Cruise Port Guide · 13 cruises visit Road Bay →
The bucket-list things to do — and the private, expert-led way to do each.
Here’s the bucket list for your day ashore: the most extraordinary thing to do at each stop, and the private, small-group, or expert-led way to make it yours — your own pace, real access, none of the crowd.
Sail aboard a private catamaran to two of Anguilla's most spectacular uninhabited cays — Sandy Island and Prickly Pear — where powdery white sand meets impossible shades of turquoise. Snorkel pristine reefs, sip chilled rum punch, and feel utterly alone in paradise.
Shoal Bay East is consistently ranked among the world's finest beaches — two miles of powder-soft white sand lapped by luminous turquoise water. Reserve a private cabana at Madeariman Reef Bar & Restaurant and snorkel the thriving reef just steps offshore.
Anguilla punches far above its size in fine dining, with more world-class restaurants per capita than almost any island in the Caribbean. A curated culinary tour stops at a legendary local chef's table and a heritage rum shack, finishing with a private multi-course lunch.
Canter along Anguilla's undeveloped eastern coastline on a barefoot beach horse ride with Seaside Stables, the island's most established equestrian outfitter. The wild dunes, sea-grape trees, and crashing Atlantic surf create an utterly cinematic setting.
Delve into Anguilla's remarkable story — from Amerindian settlements and the salt-trade era to the 1967 Revolution — on a private walking tour led by a local historian. The Wallblake House, heritage churches, and ancient salt ponds tell a story found nowhere else in the Caribbean.
Explore Anguilla's gorgeous, cliff-flanked western coastline from the water on a guided SUP and kayak safari, ducking into secret coves and sea caves invisible from shore. Crystal-clear water above healthy coral makes every stroke a window into an underwater world.
⚓ Your bucket-list concierge
Tell us your sailing and we'll send the bucket list for every port — the most extraordinary thing to do at each, and the private, expert-led way to make it yours.
No spam. The honest plan, even when it says skip the ship’s tour.