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Trendy Guide to Key West

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Full of quirky locals, chic boutiques, and hip venues, Key West is the perfect destination for trendy travelers. Spend a cool 24-hours in this eclectic area, with my guide to the hippest breakfast, lunch, and dinner spots, plus a few must-see attractions to keep you entertained in between.

Good for
  • History Buff
  • Foodie
  • Trendsetter
  • Like a Local

8 Places

3 City Tips

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Map

8 Places

Blue Heaven

Restaurants

The Ernest Hemingway Home and Museum

Specialty Museums

The Oldest House

Specialty Museums

Lagerheads Beach Bar

Restaurants

Besame Mucho

Gift & Specialty Shops

The Schooner Hindu, Hindu Charters

Boat Tours

El Meson de Pepe

Restaurants

Roof Top Cafe

Restaurants

Pjk's City Tips

  • Key West is an easily walkable city with a large number of attractions close to each other. You will always find more to see and do by walking from A to B.
  • Most of these recommendations are in the Old Town and easy to get to on foot.
  • Key West is an extremely casual city — slacks and a long-sleeve shirt are considered dressing up! However, if dining in an upscale restaurant, check the dress code in advance.
  • Blue Heaven
    Restaurants (American, Caribbean)
    See more photos
    Pjk Says:

    One of the more unique places to have breakfast in Key West, here you'll dine in a garden among chickens and cats. Expect sawdust on the ground, every table to have a different theme, and amazing Lobster Eggs Benedict!

    Good for
    • Must See
    • Trendsetter
    • Like a Local
    Tips
    • Hope for at least a half hour wait so that you can enjoy a Bloody Mary at the bar in the back.
    Plan to stay:
    1-2 hours
    From the community
    Ranked #22 of 347 restaurants in Key West
    Certificate of Excellence 2014
    • Amazing Lobster Benedict!!! 11/17/2018
    • Key West favorites 11/17/2018
    • Blue Heaven
    Address:
    729 Thomas St
    Key West, FL 33040-7334
    Phone:
    +1 305-296-8666
    Price range:
    $15 - $28
    Hours:
    Sun - Sat
    8:00 AM - 10:30 PM
    Other:
  • The Ernest Hemingway Home and Museum
    Specialty Museums
    See more photos
    Pjk Says:

    One of Key West's most famous citizens, Hemingway, used this house on Whitehead Street as a base for fishing, entertaining friends, and, of course, writing his masterpieces. His beautiful former home makes for an interesting visit for fans and non-fans alike.

    Good for
    • History Buff
    • Trendsetter
    • Like a Local
    Tips
    • The tour lasts 30 minutes. Set aside some additional time afterwards to explore a little more on your own, and to visit the bookstore/gift shop.
    Plan to stay:
    Less than 1 hour
    From the community
    Ranked #2 of 130 things to do in Key West
    Certificate of Excellence 2014
    • Cats, cats, cats - oh and yes - Hemingway... 11/17/2018
    • Just awesome 11/17/2018
    • The Ernest Hemingway Home and Museum
    Address:
    907 Whitehead Street
    Key West, FL 33040-7473
    Phone:
    +1 305-294-1575
    Price range:
    $13 - $13
    Hours:
    Sun - Sat
    9:00 AM - 5:00 PM
    Other:
  • The Oldest House
    Specialty Museums
    See more photos
    Pjk Says:

    Just a few blocks down from Hemingway House, this museum makes for a great stop off on Duval Street, and climbing its tower for the 360 degree view of the city and the ocean is a must-do to capture that iconic postcard-perfect photo.

    Good for
    • Must See
    • Art and Architecture Lover
    • Trendsetter
    Tips
    • The area around the museum has much to see, including the Sponge shop, various gift shops, and the Clinton Square Mall.
    Plan to stay:
    Less than 1 hour
    From the community
    Ranked #27 of 130 things to do in Key West
    Certificate of Excellence 2014
    • Amazing Story 11/10/2018
    • The Oldest House 11/04/2018
    • The Oldest House
    Address:
    322 Duval St
    Key West, FL 33040-6510
    Phone:
    +1 305-294-9501
    Hours:
    Mon - Tue
    10:00 AM - 4:00 PM
    Thu - Sat
    10:00 AM - 4:00 PM
    Other:
  • Lagerheads Beach Bar
    Restaurants (American, Bar, Seafood)
    See more photos
    Pjk Says:

    The kind of place that you might not stumble across on your own, Lagerheads is a small restaurant on Simonton Beach where you can enjoy a drink, a fish taco or sandwich, and the lovely sights — including the boats going to and fro.

    Good for
    • Foodie
    • Peace and Quiet Seeker
    • Beach Goer
    • Trendsetter
    • Hidden Gems
    Tips
    • Kick off your sandals and wade in the water.
    • Find Front Street and then walk towards the ocean on Simonton Street.
    Plan to stay:
    1-2 hours
    From the community
    Ranked #45 of 347 restaurants in Key West
    Certificate of Excellence 2014
    • Fun afternoon on the beach 11/06/2018
    • Relaxing 10/30/2018
    • Lagerheads Beach Bar
    Address:
    0 Simonton Street
    Key West, FL 33040
    Phone:
    +1 305-509-7444
    Price range:
    $5 - $15
    Hours:
    Sun - Sat
    10:00 AM - 8:00 PM
    Other:
  • Besame Mucho
    Gift & Specialty Shops
    Pjk Says:

    Time for a little upmarket shopping. Besame Mucho is one of the more luxurious boutiques in Key West, offering an assortment of lovely lotions, jewelry and clothing. Just try not to hum the song as you shop!

    Good for
    • Must See
    • Shopping Fanatic
    • Trendsetter
    Tips
    • Say "Hello!" to, but do not pet Betty the cat. She's usually sleeping here on the couch.
    Plan to stay:
    Less than 1 hour
    From the community
    Ranked #20 of 121 Shopping in Key West
    • An exquisitely well-curated boutique 06/14/2018
    • So Happy To Find YOU! 12/29/2017
    • Besame Mucho
    Address:
    315 Petronia St
    Key West, FL 33040-7327
    Phone:
    +1 305-294-1928
    Other:
  • The Schooner Hindu, Hindu Charters
    Boat Tours
    See more photos
    Pjk Says:

    A two-hour sunset sail on one of Key West's smaller sailboats is the ultimate 'must-do' evening activity, and perfect for couples, friends and families alike. Don't forget your eye-patch!

    Good for
    • Peace and Quiet Seeker
    • Must See
    • Trendsetter
    • Nature Lover
    Tips
    • As you sail out of the harbor, take note of the Tiki bar at The Galleon and the sunset pier at The Ocean Key (both hotels) for future reference!
    Plan to stay:
    2-3 hours
    From the community
    Ranked #14 of 266 Boat Tours & Water Sports in Key West
    Certificate of Excellence 2014
    • Birthday gift from friends............. 07/31/2018
    • Sunset cruise 07/30/2018
    • The Schooner Hindu, Hindu Charters
    Address:
    211 William St
    C-Dock at the foot of Margaret St.
    Key West, FL 33040-6644
    Phone:
    +1 305-509-1771
    Hours:
    Mon
    8:00 AM - 6:00 PM
    Tue - Sun
    9:00 AM - 5:00 PM
    Other:
  • El Meson de Pepe
    Restaurants (Caribbean, Latin, Spanish, Cuban, Central American)
    See more photos
    Pjk Says:

    One of the best bars for a late-night drink — a mojito perhaps — and to enjoy a live Cuban band is here at El Meson. This venue is just off Mallory Square where the sunset celebration is held; the perfect pre-cocktail warm-up.

    Good for
    • Must See
    • Trendsetter
    • Nightlife Seeker
    Tips
    • Sampling the stuffed plantains or masitas at the bar isn't out of the question.
    • There is a cigar maker inside the building.
    Plan to stay:
    Less than 1 hour
    From the community
    Ranked #137 of 347 restaurants in Key West
    Certificate of Excellence 2014
    • good food a little overpriced 11/16/2018
    • On Mallory Square 11/15/2018
    • El Meson de Pepe
    Address:
    410 Wall St
    Mallory Square
    Key West, FL 33040-6633
    Phone:
    +1 305-295-2620
    Price range:
    $18 - $18
    Hours:
    Sun - Sat
    11:00 AM - 10:00 PM
    Other:
  • Roof Top Cafe
    Restaurants (American, Caribbean, Seafood, Soups)
    See more photos
    Pjk Says:

    A late-night dinner at one of Key West's more upscale restaurants; what better way to round off a fabulously chic day of exploring! Share an appetizer, two main courses of either meat or seafood, and a nice bottle of wine. You can't go wrong here.

    Good for
    • Foodie
    • Must See
    • Luxury Traveler
    • Trendsetter
    Tips
    • Reserve a table outside on the second floor deck overlooking the Wrecker's Tower.
    • The sautéed clams alone are worth the entire dinner.
    Plan to stay:
    1-2 hours
    From the community
    Ranked #114 of 347 restaurants in Key West
    Certificate of Excellence 2014
    • What happened?!? 11/12/2018
    • Always a good choice 10/24/2018
    • Roof Top Cafe
    Address:
    308 Front St
    Key West, FL 33040-6615
    Phone:
    +1 305-294-2042
    Price range:
    $8 - $42
    Hours:
    Sun - Sat
    11:00 AM - 10:00 PM
    Other:
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