Key West Bachelor Weekend Guide

Duval Street After Dark

Duval Street is where your nights will happen, whether you plan it that way or not. It runs the length of Old Town and is packed with bars that stay loud until close.

Sloppy Joe's Bar

Best for: the one stop everyone expects you to make | Price: Original Sloppy Joe sandwich $7.95, Peel and Eat Key West shrimp $9.95 for a half pound

This is the bar most associated with Hemingway's Key West years, and it's usually the first stop for nearly every visiting group. It gets loud and crowded at night, which is either exactly what you want or a good reason to grab one drink and move on. Reviewers on Tripadvisor are split on it, some call it a must-do for the history and live music, others say it's overpriced and worth one visit rather than a full night.

Captain Tony's Saloon

Best for: the group that wants some history with their drinks | Price: standard bar prices, no cover

The building dates to 1852 and has been an ice house, a morgue, a cigar factory, and a speakeasy before it became a bar. Jimmy Buffett played some of his earliest Key West shows here, and the building's history alone makes it worth a stop even if you're not staying long.

The Green Parrot

Best for: live music without the tourist crush | Price: standard bar prices, no cover for most nights

This one sits a few blocks off the main Duval strip and draws a mix of locals and visitors. It's a good stop if your group wants a break from the loudest part of the street.

Get on the Water

Shared and Private Fishing Charters

Best for: a group that wants a real activity, not just bars | Price: shared charters run about $200 to $350 per person for a half day, private charters start around $550 for the boat

Splitting a private half day charter across six to eight guys often works out close to what you'd pay per person on a shared boat, and you get the whole boat to yourselves. Book this early since good boats fill up on weekends.

Sunset Sail or Jet Ski Rental

Best for: an easier afternoon activity | Price: sunset sails typically include a bar on board, jet ski rentals are billed hourly

A sunset sail is the lower effort version of a boat day and works well the day after a fishing trip. Jet skis and parasailing are also easy to book same day if the weather cooperates.

Sunset and Mallory Square

Mallory Square fills up every evening for the sunset, with street performers, local vendors, and Cuban food stands along the water. It's touristy, but it's touristy because it's actually worth doing once.

Where to Stay

Old Town puts you walking distance from Duval Street, which matters more in Key West than most destinations since parking is limited and expensive. A house with a pool is worth the extra cost given how hot and humid the days get.

Before You Book

1. Hurricane season runs June through November, so check the forecast and consider travel insurance if you're booking during those months.
2. Fishing charters and boat rentals should be booked weeks ahead for weekend dates, especially in spring.
3. Parking is scarce and expensive in Old Town. Budget for it or plan to walk and use golf carts or bikes.
4. Duval Street bars don't take reservations, so just plan to bar-hop rather than lock in a schedule.