Overseas Territory with 33 white-sand beaches, a fiercely independent culture, and no mega-ship pier. Ships anchor and tender into quiet roadsteads such as Sandy Ground, letting independent-minded travelers swim, sail to a sandbar, eat grilled lobster, and explore heritage sites without guided-peloton monotony. The trade-offs are real: infrastructure is simple, dining and transport are informal, and you must be comfortable with tender-boat logistics and a slower pace.
Typical routes
- Eastern Caribbean small-ship loops from San Juan or St. Martin — often paired with St Barthélemy, St Martin, and the British Virgin Islands.
- Luxury yacht and windjammer Leeward Islands itineraries — with a relaxed Anguilla beach day built around Sandy Ground, Sandy Island, and Prickly Pear Cays.
Ports overview
Anguilla has no deep-water cruise pier, so every call is a tender operation or a yacht anchorage. The two main drop-off points are Sandy Ground on Road Bay and Blowing Point on the south coast; a few small-ship itineraries anchor off Shoal Bay East or Meads Bay for beach days. This is an advantage for independent travelers: the island is small enough to explore on your own, but always confirm tender schedules and taxi fares.
Cruise season
December to April is the dry, high season; May to June and November are shoulder months with calm seas. Hurricane season (June–November) brings higher risk; small-ship schedules are weather-dependent.
Find your Anguilla sailing
Upcoming sailings calling at Anguilla, earliest departure first.
8 Days St Thomas Island Usvi, Us Virgin Islands Round Trip
Visits Anguilla. Also visits Charlotte Amalie, US Virgin Islands, U.S. Virgin Islands, Saint Barthélemy
SeaDream I
8 Days Philipsburg St Maarten, Netherlands Round Trip
Visits Anguilla. Also visits Sint Maarten, St Kitts and Nevis, BVI
Emerald Sakara
8 Days One-Way from San Juan to Philipsburg St Maarten
Visits Anguilla. Also visits Puerto Rico, BVI, Saint Barthélemy
SeaDream II
Why Book With Waterways Cruise?
Four decades of expertise, one dedicated advisor, and every detail handled, from your front door to the gangway and back.
Cruise Concierge
A dedicated advisor who learns your name, your travel style and your preferences, then stays with you from the first conversation to the day you return home. Not a call center. Never a stranger.
100% Custom‑Built
No cookie-cutter packages. Flights, hotels, transfers and shore days are designed from scratch around how you actually like to travel, then refined until the trip feels like yours.
40+ Years in Travel
Founded by J. Richard, a four-decade veteran of the travel industry, and focused solely on premium river and ocean cruising. Decades of ship and itinerary knowledge go into every recommendation.
Book With Total Confidence
A travel agency that is a proud member of Signature Travel Network, CLIA, ASTA and IATA.
9 Days Philipsburg St Maarten, Netherlands Round Trip
Visits Anguilla. Also visits Sint Maarten, Saint Barthélemy, Antigua and Barbuda
Wind Surf
16 Days Philipsburg St Maarten, Netherlands Round Trip
Visits Anguilla. Also visits Sint Maarten, Saint Barthélemy, Antigua and Barbuda
Wind Surf
8 Days One-Way from St Thomas Island USVI to Philipsburg St Maarten
Visits Anguilla. Also visits Charlotte Amalie, US Virgin Islands, BVI, Saint Barthélemy
SeaDream I
15 Days One-Way from Philipsburg St Maarten to Bridgetown
Visits Anguilla. Also visits Sint Maarten, St Kitts and Nevis, BVI
Emerald Sakara
18 Days One-Way from Bridgetown to Philipsburg St Maarten
Visits Anguilla. Also visits Barbados, Saint Lucia, Trinidad and Tobago
Seabourn Ovation
11 Days One-Way from Bridgetown to Philipsburg St Maarten
Visits Anguilla. Also visits Barbados, Grenada, St Vincent and Grenadines
Seabourn Ovation
22 Days Bridgetown, Barbados Round Trip
Visits Anguilla. Also visits Barbados, Grenada, St Vincent and Grenadines
Seabourn Ovation
10 Days Philipsburg St Maarten, Netherlands Round Trip
Visits Anguilla. Also visits Sint Maarten, St Kitts and Nevis, Dominica
Star Flyer
14 Days Philipsburg St Maarten, Netherlands Round Trip
Visits Anguilla. Also visits Sint Maarten, St Kitts and Nevis, Dominica
Wind Surf
Where Anguilla cruises start and end
Embarkation ports (0)
No cruises start here.
Disembarkation ports (0)
No cruises end here.
Ships by type: 17 ocean 1 expedition · a ship that visits several places here is counted once; an expedition ship that also sails as an ocean ship appears under both types.
Plan your Anguilla cruise
Anguilla cruise port guide
Cruise ports, what to see, history and practical advice.
Anguilla cruise port guide →More Caribbean cruises
Sint Maarten · Bahamas · Puerto Rico · Dominican Republic · Bermuda · Curacao · St Kitts and Nevis · Aruba
Frequently asked questions about Anguilla cruises
How many places do cruises visit in Anguilla?
1 Anguilla place are visited by 18 ships from 10 cruise lines.
When is the best time to take a Anguilla cruise?
December to April is the dry, high season; May to June and November are shoulder months with calm seas. Hurricane season (June–November) brings higher risk; small-ship schedules are weather-dependent.
Sources and further reading
Background on Anguilla draws on these references. Sailing, fare and port data come from cruise line itineraries and are refreshed regularly.
- Anguilla Tourist Board: Anguilla Official Tourism Site
- CIA World Factbook: Anguilla - The World Factbook
- Encyclopaedia Britannica: Anguilla
- Wikimedia Commons: Category:Anguilla
Created by the Waterways Cruise content team and reviewed and fact-checked by J. Richard, Sr. Cruise Travel Agent and Founder of Waterways Cruise.
Published September 9, 2026 · Last updated October 26, 2026
Fares, availability and itineraries change often. Confirm current details with your cruise line or a Waterways Cruise agent before you book.
Cruise Disclosure
Good to know: Prices are quoted per person based on double occupancy and include all applicable taxes and fees. Availability and prices can change quickly, so please continue through the booking process to confirm the latest availability and pricing before you pay.
We work hard to make sure everything on this website is accurate and up to date. However, some information may be incomplete or inaccurate, including details supplied by third parties or otherwise outside our control, and we cannot be held responsible for such errors. We work with 41 cruise line operators, that are providing cruises on 585 ships visiting 1,731 ports across 7,194 unique cruises, creating 13,822 itineraries. This is a great deal of data to continually update daily from our suppliers. If a pricing error, misrepresentation, or omission occurs, we reserve the right to adjust the pricing, correct the information, or cancel or decline any booking made in error, with notice to you. Thank you for your understanding!