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Commercial Real Estate in Key West & the Florida Keys by RE/MAXCommercial Real Estate in Key West & the Florida Keys by RE/MAX

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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

1 Henry Morgan Road W 1 $38,000,000

1 Henry Morgan Road W 1 OTHER, Florida

99 Beds 119 Baths

1 Infinity Bay Road W 145 $28,000,000

1 Infinity Bay Road W 145 OTHER, Florida

99 Beds 170 Baths

1 Media Luna Resort Road W 126 $26,000,000

1 Media Luna Resort Road W 126 OTHER, Florida

99 Beds 109 Baths

$10,000,000

Other, Florida

30 Beds 33 Baths

27340 Overseas Highway $6,900,000

27340 Overseas Highway Ramrod, Florida

3,969 SqFt

1 Lands End  West End Roatan W $6,750,000

1 Lands End West End Roatan W OTHER, Florida

25 Beds 27 Baths

328 Whitehead Street $4,995,000

328 Whitehead Street KEY WEST, Florida

5 Beds 5 Baths 2,759 SqFt 0.330 Acres

7537 Overseas Highway $3,495,000

7537 Overseas Highway MARATHON, Florida

6,750 SqFt

91865 Overseas Highway $2,300,000

91865 Overseas Highway Tavernier, Florida

15 Beds 10 Baths 10,150 SqFt

100150 Overseas Highway $2,100,000

100150 Overseas Highway KEY LARGO, Florida

58835 Overseas Highway $1,499,000

58835 Overseas Highway MARATHON, Florida

3,414 SqFt

1000 Eaton Street $1,200,000

1000 Eaton Street KEY WEST, Florida

1 Baths 989 SqFt

Pirates Road $799,000

Pirates Road Cudjoe, Florida

Pirates Road $799,000

Pirates Road Cudjoe, Florida

2.200 Acres

Pirates Road $799,000

Pirates Road Cudjoe, Florida

96,547 SqFt

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:

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Newest Key West Commercial Properties on the Market

Offered for sale is Vaca Cove a 7 unit vacation rental property located in Marathon, FL.  The property is comprised of 7 stilted waterfront homes, dockage accommodating up to 40' boats per home, resort sized pool, fishing dock/kayak launch and built in 2016.  Each home is 1,740 Sq. Ft., 4 bedroom, 3 bath, open floor plan living area, large laundry, water front porches with open water views, private spas and covered parking.  This is an active vacation rental property with established management and increasing numbers.  Please do not go to property unscheduled.  Call for more information. $6,900,000 Active

12555 Overseas Highway A MARATHON, Florida

28 Beds 21 Baths 12,180 SqFt

The BB & T building is a centrally located landmark in one of the best areas in Key West. A prestigious location for this expansive second floor condominium executive office suite. Ideally suited for any professional office; medical, attorney, accountant, investment, real estate and or continued insurance enterprise. This tastefully decorated and expansive office suite offers many desirable features: More than 1900 sq. ft., 2-private balconies facing east and west, kitchen, reception, multiple private offices, bull-pen, conference and ample storage. Common area baths located immediately adjacent to the suite. Utilities included. $5,500 Active

1010 Kennedy Drive 203 KEY WEST, Florida

1,912 SqFt

The BB & T building is a centrally located landmark in one of the best areas in Key West.  A prestigious location for this expansive second floor condominium executive office suite. Ideally suited for any professional office; medical, attorney, accountant, investment, real estate and or continued insurance enterprise.   This tastefully decorated and expansive office suite offers many desirable features:  More than 1900 sq. ft., 2-private balconies facing east and west, kitchen, reception, multiple private offices, bull-pen, conference and ample storage.  Common area baths located immediately adjacent  to the suite.  The CAM monthly fee includes the utilities; insurance, building maintenance and 24 hour security.  Seller financing available.  Office furnishings negotiable. $585,000 Active

1010 Kennedy Drive 203 KEY WEST, Florida

1,912 SqFt

3600 sq. feet of CBS Twin Tee Construction WAREHOUSE with 17' interior height Insulated and Air conditioned.  3 Overhead doors. Ample Asphalt  Parking Cabinet Shop, Window Shop, Endless possibilities ******* COULD BE SUBDIVIDED *********Additionally available 1000 sq. feet of office space plus upstairs apartment.  Pricing will depend on size of space that is  leased. $26 Active

Key Largo, Florida

1 Beds 3 Baths

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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Key West, FL 33040

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Key Largo, FL 33037

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