|
Monday
|
Tuesday
|
Wednesday
|
Thursday
|
Friday
|
Saturday
|
Sunday
|
|---|---|---|---|---|---|---|
|
2 events,
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
Free
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,...
Free
|
1 event,
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
Free
|
1 event,
-
Set sail with Santa for a joyful holiday cruise off the Key West coast! Enjoy festive views from the water, holiday spirit, and a special appearance by Santa himself — all for a meaningful cause. 💙 Minimum donation: $30 per adult. Kids 10 and Under sail for free. 🙏 100% of proceeds benefit Wesley House...
$30
|
3 events,
A stunning revue of Rodgers & Hammerstein’s most treasured songs, this elegant theatrical presentation brings five performers into a world of timeless music — from backstage intimacy to full-stage splendor. A heartfelt tribute to the golden age of Broadway. Showtimes are Tuesday-Saturday at 7:30 and on Sunday at 2pm.
$70
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...
Free
-
Hosted by All Animal Clinic Professional photos by Rob O’Neal LOCATION: At the 16’ Nautical Christmas Tree on the Harbor Walk of Lights at William St. Santa pics with pets and kids big and small, treats for all! Pictures with Santa are $25 (cash only) to benefit our local Boys & Girls Club. Get professional...
$25
|
2 events,
-
Join the Key West Cooking Show for an Evening with Chef Norman Van Aken. A legend in the Key West culinary scene, Van Aken is a James Beard Award winner and author of seven cookbooks, including My Key West Kitchen. Enjoy great conversation and food with one of America’s most acclaimed chefs. With an amzinng...
$140
|
4 events,
-
Join us on Saturday, December 6th at noon for the Key West Woman’s Club’s first-ever European Style Holiday Market, a festive community event created entirely by our own talented members. Our front courtyard at 319 Duval Street will be filled with member-made holiday gifts, baked goods, crafts, décor, and treats inspired by the charm of...
Free
-
Ho ho ho! Bring the family for a festive Key West holiday moment with Santa himself at The Shops at Mallory Square. Enjoy photos, holiday cheer, and a little island Christmas magic — perfect for families, friends, and visitors of all ages! Join us at the Shops of Mallory Square for a festive afternoon filled...
Free
-
Parade starts on Truman Ave. (at White St.) then proceeds to Duval St., then down Duval St. ending at Eaton St. The most charming hometown parade you’ll ever see with holiday floats, and tons of kids (of all ages). Of course Santa will make a guest appearance! Parade goes south down Truman Avenue to Duval...
Free
|
1 event,
|
|
4 events,
No need to gas-up the snowblower this year if you’re planning a holiday escape to the Conch Republic! Here, ‘Christmas chill’ means rockin’ your flops and kicking back island-style and one of the best ways to do that is hopping a ride on Old Town Trolley’s Holiday Sights and Festive Nights Tour! The Southernmost City...
$24.53 – $36.28
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,...
Free
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
Free
|
3 events,
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
Free
|
3 events,
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...
Free
|
3 events,
-
Join us for an enchanted evening of decorated historic inns while enjoying light sweet or savory holiday treats and holiday cheer at each property. Visit each property, explore the unique architecture and history, and delight in holiday ambiance in a tropical setting. The tours are self-guided. Free trolley transportation will be provided between properties -...
$43.93
|
5 events,
-
Come one, come all to the Great Gingerbread Build at the Harry S. Truman Little White House. This event is free and open to the public. We will have gingerbread crackers, icing, and all sorts of candies to decorate your house with or we will also have a limited amount of kits available to buy...
Free
-
Movies Under the Stars Kick off the holiday season with a magical night under the stars! In Tim Burtons beloved stop-motion classic The Nightmare Before Christmas, Jack Skellingtonthe Pumpkin King of Halloween Townstumbles upon Christmas Town and decides to bring the holiday spirit home with some spooky twists. This family-friendly favorite is full of music,...
Free
-
Sail-abrate the holiday season with one of the most popular events of th year with the crew at Danger Charters. Guests can join us for the Key West Lighted Boat Parade on either our Viewing Boat or our Parade Boat! Both options include: • Unlimited wine and beer • Passed appetizers • Festive holiday treats...
$89 – $109
|
3 events,
Make sure to visit the family-friendly Monroe County Sheriff's Animal Farm, open on the second and fourth Sundays of each month from 1 to 3 p.m. Visits are free of charge, but donations are always welcomed. The farm started as a haven for homeless animals. The first residents were Muscovy ducks and a group of...
Free
|
|
|
4 events,
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
Free
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,...
Free
|
3 events,
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
Free
|
3 events,
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...
Free
|
3 events,
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...
$72 – $84
|
|||
|
4 events,
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
Free
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,...
Free
|
4 events,
-
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...
$25 – $35
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
Free
|
2 events,
-
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,...
$168
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...
Free
|
2 events,
-
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...
$45 – $55
-
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...
$25 – $35
|
1 event,
-
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...
$45 – $55
|
1 event,
Make sure to visit the family-friendly Monroe County Sheriff's Animal Farm, open on the second and fourth Sundays of each month from 1 to 3 p.m. Visits are free of charge, but donations are always welcomed. The farm started as a haven for homeless animals. The first residents were Muscovy ducks and a group of...
Free
|
|
|
2 events,
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,...
Free
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
Free
|
1 event,
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
Free
|
0 events,
|
1 event,
Fifteen-year-old Heidi earned her college tuition by winning constitutional debate competitions across the country. In this critically acclaimed and deeply personal play, she resurrects her teenage self to examine how our founding document has shaped generations of American women. “Not just the best play to open on Broadway this season, but also the most important.”...
$60
|
1 event,
|
1 event,
|
1 event,
-
Fifteen-year-old Heidi earned her college tuition by winning constitutional debate competitions across the country. In this critically acclaimed and deeply personal play, she resurrects her teenage self to examine how our founding document has shaped generations of American women. “Not just the best play to open on Broadway this season, but also the most important.”...
$60
|
