Adventure and Romance Await on Key West's 10 Best Day Cruises

When you experience Key West from the water, you'll gain a new perspective on its rich nautical history and diverse ecosystem. The island is surrounded by a palette of blues, and you’ll easily heed the call that has lured many a pirate to sea. In fact, you can even play pirate on the regal wooden schooners Jolly II Rover and Classic Harbor Line.

Looking for a more relaxing sail? Champagne sunset cruises abound, and connoisseurs will relish the wine tasting on Danger Charters. For the consummate romantic cruise, how does dinner on Islescapes' private yacht sound?

Get up close and personal with the wide variety of sea life on excursions such as the Dolphin Safari and Key West Extreme Adventures’ heart-pumping shark tour.

Active types will find a smorgasbord of recreational activities available. Day cruises like Sebago Watersports' Power Adventure include snorkeling, jet skiing, parasailing, kayaking and paddle-boarding. Barefoot Billy's two-hour Island Jet Ski Tour takes riders on a high-octane sightseeing circuit around Key West.

The ultimate day trip is on the Yankee Freedom II to the isolated Dry Tortugas National Park 70 miles from Key West. The shallow waters surrounding the islands are perfect for snorkeling, and a history lesson awaits amid the ruins of Fort Jefferson.

No matter which of these day cruises you choose, you’ll love Key West even more once you’ve found your “sea legs.”



If you're the type that cancels all your plans during the Discovery Channel's "Shark Week," then this adventure tour is just the ticket to get your adrenaline pumping. Join the "shark whisperers," Captain Ken Harris and Captain Dave Harris, on a...  Read More



While a catamaran day cruise offers the chance to kick back and relax, the Classic Harbor Line gives guests a more genuine sailing experience. Their schooner, America 2.0, is a near replica of the first boat to win the America's Cup in 1851 with...  Read More



Fishing in Key West is a lot of fun, but it certainly isn't cheap. Private charters, which charge approximately $600 per group for a half-day tour (excluding gratuities), may not be ideal for families with young children. Gulfstream Fishing has...  Read More



With its distinctive red sails flying high each evening as the sun goes down, it's no wonder that the Schooner Jolly Rover II is the most photographed ship in Key West. The captain and crew encourage you to play pirate on the classic 80-foot...  Read More

Sebago Watersports
Photo courtesy of Schooner Appledore II


Sebago Watersports has it all: watersports, sunset sails, eco-tours, snorkel trips and parasailing. For a sports sampler, try their day-long Power Adventure on a 60-foot catamaran. They'll sail you to their secluded water park area for a day of...  Read More



Foodies with a passion for the sea will rejoice when they set sail on a three-hour dinner cruise, complete with sunset, on Islescapes' 33-foot motor yacht. The boat is fitted with a barbecue grill where Captain Alex and his first mate cook...  Read More



For over 20 years Barefoot Billy's in Key West has been providing recreational equipment rentals and tours both on water and on land. Rentals include Jet Skis, paddle boards, kayaks, Hobie Cats, bicycles and scooters. They're best known for...  Read More



There's one thing both kids and adults love about the sea: dolphins. Hop aboard Dolphin Safari's six-passenger boat for a chance to see them in the wild. Along the way, you'll come across other sea life like manatees, sea turtles and stingrays....  Read More



Key West is famous for its circus-style sunset celebration on Mallory Square. For a more upscale (and less crowded) experience, hop on Danger Charter's Wind and Wine Sunset Sail, where you'll have a peaceful front row seat to the sun's...  Read More



About 70 miles from Key West, the Dry Tortugas National Park is comprised of seven islands, straddling the Gulf of Mexico, Caribbean Sea and Atlantic Ocean. This remote treasure is only accessible by seaplane, private boat or the Yankee Freedom...  Read More


Meet Claudia Miller

Claudia Miller has been writing about South Florida for over 17 years--seven from Key Largo. A budding photographer, she can usually be found stalking a sunset. Despite being a tad...  More About Claudia