Travel Addicts: Key West

Do you love traveling? Do you love making money? Do you hate spending that love money on overly expensive hotels and sightseeing tours? Fear not fellow Outblushers, there is a new travel sheriff in town! Ashley, Outblush Operative, will be helping those bitten by the wanderlust bug plan their upcoming vacays in style...and on the cheap! What more could a gal ask for?

Erin writes:My parents are planning a trip to Key West in January to celebrate my dad getting through radiation treatments. He'll be weak, but he's determined to do outdoors stuff like biking and walking around the historic city area. Can you suggest some things to do that would excite both young and middle aged couples? Budget is not an issue, and there will be no children attending.

Wow! The news about your father is amazingly wonderful, Erin! I know through personal experience how difficult radiation can be, but I also know how difficult it is for the family members as well. So kudos to all of you for getting through the big fight! I'm also handing out kudos to having such rockin' parents (Key West? Really?!) Envy is green, and so am I. You guys really picked a fantastic place for January weather, and with an open budget the sky is the limit! I hope ya'll have a blast - you most certainly deserve it!!

1) Old Town Trolley Tours - I know it is kind of kitschy, but they are wonderful (the one in Savannah is a-ma-zing). Not only do you get a uniquely entertaining tour guide, but you also have the option of jumping on and off the trolley as little (or as much) as you want. There are 12 stops in Key West, and an absurd amount of things to keep you all busy. This also gives your dad the option of taking it easy, while still being outdoors and in the center of the action.

2) Sunset Dinner Cruise - Islescapes is a wonderful way to enjoy the ocean if swimming in it isn't your thing (Jaws, anyone?). Islescapes provides a 33-foot yacht and a personal chef! Not only do they specialize in the beautiful Key West sunset dinner cruise, they also provide private snorkeling expeditions. The price is a teensy bit up there (in comparison to hanging out on dry land), but the views are breathtaking and the experience would be wonderful!

3) The Key West Food & Wine Festival - This looks freakin' fantastic! Food? Wine? People watching? Where do I sign up? This is a wonderful way to really get the local flare in one location. (Did I mention wine?) Loads of wine, food, cooking classes, and local funky events. My wine rep cousin hit this place up last year, and had nothing but rave reviews for it. This runs from January 27-30.

4) Dry Tortugas National Park - This place is stunning. It is a preserve for Fort Jefferson and the Dry Tortugas (Dry Turtles). It boasts amazing coral reefs along with the legend of numerous shipwrecks and buried treasure (Aaaaarrrr Matey!!!). The snorkeling that can be done here is supposed to be out of this world, as is the saltwater fishing and bird watching. The island is only accessible via seaplane or ferry. (Trivia Time! Fort Jefferson is the largest masonry structure in the Western Hemisphere!! Ooooh! Aaaaah!)

5) Key West Cemetery - I know, I know....doom and gloom, doom and gloom. Normally cemeteries are NOT my thing, but this place is so quirky and embodies (cymbal strike!) such a quirky and uniquely Key West flare, that you have to check it out. Humorous headstones with epitaphs like "I told you I was sick" litter the grounds, with some headstones stacked several high. Go check it out - you will leave with some truly unique and hysterical pictures and memories!

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Prudence Booker

Posted on 10.13.10 at 2:47 PM

I have been planning a January trip to Key West and this list of great things to do is just what I need to complete my plans. Thanks OutBlush!


Posted on 10.13.10 at 3:43 PM

I've been meaning to go to Key West and will definitely have to check that quirky cemetery out! Yaaaarrrrrrgg!


Posted on 10.13.10 at 3:48 PM

There is no place like Key West; I love it and would move there in a NY minute. Just know, it will be crowded but friendly. The food is beyond belief. The Southernmost on the Beach has a great restaurant.


Posted on 10.13.10 at 4:16 PM

Also... second the Trolley Tours! And the Maritime Museum. And the Hemingway House! Mallory Square at sunset is the place to be.

One Ring to Rule Them All

Posted on 10.13.10 at 4:52 PM

I think somebody knew that ;*)

Y'all have fun!


Posted on 10.14.10 at 5:51 AM

Great summary! I've only been to Key West once, and it was a few years ago, but after reading this article, I'd love to go back! to convince husband that we could use a vacation...


Posted on 10.14.10 at 1:19 PM

Don't forget to just take a night to go to Mallory Square and see one of the best sunsets in the world. They have street performers and artists there for you to watch while you sit there and wait for the sun to go down. I would get there about an hour before sunset. I love just sitting there watching the boats/ocean. Good times with good friends. And it's FREE!


Posted on 10.15.10 at 5:26 AM

Just got back from Key West a few months ago! Listen to the other outblushers! Mallory Square at sunset is a MUST. El Meson De Pepe restaurant at Mallory Square was the best meal we had (have the sangria!) Don't forget SNORKELING! The fish are gorgeous down there. Have fun!

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