`
Have a question? Call 844-308-0080

Annual Events in Key West

 

August 2018

22nd Annual Key West Lobsterfest

August 9-12, 2018

Marking the official opening of lobster season, this is a big party on Duval. Event features street fairs, live music, arts & crafts. Street fair with free live concert on Saturday, from Noon until 11:00 PM on lower Duval. 

Learn More Here

9th Annual Key West Brewfest

August 30 - September 3, 2018

This popular event features more than 150 varieties of beer, including many award-winning micro brews. Event includes seminars, tastings, pool parties, and meals. The big event is the Signature Tasting on Saturday, September 2nd at South Beach. Cost is $75 a person for that event and advance tickets are required. 

Learn More Here


September 2018

9th Annual Key West Brewfest

August 30 - September 3, 2018

This popular event features more than 150 varieties of beer, including many award-winning micro brews. Event includes seminars, tastings, pool parties, and meals. The big event is the Signature Tasting on Saturday, September 2nd at South Beach. Cost is $75 a person for that event and advance tickets are required. 

Learn More Here


October 2018

Stone Crab Season Opening

October 15, 2018

The official season opens for 2018 on October 15th and runs through May of 2019. This is the most delicious local seafood and highly anticipated. Only the claws are taken and the crab is released back into the wild to reproduce new ones. Stone crab is only native to this region and is considered a seafood delicacy. 

37th Annual Goombay Fest 2018

October 19-20, 2018

This street party brings out all the locals to Bahama Village and features street fair cuisine (conch ceviche made fresh is popular), vendors selling a variety of wares, and live music at the bottom of Petronia. This is a free, family-friendly event and runs from Noon until Midnight. 

Learn More Here

Fantasy Fest 2018

October 19-28, 2018

39th Annual Key West Fantasy Fest is a week-long celebration and Key West's biggest party of the year. Many of the events are adult-only and not appropriate for children. This year's theme is "Oh...The Games We Play!" The structure of this event has changed in that creativity of costume is the focus over all else. 

Learn More Here

Headdress Ball

October 25, 2018

A costume contest featuring dazzling headdresses created over many months then worn and displayed in this awe-inspiring event. HUGE works of art, with each being more inventive and imaginative than the previous. Grant prize is $1,500. Located at the Truman Waterfront Amphitheater, end of Southward Street. Buy tickets early has this event sells out. Call 305-294-4603 for tickets.

27th Annual Meeting of the Minds 2018

October 31-November 4, 2018

Parrothead convention and nirvana benefiting charity. Many events are members only. Live shows include members of Jimmy Buffet's band. Highlights include the Margaritaville Street Fest on Friday from 1:00 PM - 5:30 PM on the 500 block of Duval near Fleming. This is free and open to the public. 

Learn More Here


November 2018

27th Annual Meeting of the Minds 2018

October 31-November 4, 2018

Parrothead convention and nirvana benefiting charity. Many events are members only. Live shows include members of Jimmy Buffet's band. Highlights include the Margaritaville Street Fest on Friday from 1:00 PM - 5:30 PM on the 500 block of Duval near Fleming. This is free and open to the public. 

Learn More Here

26th Annual ABC 5K Walk/Run

November 3, 2018

Sponsored by Zonta, this running race benefits women's health screenings and breast cancer awareness in the Lower Florida Keys. Race begins and ends at Salute on Higgs Beach. Registration cost is $25-$35, depending on when you register. 

Learn More Here 

Key West Film Festival

November 14-18, 2018

Independent films are recognized in this annual event. Awards for narrative feature film, LGBT feature film, documentary, Florida feature film, and foreign feature film. Events include movie screenings, a kick-off party, and awards gala. 

Learn More Here

Thanksgiving in Key West 2018

November 22, 2018

Traditional turkey is served in a tropical setting as residents and visitors celebrate the annual holiday. Many local restaurants have special Thanksgiving menus.


December 2018

9th Annual TRIKW Triathlon

December 1, 2018

Athletes swim, run, and bike among Key West's ideal scenery and conditions. More than 500 competitors are expected. Two race distances are available: Spring and the twice-as-long Olympic. 

Learn More Here 

Tree Trimming Party

December 2, 2018

The dock-front at Schooner Wharf Bar hosts this annual holiday tree decorating party, craft fair, and toy drive. Bring an ornament and get a free holiday cocktail. Prizes available for best ornaments. Features live island music by The Last Mango. 5:00 PM, 202 William Street. 

Key West Holiday Parade

December 3, 2018

This family-friendly event is especially popular among the kids with all of the free candy given out! Parade begins at Bayview Park in Key West then heads down Truman Ave. to Duval Street. Best viewing is along Truman Ave. in Old Town, Key West. This is a free event.

Key West Lighted Bike Parade

December 5, 2018

This event benefits the Wesley House Family Services. A neighborhood parade, it features bicycles adorned with holiday lights and decor. Begins at 7:00 PM (check-in is at 6:00 PM), Bayview Park. Free event with a donation of an unwrapped children's gift. 

Hanukkah in Key West 2018

December 2-10m 2018

Key West is home to one of Florida's oldest Jewish communities - with Jews settling here when the city was incorporated in 1832. During Hanukkah, a large menorah is lit in front of the synagogue each night of the holiday, with Rabbi and congregants gathering for the "festival of lights". A latke and salmon feast is held the first night. Stop by 750 United Street and celebrate.

28th Annual Key West Lighted Boat Parade

December 15, 2018

Vessels of every size and shape deck their hulls and light up the night with their creativity and originality to the delight of locals and visitors. Santa Claus has been spotted at the helm, ditching his sleigh for a center console or sailboat with mistletoe hanging from the mast. His first mates have included gingerbread men and the Grinch. Other times, dolphins have replaced cold-weather reindeer, ushering in Santa's sleigh packed with lighted presents. Boats will come into the Key West Bight (Historic Seaport) and pass in front of the judges' stand at Schooner Wharf Bar. Festivities start at 6:00 PM with the Gerald Adams Steel Your Heart Band, and the parade begins at 8:00 PM. Live music all evening with yuletide favorites, plus a traditional ham dinner served from their galley. To register your boat or for more information, please call (305) 292-3302.

Key West New Year's Eve Celebration

December 31, 2018

Celebrations include the lowering of the Conch Shell over Sloppy Joe's on lower Duval Street, the lowering of the famous Key West Drag Queen, Sushi, in a huge red high-heeled shoe over the Bourbon Street Complex on upper Duval Street, the lowering of a Key Lime wedge on the Sunset Pier, and the lowering of the "pirate wench" from the mast of a Schooner in the Historic Seaport.

 

Make a Reservation

Manage Reservations
Need assistance? Call 844.308.0080
Pool and garden at our key west bed and breakfast

Photo Gallery

Tour our beautiful Key West hotel through photos in our gallery. View our lush grounds and gardens, cozy rooms, property map, and tranquil pools.

Learn More

On the Beach after a wedding in key west

Wedding Gallery

You’ve always pictured your perfect wedding day. View the photos in our Wedding Gallery to see what your destination wedding can be like at Westwinds Inn.

Learn More

Key West beach and palm tree

Calendar of Events

There’s always something going on in Key West, from food and literary festivals to fishing and sailing tournaments. View our Events Calendar for the latest happenings.

Learn More