A Key West Bachelor Party City Guide to Plan Your Weekend

Admittedly, Key West can be tricky to get to—it requires a flight with connections or a road trip from Miami—but the effort is rewarded with a laid back beach town full of fun energy. A Key West bachelor party is the ultimate guys' weekend for the groom looking to spend time in the sun or on the water, drink plenty of frozen cocktails, or eat delicious seafood. While you won't find Vegas-style nightlife in this southernmost point of the Sunshine State, you will find plenty of character in this one-of-a-kind destination.

What Are Some Key West Bachelor Party Ideas?

Key West is known for its charm and quirk. It's where Jimmy Buffett created the sailor-inspired Margaritaville, and where Hemingway penned some of his best works. But you don't have to be Parrotthead or bibliophile to enjoy this tropical paradise—you just need to embrace the low-key charm with adventures on land and at sea. (And check out The Knot Shop for group gifts to make more of the ultimate weekend.)

For the Pirates at Heart

There is plenty to do on the water in Key West—and plenty of water to be found. For starters, you and the guys can charter a boat for sportfishing, or if you'd rather be in the water, a boat can be chartered for a half day of snorkeling Key West's beautiful reefs. Then there are water sports, including parasailing and jet skiing, a sunset sail that includes a full bar while you take in the sights, or kayaking around Island T'ing on an eco-tour.

For the Land Lubbers

There's plenty of fun to be had on shore, too. Take a tour of Hemingway's House and it's famous six-toed cats, bike the entire perimeter of the Key to the southernmost point of Florida, or take a seafood-lover's tour that includes tastings and insight into Key West's unique history and culture.

For the Drinkers

Home of Margaritaville, you won't be wanting for places to drink in Key West. From a Key West pub crawl along its famous Duval Street to a rum tasting at Key West First Legal Rum Distillery and tropical drinks at the famous Willie T's, there are plenty of opportunities to indulge.

What Do You Do at a Bachelor Party in Key West?

There's a lot to do in Key West, but you can easily fit everything in—from kayaking and sailing to drinking and eating—using our ultimate three-day Key West bachelor party itinerary.

Day 1

Morning: Start the day with breakfast or lunch at The Breakfast Club, too, a great spot that serves comfort food classics including five types of eggs benedict (try the lobster bene), five styles of rostis, and a monster burrito. Oh, and did we mention 12 varieties of bloody Mary's?

Afternoon: Get to know the town you'll be staying in by renting bikes and exploring Key West. Bikeman Bike Rentals delivers bikes to your hotel or AirBnB and offers multiple day rentals so you can use your wheels to get around all weekend. After getting the lay of the land, head to Dante's Key West for its pool bar. Though not as rowdy as a Vegas-style pool party, Dante's pool gets packed on the weekends with locals and tourists alike who want to enjoy good drinks, a live DJ, and delicious bar food. Tiki bars surround the pool, and you can saddle up at a poolside cabana or table with your group (no reservations are taken, so get here a little early if you want to grab a good spot).

Evening: If you can manage one more adventure, plan for a later dinner tonight so you can do some after dark paddling. Heading out at sunset, you'll make your way in LED-bottom kayaks or paddle boards to enjoy the Florida coast at night, a one-of-a-kind experience. Don't worry about cleaning up before heading out for the night (remember: Key West is super casual). Dinner and drinks tonight is at the Stoned Crab, where everything is caught fresh and locally (try a build-your-own steamer and definitely get a seafood tower for the table). For your first night out head to Sloppy Joes where you can listen to live music while enjoying a rotating list of beers. (If you had a guy miss out on the weekend, they can join in on the fun by tuning into the bars four live web cams!)

Day 2

Morning: Get an early start to the day with a quick breakfast at Keys Coffee Co., where you can grab cold brew, lattes, or Cuban coffees and delicious breakfast sandwiches like the Havana (grilled ham, eggs, and swiss on Cuban bread) or the Sunrise Tacos (two sunny-side up eggs, with bacon, ham, cheese, and sriracha on a corn tortilla) along with breakfast pastries and bagels.

Afternoon: Today will be spent on the water: Book a "Do It All Adventure" with Sunset Watersports for the ultimate day of play. On this six hour boat ride, you'll get a chance to snorkel, paddle board, hydro bike, kayak, water ski, and kneeboard, plus have your fun on inflatable slides, banana boat rides, a watery climbing wall, and water trampolines. Lunch, sodas, and unlimited draft beer are included in the package, and there's a cash bar on board too.

Evening: After cleaning up a bit, head to the world famous Willie T's for happy hour. Here you'll find a large assortment of tropical cocktails, including their beloved mojitos, daily specials, and plenty of live music. Then head to dinner at El Meson de Pepe for authentic Cuban fare including ropa vieja and churrasco. After you've filled up, it's time to hit Key West's Duval Street, home to its best and most lively bars. Consider booking a pub crawl to make sure you hit as many as possible, or guide yourselves to spots like Flying Monkeys Saloon (for frozen drinks), Rick's Upstairs (a great place for dancing and DJs), The Bull (enjoy great cocktails in this old-school dive and outdoor space), and Captain Tony's Saloon (a Key West treasure).

Day 3

Morning: Treat yourselves to brunch at La Grignote, a French-style cafe with made-fresh daily pastries, croissant breakfast sandwiches, and Belgian waffles, plus coffee, tea, beer, and fresh mimosas.

Afternoon: If you're up for another day on the water, consider chartering a boat and guide to take you for the ultimate day of sportfishing, where you'll reel in big catches like tuna and marlin. If you'd rather stay on land, plan a trip to Key West First Legal Rum Distillery for a behind-the-scenes tour, tasting, and mojito-making class.

Evening: For your last night, head to happy hour at Mangoes back on Duval Street where the big open-air patio looks out on all the action. Then it's dinner time at Hog's Breath, where you'll feast on fresh oysters, Gulf shrimp, stone crab claws, and entrees including whole hog bbq nachos, baja fish tacos, and the hog dog—a quarter-pound char-grilled hot dog with relish, chopped onion, and housemade potato chips. Choose between the Rum Bar at the Speakeasy Inn, the Green Parrot (a Key West institution for drinks and live music), or the Garden of Eden clothing-optional rooftop bar on top of The Bull for your last night out.

Where Should I Stay in Key West for a Bachelor Party?

Though it may take some effort to get there, Key West is a small town—only about 7 square miles—and you can walk or bike to just about every destination once you arrive in town. If you want to be close to the heart of the action, stay near Duval Street, but you'll be hard-pressed to find a bad location in this charming key.

Best Key West Bachelor Party Hotels

• Pier House Resort and Spa is a luxe spot to stay right on the water in Key West in walking distance to Mallory Square, Hemingway House, and plenty of watersport action.
• The Laureate Key West offers three-bedroom suites that can sleep up to ten, plus a great outdoor pool and even grocery delivery service.
• Key West Marriott Beachside Hotel has access to a guest-only white sand beach, a large pool, and access to the Key West Golf Club.

Best Key West Bachelor Party AirBnBs

• The Americana Tropicale Houseis a short jaunt from Duval Street and can sleep up to 10 with a private pool in the backyard.
• The Louisa Househas a unique historic flare, a private pool, and is just a half block from Duval Street. (Sleeps up to 8.)
• For larger groups of up to 12, consider renting Two Private Cottages with a shared hot tub and private parking for a great price.

For other home rental options, we've found success using sites like VRBO and HomeAway.com.