Model train and figure in a colorful outdoor theme park setting.

Sightseeing

From quirky tours to can’t-miss landmarks, sightseeing in The Florida Keys is anything but ordinary - on island or at sea. Hop on a trolley or the iconic Conch Train, set sail on a charter, or wander museums filled with history, art, and stories you couldn’t make up if you tried. Key West’s haunted tours add a spooky thrill, while scenic drives and hidden stops up and down the island chain reveal the Keys’ offbeat charm. These listings connect you with the guides, tours, and attractions that turn “just looking around” into a true island adventure.

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Key West

Key West Water Tours

Thrilling 2-hour guided jet ski tours exploring stunning Key West waters!

Key West

Tiki Boat Adventures Key West Sandbar Charters

Tiki Boat Adventures — private tiki-bar boat charters in Key West for sandbars, sunsets & island-style fun.

Key West

Six Fins Charters

Private luxury boat and jet ski charters in Key West — explore hidden reefs, sandbars, and dolphin playgrounds.

Marathon

Two Conchs Fishing Charters

Capt. Jack Carlson has guided the Keys for more than 20 years, and all three of his sons run boats now too, which is how one family ends up with a fleet this size. More than 20 boats from 17 to 43 feet means the boat gets matched to your day, whether that is poling a flat for bonefish or a long run out to the Dry Tortugas.

Islamorada

Reef Quest Tours

ReefQuest Tours: Explore the vibrant reefs, wildlife, and sandbars of the Florida Keys on tailor-made, eco-educational boat adventures.

Key West

Off the Charts!

Off the Charts! offers personalized fishing charters, eco-tours, and sandbar excursions aboard a 32' Whitewater center console in Key West. Led by a captain with over 40 years of experience, they provide all necessary gear, safety equipment, and fishing licenses are included.

Key West

Green Turtle Charters

Private charters in Key West offering sandbar trips, snorkeling, eco-tours, and dolphin watching.

Key West

After Hours Yacht

Private yacht charters in Key West for unforgettable sunset cruises and day trips.

Key West

Florida Keys Air Tours LLC

Experience safe, scenic air tours and expert flight training in the Florida Keys—based at Key West International Airport.

Key West

Aloha Sailing Key West

A small, captain-run sailing charter out of Stock Island Marina Village, building each trip around what you actually want: backcountry anchorages, uninhabited islands, snorkeling in the national marine sanctuary. For the ambitious, a three day voyage out to Fort Jefferson in the Dry Tortugas.

Key West

Key West Express

Key West Express — high‑speed ferry service from Fort Myers Beach and Marco Island to Key West for relaxing day trips or island adventures.

Key West

FishMonster & IslandJane Charters

A family run outfit fishing Key West since 2006, with boats at three Old Town docks: a 64 foot air conditioned catamaran running $85 half day party trips, a fleet of sportfishers, and a 52 foot sailing ketch for sunset charters and weddings. Fishing license and bait come included in the party boat fare.

Islamorada

Reef Marine

Boat rentals, snorkel & fishing charters across the Florida Keys

Key Largo

Captain Stewys Charters

Captain Stewy's Charters offers private, personalized boat excursions in Key Largo, specializing in snorkeling trips, sandbar tours, eco tours, and sunset cruises for up to six guests.

Islamorada

Deep Sea Scuba

Deep Sea Scuba & Snorkel in Islamorada offers top-quality personalized scuba diving, snorkeling, eco-tours, PADI training, and six-pack charters, all backed by over 25 years of safety-focused experience.