Key West Historical Sightseeing and Refreshment Tour

Key West is famous as mainland America's Caribbean resort town. Here, time slows down as the island vibes take over. But there is more to this island than umbrella drinks and warm breezes.
Key West has an incredible history, from its origins as a maritime village that profited heavily from salvaging wrecked ships and crews along the Great Florida Reef a few miles offshore, to the creation of the micro-state known as the Conch Republic. While in Key West, you will want to visit many of the sites that make the island distinct such as the Key West Lighthouse, the Hemingway House, the Little White House, and Southernmost Point.

On this tour, you will visit all of these and more, stopping for refreshments along the way at many of the island's signature restaurants and bars. You will hear stories of some of the island's more famous residents along with some lesser-known tales that have given Key West its unique place in American culture and history.

Meeting Point

10 Mallory Square

10 Mallory Square, Key West, FL 33040, USA

The tour begins at the Florida Keys Historical Military Memorial in Mallory Square. Look for the US flagpole surrounded by a semicircle of stone pedestals.

What's included:

• Audio Guide
• Voice Map Audio Tour App

Not included:

• Smartphone
• Headphones
• OPTIONAL: Admission to Truman Little White House ($22.95)
• OPTIONAL: Admission to Hemingway Home and Museum ($18.00)
• OPTIONAL: Admission to Key West Lighthouse ($15.50)

What to expect:

Duration: between 1 hour, 30 minutes and 3 hours

Mallory Square

400 Wall St, , 33040-6633, Florida

This is the starting location for the tour. Here, you can enjoy street performers and visit the shops before starting the tour. If you are starting your tour in the morning, then coffee is available at nearby Cuban Coffee Queen.

5 minutes

Key West Shipwreck Museum

1 Whitehead St, , 33040-6634, Florida

This is an optional visit for travelers interested in learning more about Key West's origins as a shipwrecking community.

Pass by without stopping

Mel Fisher Maritime Heritage Museum

200 Greene St, , 33040-6516, Florida

We discuss treasure hunter Mel Fisher during the audio tour and for those who want to learn more, the museum has artifacts and a detailed account of Mel's story.

Pass by without stopping

Capt. Tony's Saloon

428 Greene St, , 33040-6567, Florida

Stop in for a drink, appetizer, or lunch and see some of the named barstools that have supported the backsides of famous customers, or the tree growing in the middle of the saloon as discussed in the tour.

20 minutes

Sloppy Joe's

201 Duval St, Key West, FL 33040, USA

This optional stop is one of Key West's most famous restaurants. Stop in and check out some live entertainment and some food/drink.

20 minutes

Kermit's Key West Key Lime Shoppe

200A Elizabeth St, , 33040-6613, Florida

Kermit's sells Kery Lime Pies, but if you want a frozen treat during your walk, grab a frozen Key Lime Pie Bar on a stick.

Pass by without stopping

Truman Little White House

111 Front St, Naval Air Station , 33040-8311, Florida

We discuss the Little White House as a presidential retreat during the Truman Administration. Tours are available for those who want to learn more about this location.

10 minutes • Admission Ticket Not Included

US 1 Mile Marker 0

490 Whitehead St, 33040-6545, Florida

Pass by the beginning of the longest north-south road in the nation, starting here in Key West and running to the Canadian border at Fort Kent, Maine.
This location is a great opportunity for a selfie or group photo.

5 minutes

Margaritaville - Key West

500 Duval St, Key West, FL 33040, USA

Optional stop for Parrotheads who want to visit the first Margaritaville store/restaurant that started a business empire for singer/songwriter Jimmy Buffett.

Pass by without stopping

The Ernest Hemingway Home and Museum

907 Whitehead Street, 33040-7473, Florida

Visit the home of writer Ernest Hemingway, who lived here for nine years, writing several famous works inside these walls. The house has many six-toed cats descended from Hemingway's original pet that visitors can interact with.
We discuss Hemingway's time on Key West during our walk, but tours of the home are available for those interested in learning more

10 minutes • Admission Ticket Not Included

Key West Lighthouse and Keeper's Quarters Museum

938 Whitehead St, , 33040-7423, Florida

Walk the grounds of the lighthouse and learn about its first light keeper during our walk. Separate admission is available if you want to view the interior of the keeper's house and climb the 88 steps to the top for a bird's eye view of Key West and the Gulf of Mexico.
Admission is free for active military.

15 minutes • Admission Ticket Not Included

Southernmost Point

Whitehead Street, , 33040, Florida

This is the end point of our tour. The Southernmost Point Bouy is another great location for a selfie or group photo to commemorate your time in Key West.

15 minutes