Key West, Florida - Jim Flynn's BestWeekends

Key West, Florida

Key West, Florida Overview

At the southern tip of Florida and only 90 miles from Cuba sits the southern most U.S. city of Key West. Once the base for Caribbean pirates and later home to Ernest Hemingway and Tennessee Williams, Key West also served as the winter White House for President Truman and the inspiration for the drawings of John James Audubon.

Inhabitants are a colorful blend of eclectic artists, writers and others just escaping from everyday life. Everyone has a story and they’re more than willing to share it with you. No one seems to care about the rest of the world, only about enjoying life every single day. This is Jimmy Buffet’s headquarters and the site of the annual Parrot Head convention. Sunshine, tropical breezes, crystal clear water and a never ending party make this an ideal weekend getaway.

Where else would you find a restaurant that celebrates Thanksgiving every Thursday night or a town that sponsors bed races down its main street or a place where restaurant owners call the local jail first when employees don’t show up for work?
Unlike other parts of Florida dominated by fast food restaurants and neon signs, Key West is more like a tropical Caribbean island with tall palm trees, incessant sunshine, crystal blue waters, cascading bougainvillea and colorful hibiscus.

Duval Street, the center of most activity is lined with countless open air restaurants and bars, live music, souvenir shops, clubs and B&B’s. You could spend your whole weekend here just making (or drinking) your way from one end to the other.

Each day ends and evening begins in Mallory Square with the Celebration of Sunset. The Square is filled with hundreds of people, street vendors, and street performers and the sunset is the most glorious you will ever see.

When warm is what you want, there is no better weekend destination than Key West.


When To Go

This content is only available to active members. Please Login or visit our membership page for details.

Getting There

This content is only available to active members. Please Login or visit our membership page for details.

Getting Around

This content is only available to active members. Please Login or visit our membership page for details.

Things To Do

This content is only available to active members. Please Login or visit our membership page for details.

Dont Miss

This content is only available to active members. Please Login or visit our membership page for details.

Good to Know, Good to Go

This content is only available to active members. Please Login or visit our membership page for details.

Special Things

This content is only available to active members. Please Login or visit our membership page for details.

Where To Stay

Casa Marina Resort

Geography:
,

OVERVIEW If a full service hotel is what you are seeking, The Casa Marina will fit the bill. Opened in 1920 it has the charm of an old world hotel with all the modern amenities. It is located just outside the heart of town on the largest private beach on the island. Many of the...…

View Property Details

La Mer/Dewey House

Geography:
,

OVERVIEW Staying here is getting the best of all worlds. La Mer and Dewey House are delightful, private and intimate oceanfront B&B’s, but are part of the adjacent Southernmost Hotel which has three pools, two outside bars and a fishing pier.  Also part of the complex is the Southernmost Beach Cafe an open air restaurant...…

View Property Details

Ocean Key Resort

Recognition:
Geography:
,

OVERVIEW If location is everything, then the Ocean Key Resort has it all. Situated at the end of bustling Duval Street and right on the Gulf, the Resort stands next to Mallory Square the site of the nightly sundown festival. THE ROOMS The 100 rooms are decorated in vibrant island colors and look out on...…

View Property Details
We have a lot more recommended accomodations, but you must be a member to view them! Please login or become a member.

Where To Eat

Antonia’s

The yellow flag on the white clapboard building above two bay windows on Duval means you have found one of the best Italian restaurants in Key West, Antonia's. Owners Antonio Berto and Phillip Smith (also the chef) have created a comfortable, yet sophisticated restaurant in a candlelit wood paneled room with a cozy bar, creative…

View Restaurant Details >

Cafe Marquesa

Warm yellow/gold walls, accented by dark mahogany molding and large mahogany framed mirrors create an inviting atmosphere for Cafe Marquesa, an intimate 50 seat spot about two blocks from Duval. Add wide-paned windows with views to the street, shaded table lamps, crisp linens and you have the makings for a very romantic meal. The open…

View Restaurant Details >

Cafe Sole

'A meal in Provence' is how Café Sole describes itself and that is a very apt description. The setting and the wonderfully prepared seafood with a French influence can transport you to the French countryside. Owners John and Judy Correa have created a very special place that is will be a highlight of your trip to Key…

View Restaurant Details >
We have a lot more recommended dining locations, but you must be a member to view them! Please login or become a member.

Advance Search

Use our handy tool to search for the perfect weekend with all the features you prefer. Search by accomodation type, recognition, geography, amenity and more. Search now!

May 2020: Little Nell

This months featured property is… charming and sweet. THE ROOMS In 2017, Champalimaud Design refreshed all 86 rooms and suites and all guest floor corridors. The approach was to reinvigorate the spaces to be fresh, light and welcoming, utilizing palettes of blue, tan and grey to complement the relaxed nature of Aspen. Key features include… read more.

Notes From the Road

Hear about our latest discoveries
before anyone else!

CLICK HERE TO SIGN UP!