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Valentine's Day Dinner at Yellowfin Bar & Grill

Valentine's Day Dinner at Yellowfin Bar & Grill

Join us for a romantic waterfront dining experience from 5PM to 9PM on Valentine’s Day, Friday, February 14. Enjoy a complimentary glass of rose and chocolate dipped strawberries to take with you when you purchase a menu item.

January 2020

Florida Keys Seafood Festival

A family-friendly event with local fresh Keys seafood, drinks, marine-related crafts, youth activities, and live music.

happening date

DateSat, Jan 18, 2020

22nd Annual Key West Half Marathon & 5k

Recognized by Runners World magazine as one of the 10 great half-marathons of the winter season, the race follows a 13.1-mile course that includes Old Town Key West and the scenic waterfront.

happening date

DateSun, Jan 19, 2020

Key West Craft Show

The Key West Craft Show is a two day juried outdoor craft festival. This nationally recognized Craft Show brings over 100 fine and skilled craft artists to this beautiful historic area of Old Town Key West.

happening date

DateSat, Jan 25, 2020

Key West Food & Wine Festival

From Jan. 26 - Feb. 2, top chefs and restaurateurs display culinary creativity and the Keys' indigenous cuisine in a flavorful schedule of events for food lovers. Highlights include the lively "Old Town Uncorked," neighborhood wine strolls, food and wine pairings, intriguing seminars, winemaker dinner series and a grand tasting.

happening date

DateSun, Jan 26, 2020

Mile 0 Fest

Mile 0 Fest Key West is a "must see" music festival in the burgeoning Red Dirt & Americana music scene. Take in big shows at Truman Waterfront Park Amphitheatre, a state-of-the-art facility located blocks off the hopping streets of Duval, or get into a stripped down acoustic set with your favorite band leader at one of the theaters or bars off Duval. Many activities and memorable experiences await.

happening date

DateTue, Jan 28, 2020

February 2020

Key West Home Tours: “Be My Valentine”

Tour a series of elegant and unique private homes of Key West, ranging from exquisite restorations to creative renovations, and interior design that complements each. February tours are offered 10 am to 4 pm February 14-15. Transportation between homes is not provided. Tickets are $35 in advance and $45 on tour days. Proceeds benefit the foundation's Oldest House Museum, grant and scholarship programs.

happening date

DateFri, Feb 14, 2020

Valentine's Day Dinner at Yellowfin Bar & Grill

Join us for a romantic waterfront dining experience from 5PM to 9PM on Valentine’s Day, Friday, February 14. Enjoy a complimentary glass of rose and chocolate dipped strawberries to take with you when you purchase a menu item.

Ticket Price


Old Island Days Art Festival

The 55th annual juried outdoor fine art festival features over 70 local and national artists who are to grace the streets with fine art ranging from jewelry, paintings, photography and sculpture. Bring the kids to create an art piece at the children’s art booth. Staged from 10 a.m. - 5 p.m. February 22-23 at Whitehead and Caroline Streets in Old Town Key West.

happening date

DateSat, Feb 22, 2020

March 2020

St. Patrick's Day Bar Stroll

Walk, don't run! This annual gathering has been a local favorite since 1979, held across 10 bars in Old Town, Key West. Purchase a beer ticket and t-shirt for $30 and start the stroll at noon with an after party at Schooner Wharf. Proceeds benefit the Florida Keys Boys & Girls Club and the Cancer Foundation.

Ticket Price


April 2020

38th Annual Conch Republic Independence Celebration

This multi-day festival celebrates Key West's momentary secession from the United States, prompting the "Conch Republic" nickname. Enjoy an array of eccentric events, from whacky drag races to a dog costume contest. Programming is mostly free and family-friendly. Runs April 17-26.

happening date

DateFri, Apr 17, 2020

May 2020

Key West Songwriters Festival

Celebrate the art of songwriting during the annual Key West Songwriters Festival. The five-day event focuses on songwriters behind the music that you know and love. Jam sessions and performances take place across the island, on boats and beaches; in bars and theaters. Most events are free. This year's festival headliners include Luke Comb, Matt Stell and Niko Moon. May 6-10.

happening date

DateWed, May 6, 2020

Keys100 Ultramarathon

Race across the islands of the Florida Keys and take in turquoise horizons of the Florida Straits. This iconic ultramarathon is a series of point-to-point races that begin in Key Largo (100 miles due north) and end in Key West. Individual and relay races raise money for a good cause.

happening date

DateSat, May 16, 2020

June 2020

Key West Pride

Key West has long been a community that sees itself as "one human family," welcoming people from all walks of life. The island gets especially colorful during Key West Pride, with over-the-top programming that includes drag shows, a street fair, a gay film festival and a spirited pride parade. June 3-7.

happening date

DateWed, Jun 3, 2020

July 2020

8th Annual Key Lime Festival

Celebrate the citrus that's beloved across the Keys during this annual festival in Key West. Popular events include the Key Lime Cocktail Sip & Stroll, culinary events, key lime pie drops, and a spectacular firework show as finale. July 2-5.

happening date

DateThu, Jul 2, 2020

Hemingway Days

Ernest Hemingway was quite the character, with hobbies and interests that continue to fascinate the island he once called home. This annual event celebrates the late writer, angler, and drinker during a host of activities that include a Papa Look-Alike Contest, the 'running' of the bulls, and the Stock Island Marina Village Key West Marlin Tournament. July 16-19.

happening date

DateThu, Jul 16, 2020

Mini Lobster Season

Get a headstart on catching these delectable crustaceans during mini lobster season, which allows recreational anglers to get their hands on the local catch before the commercial fishermen do. Read up on the FWC rules and make sure to plan ahead of time – this two-day event draws quite the crowd. July 29-30.

happening date

DateWed, Jul 29, 2020

August 2020

24th Annual Lobster Festival

Fresh Florida lobsters, cold drinks and great music are all part of the annual Lobster Fest in Old Town, Key West. Programming includes pub crawls, street festivals, lobster boils and more.

happening date

DateThu, Aug 6, 2020

October 2020

Fantasy Fest

Fantasy Fest is a time for adults to enjoy the garden of earthly delights! Parties, costumes, body paint, headdress balls, and a street fair culminate into the raucous Fantasy Fest Parade, known around the world for its bigger-than-life floats, costumes, and performances. This is the biggest event of the year, so make sure to plan well in advance. Oct. 16-25.

Ticket Price


Bahama Village Goombay Festival

Pay homage to the cultures of the Caribbean with Goombay, a family-friendly street party that kicks off Fantasy Fest every year. This neighborhood celebration features island fare, a lively parade, arts and crafts, and lots of music, from gospel to reggae. Runs Oct.16-17 from noon until midnight.

happening date

DateFri, Oct 16, 2020

Meeting of the Minds: Parrot Heads in Paradise

Jimmy Buffet fans meet all across the globe, but is there a more fitting location than Key West? Head down to the original Margaritaville to enjoy Trop-Rock and raise money for national charities and community projects. Oct. 29-31

happening date

DateThu, Oct 29, 2020

November 2020

Super Boat International (Powerboat)

It's not November in Key West without Powerboat! Now in its 40th year, this annual race features boats exceeding 140mph right off the island. Parties, parades, and boat shows are all part of the fun. Nov. 8-15.

happening date

DateSun, Nov 8, 2020

December 2020

Key West Triathlon

Key West's flat terrain and generous waterfront makes this annual triathlon a momentous way to close out the year. Triathlon, duathlon, aquabikes and aquathlons are in the works for this year's 2020 Mack Cycle Tri Key West Olympic & Sprint.

Ticket Price

Oceans Edge activities-cross-sell


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Oceans Edge adventures-cross-sell


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