It’s Friday morning and you just stepped off your day-cruise from whatever gorgeous location you were just at. You have landed afoot at the Key West Historic Seaport. It’s early, you need coffee and you especially need to figure out how to maximize your time as you only have twelve-hours before you sail off to the next lovely location. 

1. But first, coffee. 

Follow the sound of the roosters, literally. Nestled on Margaret Street, you’ll find the deliciously, strong, coffee from one of our favorite places, Cuban Coffee Queen. With all of the Cuban Coffee specialties that you could have ever dreamed of and over 20 types of breakfast sandwiches and other easy-to-eat-with-your-hand delicacies, this yummy establishment will not disappoint. Their coffee is strong but their mantra is stronger — “Drink more Cuban Coffee and do stupid things faster.”

       2. Going up, on a Friday. 

Technology is a beautiful thing. In the time it took you to drink your coffee (and order one to go, duh) you have managed to find and book a parasailing ride with one Key West’s hottest watersport companies, Sunset Watersports. There is no better view of the Key West Historic Seaport than from high above the sea and up in the air. In those 8 to 10 minutes floating in the sky and imagining life as a bird, it is impossible not to feel blissfully happy with your birds-eye view of Key West. Regardless of any fear you may have, there truly is no better way to jumpstart your morning.  

        3. You’re on island-time, baby!

• Disclaimer, this blog is being written by someone who is terrified of heights and after pushing herself to the limit of parasailing 300 feet in the air — I need a drink despite the time.  

So you are on island time, you have approximately 8ish hours left to play with and (like me) you need a celebratory “I was-just-suspended-300-feet-in-the-air” drink.  Located in the heart of Old Town, is the wonderfully refreshing Waterfront Brewery. With a rotating assortment of beers brewed on-site and a tasty selection of seafood, your options are seemingly endless. From their signature Crazy Lady beer to their Lazy Way IPA or Island Life Lager, you have officially stepped into a beer lovers haven. Brewed with local honey and that tasty subtle goodness, we highly recommend their Crazy Lady Honey Blonde! Paired with their dangerously delicious seafood ceviche appetizer, yeah, you may never return home. (Not sorry).

       4. Two birds, one Key West stone. 

With about six hours before your cruise leaves you stranded, you and your group have literal moves to make. Voted one of Key West’s premier shopping locations and with over ten shops to choose from, get your vitamin-c fix while exploring the Historic Seaport’s waterfront shopping along our famous Harborwalk. From art galleries to surf shops or authentic Key West treasures, you cannot go wrong with some Key West retail therapy. We take a size in everything at Hammerhead Surf Shop in case you were wondering. 

• Side note, to truly maximize your time, we highly recommended detouring for about thirty minutes, grabbing a fresh-squeezed lemonade from Fishermans Cafe and visiting the wonderfully renovated Sails to Rails museum across the street from Local Color (fantastic shop with the perfect selection of jewerly and him & her apparell) on Caroline street. With state-of-the-art exhibits, unique artifacts and the only scale model of Fort Jefferson Museum at the Dry Tortugas, you’ll be happy you made the decision to stop. You can even take all the credit for this wonderfully genius idea. You’re welcome.

       5. 5 o’clock + somewhere = who cares 

So it’s 5 o’clock and happy hour has commenced all over Key West. Live music has taken over the sounds of roosters and seagulls and you are torn on how you want to spend your last few hours at the Historic Seaport. With their blunt slogan in tow, “for fresher seafood, you’ll have to catch it yourself,” Conch Republic Seafood Company truly lives up their all the hype surrounding their establishment. 

Continuously voted one of the best happy hours in all of Key West, Conch Republic Seafood Company not only mixes up some of the best cocktails and offers the hottest daily entertainment but they serve the freshest seafood on the island. Every morning their boats tirelessly strive to reel in the freshest catch. We can assure you, there is no better way to compliment your overall experience than visiting one of the island’s most beloved restaurants. 

       6. Do it for the gram! 

So your cruise leaves relatively soon, you have dabbled in happy hour and you are now feeling adventurous.  Located approximately two minutes from Conch Republic Seafood Company (but putting you further away from where your cruise ship dropped you off at) is the world-famous Schooner Wharf Bar and Galley. Their second-floor tower bar makes for not only one of the best photo-ops in all of Key West but is one of the hottest locations to catch that quintessential Key West sunset.

The Key West Historic Seaport has something for everyone. Conveniently located in Old Town, the Key West Historic Seaport has done a phenomenal job of honoring its past and holding on to its character. Evolving into 20 acres of world-class dining, one of a kind shops, live music, museums, year-round events and a variety of watersports & fishing excursions, the famous “Welcome to Paradise” could not ring truer when you are here. Whether you are visiting for a weekend getaway or on a twelve-hour day cruise, our historic roots have truly laid down the foundation for a modern yet preserved and thriving seaport. 

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• Sunset Watersport image is provided via Sunset Watersports Instagram.