Old Town Key West - The legends, lore, and history that made it what it is today

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Key West

Duration: 1 hour and 30 minutes

Languages: English

Guru: whiskey

Registered on 25 February 2026

History Nerd that loves learning and sharing.

Free reservation and cancellation

Pay-what-you-want tour, no set price, reservation and cancellation are free

Tour description

Walking tour of the heart of Key West from the seaport to Mallory square, the Mile Marker 0 sign, and all the charm and history of Old Town.

Walk thru a residential area, see the docks that started it all, hear the stoires that made Key West famous. Stop and enjoy food or drink if you wish. Understand why US Presidents, writers, athletes, and many others have made this home full time, part time, or just visited. You will pass by numerous places to get photos and a few hidden gems. Hear about the legends made famous in songs, books, and movies while being at the spots that inspired that lore.

This is your tour so we can adjust pace per your requests. We allow the wind and your energy to help navigate this historic area.

Highlights

What will we see on this tour?

Meeting point:

Custom House by park in front of building

I will have a bright shirt on in front of the custom house near the cruise ship dock next to the civil war monument in the square.

Outside visit

Mallory Square

Site of sunset celebration

Outside visit

Seaport

The industry that built this city

Outside visit

Mile Marker 0

The iconic photo

How much does this tour cost?

Free tours don't have a fixed price. At the end, each person contributes to the guide the amount they consider fair based on their satisfaction. As a guideline, Guruwalk recommends between €15 and $50 per participant.