Cruise Port Guide · 392 cruises visit Key West →
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 70 miles into the Gulf to America's most remote national park — a Civil War-era fortress rising from turquoise shallows. Snorkel pristine coral reefs, explore Fort Jefferson's massive battlements, and witness a wilderness most travelers never reach.
Step aboard a private luxury catamaran for an intimate sail across the famous Key West sunset horizon. Snorkel living coral reefs by day, then toast the legendary Mallory Square sunset with champagne as the sky erupts in gold and crimson.
Step inside the sun-drenched Spanish Colonial mansion where Ernest Hemingway wrote some of the 20th century's greatest novels. Meet the legendary six-toed cats, wander the lush gardens, and hear the stories only an insider guide can tell.
The definitive introduction to Key West — a narrated journey through 100+ points of interest aboard an iconic orange-and-green trolley, with the freedom to hop off and explore at will. Perfect for first-timers who want to see everything without missing a thing.
America's original Key West sightseeing experience — a beloved 90-minute narrated journey aboard the legendary Conch Tour Train through Old Town's most storied streets. Sixty years of storytelling tradition make this an unmissable piece of living Florida history.
Descend into Key West's swashbuckling wrecking heritage at this theatrical, landmark museum on Mallory Square. Live actors, authentic 19th-century artifacts, and a climb to the 65-foot wreck-spotter's tower make this one of the island's most unforgettable cultural experiences.
⚓ 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.