Best Day Cruises in Key West

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 nature-viewing excursion to the backwaters of Key West. Hop aboard the 34-foot, eco-friendly catamaran as the crew lures bull sharks, lemon sharks and nurse sharks (among others) to the boat. Stingrays, turtles, dolphins and other marine life are also common sightings during the voyage. As the only shark tour in the continental U.S., the staff is very knowledgeable about wildlife habits and the history of Key West. Snacks and polarized glasses are provided, but be sure to bring your camera.

Recommended for Day Cruises because: For an adrenaline pumping day on the water, look no further than this shark-filled eco-tour.

Claudia's expert tip: Tour times may vary due to season, tides and weather conditions.

Read more about Key West Extreme Adventures →

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 teak decks and mahogany trimmings. Their romantic sunset sail includes champagne, wine, beer, soft drinks and water, as well as a cheese display and shrimp cocktail. The daytime sail offers the same type of beverages, and passengers are encouraged to pack a picnic lunch. The key word here is sail: when the engines turn off, guests witness the power of the wind and the talent of the crew. They also offer packages for events like the Wrecker's Race, the holiday-themed Lighted Boat Parade and New Year's Eve. Note that they only sail in Key West November through mid-May.

Recommended for Day Cruises because: While a catamaran day cruise offers the chance to kick back and relax, the Classic Harbor Line gives guests a more genuine sailing experience.

Claudia's expert tip: Make your reservations early for annual events like the Wrecker's Race and Lighted Boat Parade.

Read more about Classic Harbor Line Key West →

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 the solution with a six-hour deep sea excursion at prices of $65 for adults and $38 for children under 12. Best of all the wee ones (under five) are free. This includes parking, bait and license; add $5 for rod rental. Their 58-foot Gulfstream IV party boat comes equipped with an air-conditioned cabin, restrooms and snack bar. Anglers can haul in grouper, snapper, mackerel, kingfish, tuna and sharks. The mates will become your best friends, as they help you bait your hook, gaff your catch and clean your fish. (Don't forget to tip.) Head straight to a local restaurant and have it cooked up for dinner.

Recommended for Day Cruises because: Budget-conscious families can enjoy an action packed day of deep sea fishing at reasonable prices on this well-appointed party boat.

Claudia's expert tip: Don't bring spray sunscreen or bananas. The sunscreen can stain the boat, and maritime lore deems the fruit bad luck.

Read more about Gulfstream Fishing, Inc. →


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 coastal topsail ship and tell the tales of scallywags, rum runners and privateers. They'll even let you take a turn at the wheel or help hoist the sails. While they only serve water, guests are encouraged to bring their drink of choice and perhaps a light picnic. As the wind fills the sails and you soar around Key West, you'll see sights like Fort Zachary Taylor, the Harry S. Truman Little White House and glamorous Sunset Key. When they fire the cannon at sunset, it's a blast. Find them docked in the Historic Seaport just outside The Conch Republic Seafood Restaurant.

Recommended for Day Cruises because: Good for families and couples, this sunset sail is bound to bring out the scallywag in everyone, especially when it's time to fire the cannon.

Claudia's expert tip: If you plan on being in town for several days, they offer $10 off your second sail and your third sail is free.

Read more about Schooner Jolly II Rover →

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 reef snorkeling, jet skiing, parasailing, kayaking and paddle-boarding. Other toys as like banana boats, a jumbo watermat, water trampoline and water slide add to the fun. The all-inclusive adventure includes breakfast, lunch, snacks and beverages (including beer and wine). For their champagne sunset tour, you'll board the Appledore V, a traditional 19th century 2-masted schooner. If you've always wanted to play pirate, this is your chance. They'll let you help hoist the sails or take a turn at the wheel. As the sun sets, enjoy a glass of bubbly, boutique wine, sangria or beer. Paired with fresh fruit and artisan cheeses, this makes for the perfect romantic evening.

Recommended for Day Cruises because: Sebago Watersports has it all from an all day adventure with a watersports smorgasboard to a romantic champagne sunset sail.

Claudia's expert tip: If you plan on jet skiing and were born after January 1, 1988, make arrangements to take a temporary safe boating test before any tours.

Read more about Sebago Watersports →

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 their two-hour Island Jet Ski Tour, which takes riders on a high-octane sightseeing tour around the entire island. They also offer an Ocean Discovery Tour with clear bottom kayaks and paddleboards. There are three departure locations: Casa Marina Resort, Reach Resort, and Marriott Beachside Resort. Staying someplace else? Barefoot Billy's offers a free shuttle with Jet Ski Tour reservations.

Recommended for Day Cruises because: Barefoot Billy's is best known for their two-hour Island Jet Ski Tour, which takes riders on a high-octane sightseeing tour around the island.

Claudia's expert tip: Book your Barefoot Billy's Island Jet Ski Tour on-line and save 10% off the regular price.

Read more about Barefoot Billy's Watersports →

Dolphin Safari
Photo courtesy of Dolphin Safari

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. Toss some pineapple in the water and watch the tropical fish go crazy. You'll usually spot at least one pod of playful dolphins frolicking on the open water. Friendly and curious creatures, they'll swim near the boat for photo-ops. The trip also includes 45 minutes of snorkeling in the reefs, and equipment is included. Parents can hop in the shallow water first while kids stay on the boat snacking on fruit and Rice Krispies Treats. Then they can join mom and dad with fun-noodles and life jackets. Book the afternoon tour, and you'll wrap up your time on the water with a colorful Key West sunset.

Recommended for Day Cruises because: Dolphin Safari delights passengers of all ages with dolphin-sightings, snorkeling and sunsets.

Claudia's expert tip: Book the afternoon cruise to catch the colorful sunset from a prime perch on the water.

Read more about Dolphin Safari →

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 departure, replete with world-class wines. Each cruise is limited to a maximum of 25 people, which creates an intimate cocktail party vibe. Eight different fine wines, a selection of cheese, fresh fruits, beer, and hors d'oeuvres are served aboard the Danger Prize, a 65-foot schooner. A mellow mix of reggae, Jimmy Buffet, Salsa and Bossa nova music plays over the speakers in rhythm with the wind rippling the canvas sails. As the sun slips below the horizon, keep an eye out for the Keys' mystical green flash.

Recommended for Day Cruises because: Skip the crowds on Mallory Square for a peaceful sunset sail and wine tasting.

Claudia's expert tip: Ask someone to take your photo as the sun goes down. Add in a kiss for the best romantic souvenir.

Read more about Danger Charters →

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 II--a high-speed catamaran that departs from Key West. The shallow waters surrounding the islands are perfect for snorkeling amid the ruins of Fort Jefferson. Tour the fort to learn about its construction and Civil War prisoners like Samuel Mudd--the doctor who assisted John Wilkes Booth after his injury. Prices start at $165 and include park entrance, meals, snorkeling and tour of Fort Jefferson.

Recommended for Day Cruises because: A lesser-known national wonder, the Dry Tortugas make for a fascinating day trip filled with snorkeling, nature and history.

Claudia's expert tip: Depending on the weather, the ride can be rough for those prone to sea sickness.

Read more about Yankee Freedom II →


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