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There are a vast array of activities available to those visiting this paradise. First "activity" would be to do nothing and simply relax! Key West is well known for its laid back attitude from its people to its bars and restaurants to its dress code. Flip flops, shorts and t-shirts are de rigeur here and welcomed island-wide. One can also partake in the many and varied restaurants and bars KW has to offer. From fine gourmet dining to conch fritters and a cold beer, Key West has something for every taste, and is especially known for its ultra-fresh seafood. And who can forget (well after night out, maybe you can!) Key West's night life? The famous Duval Street, the backbone of KW is known for claiming victims who attempt the "Duval Crawl" as some call it. Try it and you'll see where the name comes from. And if the selection seems overwhelming, any hotel or B&B front desk, or any local for that matter will be more than happy to offer suggestions, if asked. Go for it! Take time to explore other areas besides Duval too. There are some very cool places off Duval like Schooner Wharf Bar, Green Parrot and Don's Place to only name a few.
Water sports, this is a biggie, Key West is an island, go figure. Deep sea fishing of all kinds, kayak eco-tours, parasailing, jetskis, speedboat and snorkel tours, windsurfing, water skis, banana boats - you name it- it's all there. Sunset cruises are beautiful, there are many options here; again your hotel can offer suggestions to make sure you make the right choice.
Floridays is a beautiful 60 foot sailing yacht that takes people to the reef for snorkeling twice a day and does a sunset sail each evening. They serve beer, wine, champagne and margaritas. The crew is fabulous and they take very limited amounts of passengers so it's not crowded and you get to know the crew and fellow sailors.
The Catamaran Echo Moet and Chandon Sunset Sail offers a more intimate and romantic way to watch the sun set off of Tanker key while drinking a fine selection of champagne, wine, or beer and munching on gourmet cheeses and tropical fruits.
Danger Charters offers a full day ECO tour and a half-day sailing, snorkeling and kayaking tour that ends with watching the sunset as you sail back into Key West. In addition they also offer a sunset sail that features wines from around the world and hors d'oeuvres to compliment them on there Wind & Wine Sail.
Restless Native offers a tapas dinner sunset sail.
A private charter company is Fun In The Sun Charters. They offer combination trips and give you the ability to customize your day. Not only can you choose to snorkel, but you can add other activities such as fishing, relaxing sandbar trips, spearfishing, lobstering, and pretty much anything else you wish. They go to many of the low boat traffic areas that have an array of undisturbed wildlife to be seen. The boat can hold up to 6 people . Prices are negotiable when booking direct.
Tortuga Sailing Adventures offers private crewed charters for up to 6 guest aboard S/V Tortuga, a 42' luxury sailing catamaran. The all inclusive sailing tours are totally customized and rates are based on time aboard starting at 4 hour day trips at $106/pp. Overnight guests stay for up to 6 days/nights and are offered extreme vacation getaways to as far as the Dry Tortugas. The spacious yacht has all state of the art equipment & toys. The crew is experienced, friendly and professional. TortugaSailingAdventures.com provides in-depth details on all excursions.
So when not relaxing, eating or drinking, what else does Key West have to offer? Here are some "must sees": Sunset celebration at Mallory Square, with the requisite Mojito in hand, and be sure to watch the One Man Cat Show for amazing feline feats; Ernest Hemingway's House for Hemingway and cat lovers; Mel Fisher's Museum; Southernmost Point in the United States- touristy, but you just have to get a picture; The Lighthouse; a visit to the Key West Winery with free tasting and a very unique selection of wines; The Pepper Store for hot sauce lovers; BO's Fish Wagon for a Grouper Sandwich; The Green Parrot just to see the oldest bar in the Keys and its amazing jukebox; take the ferry, or fly if you can afford it, and spend the day in the Dry Tortugas National Park; Fausto's Gourmet Market, even just to look at the selections... this is just to name a few! Be sure to visit the Audubon House and enjoy the beautiful gardens. Take a tour of this house and take in the history. Do not miss the Butterfly Conservatory, it is beautiful. The Aquarium, although small, is also fun.
Shopping is another big thing to do. You won't find your typical mall here. From cheesy t-shirt souvenir shops, to designer (local and otherwise) clothing, art galleries, jewelry, antiques, there's something for everyone here. Browsing was never more fun! Do not miss the Kino store near Mallory Square. These are handmade leather sandals that are very affordable ($10-$12 per pair), come in a variety of styles and colors, and are oh so comfortable. The Sunset Celebration at Mallory Square also has many vendors selling their own handmade items.
Now that you know what there is TO DO (and this only scratches the surface) there are a few things NOT to do in Key West. DO NOT bring or rent a car - you can rent a scooter or a bike for a nominal charge (talk to those front desk people because sometimes they might even have a coupon or two) and that is the real way to see the island. There is also the CityTours Trolley that will drop you off at key tourist location spots throughout the city and pick you up while giving you local history along the ride. The trolleys run every 15 minutes, so it is a good way to get around to all of Key West's hot spots. DO NOT judge a book by its cover - some of the most "hole in the wall" places are the best and you will have a great time. DO NOT be surprised by anything you see or hear. Key West is a laid back place with very liberal ideas, which is a big part of its charm. Leave your pre-conceived notions at home and chill. That's how to appreciate Key West!!!