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  • Key West History
  • Key West Architecture
  • Tour Overviews
    • Tour 1: Mallory, Front and Greene Streets
    • Tour 2: Harborwalk & Caroline Street
    • Tour 3: Fleming Street
    • Tour 4: Southard Street
    • Tour 5: Truman Annex & the Forts
    • Tour 6: Whitehead Street
    • Tour 7: Literary Landmarks
Sunrise: 07:11 AM EST - Sunset: 06:02 PM EST
Tour 2: Harborwalk & Caroline Street
Click map to see the route
Outstanding examples of the West-Indian flavored tropical architecture that distinguishes Key West are found along Caroline Street--the earliest, rather posh neighborhood. Along the way, see the metal Presidential Gates leading into the former 1823 Naval Station, now privatized as Truman Annex, Milton W. Curry's turn-of-the-century mansion, two Porter Family multi-generation manses, Robert Frost's cottage, and the waterfront HarborWalk along the Key West Bight. Traverse the sights by foot or bike and you will be rewarded.
Places to stay:
Historic Key West Inns
Mermaid & Alligator Bed & Breakfast
Tropical Inn
Island City House
The Marquesa Hotel
Heron House
Sunset Key Cottages, a Westin Resort
Amsterdam’s Curry Mansion
The Westin Key West Resort & Marina
Things to do:
The Hemingway Home & Museum
Greg Henke Massage
Sharon Wells Online Gallery
Blue Turtle Gallery
Eaton Street Bikes
Places to eat:
D’vine Wine Gallery
Fausto’s Food Palace
Sarabeth’s
Hyatt-Shor
5 Brothers Sandwich Shop
© Blue Light, LLC 2021


Sharon Wells' Key West Historic Old Town Walking and Biking Guide App for iPhone, iPod Touch and Android Devices






Sharon Wells, an historian and preservationist in Key West since 1976, wrote and published the Key West Walking Guide to Historic Key West as an annual magazine in 1984. Since that time, more than two million issues have been enjoyed by travelers to the Southernmost island. Wells, the state's historian for the Florida Keys for 18 years, gathered the images and stories of the island and its people for many years.

The self-guided tours, neighborhood by neighborhood, with accompanying maps, directions, and photographs, let visitors explore Key West's historic, architectural, cultural and botanical resources at their own pace. All the treks, virtually building by building, led visitors to streets or lanes in the heart of the historic district. Actually, there are three historic districts that welcome people--Old Town, Expanded Key West, and Key West Naval Station. More than 3,000 wood frame structures exist. And nearly every one is distinctive.

The Key West Walking Guide, which became a handbook for visitors, writers, artists and journalists, showcased the traditions, local lore, the fun and the funky, and the island's cultural--artistic and literary--heritage.

Truly the best way to enjoy the historic architecture, to see the wildly lush tropical flora, to meet locals, to enjoy the vistas and parks, to look in all the nooks and crannies and to explore the hidden gems and not so hidden treasures is to Walk, Wander or Ride around our island.

For such a small town, set in an extraordinary waterfront locale, between the Gulf and the Atlantic, Key West offers a remarkable experience.

The Key West Walking Guide has provided the best venue to discover the island for 25 years!




For more information visit us on Facebook or contact us at info@walkbikeguide.com