Key West Suggested Itineraries

By Viator, June 2015

5 223 Reviews | Add your review

The self-styled Conch Republic has always danced to its own drumbeat, on the southernmost, and perhaps most eccentric point of continental USA. A party island, artists’ haunt, cruise-ship favorite and GLBT-friendly resort, Key West floats off the west coast of Florida’s southern tip.

Day 1: Key West Characters

When you’re talking characters and Key West, the name Hemingway is bound to crop up. The notoriously macho author lived on Key West for more than a decade from 1928, and raffish Key West characters and locations feature in his novel To Have and Have Not. You can visit Hemingway’s lovely Old Town home and meet the 60-plus descendants of the author’s cats, many inheriting the extra toes of his original felines. Old Town was also where US President Harry S. Truman chose a Caribbean-style getaway as his winter White House on Key West. Eisenhower and Kennedy also stayed at the house at 111 Front Street, which is open for guided tours.

Day 2: Conch tours and mansions

Get with the conch theme and jump aboard the Conch Train , a hit with young and old since 1958. The 90-minute train ride begins on Front Street and loops through Old Town Key West. Bone up on the island’s conch history at Heritage House, browse pirate plunder at the Pirate Museum, and see treasures from the deep at the Shipwreck Museum. Salvage from shipwrecks was used to decorate many a mansion on Key West, including the Classic Revival Audubon House which features original artworks by the great bird artist J. J. Audubon.

Day 3: Dip your toe in the water

This being Key West, you’re going to get your feet wet at some stage, whether your favorite outdoor activity is dolphin-watching, snorkeling, parasailing, fishing or jet-skiing. If you can’t decide where to start, the full-day Power Adventure combines a catamaran sail across the Gulf of Mexico, kayaking in the mangroves, parasailing, kayaking and snorkeling. Go for a cruise and view Key West from the water, or clink champagne flutes on a romantic sail into the sunset.

Tours & Tickets

See all

Champagne Celebration Sunset Cruise

5 star rating: Highly Recommended 58 Reviews

Get out on Key West’s beautiful Atlantic waters to sip Moët & Chandon champagne while enjoying the sunset. Included in the tour price are ...  Read more

Location: Key West, Florida
Duration: 2 hours (approx.)

From USD $79.49

Key West Dolphin Watch and Snorkel Cruise

5 star rating: Highly Recommended 23 Reviews

Get in touch with one of nature's friendliest mammals on this relaxing 3-hour dolphin cruise from Key West. Sail alongside playful dolphins and take in the ...  Read more

Location: Key West, Florida
Duration: 3 hours (approx.)

From USD $67.59

Ultimate Express Water Adventures

4.5 star rating: Recommended 7 Reviews

Embark on one of the best cruises in Key West! After climbing aboard the express power catamaran, immerse yourself in nature as you swim in the warm, clear ...  Read more

Location: Key West, Florida
Duration: 3 hours 30 minutes (approx.)

From USD $149.89

Day Sail in Key West by Private Charter

Live the high life on this private chartered day sail in Key West. Set sail on your boat for a 90-minute adventure around the Florida Keys and view the city  ...  Read more

Location: Key West, Florida
Duration: Flexible

From USD $294.99

Key West Glass-Bottom Boat Tour with Sunset Option

4.5 star rating: Recommended 16 Reviews

See the only living coral barrier reef in the continental United States on this two-hour glass-bottom boat tour from Key West! As you relax on the cruise, look ...  Read more

Location: Key West, Florida
Duration: 2 hours (approx.)

From USD $46.39

Key West Full-Day Power Adventure: Sailing and Water Sports

5 star rating: Highly Recommended 15 Reviews

This Key West experience lets you enjoy all that the island has to offer. Sail on a sleek catamaran along the smooth waters of the Gulf of Mexico and choose ...  Read more

Location: Key West, Florida
Duration: 6 hours (approx.)

From USD $143.99

Conch Tour Train

5 star rating: Highly Recommended 20 Reviews

Experience the best of Key West on the famous Conch Tour Train! One of Florida’s most popular attractions, the Conch Tour Train has been entertaining ...  Read more

Location: Key West, Florida
Duration: 90 minutes (approx.)

From USD $30.45

Key West Ghost and Gravestone Tour

4 star rating: Recommended 9 Reviews

Join your gravedigger guide aboard the Trolley of the Doomed for a journey through Key West's darker side! Take an evening trolley ride down the narrow, dark ...  Read more

Location: Key West, Florida
Duration: 90 minutes (approx.)

From USD $35.70

Key West Shark and Wildlife Catamaran Tour

5 star rating: Highly Recommended 21 Reviews

Delight in close-up views of sharks and a variety of other marine life on this 2-hour boat tour from Key West. In an eco-friendly catamaran, travel through ...  Read more

Location: Key West, Florida
Duration: 2 hours (approx.)

From USD $78.99

Helicopter Flight Over Florida Keys

Discover the sensational beauty of the Florida Keys from the air on this helicopter tour. Choose between two options: See the changing colors of the sky over ...  Read more

Location: Marathon, Florida
Duration: Varies

From USD $158.99

See all

Viator uses cookies to improve your experience on our website. Learn more about how we use cookies and how to change your cookie settings | Close message