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

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

112 Bounty Lane N $5,990,000

112 Bounty Lane N KEY LARGO, Florida

5 Beds 5 Baths 4,822 SqFt 0.180 Acres

3574 Overseas Highway 1-7 $4,800,000

3574 Overseas Highway 1-7 MARATHON, Florida

5 Beds 4 Baths 7,706 SqFt

100099 Overseas Highway $4,749,000

100099 Overseas Highway KEY LARGO, Florida

2 Baths 4,680 SqFt

30770 Overseas Highway $3,995,000

30770 Overseas Highway Big Pine, Florida

12,560 SqFt

919 - 921 Duval Street $3,750,000

919 - 921 Duval Street KEY WEST, Florida

9 Beds 6 Baths 4,173 SqFt

10 Ocean Drive E $3,699,000

10 Ocean Drive E MARATHON, Florida

5 Beds 3 Baths 2,832 SqFt 0.290 Acres

96180 Overseas Highway $3,600,000

96180 Overseas Highway KEY LARGO, Florida

3 Beds 3 Baths 1,445 SqFt 0.960 Acres

770 107th Street Ocean $3,500,000

770 107th Street Ocean MARATHON, Florida

33,977 SqFt

770 107Th St Ocean $3,500,000

770 107Th St Ocean MARATHON, Florida

101350 Overseas Highway $3,250,000

101350 Overseas Highway KEY LARGO, Florida

2 Baths 6,674 SqFt

155 Atlantic Circle Drive $3,100,000

155 Atlantic Circle Drive KEY LARGO, Florida

3 Beds 2 Baths 2,694 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:

Newest Key West Commercial Properties on the Market

Prime Commercial Real Estate in Big Pine Key. The property offers 125 footage on US1 and 200 feet deep. With access from the front of the building to the back. Back of the property is fenced with extra storage facilities. Metal building, metal roof, two half baths, two lofts, front office space. $1,545,000 Active

31133 Ave A Big Pine, Florida

2 Baths 2,460 SqFt

Come and Use this precious space at a prime location! There is so much foot traffic in this area. Your business here at 300 Southard Street Unit 103 is at a Great location. Parking space provided as well. Renting for $950. Ideal spot right by Truman Annex and in between Southard Street and Thomas Street. $950 Active

300 Southard Street 103 KEY WEST, Florida

5 Baths 135 SqFt

Hard to find office space available at Conch Harbor Retail Center. Suitable for office, at the corner of Caroline and Grinnell Streets. Men and Women's bathrooms, outdoor seating in courtyard. Neighbors include Prime 951 Steakhouse, Dante's Pool Bar and Restaurant and West Marine. Sales tax is in addition to rent quoted, minimum one-year lease. $4,328.33 Active

951 Caroline Street 207 KEY WEST, Florida

2 Baths

2,705 SF lot in X Flood Zone on White Street in Key West. Zoned HNC-1, see documents tab for land uses. Buyer to verify if any build back rights. Owner is a licensed FL Realtor. $499,000 Active

1212 White Street KEY WEST, Florida


[button size=”large” url=”https://homes.floridakeyscommercial.com/i/newest-commercial-properties-for-sale-in-key-west-fl” expand=”true” color=”#dd3333″]View All[/button]