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Key West, FL
Weekend Vacation Getaway

Destination 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.

Click picture to enlargeKW SchoonerStreet PerformerAudubon Garden

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.


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Click picture to enlargeConch TrainSouthernmost Point USBlue Heaven

Making Your Travel Plans

To make your travel plans you can go to our Weekend Planner for all the contact information.

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Getting There

You can reach Key West by air from anywhere in the country, usually with a stop in Atlanta or Miami first. Or, you can fly into Miami, rent a car and drive down through the keys to Key West. The trip is about 3 1⁄2 hours and is really an enjoyable ride with beautiful blue waters on each side of the highway. I like to stop half way down in Islamorada for lunch or to stay overnight at the delightful Cheeca Lodge (have one of their mangoritas) and then continue on to Key West. Islamorada is the bone fishing capital of the world, so if you are a fisherman, it’s not a place to miss.

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When To Go

Key West is a great weekend destination all year with the exception mid-summer when the heat can be oppressive and late summer/early fall which is hurricane season. 

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Getting Around

The island measures only 4 by 2 miles so you will not need a car in Key West as most activities are within walking distance. Bikes and mopeds are the preferred methods of transportation and rentals are available everywhere. Taxis and pedicabs (rickshaw like cabs on bicycles) are also readily available.

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Accommodations/Dining

There’s no longer any need to roll the dice on where you stay or to settle and stay at a “safe” national chain. BestWeekends Travel Advance Team takes the worry out of where to stay when you go away.

The BestWeekends Travel Advance Team does all the work for you. We research each destination by scouring the guidebooks, articles, blogs, reviews and rating systems. Then we visit the destination and stay in the properties. Finally, we talk to the locals to be sure we didn’t miss anything. The result: we post on our site only the best of what we experienced. You can book with confidence knowing that “we’ve been there” and that no one pays us for a review. Inside see our Featured Properties.

When you are away on vacation, there’s few things worse than a bad dining experience. We agree, so we follow the same process for identifying restaurants as we do for accommodations, but with an extra step. We believe that the best dining experience has the strongest combination of food, ambiance and service. Good food is a given in our recommendations, but the best food in the world just doesn’t taste as good in a poor setting and the best setting with poor service just doesn’t cut it for us. The BestWeekends Travel Advance Team only presents those restaurants that meet our strict criteria. Mangia….enjoy! Inside see our Favorite Restaurants.

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Things To Do

Key West is a water sports haven offering everything from world class deep sea fishing to scuba and snorkeling in clear blue water to jet skiing, parasailing, challenging bone fishing and just about anything else you can think of relating to the water. Most accommodations have pools, but there are also wonderful beaches to enjoy.

The island is steeped in history and offers the opportunity to go back in time to the days of pirates, shipwrecks, Hemingway, Tennessee Williams and more through museums and island tours. Golf is nearby, there are two excellent theatres with road shows of top productions, excellent art galleries are scattered throughout the town and there is, of course, shopping everywhere. Sunsets here are legendary and merit their own festival each evening. The feel is very laid back. Every day seems like a celebration of life. Full list of Things To Do.

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BestWeekend' s Exclusives

After selecting our favorite places to stay and eat, we sat down and made a list of all the other things that would save you time and make your stay more enjoyable. The result is “Special Things” and “Good To Know, Good To Go,” BestWeekends Exclusives.

Special Things identifies unique, fun and romantic things for couples to do together in a particular destination. Good to Know is our list of the “best” of everything from breakfast to burgers, cocktails to after dinner fun and much, much more. Why stumble around trying to find the “best”….we’ve already done it for you!

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Don't Miss

  • Sunset at Mallory Square (Gotta do it once)
  • Any meal at Louie’s Backyard
  • Breakfast at Blue Heaven and Pepe’s
  • Pub crawl on Duval
  • Snorkeling
  • Drag show at La Te Da
  • Butterfly Conservatory

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News and Resources

Key West News is an on-line source for KW info.

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