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My Love Affair With Key West

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My experience with Key West spans over 25 years. Beginning with a couples getaway, followed by multiple visits with friends and family including planning and enjoying two family weddings. My children,now adults with children of their own, enjoyed bicycling the island, snorkeling, kayaking,shopping, visiting museums, going on Ghost Tours, sampling great and unusual food, marveling at the performers on Mallory Square and being exposed to art and music of every type. Adult adventures included visits to the Dry Tortugas, intimate dining spots and nightlife, music and entertainment for all tastes!

Good for
  • History Buff
  • Thrill Seeker
  • Shopping Fanatic
  • Art and Architecture Lover
  • Nightlife Seeker
  • Nature Lover
  • Foodie
  • Peace and Quiet Seeker
  • LGBT
  • Beach Goer
  • Luxury Traveller
  • Like a Local

10 Places

19 City Tips

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Map

10 Places

Sandy's Cafe

Restaurants

Fort Zachary Taylor Historic State Park

Historic Sites, Beaches, State Parks

Tropic Cinema

Movie Theatres

The Flaming Buoy Filet Co.

Restaurants

Blue Heaven

Restaurants

Better Than Sex - A Dessert Restaurant

Restaurants

Key West Butterfly and Nature Conservatory

Nature & Wildlife Areas

Fort East Martello Museum

Art Museums, History Museums

El Siboney Restaurant

Restaurants

Mallory Square

Piers & Boardwalks, Parks, Points of Interest & Landmarks

Mary S's City Tips

  • Deserves it's own post - The Flaming Buoy hidden on the corner of Packer and Virginia Streets. If you want fancy, go elsewhere. If you want great food, superlative service...
  • Art galleries featuring local and internationally known artists dot Old Town. My favorite international artist is Peter Lik; favorite local is the Red Door Gallery on Caroline.
  • Night life should include people watching on Duval at the Whistle Bar, dancing at the Green Parrot or Hog's Breath, Irish Kevin's or Captain Tony's! Must see - visit Inga at Aqua!
  • Eat reasonably priced but excellent Cuban food at El Siboney (it is easily accessible but not in the tourist area.) Eat brunch or dinner at Blue Heaven or Salute Sur La Mer.
  • Don't avoid the museums. East Martello: even the kids will want to go back. Hemingway House; the Little White House/Light House Museum; the Audubon House;
  • Do go to Mallory Square Sunset Celebration with it's local artisans selling their wares and amazing street performers including Cat Man. The resplendent sunset is the real star.
  • Don't try to navigate by car unless it is your last option. Rent bikes for your trip. Many vendors will give you a discount for the week and will drop off and pick up.
  • If you just need a break from the crazy, busy buzz of Duval, you must stop at the Butterfly Conservatory. Breathtaking and worth a revisit. Shop here for one of a kind items.
  • Plenty of places for iconic, reasonable sea food. I like to go one island over (Stock Island) to visit the traditional Rusty Anchor and the fabulous Hogfish Bar and Grill.
  • For romantic venues, go to Louie's ($$$), Kelly's ($$) (I am partial to this site because my son's reception was here), Santiago's, Cafe Marquesa and Better Than Sex for dessert.
  • My favorite places to shop for beautiful, one of a kind gifts or memories are Bessame Mucho in Bahama Village or Glass Reunions on Duval. I buy tee shirts at the Green Parrot.
  • So, you've been dancing and reveling all night and you want to get some great, greasy pizza to satisfy your late night craving. Bike up to Mr. Z's on Southard, right off Duval.
  • Sloppy Joe's is usually on most tourist's lists. It is crowded and over-hyped but the music is usually good and the food is fine. The original is Captain Tony's, a few doors down.
  • Get at least one photo taken in front of the massive "90 miles to Cuba" buoy. Be prepared to wait in line.
  • Kayaking in the mangroves, parasailing, jet skiing, scuba diving....many great choices for adrenaline junkies. Go to the south side of the island; less busy.
  • A trip to the Dry Tortugas on a Fast Cat is worth every penny. The snorkeling is epic, the tour of the Fort is memorable (very hot!). The island is inhabited only by park rangers.
  • Have a sandwich at BO's Fish Wagon, fresh oysters, shrimp at Turtle Kraals, Half Shell Raw Bar or watching the passing parade at Caroline's on Duval.
  • Places to stay: Coconut Beach is a time share but sometimes has rentals available. Ambrosia is lovely. Alexander Palms or Angela's are more affordable, clean, great staff.
  • You are biking the streets and are hit with a pop up shower. Have a drink at the Green Parrot. Nice mix of tourists and locals in the oldest bar in KW! Best music in town.
  • Sandy's Cafe
    Restaurants (Latin, Cafe, Cuban)
    See more photos
    Mary S Says:

    You want to eat a great Cuban sandwich but are chilling at the pool? Call Sandy's! They deliver!

    Good for
    • Family
    From the community
    Ranked #76 of 343 restaurants in Key West
    Certificate of Excellence 2014
    • Best cuban in towm 19/10/2018
    • It was ok 03/10/2018
    • Sandy's Cafe
    Address:
    1110 White St
    Key West, FL 33040-3394
    Phone:
    +1 305-295-0159
    Hours:
    Mon - Fri
    5:00 am - 12:00 am
    Sat - Sun
    7:00 am - 12:00 am
    Other:
  • Fort Zachary Taylor Historic State Park
    Historic Sites, Beaches, State Parks
    See more photos
    Mary S Says:

    A national park with a beach you can snorkel from. Pack a lunch. It is worth a day trip. There are picnic tables, shady trees and an historic fort to explore.

    Good for
    • Beach Goer
    • Thrifty Traveller
    • Like a Local
    • Solo
    • Friends
    • History Buff
    • Couples
    • Senior
    • Family
    Tips
    • Minimal fee to enter. Stop at the Green Parrot for a drink on the way back to your hotel!
    Plan to stay:
    More than 3 hours
    From the community
    Ranked #26 of 129 things to do in Key West
    Certificate of Excellence 2014
    • Absolutely beautiful spot - a real treat. 19/10/2018
    • Truly beautiful state park. 18/10/2018
    • Fort Zachary Taylor Historic State Park
    Address:
    601 Howard England Way
    Key West, FL 33040-8395
    Phone:
    +1 305-292-6713
    Hours:
    Sun - Sat
    8:00 am - 5:00 pm
    Other:
  • Tropic Cinema
    Movie Theatres
    See more photos
    Mary S Says:

    Tropic Cinema is a gem off the main drag on Duval. Need a litte quiet time? Check the listings for films or events at this lovely, vintage cinema.

    Good for
    • Peace and Quiet Seeker
    • Trendsetter
    • Hidden Gems
    • Like a Local
    • Solo
    • Friends
    • Couples
    • Senior
    • Family
    • Art and Architecture Lover
    Tips
    • Tell them Jane sent you!
    Plan to stay:
    2-3 hours
    From the community
    Ranked #2 of 13 Fun & Games in Key West
    Certificate of Excellence 2014
    • UnMatched 17/09/2018
    • Old School Theatre 06/08/2018
    • Tropic Cinema
    Address:
    416 Eaton St
    Key West, FL 33040-6512
    Phone:
    +1 877-761-3456
    Price range:
    USD 11 - USD 11
    Other:
  • The Flaming Buoy Filet Co.
    Restaurants (American, Caribbean, Seafood)
    See more photos
    Mary S Says:

    Already reviewed this restaurant but it is one of my favorites. Great food, fabulous service!

    Good for
    • Foodie
    • Must See
    • Friends
    • Couples
    • Senior
    • Family
    Tips
    • Not an extensive wine list but great choices!
    Plan to stay:
    2-3 hours
    From the community
    Ranked #9 of 343 restaurants in Key West
    Certificate of Excellence 2014
    • Great restaurant! 23/09/2018
    • A gem a bit remote from downtown. 22/09/2018
    • The Flaming Buoy Filet Co.
    Address:
    1100 Packer St
    Key West, FL 33040-3263
    Phone:
    +1 305-295-7970
    Price range:
    USD 9 - USD 32
    Hours:
    Sun - Sat
    6:00 pm - 9:30 pm
    Other:
  • Blue Heaven
    Restaurants (American, Caribbean)
    See more photos
    Mary S Says:

    The best brunch I have ever had! I love the Rooster special and their Eggs Benedict. Try the Lobster Benedict in season.

    Good for
    • Foodie
    • Friends
    • Couples
    • Senior
    • Family
    • Trendsetter
    Tips
    • There are chickens running around the premises. Great gift shop. Go early or plan to have a Mimosa or Bloody Mary while you wait.
    Plan to stay:
    1-2 hours
    From the community
    Ranked #23 of 343 restaurants in Key West
    Certificate of Excellence 2014
    • Breakfast 23/10/2018
    • Loved the atmosphere! 22/10/2018
    • Blue Heaven
    Address:
    729 Thomas St
    Key West, FL 33040-7334
    Phone:
    +1 305-296-8666
    Price range:
    USD 15 - USD 28
    Hours:
    Sun - Sat
    8:00 am - 10:30 pm
    Other:
  • Better Than Sex - A Dessert Restaurant
    Restaurants
    See more photos
    Mary S Says:

    Desserts that you will remember always served in a romantic atmosphere!

    Good for
    • Foodie
    • Must See
    • Friends
    • Couples
    • Trendsetter
    Tips
    • After dinner, take a bike or stroll here for dessert. Convenient to Duval but darkly romantic.
    Plan to stay:
    1-2 hours
    From the community
    Ranked #21 of 343 restaurants in Key West
    Certificate of Excellence 2014
    • Deliciously Decadent 21/10/2018
    • Disappointed - wouldnt go back 19/10/2018
    • Better Than Sex - A Dessert Restaurant
    Address:
    926 Simonton St
    Key West, FL 33040-7448
    Phone:
    +1 305-296-8102
    Price range:
    USD 7 - USD 14
    Hours:
    Thu - Tue
    6:00 pm - 12:00 am
    Other:
  • Key West Butterfly and Nature Conservatory
    Nature & Wildlife Areas
    See more photos
    Mary S Says:

    I have visited multiple times. Get out of the heat and visit the exquisite gardens with places to sit and enjoy the main attraction - the population of gorgeous butterflies.

    Good for
    • Peace and Quiet Seeker
    • Must See
    • Solo
    • Friends
    • Couples
    • Senior
    • Family
    • Nature Lover
    Tips
    • There is a fee to enter. The gift shop is worth a visit on it's own.
    Plan to stay:
    1-2 hours
    From the community
    Ranked #1 of 129 things to do in Key West
    Certificate of Excellence 2014
    • What a surprise! 23/10/2018
    • Interesting collection of Butterflies 23/10/2018
    • Key West Butterfly and Nature Conservatory
    Address:
    1316 Duval St
    Key West, FL 33040-3132
    Phone:
    +1 305-296-2988
    Hours:
    Sun - Sat
    9:00 am - 5:00 pm
    Other:
  • Fort East Martello Museum
    Art Museums, History Museums
    See more photos
    Mary S Says:

    This museum is my favorite "off the beaten track" musuem. A mixture of history, art and KW quirkiness! Early history with weird local legends interspersed.

    Good for
    • Peace and Quiet Seeker
    • Must See
    • Hidden Gems
    • Solo
    • Friends
    • History Buff
    • Couples
    • Senior
    • Family
    • Art and Architecture Lover
    Tips
    • Donation required. Go to the top of the tower for a spectacular view; visit Robert the doll and go through the Cuban history wing.
    Plan to stay:
    1-2 hours
    From the community
    Ranked #33 of 129 things to do in Key West
    Certificate of Excellence 2014
    • Came for the doll 18/10/2018
    • Very interesting spot 03/10/2018
    • Fort East Martello Museum
    Address:
    3501 S Roosevelt Blvd
    Key West, FL 33040-5209
    Phone:
    +1 305-296-3913
    Hours:
    Sun - Sat
    9:30 am - 4:30 pm
    Other:
  • El Siboney Restaurant
    Restaurants (Caribbean, Latin, Spanish, Soups, Cuban)
    See more photos
    Mary S Says:

    Out of the way restaurant with a "mom and pop" feel. Great Cuban food even kids will love! Take the family or make it a date night. Have a carafe of sangria.

    Good for
    • Foodie
    • Thrifty Traveller
    • Solo
    • Friends
    • Couples
    • Senior
    • Family
    Tips
    • Economical. No reservations. Not open on Sunday!
    Plan to stay:
    1-2 hours
    From the community
    Ranked #35 of 343 restaurants in Key West
    Certificate of Excellence 2014
    • Had lots of recommendations, but.. 22/10/2018
    • Best cuban food i have ever had 20/10/2018
    • El Siboney Restaurant
    Address:
    900 Catherine St
    Key West, FL 33040-3202
    Phone:
    +1 305-296-4184
    Price range:
    USD 1 - USD 20
    Hours:
    Sun - Sat
    11:00 am - 9:30 pm
    Other:
  • Mallory Square
    Piers & Boardwalks, Parks, Points of Interest & Landmarks
    See more photos
    Mary S Says:

    The arts and crafts by local artisans would be a good enough reason to come to Mallory Square for Sunset Celebration. The street performers and the sunset are fabulous.

    Good for
    • Must See
    • Beach Goer
    • Solo
    • Friends
    • Couples
    • Senior
    • Shopping Fanatic
    • Family
    • Nature Lover
    Tips
    • Find The Cat Man, Dominique. My personal favorite. Food and drinks are available too.
    Plan to stay:
    2-3 hours
    From the community
    Ranked #3 of 129 things to do in Key West
    Certificate of Excellence 2014
    • Always fun 22/10/2018
    • COOL SPOT TO WATCH THE SUN SET OVER THE WATER 22/10/2018
    • Mallory Square
    Address:
    400 Wall St
    Key West, FL 33040-6633
    Other:
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