The start of every holiday season sees the iconic old Custom House, now the Key West Museum of Art & History, transformed into a bustling annual Holiday Concert & Bazaar with artisans, musicians, and future filmmakers.

Key West is a town that just can’t seem to put its decorations and costumes away. Wesley House Family Services’ Annual Holiday Village and BeLighted Bike Ride is a great way to get into the season. A starting line comprising a “village” out at the Coffee Butler Amphitheater in Truman Waterfront sees costumed riders take to Whitehead and Duval Streets for one of the most colorful displays all year.

The Annual Offshore World Championship in Key West fills hotels, packs bars and restaurants, and provides an important bump to the start of the season. Each year sees even more boats and global teams participating in the week of races and special events in a community where the roar of engines can be heard from just about every major spot.

Visitors and locals can now spot a splash of color in downtown Key West following this summer’s state-mandated removal of the rainbow crosswalks at Duval and Petronia Streets.

As repeat visitors have come to know, there is a party in Key West for just about anyone. Adorable pets in costumes strutting before a live audience? That’s the pet masquerade. Into skulls, monsters, and Day of the Dead tributes? Check out the Zombie Bike Ride. Colorful floats with enough hurled beads to trigger Mardi Gras flashbacks? Watch the Fantasy Fest parade.

Each year, a red carpet of sorts is rolled out for a handful of islanders and contestants vying to be the latest duo inducted to Key West’s longstanding “royals.” Specifically, in a town filled with noted personalities and artists, candidates hope to become the reigning “King” or “Queen” by raising the most money for charity. These days, that charitable beneficiary is the Florida Keys SPCA.