Key West is a prime destination for bachelor and bachelorette parties. There’s nightlife. There’s water sports. There’s delicious restaurants. And best of all, anything goes! Bond with your bros or connect with your gals and get a little wild in Key West before you get hitched with this guide to planning the ultimate Key West bachelor/bachelorette party.
First thing’s first: A great way to get around the island is by renting bicycles or electric cars, so make arrangements ahead of time or the day of your arrival. Once you’ve settled in, you’ll quickly realize the beauty of renting a Key West Vacation Home is that you’ll have your own private pool paradise during your bachelor/bachelorette weekend. Whether it’s nursing a hangover, soaking up the sun or night swimming after an evening on Duval, this is where you’ll make memories.
For a pool party scene, look no further than Dante’s at the Historic Seaport. Expect a lively crowd of both locals and visitors enjoying drink specials, bar bites and a DJ spinning on the weekends. Hit up Smathers Beach for an afternoon of sun, sand and surf that promises to have a festive party vibe, especially in the springtime.
Two words: Duval Crawl. Key West’s entertainment corridor is teeming with bars and clubs blaring live music and slinging strong drinks day and night. Start with Sloppy Joe’s and work your way up from there ducking into whichever scene strikes your fancy. And don’t forget—the open container law is lax and “to go” cups are a thing.
For the Bachelors
There’s nothing like a fishing charter for some serious male bonding. Whether it’s a backcountry flats fishing excursion or a deep sea adventure, put the beers on ice and hop aboard.
If fishing is not exactly your thing, there’s so much more to discover in Key West’s abundant waters from snorkeling to jet skiing, parasailing, paddle boarding and diving. Day drinking is also a beloved pastime and the Historic Seaport is an ideal spot to take in the views of the marina while downing a cold beer or bloody Mary at Schooner Wharf, Alonzo’s or Waterfront Brewery.
At lunchtime, head to Half Shell Raw Bar for fresh oysters, peel n’ eat shrimp and cold beers in an open air setting on the Historic Seaport.
Celebrate in style at A&B Lobster House, the only restaurant in Key West with a cigar bar. Indulge in prime steak, lobster, red wine and martinis followed by a nice stogie in the lounge after dinner. Here’s your Duval Street itinerary: Get your night started with craft beers at The Porch followed by a raucous sing-along with the band at Irish Kevin and then swing by the Green Parrot late night for root beer barrels (that’s a shot of root beer schnapps plunged into a rocks glass of Miller Light), darts and a killer jukebox. At some point, the night’s going to devolve into a trip to the Red Garter, so be prepared!
For the Bachelorettes
Get your morning started right with brunch at Blue Heaven on Petronia Street in the heart of Bahama Village. The sprawling backyard is shaded by ship’s sails and palm trees for a seriously chill vibe and the delectable menu includes surf and turf eggs benedict and banana pancakes. Petronia is also home to some of the island’s best boutiques, so checkout Besame Mucho and Wanderlust for a shopping afternoon. Don’t skip the chance to indulge in a spa day with your ladies at Ocean Key House offering rejuvenating spa packages that include time to unwind in a Japanese soaking tub.
For lunch, Two Friends is an awesome spot to enjoy the ambiance just off Duval Street with a grouper sandwich and a strong rum punch.
Enjoy dinner on the water at Pier House where they specialize in fresh seafood with an impressive wine list. Splurge and order a bottle of Champagne to toast the end of your singlehood. Afterwards, indulge your sweet tooth at the dessert only restaurant Better Than Sex for sexy desserts and glasses of wine with the rims dipped in chocolate or caramel.
Get a little wild later on Duval with a drag show at Aqua Nightclub followed by hooting and hollering from the balcony at the Bull & Whistle.