Key West, Florida

Where to go on a Bachelor Trip in Key West

After months of planning, you land on Key West for a bachelor party in the Conch Republic, but you have no idea where to begin looking for recommendations on where to eat, drink, party and maybe sleep. 

Cosmopolitan Dream

The Grand Maloney

Southern Palms 

Commodore's Compound

The Curry House


Happy Hour:

Boat House Bar & Grill - Happy hour starts at 4pm and goes until 6:30pm. It includes half off well drinks, house wine, draft beer and an extensive list of small plates. They’re known for their boathouse bread, lobster bisque and margaritas. 


Galleon Resort Tiki Bar - After happy hour, stroll over to the Galleon Resort Tiki bar to check out one of the best sunset views in town and try a delicious mojito before dinner.


Louie’s Backyard - Belly up to the After Deck bar for an oceanfront piña colada that is sure to quench the summer heat, then make your way to their upscale, Caribbean-influenced restaurant that has been one of Key West’s most cherished settings. 

Bar Stop:

Sloppy Joes - Don’t miss one of Key West’s most infamous bars, Sloppy Joes, offering live music, dancing and a tap-room to keep up with every sports game. This is a spot you and your boys have to stop by to kick off your weekend. 

Bar Stop:

Green Parrot - Looking for a watering hole to end your night? Look no further than the Green Parrot which has been around since the late 1800s. Green Parrot is also known to have the BEST live music lineup in town. Random Fact: During WWII, this corner bar, formerly known as the Derby Bar, became a bar for the submarine sailors to come to after a long day at work. 



Ana’s Cafe Cubano (Green St. location) - You may or may not be lagging behind this morning. Ana’s is a coffee spot loved by locals and will be just what you need to kick off day two. Must grabs: iced café con leche and a cuban biscuit. 

To Do:

Fury Jet Ski Tour - This jet ski tour is a 90-minute tour around the island. It leaves from the Galleon Marina. Don’t be surprised if you spot some dolphins on this must-do trip! (If you’re interested in booking this while staying with Brighwild, let one of our GEMs know and they’ll get you set up.) 


Conch Republic - Nicknamed the “Conch Farm,” this fully open air restaurant is situated along the Historic Seaport where all of its products are delivered everyday by boats docked directly in front of the building. Don’t miss out on their well-known conch fritters. 

Pre Game:

Back at Home - Aloe up and get ready for the night with some beers and vodka sodas at home…and maybe throw in a water or two?

To Do:

Sunset Celebration at Mallory Square - The Sunset Celebration is a nightly arts festival held at Mallory Square Dock and is something you should not miss. There are dozens of street performers, food carts and arts and crafts exhibitors that’ll make you feel immersed in Key West culture. And best of all: Our amazing sunsets. Calculate the sunrise for your trip HERE


Bagatelle - Just steps away from Mallory Square, book a reservation at Bagatelle to enjoy some of the best and most fresh seafood.

To Do:

Duval Bar Crawl - Key West is known for some of the best bars in the country and you certainly don’t want to miss any of them. The Duval Bar Crawl is the perfect way to see the top hits.



The Breakfast Club, Too - Need to cure last night’s hangover? We’ve got you set. Bloody Marys. Pancake Charcuterie Boards. Egg Benedicts. Mimosas. Trust us on this one.

To Do:

Dante’s Restaurant & Pool Bar - Wanting to get a dip in the pool and enjoy a daiquiri before your flight? Stop by Dante’s and grab a tan while you still can.  

To Eat:

5 Brothers Grocery & Sandwich Shop - Serving up delicious coffees and authentic Cuban sandwiches, everything is grab-and-go and their daily lunch plate specials like picadillo, ropa vieja and oxtail are not to go unnoticed.

Other places we recommend checking out should time allow: 




  • Smathers Beach
  • Higgs Beach  


Dinner Spots



For any additional recommendations tailored to your group, reach out to your in-the-know GEM once you select a stay with Brightwild and they’ll point you in the right direction. Happy bachelor partying!