My Key West Bachelorette Party Picks: An Editor's Take on the Best Spots

I have always found the best way to plan a trip is to seek out expert advice from someone who's actually been there. So as a wedding editor who recently got to visit Key West to plan the ultimate low-key bachelorette party, I'm sharing a real recap of my trip as well as my favorite under-the-radar spots and authentic local finds. This is not an exhaustive list of everything to see and do in Key West. (You can find that in our full bachelorette city guide.) Instead, it's my honest take on what I loved and would do again, including my curated recommendations for a trip that goes beyond the expected.

The Vibe We Were Going for in Key West

On our visit, a local told me Key West is equal parts New Orleans, Nashville and Miami, and honestly, I can see the resemblance. Historic charm abounds, the sound of live music fills the streets nightly and there's noticeable Cuban and Caribbean influence in the food, drinks and culture. But the southernmost city in the Florida Keys (and the continental U.S.) also has a vibe all its own. It's a perfect fit for a relaxed bachelorette party destination—there's no big-city hustle and bustle here, just a laid-back island lifestyle and an easygoing energy that makes the whole weekend feel effortless.

To truly embrace the Keys mindset, resist the urge to overschedule and instead, keep the itinerary unhurried. Our trip managed to hit that sweet spot between taking it easy and having plenty to do.

Winslow's Bungalows

Where We Stayed (and Why I Would Book It Again)

Winslow's Bungalows: A collection of charming white cottages nestled amongst tropical foliage and hidden pathways, this resort feels like a secret garden hideaway. Our stay included daily breakfast and access to three pools scattered around the property, plus most rooms feature a porch, patio or other outdoor space. The location is close enough to the action on Duval Street but also far enough removed to be a quiet escape, making it the best place to stay in Key West for a girls' trip.

Why it worked

I loved how walkable the bungalows were to everything downtown. It made it so easy to pop out for coffee in the morning or head back to the room for a little pool time. The pools felt secluded and serene, which is ideal if your group is more into relaxing in the sun than poolside parties. Plus, the lush surroundings put you in the island mindset immediately.

What I would consider next time

Staying in the center of it all, but still a bit removed from the late-night partiers on Duval worked well for our trip. But if you're looking for more of a beach getaway, I'd recommend the historic Casa Marina. Perched on the largest private beach in Key West, this 1920s landmark will make you feel like a Jazz Age socialite escaping to the Keys.

For the best of both worlds, stay downtown but book a beachfront daybed or cabana experience at Casa Marina for a few hours. This is a great option for a relaxing last day in Key West before heading home. We had a luxurious few hours on their beach prior to our flight, and it was the perfect reset after a busy few days.

Images (clockwise from top left): Caribbean Coffee Roasters, Cafe Sole, Hogfish and pizza from Roostica

Editor-Approved Food and Drink Spots in Key West

Yes, everyone knows about Blue Heaven and Sloppy Joe's…and you should visit those iconic favorites. But here are our under-the-radar editor's picks for the best Key West bachelorette party restaurants and bars, with input from the locals.

Hogfish Bar & Grill: This is the hidden gem the locals don't want you to know about. You'll have to grab a rideshare out to Stock Island to get here, but the fresh seafood is well worth the trip. Hogfish hearkens back to a simpler time in the Florida Keys, when you could grab a seat at a picnic table on the dock and dine on fish straight off the boat. Any preparation of the signature hogfish is a must-try (it comes grilled, blackened or fried), as well as the Bahamian conch salad and yellowtail with scallops. And if you're lucky enough to be there when the grouper with pesto cream sauce is the day's special, don't ask questions—just get it.

Café Solé: One editor recommended this elegant, yet relaxed café where French cuisine and fresh, local seafood combine. Try the hogfish with red pepper hollandaise or yellowtail in a beurre blanc of lobster for a special dinner and night out.

Kaya Island Eats and the Key West EmPOURium: Hawaiian dishes by way of the Keys are on the menu at this casual island eatery on Duval Street. Here, the chef hails from Maui, the mai tais are on point and the backyard bar turns into a live music venue and karaoke lounge at night. Come for the ahi poke nachos, then reserve their VIP karaoke room if you really want your moment in the spotlight.

Roostica: Owned by the same team as Hogfish Bar & Grill, this wood-fired pizza joint is also off the beaten path on Stock Island. Using authentic Italian ingredients, their creative pizzas (we went for the Fig and Pig) and massive charcuterie boards are designed for sharing. Bonus: the outdoor seating area gives Tuscan garden vibes.

Square Grouper: We got a local tip that the Key Lime Martini at Square Grouper is the best in Key West, and honestly, we're still dreaming about it. I think the not-so-secret ingredient is their house-made key lime curd, paired with a graham cracker rim. Grab a round and enjoy the ambience of their outdoor patio.

Caribbean Coffee Roasters: A local suggested we hit up this coffee spot, and it didn't disappoint. They roast their own beans in-house and have an impressive selection of seasonal lattes and iced coffees. I highly recommend the coconut cold brew for a morning pick-me-up with a tropical twist.

Images (clockwise from top left): When and If sunset cruise, The Old Town Trolley Tour, Tijon Fragrance Lab, Key West First Legal Rum

The Key West Experiences That Made the Trip

What's a bachelorette party without a few group activities? The trick is finding things to do in Key West that appeal to a wide range of personalities and interests.

Key West First Legal Rum Mojito Class: The culinary duo behind Key West First Legal Rum distillery, Chef Paul Menta and his wife, Crystal, are seriously "cool couple coded." (They were married inside a cenote in Mexico complete with underwater wedding photos. Say less.) While traveling to Cuba to share their rum with the locals (another bold move), they learned the secrets to making an authentic Cuban mojito. Hint: It's always stirred, never shaken. Now Crystal is leading the distillery's private mojito classes, so you can mix and muddle your own minty cocktail with a Key West twist. We had a blast learning the art of mojito-making from Crystal, starting with a tour of the distillery and ending with a mini dance session while mixing our drinks.

Creating a Personalized Fragrance at Tijon: Want a souvenir that's totally unique to you and your crew? A fragrance-making class at Tijon is a fun way to customize your signature scent. We started the experience by selecting a base fragrance, then personalizing it with three additional oils chosen from a selection of over 300. I'm obsessed with my custom scent and will think of Key West every time I wear it.

Sunset Sail on When and If: Boarding the 1939 vintage schooner When and If made me feel like a vintage Hollywood starlet. (Attention, The Marvelous Mrs. Maisel fans…this boat was used on the show!) This stunning ship sets sail from a historic seaport and gives passengers a chance to hoist the sails, enjoy the scenery and have a drink or two. We ended the cruise by toasting to the sunset with a glass of champagne and firing the mini cannon to announce our return to shore.

Key West Cooking Show: If you love to cook, this is an entertaining way to suss out the secrets behind the local dishes, while getting to taste everything yourself. On our visit, we learned how to make swordfish piccata, a bright and refreshing conch salad and a smooth and creamy flan. They also hold cocktail classes and a key lime pie making class.

Old Town Trolley Tour: A veritable treasure trove of dad jokes, this tour gives a fun and funny overview of the history of Key West. You can also hop on and off all day, making it a convenient way to get around and see the sights.