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Trip List by pahhobbs

Key West Before It's Too Hot

May 10, 2006  My Love of Key West and All It Has To Offer
3.0 of 5 stars based on 19 votes

This is a list for first timers to Key West or for people who've only visited once or twice.

  • Explore locations featured in this Trip List: Key West
  • Category: Perfect weekend
  • Traveler type: Sightseeing, Shopping, Never been before
  • Appeals to: Couples/romantics, Honeymooners, Singles, Large groups, Tourists
  • Seasons: Winter, Spring, Summer, Fall
  • 1. Hemingway House

    This is the home that Ernest Hemingway and his wife owned and lived in while in Key West. Hemingway wrote a couple of his novels while living here. There is a lot of folklore about Ernest and his drinking days while in Key West. It is a great place to get the flavor of what the man was like.

  • 2. Old Time Trolley

    This is one of two "tour" type ways to get the history of the area as well as see the City. The Conch Train is the other. You board at Mallory Square and it makes 15? stops along the way. You can get on and off to explore what you've just learned about. It is a great way to see the entire City and what it has to offer and then go back to spend more time at what struck your fancy. Also a great way to go shopping and drop your bags at your hotel. If you plan this right, you can take the tour, do your shopping, have lunch , drop everything back at the hotel and get dropped back off at Mallory Square in time for Sunset Festival.

  • 3. Roof Top Restaurant

    This restaurant is in the Front Street area close to Mallory Square. You must go by and have a drink or even lunch/dinner. You sit high up in the tree tops and overlook the Front Street area (the end of Duval Street). In the evening they have twinkling lights which makes it very romantic. They make their own soups and chowders which are absolutely to die for! A margarita that is just about the best anywhere goes quite well.

  • 4. Mallory Square
    Mallory Square, Key West, Florida Keys

    Every evening just before the most beautiful sunset you will ever experience, many vendors and street performers gather on the boardwalk of Mallory Square. There are fire eaters, jugglers, a cat acrobatics show, magician, and many, many more. There is live music, drinks, food, etc. You simply must visit at least one night while in Key West. This is a really fun thing to do and great for singles, couples, honeymooners and families. There truly is something for everyone.

  • 5. Duval Street
    Duval Street, Key West, Florida Keys

    This street stretches about 4 miles from end to end. There is every shop you can imagine along with eateries and places for a nice cold beverage. This is one of the best people watching places in the world! You really have to spend an evening just strolling from one end to another. Chances are you will never make it without stopping in somewhere and not leaving! It is a challenge that you can extend to yourselves over and over again.

  • 6. Crowne Plaza Key West (La Concha)
    Crowne Plaza Key West La Concha, Key West, Florida Keys
    Show Prices
    Avg price: $415

    This is one of the best places to stay in all of Key West. It is a little pricey, but within walking distance to just about everything. A must do at this hotel is to go the the roof top bar and watch the sunset. It is absolutely incredible! There is a restaurant downstairs for a snack when you're through and they sometimes have entertainment in the evening.

  • 7. Green Parrot Bar
    Green Parrot Bar, Key West, Florida Keys

    This is one of the most fun places you could visit anywhere! This is a locals bar where you just never know what you are going to see. The bartenders are so much fun. They have the best juke box ever! The drinks are very reasonable and they serve popcorn all the time. It is located on the corner of Southard and Whitehead. Open every single day of the year -- even Christmas where it is the most fun of anywhere in town to spend the afternoon.

  • 8. Columbia Collection

    This is a great little shop on Duval Street just across the street from The Bull. They have local artists things as well as all kinds of whimsical things. Jewelry, cards and a few other things are offered here too. Once you go, you'll make a point to stop in every time you are in Key West.

  • 9. The Bull/Whistle Stop/Garden of Eden

    This is a watering hole with 3 levels. The first floor is The Bull. They have entertainment and an open air bar that looks over Duval Street. This is a very fun place for a drink or two. The Whistle Stop is another bar on the 2nd floor and the Garden of Eden is a "clothing optional" bar on the 3rd floor. During Fantasy Fest in October this is the best seat in town!

  • 10. Pepe's Cafe
    Pepe's Cafe, Key West, Florida Keys

    A locals favorite for breakfast, lunch or dinner. They make their own soups daily which are delicious. Try the steak smothered in pork chops for 2 for something to go home to tell your friends about. Outside seating and bar for people watching. They serve delicious fresh-squeezed margaritas.