Best events this weekend in Summerland Key

Date and Time

Fri, 23 Jan, 2026 - 06:30 PM

Location

Boondocks Grille and Draft House, 27205 Overseas Hwy, Summerland Key, FL 33042-5344, United States

Friday, January 23. 2026 Boondocks 27205 US HWY 1 Mile Marker 27.5 Ramrod Key, FL 33042 Join Howie and The Mile Marker 24 Big Band at the largest tiki bar in the Florida Keys!. Meet and Greet 6:00pm, showtime 6:30pm-9:30pm. No cover charge & open to... Read More

Date and Time

Fri, 23 Jan, 2026 - 07:00 PM

Location

Looe Key Tiki Bar & Grill, 27340 Overseas Hwy,Summerland Key, Florida, United States

Come join us for our return to Looe Key for another night of electric fun, high energy, and your favorite rock songs!... Read More

Date and Time

Sat, 24 Jan, 2026 - 09:00 AM

Location

Cudjoe Gardens Marina, 477 Drost Dr, Summerland Key, FL 33042-4026, United States

Saturday, January 24th, 2026 9am – 2:30pm Join us for a leisurely paddle around Cudjoe Key, followed by a post-paddle party and libations at Bent Prop, a silent and live auction, and raffles to benefit the Florida Keys SPCA Clinic Fund. We recommend bring... Read More

Date and Time

Sat, 24 Jan, 2026 - 07:00 PM

Location

Boondocks Grille and Draft House, 27205 Overseas Hwy, Summerland Key, FL 33042-5344, United States

Join us Saturday - for the usual fun, music and shenanigans Bring your Partner, your friends, neighbors and dancing shoes... Read More