Nov
14
Wed
2018
Key West Film Festival
Nov 14 – Nov 18 all-day

Showcasing films that exhibit excellence in storytelling, the festival’s lineup is to feature screenings and special events hosted at landmark venues throughout Key West, including the San Carlos Institute, Studios of Key West and Key West Theater. The four-day program is to include several films from multiple genres and categories as well as social events with filmmakers, actors and film lovers.

Nov
16
Fri
2018
Waterfront Playhouse presents: Carmen by Request
Nov 16 – Nov 17 all-day

Key West’s own “Conch Diva” returns to grace to stage bringing along some of your favorite performers. Showtimes 8 p.m.

Nov
24
Sat
2018
Big Pine & The Lower Keys Island Art Festival
Nov 24 all-day
Big Pine & The Lower Keys Island Art Festival

Highlights of this holiday event, set for the Saturday after Thanksgiving each year, include live music by local entertainers, food, exhibits and booths featuring locally produced arts and crafts. Festivities traditionally take place on the grounds of the Lower Keys Chamber of Commerce, MM 31 oceanside.

Dec
1
Sat
2018
Key West Triathlon and Expo
Dec 1 all-day
Key West Triathlon and Expo

The Key West Triathlon and Expo expects to host a maximum of 1,000 participants and some of the sport’s best known triathletes; TRIKW allows you to bask in the warm weather and the waters of the Atlantic Ocean while the rest of the country is experiencing winter. Olympic and Sprint distances.

Dec
28
Fri
2018
59th Annual Key West House & Garden Tours
Dec 28 – Dec 29 all-day
59th Annual Key West House & Garden Tours

Presented by the Old Island Restoration Foundation, the annual self-guided tours from 3-7 p.m. each day showcase festively dressed Key West homes and gardens. Tickets are $30 in advance, $35 day-of-tour. Proceeds benefit the foundation’s museum and programs.

Jan
10
Thu
2019
Uncorked … the Key Largo & Islamorada Food & Wine Festival
Jan 10 – Jan 20 all-day
Jan
18
Fri
2019
59th Annual Key West House & Garden Tours
Jan 18 – Jan 19 all-day
59th Annual Key West House & Garden Tours

Tour elegant and unique private homes of Key West, ranging from exquisite restorations to creative renovations, and the interior design that complements each. January tours are offered 3 to 7 pm each day. Transportation between homes is available via Conch Train for $40 each, seating is limited. Tickets without transportation are $30 in advance and $35 on tour days. Proceeds benefit the foundation’s Oldest House Museum, grant and scholarship programs.

Feb
15
Fri
2019
59th Annual Key West House & Garden Tours
Feb 15 – Feb 16 all-day
59th Annual Key West House & Garden Tours

Tour elegant and unique private homes of Key West, ranging from exquisite restorations to creative renovations, and the interior design that complements each. January tours are offered 3 to 7 pm each day. Transportation between homes is available via Conch Train for $40 each, seating is limited. Tickets without transportation are $30 in advance and $35 on tour days. Proceeds benefit the foundation’s Oldest House Museum, grant and scholarship programs.

Feb
16
Sat
2019
59th Annual Key West House & Garden Tours
Feb 16 – Feb 17 all-day
59th Annual Key West House & Garden Tours

Tour elegant and unique private homes of Key West, ranging from exquisite restorations to creative renovations, and the interior design that complements each. January tours are offered 3 to 7 pm each day. Transportation between homes is available via Conch Train for $40 each, seating is limited. Tickets without transportation are $30 in advance and $35 on tour days. Proceeds benefit the foundation’s Oldest House Museum, grant and scholarship programs.

Mar
2
Sat
2019
Conch Shell Blowing Contest
Mar 2 all-day

An island tradition for over 50 years, this unique contest celebrates the historic importance of conch in the Keys and features contestants in several age categories attempting to make “music” with fluted conch shells. Contest located in the garden of the Oldest House, 322 Duval Street, free and open to all ages. Registration begins at 10 a.m., contest starts at noon.

Mar
15
Fri
2019
58th Annual Key West House & Garden Tours
Mar 15 – Mar 16 all-day

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 and March tours are offered 10 am to 4 pm each day. Transportation between homes is not provided. Tickets are $30 in advance and $35 on tour days. Proceeds benefit the foundation’s Oldest House Museum, grant and scholarship programs.

Mar
16
Sat
2019
58th Annual Key West House & Garden Tours
Mar 16 – Mar 17 all-day

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 and March tours are offered 10 am to 4 pm each day. Transportation between homes is not provided. Tickets are $30 in advance and $35 on tour days. Proceeds benefit the foundation’s Oldest House Museum, grant and scholarship programs.

Jul
31
Wed
2019
Actual Bank Robbers
Jul 31 @ 10:00 pm – 10:00 pm

On stage 10:00pm to 2:00am.

Aug
1
Thu
2019
Actual Bank Robbers
Aug 1 @ 10:00 pm – 10:00 pm

On stage 10:00pm to 2:00am.

Aug
2
Fri
2019
Actual Bank Robbers
Aug 2 @ 10:00 pm – 10:00 pm

On stage 10:00pm to 2:00am.

Aug
3
Sat
2019
Actual Bank Robbers
Aug 3 @ 10:00 pm – 10:00 pm

On stage 10:00pm to 2:00am.

Aug
4
Sun
2019
Actual Bank Robbers
Aug 4 @ 10:00 pm – 10:00 pm

On stage 10:00pm to 2:00am.

Aug
5
Mon
2019
Actual Bank Robbers
Aug 5 @ 10:00 pm – 10:00 pm

On stage 10:00pm to 2:00am.

Aug
6
Tue
2019
Actual Bank Robbers
Aug 6 @ 10:00 pm – 10:00 pm

On stage 10:00pm to 2:00am.