The Greyhound bus ride from Miami to Key West takes at least four hours with frequent stops and costs under $50, but you get free sightseeing along the way on the 113-mile Overseas Highway that includes a 7-Mile-Bridge.
With beach gear in tow, head out in the morning by bike to the Fort East Martello Museum to see Chucky of the horror movie franchise or rather the life-size doll named Robert who inspired the character and still inspires terror. Admission is $10, but a student ID will get you in for $5. Pedal back to Smathers Beach, considered one of the best gay beaches in the U.S. The 2-mile-long stretch of public sand has everything you need for the day, including water sports, volley ball and food trucks.
When you tire of beach fun, return to Old Town to shop seashells, straw hats and trinkets at the picturesque straw market at Bahama Village, a somewhat gentrified neighborhood of shops and eateries. It has a Caribbean flavor in its architecture and music with many residents descendants of original settlers from the Bahamas.
Late afternoon join the crowd at Mallory Square for the nightly sunset celebration with all manner of street performers (including cats), local artists and vendors selling everything from T-shirts to conch fritters. All this wild entertainment won't cost you a dime.
Spend the evening doing the Duval Crawl, Key West's trade-marked version of a pub crawl along Duval Street where every bar is gay-friendly. You'll find plenty of happy hours, drink specials, cheap bar food and live music without cover.