Stop by Festival Headquarters anytime during the week to pick up badges, get event information, meet up with other Friends, and grab a refreshing pina colada (badge holders get $1 off).

There are many places to eat lunch in Key West. But there’s only ONE place to have lunch with a legend. Join us for Key West’s only all-inclusive dine-in musical experience, revisiting the glory days of 1970s Key West when a young songwriter named Jimmy called this island home.

Acclaimed musician, actor, and Buffett historian Caleb Hogan appears in-costume as the man himself in a show blending live music, storytelling, humor, and of course...Cheeseburgers! Enjoy a journey back in time to a place where artists and misfits lived the eclectic Bohemian dream, and our favorite "grandson of a sailor" roamed the land.

Part lunch theater, part tribute concert, and part educational adventure, a Pirate Looks Back is a one-of-a-kind musical celebration of the songs, spirit, and the island where the legend began. This show is a MUST-SEE for all Buffett fans, music enthusiasts, or anyone looking for Key West’s most entertaining lunch experience.

Your ALL-INCLUSIVE ticket to this performance includes one cheeseburger with chips and one drink from the bar’s lunch menu. Additional beverages and drink specials will be available for purchase from the bar.

Embark on a laid-back afternoon adventure designed with Just a Few Friends guests in mind, as you board a state-of-the-art Corinthian catamaran and cruise into the serene Key West backcountry to a secluded sandbar or shallow-water hideaway within the Marine Sanctuary.

If you’re arriving early for the festival, this is the perfect way to connect with fellow “friends,” settle into island time, and start the weekend on the water. Spend your afternoon kayaking or paddleboarding through crystal-clear waters, spotting local wildlife, or simply relaxing with your toes in the warm sand and a cold drink in hand.

Enjoy a complimentary lunch along with beer, wine, seltzers, sodas, and water, all included. With equipment and instruction provided, it’s an easy, social, and immersive way to experience the natural side of Key West before the music and festivities begin.

Ease into the weekend with an informal gathering at the legendary Chart Room inside the Pier House Resort. On Wednesday from 5:00 to 8:00 PM, you’re invited to mix and mingle with the Key West Parrot Heads and fellow attendees before the festival officially kicks off. This historic hideaway—where a certain island-loving troubadour once pulled up a barstool—sets the perfect tone for what's to come. Raise a glass, swap a few stories, and meet just a few friends.