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3 things to do in Key West on a date night done right


By Alyson Sheppard, Jan 2020

things to do in key west date night


Taking a vacation to tropical and quirky Key West, the southernmost point in the continental U.S., offers plenty of opportunity for romance. Whether you're on a couples trip or traveling with the kids, free up your evening and enjoy a date night with one of these three fun and romantic things to do in Key West.

Key West sunset, Gulf of Mexico with yachts and boats on the background

Take in the brilliant colors of Key West's sunset aboard an evening sailboat cruise.


1. Sail away into the sunset

Sip Champagne while watching the sun go down aboard a dreamy evening sailboat cruise. Classic Harbor Line's sunset sail takes you out on the turquoise waters surrounding the island on a 105-foot wooden boat. On this peaceful, two-hour tour, the crew serves wine, bubbly and beer, along with light hors d'oeuvres such as shrimp cocktails and cheese and crackers. Relax and watch the sky cycle through vibrant colors; maybe you'll even spot the elusive green flash, a local phenomenon in which the top of the sun appears to turn green just before it sets.

American flag attached to porch of house

Why are the porch ceilings in Key West painted blue? Find out on a haunted pub crawl.


2. Bone up on spooky trivia at a haunted pub crawl

According to local folklore, porch ceilings are painted blue in Key West to keep bad spirits at bay. These are the kind of tidbits you learn on the Bone Island Haunted Pub Crawl & Ghost Tour, a late-night walking tour offered by Key West Pub Crawls. Your master storyteller guide will relate countless interesting facts and weave several spooky tales on this two-hour excursion. In addition to seeing haunted local architectural landmarks, you'll dip into some of the island's world-famous bars and enjoy discounted drinks. Ghost sightings aren't guaranteed, but fun is!

3. Get eccentric at a famous drag show

Key West prides itself on inclusiveness. Pirates, writers, freed slaves and Native Americans have called the island home, and it has an especially rich LGBTQ history. The island's LGBTQ culture is still thriving today, especially at 801 Bourbon. The fabulous drag bar has been entertaining Key West for three decades; grab a drink downstairs to people-watch and then head upstairs to watch the 801 Girls. The twice-nightly cabaret drag show is so legendary that it was the subject of an anthropology book that analyzed the cultural impact of the lively performances.

There are plenty of entertaining things to do in Key West and plenty of ways to craft a date night to remember. The island's charm, which it owes to its proximity to the Caribbean and its diverse heritage, is why celebrities such as Ernest Hemingway and Jimmy Buffett have put down anchors here. And it's what will keep you coming back vacation after vacation.

Get your adventure started: Check out our Key West vacation packages today!

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