Key West

Why Key West for a Bach Trip

Key West is the bach trip destination for groups who want a weekend that feels like a different country. It is the southernmost point of the continental US, four hours from Miami, and operates on its own laid-back-island-time wavelength. Duval Street is two miles of bars, restaurants, drag shows, and live music, all walking distance from the cruise port. The water is calm and clear. Sunset at Mallory Square is a daily city-wide event. The bachelorette circuit here goes back generations.

The trade-off is access. Getting to Key West means flying into Key West Airport (limited connections, expensive), flying to Miami and driving four hours through the Keys, or a long road trip from anywhere else. Once there, lodging is expensive and inventory is tight. But the weekend itself is unlike anywhere else.

Where to Base Your Group

Old Town is the only base that makes sense; everything else means you are commuting. The area between Duval Street and the waterfront puts you walking distance to bars, restaurants, and the sunset celebration. Hotels: The Marker Resort, Margaritaville Beach House, Ocean Key Resort. For groups, conch houses in Old Town (historic Bahamian-style cottages) sleep six to twelve and rent for $1,500 to $4,500 per night; book four months out for high season. The Casa Marina is the classic resort option for crews of four.

Skip Stock Island, Key Haven, and Big Coppitt; they are cheaper but the 15 minute drive into Old Town breaks the walking-everywhere magic.

When to Go (and When to Avoid)

Best months: November through April. Weather is mild (70s and 80s), water is swimmable, no hurricanes. Summer (June through October) is hot, humid, and hurricane-prone but lodging is cheaper. Avoid Fantasy Fest week (late October, the city goes full Mardi Gras), Powerboat Races (early November), and the Hemingway Days festival (mid-July); rooms triple. Spring break (March) is busy but manageable for bachelorette groups.

The Day Scene

Sandbar tours are the must-do. Local outfitters (Sebago, Honest Eco, Sunset Watersports) drop your group on a half-submerged sandbar in the backcountry with a cooler of drinks; expect $80 to $150 per person for half day. Snorkeling at the Florida Reef (the only living coral barrier reef in the continental US) is an easy add. Jet ski tours circle the island in 90 minutes. Ernest Hemingway House (with the famous six-toed cats) is a 45 minute morning. The Conch Tour Train or Old Town Trolley both give the city overview in 90 minutes; budget option for orienting your group. Smathers Beach is the swimmable beach (Higgs Beach is locals' choice).

The Night Scene

Duval Street is the entire night scene. Sloppy Joe's is the Hemingway-tied historic bar, fun for one drink. Captain Tony's Saloon is the original pre-Sloppy Joe's, more local feel. Irish Kevin's has the live cover band that anchors a great Duval night. Bourbon Street Pub has the drag show worth the cover. For dancing, Rick's upstairs or Aqua. The Green Parrot is the dive bar that has been there since 1890; locals end up here. The Garden of Eden (clothing-optional rooftop bar) is the most-Key-West venue in Key West.

Food and Drink Worth Planning Around

Seafood and Cuban food are the moves. Blue Heaven is the must-do brunch (outdoor garden with chickens, expect a wait). Half Shell Raw Bar is the classic seafood spot on the water. Latitudes on Sunset Key requires a short ferry ride for the splurge dinner. Louie's Backyard for the upscale-with-water-view experience. Cuban: El Siboney for authentic, Sandy's Cafe for the late-night Cuban sandwich. Conch fritters at any of the dives along the harbor. Key lime pie at Kermit's or Blue Heaven.

Pro Tips

Book lodging at least four months out; Old Town inventory is tiny. Rent bikes or scooters; cars are useless and parking is a nightmare. Mallory Square sunset is free and worth doing once even if it is touristy. Sandbar trips are the best money spent in town; book two weeks ahead. The drive from Miami is four hours each way; if your group is tight on time, fly into Key West directly even if it costs more. Bring sunscreen seriously; the southern Florida sun is no joke. And the Southernmost Point buoy line is a 30 minute wait for a 5 second photo; go at 6 AM if you must.