A Guide to the Perfect Valentine’s Day at the Historic Seaport

Planning a special Valentine’s Day can be very stressful. Not knowing what restaurant to make reservations for, what movie to get tickets to go see or being clueless on what gift to purchase. The Historic Seaport has made it easy for you with a guide to the perfect Valentine’s Day in Key West.

  1. Get your morning started with a cup of fresh coffee paired with a tasty breakfast sandwich at Cuban Coffee Queen or Fisherman’s Cafe. On the side of Cuban Coffee Queen is the popular mural that is full of color and the perfect Key West background to snap a picture with that special someone.

2. Walk along the harborwalk waterfront to your morning parasailing adventure for two and get the best view of Key West from high in the sky. We recommend booking your trip with Fury Water Adventures, Sebago Watersports or Sunset Watersports. All three companies are conveniently located at the Historic Seaport. Afraid of heights?  Not to worry, there are plenty of other water excursions. You and your Valentine can book a spot on a party cat, kayak or paddle board, snorkel or dive, or simply enjoy the sunset by setting sail with any number of Historic Seaport boat and sailing charters. Click HERE for the entire list.

Happy couple Parasailing in Dominicana beach in summer. Couple under parachute hanging mid air. Having fun. Tropical Paradise. Positive human emotions, feelings, joy.

3. Trust us when we say you won’t run out of restaurant options while at the Historic Seaport. Grab a bite to eat at any one of the following eateries and enjoy the flavors of Key West.

    1. B.O.’s Fish Wagon
    2. Conch Republic Seafood Company
    3. Half Shell Raw Bar
    4. Schooner Wharf Bar
    5. The Waterfront Brewery
    6. Turtle Kraals

Relax and savor every bite while watching tall ship schooners and catamarans come and go from the marina. *If you’re dining at The Waterfront Brewery, check out the rooftop for an amazing view of the Historic Seaport.  You might even get to hear tunes from anyone of the live music acts who frequent the Brewery. Turtle Kraals has a Tower Bar where you can eat and drink as well for a beautiful view.


4. Head down Lazy Way Lane for some shopping!

    1. AER Photography and Art Gallery
    2. Dragonfly Imports
    3. Stingray Steve
    4. Yours and Mayan Imports


There are always more unique and fun shops located at the Historic Seaport for you to browse through and find that perfect gift.

    1. Bumble Bee Silver Company
    2. Good Day on a Happy Planet
    3. Hammerhead Surf Shop
    4. Key West Bait & Tackle
    5. Local Color
    6. Mac’s Sea Garden


5. For a different dinner option than your standard sit-down restaurant, give Captain Alex Aller from Islescape Dinner Cruises a call. Celebrate love on the water aboard a romantic private sail, gourmet dinner and incredible view of the famous Key West sunset.


6. Once you dock at the marina, hop off and put on your dancing shoes! Head to Schooner Wharf Bar for live music and a drink to end the evening. Dance the night away to one of the many great performers who take the Schooner Wharf stage.


Leave the dinner and movie scene for another night and switch chocolates for conch fritters! Start planning an unforgettable adventure this Valentine’s Day at the Historic Seaport

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