Join us for a festive Christmas cruise featuring live holiday music and cheer! Please join us for this special Key West holiday cruise tailored for friends, family, and all your loved ones during the Christmas season. Step aboard our beautiful 105-foot Schooner America 2.0 in full holiday decor for a 1.5-hour cruise in Key West...
Our Hugh’s View roof terrace offers the best views in town, and an ideal spot to catch the sunset and a drink with friends. The bar is open, admission is free, and everyone looks great in the golden twilight. Free and open to the public on Monday's and Tuesdays from 6pm-8pm
Test Your Knowledge & Tastebuds every Monday from 6:00 to 8:30 PM for a sizzling evening of fun, food, and friendly competition at Trivia Night at the Key West Cooking School! Gather your team or come solo and make new friends as we challenge your brain with a mix of pop culture, history, food facts,...
Our Hugh’s View roof terrace offers the best views in town, and an ideal spot to catch the sunset and a drink with friends. The bar is open, admission is free, and everyone looks great in the golden twilight. Free and open to the public on Monday's and Tuesdays from 6pm-8pm
Tuesday, December 23rd, 2025, 6-8pm Join us for a festive evening at the Key West Harry S. Truman Little White House. You will start with a cup of eggnog or a hot toddy and some holiday cookies. Then you will take a tour of the house to see all the beautiful, traditional holiday decorations and...
Enjoy Christmas morning the Key West way – sailing! Enjoy the vibrant colors of Key West as you sip champagne, dine on a delicious brunch, and glide through crystal clear surrounding waters on one of Key West’s premiere holiday cruises. This Christmas brunch Key West-style features complimentary mimosas, bloody marys, champagne, wine, beer, soft drinks,...
Join us every Thursday from 2 pm to 7 pm at the Truman Waterfront for fresh produce grown in Homestead, gorgeous orchids & native plants, artisan selection of meats and cheeses, pickles, honey, nuts & dried fruits, natural soaps and so much more. You’ll find Key West crafts, gifts and the perfect souvenir to take...
66th Annual Home Tours presented by Old Island Restoration Foundation! Our 66th Home Tours will bring you joy and excitement to local homes that are opened for your viewing pleasure. Strolling through Key West, do you ever wonder what lies behind a beautiful, historic, intriguing, and private door? Each month features different homes, so enjoy...
Tuesday, December 26th, 2025, 6-8pm Join us for a festive evening at the Key West Harry S. Truman Little White House. You will start with a cup of eggnog or a hot toddy and some holiday cookies. Then you will take a tour of the house to see all the beautiful, traditional holiday decorations and...
66th Annual Home Tours presented by Old Island Restoration Foundation! Our 66th Home Tours will bring you joy and excitement to local homes that are opened for your viewing pleasure. Strolling through Key West, do you ever wonder what lies behind a beautiful, historic, intriguing, and private door? Each month features different homes, so enjoy...
