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Southern Loop: Key West to Key West Itinerary

Key West, Florida, the southernmost town in the continental United States, was once home to pirates and salvage operations. Today, Key West is a paradise for all who long to get away from the fast pace of everyday life. This Key West to Key West itinerary is only a sample. Your captain will work with you to create a personalized itinerary based on your preferences and the weather at the time of your charter.

key west to key west itinerary
Key West Southernmost Point. Photo by Rob O’Neal/Florida Keys News Bureau.

Day 1 | Key West

Although Key West is in the United States, you will feel like you are in the Caribbean. Spend the afternoon browsing eclectic shops, visiting museums to learn about Key West’s colorful past, or bar hopping on Duval Street. Take a hike, visit the shipwreck museum, and learn about all the shipwrecks in the area. Visit the Hemingway House, home to famed author Ernest Hemingway. He wrote many of his novels in Key West. Some believe the saloon at what is now Captain Tony’s was the inspiration for a bar Hemingway called “Freddy’s” in his Key West novel To Have and Have Not.

Hemingway House. Photo by Rob O'Neal/Florida Keys News Bureau
Hemingway House. Photo by Rob O’Neal/Florida Keys News Bureau.

The sunset festival in Mallory Square happens every night and kicks off about an hour before sunset. This festival features local foods and street performers.

After enjoying the sunset, have dinner at one of Key West’s seafood restaurants. Try The Thirsty Mermaid or Blackfin Bistro.

Day 2 | Key West to Marquesas Keys

Spend your second day in Key West snorkeling the recently sunk Vandenburg wreck, checking out the local beach scene, or shopping. In the evening, visit The Red Barn Theater. They put on shows almost nightly. Shows are usually humor based and are very enjoyable. For dinner, try Louie’s Backyard, Bagatelle, or Abbondanza.

Days 3 and 4 | Marquesas Keys (two days)

The Marquesas Keys are the only natural atoll in the Western Hemisphere. Scattered around the Marquesas Keys, you will find incredible wrecks and reef fishing. View the wildlife, such as rays, sharks, sea turtles, and birdlife.

This is a paradise for snorkeling and diving, and numerous sites are yet to be discovered. Large coral pinnacles are a famous site not far from the islands. The continuation of the Marquesas reef line is where you can find some spectacular caves and overhangs with extremely high visibility. At night, the pitch-black sky is perfect for stargazing.

Days 4 and 5 | Dry Tortugas (two days)

Set out early for the four-hour cruise to the Dry Tortugas National Park. The park comprises seven tiny coral-and-sand islands and is accessible only by private boat, ferry, or seaplane. If you like, fish along the way and maybe catch some fresh fish for dinner.

Arrive at Fort Jefferson National Park and spend the day exploring. The Civil War-era Fort Jefferson, one of the most significant masonry structures in the Western Hemisphere, is the remote park’s awe-inspiring centerpiece. This is a fantastic place for jet skiing, paddle boarding, fishing, and snorkeling.

A snorkeler swims along the moat wall at Fort Jefferson in Dry Tortugas National Park. Photo by Rob O'Neal/Florida Keys News Bureau.
A snorkeler swims along the moat wall at Fort Jefferson in Dry Tortugas National Park. Photo by Rob O’Neal/Florida Keys News Bureau.

Day 6 | Marquesas Keys to Key West

Depart in the early morning for Key West. It’s about an 8-hour run back to Key West, so arrival should be in the early afternoon. End of your Key West to Key West itinerary. You will return not only with a suntan but also with memories that will last a lifetime.