Escape attempts, rampages and dirty tricks. Life in the clink has never been short of drama and intrigue. Visit Old Prison to uncover more about what went on behind its doors.

To visit this historic jailhouse, make tracks to The Valley. There are lots of other worthwhile attractions in the area, such as Shoal Bay Beach, Rendezvous Bay Beach, and Cuisinart Resort Golf Course.

Plan a trip to see Old Prison

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Aurora Anguilla Resort & Golf Club

per person

Oct 8 - Oct 13

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to The Valley (AXA)

9.6/10 Exceptional! (157 reviews)

Traveling for our Honeymoon & this Resort was Amazing. From inception the staff was incredible. They communicated with me to make arrangements for transportation, the entire process was seem less. The stag goes way above & beyond ! In Al my years of traveling I haven’t met so much genuine, good hearted staff as they are .. I mean Every single 1 of them . Jessica in amazing! She welcomed us with drinks & told us to relax while she checked us in , no lines no frustrations. The resort director is amazing! He transported us to dinner himself and took amazing care of us ! The restaurants amazing ! Be prepared to be in a food coma , we dined in D Richards steak house absolutely Devine ! The cleanliness in this resort is exceptional! 10 stars !

Reviewed on Jul 30, 2025

Sheriva Luxury Villas and Suites

Save 100% on your flight

per person

Oct 8 - Oct 13

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to The Valley (AXA)

No reviews

Zemi Beach House, LXR Hotels & Resorts

per person

Oct 19 - Oct 24

found 11 hours ago

Roundtrip flight included

Boston (BOS) to The Valley (AXA)

9.6/10 Exceptional! (230 reviews)

Our second visit. It was a nice stay!

Reviewed on Jul 8, 2025

Browse tours and tickets to explore Old Prison

Tours & day trips

See all 35 activities

Anguilla Getaway Cruise

Free cancellation available

Private & custom tours

See all 14 activities

Two Islands, Twice the Fun

Free cancellation available

Food, drink & nightlife

See all 4 activities

St Maarten’s Carnival Festival Village Experience and Beach

Free cancellation available

Popular places to visit

Great spot only accessible by boat from crocus bay are you have to climb down a rope to get there. The water is crystal clear ,great snorkeling , bird watching, and is one of the most serene places on the island of Anguilla.

Little Bay

Commune with nature and explore the great outdoors at Little Bay during your travels in The Valley. Stroll along the beaches or experience the area's art scene.

Shoal Bay Beach

If a restful vacation is part of your travel plans, Shoal Bay Beach might be the perfect place to seek out during your trip to Shoal Bay. You can enjoy the restaurants while in the area.

National Trust of Anguilla

You can learn about the history of The Valley with a trip to National Trust of Anguilla. Stroll along the seaside in this quaint area, or check out its top-notch restaurants.

Stone Cellar Art Gallery

You can spend an afternoon exploring the galleries in Stone Cellar Art Gallery during your travels in The Quarter. Stroll along the beautiful beaches in this quaint area, or check out its lively bars.

Wallblake House

You can spend time exploring the galleries in Wallblake House during your travels in The Quarter. Stroll along the seaside in this quaint area, or seek out the snorkeling spots.

Scrub Island

Commune with nature and explore the great outdoors at Scrub Island during your travels in Cedar Village. Stroll along the beautiful beaches in this quaint area, or check out its lively bars.