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A Walking Tour of Key West, Florida with a Map

A Walking Tour of Key West, FloridaWhere in the world can you go and walk from the Atlantic Ocean to the Gulf of Mexico in less than an hour?  The answer is Key West, Florida.  The island actually sits between the two bodies of water which makes exploring this quaint town a fascinating and educational journey.  Because of its small size, walking is the main form of transportation in Key West.  And a walking tour is by far the most interesting and informative way to get to know this island, rich in lush scenery, American history and Bahamian inspired architecture.

Start: The Southernmost Point in Key West

Southernmost Point
Whitehead Street and South Street, Key West, FL 33040

Starting out at the very south end of the island, you will find yourself at the Southern Marker for the southernmost point of Key West; the southernmost point in the Continental U.S.A.  Take in the beauty of the Atlantic Ocean and take advantage of a unique photo opportunity at this famous, historical marker. Walking north on Whitehead Street, you can leisurely view Key West’s classic conch homes and inns, with palatial two-story porches, shutter flanked windows, charming framework and white picket fences overflowing with colorful foliage.  Weaving up and down side streets along the way, you’ll also find various eatery gems off the beaten path. As you head north along Whitehead, you may want to stop and visit the Key West Butterfly & Nature Conservatory. Take a quick right on Truman Ave to Duval Street and pick up some souvenirs at Key West’s Truval Village Market Place.

Earnest Hemingway & Mile Marker Zero

Head back down Truman to Whitehead St and continue heading north a block and you will find the Ernest Hemingway House & Museum. Right after that you will find some great souvenirs at the Bahama Village Market and a few blocks more will take you to Mile Marker Zero. Continue down to 410 Caroline Street where you will come across a tiny cottage once visited by the famous poet Robert Frost. The building is now open as the Heritage Museum.  Trek down a block or so to discover the Harry S. Truman Little White House and the Curry Mansion Inn which was purchased in 1975 by a New York couple named Edith and Al Amsterdam whose family still operates it today as one of Key West’s most popular bed and breakfasts.  Beautiful columns and balconies adorn this 28 room inn filled with eclectic antiques.  Guests can enjoy a full breakfast and happy hour drinks daily.

History, Art, Ghosts & Key Lime Pie

Continue heading north on Whitehead and you will pass the Audubon House & Tropical Gardens, a quick jaunt down front street will bring you to the Museum of Art & History (Customs House) and right on the corner of Front St and Whitehead St. you can book a Haunted Tour of Key West at the infamous Ghosts & Gravestones or visit the Key West Aquarium right next door. Head north-east on Front St and a few blocks down is Ripley’s Believe it or Not. Across the street on the corner of Duval and Front St., you can stop in for a slice of Key West’s Famous Key Lime Pie at Kermit’s Key Lime Pie Shoppe.

The Seaport Harborwalk, Dinner & Drinks

Make your way down Duval and turn East on Caroline Street to Margaret Street and you will soon find yourself at the Seaport Harborwalk. Stroll the seaport to Schooner Wharf Pub and eat fresh seafood while you sit amongst towering ships docked in the marina.  Take a snorkeling or sunset cruise out to a coral reef in the Gulf of Mexico.  Also, visit the Conch Republic restaurant for open air, waterfront dining in a laid back, casual atmosphere.  There are several large hotels and resorts along the water that you can visit for a drink or dinner.

Mallory Square Sunsets

Further down along the water, you will discover the bizarre and beautiful charm of Mallory Square where the sunsets are magnificent and the entertainment – a tad weird.  Fire eaters, jugglers, daredevils and more make Mallory Square Key West’s own little circus.  It’s a must see!

Key West’s Spirited Nightlife: Irish Kevins & Sloppy Joes

Backtrack a bit to Duval Street and wrap up your tour with singing and dancing at the World Famous Irish Kevin’s where singing along with the entertainment is sure to be the highlight of your day. If belting out some fun tunes isn’t your style then Key West’s free spirited nightlife awaits you. Visit Sloppy Joes, Hogsbreath, Margaritaville and more, for tropical cocktails and lively music.  No need to worry about appointing a designated driver, remember you’re on foot and there are plenty of Cabs & Uber drivers patrolling 24/7 to bring your tired feet back to your hotel or vacation rental when you are done for the day!

If you prefer to take a Trolly, Old Town Trolly Tours hits most of the same places from the comfort of the Trolly so you can save your sandals.

Key West Walking Tour Map

To view the map below in a new window click here.

Hot Key West Business Opportunities

101600 Overseas Highway $20,000,000

101600 Overseas Highway KEY LARGO, Florida

3 Beds 3 Baths 3,717 SqFt

139 Seaside Avenue $10,500,000

139 Seaside Avenue KEY LARGO, Florida

5 Beds 7 Baths 6,740 SqFt

5730 4Th Avenue $9,995,000

5730 4Th Avenue Stock Island, Florida

9 Baths 6,444 SqFt

1622 Overseas Highway $9,900,000

1622 Overseas Highway MARATHON, Florida

3,400 SqFt

12685 Overseas Highway $8,500,000

12685 Overseas Highway MARATHON, Florida

5,607 SqFt

517 Duval & 518 Bahama Street $7,500,000

517 Duval & 518 Bahama Street KEY WEST, Florida

4 Baths 7,854 SqFt

3428 Roosevelt Boulevard N 1,2,3,4,5,6 $5,995,000

3428 Roosevelt Boulevard N 1,2,3,4,5,6 KEY WEST, Florida

7 Baths 8,046 SqFt

$5,250,000

Key Largo, Florida

2 Baths 4,680 SqFt

96180 Overseas Highway $4,650,000

96180 Overseas Highway KEY LARGO, Florida

3 Beds 3 Baths 1,445 SqFt 0.960 Acres

919 - 921 Duval Street $3,750,000

919 - 921 Duval Street KEY WEST, Florida

9 Beds 6 Baths 4,173 SqFt

101350 Overseas Highway $3,250,000

101350 Overseas Highway KEY LARGO, Florida

2 Baths 6,674 SqFt

1100 Indies Drive S $2,725,000

1100 Indies Drive S Duck, Florida

4 Beds 4 Baths 3,402 SqFt 0.290 Acres

100150 Overseas Highway $2,400,000

100150 Overseas Highway KEY LARGO, Florida

2,436 SqFt

352 Seaview Drive E $2,200,000

352 Seaview Drive E Duck, Florida

2 Beds 3 Baths 1,440 SqFt 0.190 Acres

218 Bristol Court $1,999,000

218 Bristol Court Tavernier, Florida

3 Beds 2 Baths 1,628 SqFt 0.150 Acres

Are You Looking for Commercial Property in the Florida Keys?

Use our site to search commercial real estate in Key West and all of the Florida Keys. Unlike the “big name” sites out there, our site is directly connected to our local MLS and is updated with new properties every HOUR. By creating a Property Manager account you can stay on top of the newest businesses that go up on the market and get Price Change alerts so you can stay ahead of other buyers and beat them to the best deals!

In the meantime, check out these 1-click searches:

  • All Businesses for Sale
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  • Hotels, Motels & Bed & Breakfasts
  • Bars & Restaurants
  • Marinas for Sale in Key West
  • Investment Properties
  • Business Opportunities

Newest Key West Commercial Properties on the Market

Great opportunity to purchase a SIX UNIT corner property!  All units are spacious with 2 bedrooms and 1 bath. Separately metered for water and electric.  Five units are month to month and one unit has a lease ending 9/2023. Close to dining, resorts, marina, and only minutes to Key West.  Ideal for investors, perfect for employee housing or owner occupier with rental income.  Prime corner 125x50 lot with ample off street parking. Sale is subject to court approval of Personal Rep. for the Estate of Co-Seller. $1,750,000 Active

6336 2nd Street Stock Island, Florida

6 Beds 6 Baths 5,394 SqFt

Endless possibilities! Rare multi-use commercial/residential building located in prime location in Old Town, Key West. Now available, 2000 sq.ft. commercial space on ground floor with 2 bathrooms and bonus office/storeroom. Upstairs are (3) three large residential apartments with a terrace. All the units have independent entrances and separate electric meters. The first apartment has 3 large bedrooms, 2 full bathrooms, stainless steel appliances & spacious balcony. The second apartment has a new kitchen with 2 bedrooms, 1 bathroom. The third unit is a large studio with full kitchen and bathroom. Enjoy the proximity to the beaches, restaurants, shopping and all the attractions. This mixed-use property is a must see! Perfect for 1031 exchange, investor, employee housing or owner occupier. As per request, rental income and annual expenses are available. Schedule your viewing today! $2,900,000 Active

1110 White Street KEY WEST, Florida

6 Beds 6 Baths 3,657 SqFt

Fantastic space available in the heart of the evening crowd across from the Opal and Ocean Key House Hotels and steps away from world famous Mallory Square, Key West's popular Sunset Celebration. High traffic location with cruise ship passengers and tourists using the old town train & trolley stationed right across the street. Ground level storefront with large display windows and approximately 1250 sq. ft. of retail space with an additional 950 sq. ft. of space that could be combined next door for a total of 2,200 sf. ft. Triple net expenses and sales tax are in addition to the amount quoted $8,300 Active

308 Front Street KEY WEST, Florida

1 Baths 9,411 SqFt

Fantastic space available in the heart of the evening crowd across from the Opal and Ocean Key House Hotels and steps away from world famous Mallory Square, Key West's popular Sunset Celebration. High traffic location with cruise ship passengers and tourists using the old town train & trolley stationed right across the street. Ground level storefront with large display windows and approximately 950 sq. ft. of retail space with an additional 1250 sq. ft. of space that could be combined next door for a total of 2,200 sf. ft. Triple net expenses and sales tax are in addition to the amount quoted $6,308 Active

304 Front Street KEY WEST, Florida

1 Baths 9,411 SqFt

View All

Posted in: Events, Key West, Things to Do, Venues & Attractions Tagged: Audubon House & Tropical Gardens, Bahama Village Market, Conch Republic, Curry Mansion Inn, Customs House, Duval St, Duval Street, Ernest Hemingway House & Museum, Ghosts & Gravestones, Harry S. Truman Little White House, Hemingway House, Heritage Museum, Hogsbreath, Irish Kevins, Kermit's Key Lime Pie Shoppe, Key West, Key West Aquarium, Key West Butterfly & Nature Conservatory, Key West Florida, Mallory Square, Margaritaville, Mile Marker 0, Mile Marker Zero, Museum of Art & History, Museum of Art & History (Customs House), Old Town Trolly Tours, Ripley's Believe it or Not, Schooner Wharf Pub, Seaport Harborwalk, Sloppy Joes, Southernmost Marker, Southernmost point, things to do, things to do in Key West, Truval Village Market Place, walking tour, Whitehead St

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