Old Town North

Everything you desire in island living.

Technically Old Town has always been the area South of White Street and West of Casa Marina. However, due to its size, Realtors have begun differentiating between what is North and South of Truman Ave. Old Town North encompasses every street from The Gulf of Mexico south of White Street to Truman Ave. The gated community of Truman Annex is not used in this area, although it also technically falls within this area.

Old Town Key West is what you see advertised the most. It has it all: shops, restaurants, bars, theatre, culture and of course the beautiful Conch architecture. The walking and biking accessibility to everything from the Gulf to the Atlantic makes this location extremely desirable. The fact that the coveted X flood zone also falls within certain areas of Old Town lends to the allure.

Old Town North is host to The Key West Historic Seaport District which is the Caroline Street corridor that surrounds the Key West Bight. This is another area that is close to my heart because of my wife’s family who have deep roots in this area dating back to 1909. Enjoy a cocktail or shrimp platter at one of the many bars & restaurants along the boardwalk. Whether you are looking for casual or upscale dining, you will certainly find it at the Historic Seaport. At Christmas time, be sure to check out the amazing nautical themed decorations and lights that surround the boardwalk as well as the Schooner Wharf Lighted Boat Parade. There are many charter fishing boats, recreational snorkeling, parasail and sunset cruise boats docked here as well as boat slips for sale if that is your desire.

If you follow the boardwalk west all along the water, you will end up at Mallory Square. If you have never been, it’s a “must-do” for your time in Key West. Each night the sunset is celebrated with local street performers and artists selling everything from original paintings, jewelry and clothing. Once you are settled with Island Life, be sure to take your many visitors to this attraction. It’s best to arrive 90 minutes before sunset, so you can take in a few different acts and peruse the artists.

Old Town North also encompasses the historic Key West Cemetery. It is located in the northeast section of Old Town, and it is estimated that as many as 100,000 people are interred there with gravestones dating back to the mid 1800’s. Whether you love or disdain cemeteries, nothing beats taking a relaxing bike ride through the Key West cemetery where you have open sky and unobstructed views of 19 acres. These unobstructed views also make homes around the cemetery quite fetching.

Of course, I must mention the world famous Duval Street. Old Town North features the “rowdy” end of Duval Street where tourists, spring breakers, and 20-somethings go to party. During Fantasy Fest and New Year’s Eve, the 300 block is jam packed. If nightlife or day drinking is your thing, be sure to check Sloppy Joe’s and Captain Tony’s off your bucket list.

Don’t be fooled, Key West living is MUCH MORE than just this area of Duval Street! We are a community. We are culture. We are foodies. We are philanthropists.

Here are a few more reference links for you located in Old Town North:

Culture: The Studios of Key West, The Key West Theater, The Waterfront Playhouse, and The Red Barn Theatre.