More Events
Sip n' Paint:
Celebrate Spring, Island Style!
Thursday, March 20, 2025 — — Southernmost Beach Resort
We are "painting" a garden. Canvases can be painted separately or as a group. So much fun!
One of a kind painting events- Paint the Tale!
Price is $30 per person: includes all paint and supplies.
Entertainment and stories with Amy and of course your choice of cocktail or mocktail!
Seating is limited to 40 people! BUY TICKETS FAST. THESE will sell out!
Tickets: $30
Taste of Key West
Monday, March 24, 2025 — — Truman Waterfront Park
This open-air event promises an assortment of beverages and palate-pleasing small plates. Local Restaurants and Vintners Present the perfect Taste of Key West at our 30th Annual Celebration!
A.H. Monroe & Republic National Distributing Company bring the community together for Cuisine, Craft Beer & Fine Wines! Cheers!
TASTE VIP PASS - $150 / person - includes lighted VIP tent with tables and chairs to sit and enjoy your Taste of Key West experience, upscale, butler-passed Hors d'oeuvres will be presented intermittently throughout the evening, an Educated sommelier to discuss the finest wines only available in this exclusive area, The VIP badge grants you unlimited food and wine samples, a Taste of Key West wine or pint glass and plate. Flexible Seating within the VIP Tent.
2 For Taste - $75 - includes 2 glasses, 2 plates and 60 tickets
Admission is Free.
To enjoy these scrumptious small bites, fine wine and spirits – you will also be able to purchase a glass, plate and tickets on site
These will be available for purchase at the ticket booth the day of the event - Monday, March 24th.
$1 / ticket (each bite size portion is usually 4-6 tickets)
$5 / wine glass
$5 / pint glass
$5 / plate
Tickets: $75-$150
Buckets N Boards
Wednesday, April 2, 2025 — — Marathon Performing Arts Center (at the Marathon High School)
Buckets N Boards is a hilarious and high-energy show chock-full of amazing percussion, ridiculous songs, spectacular tap dancing, inventive instrumentation and an incredible variety of musical talents!
Matthew Levingston and Gareth Sever have hand crafted a fresh and unique clean comedy experience for the entire family to enjoy! The show was born from their shared passion for music, comedy, and rhythm, but it truly comes to life through the nonstop hilarious interaction between these two AND their audience.
Buckets N Boards have toured the world and are currently one of the top requested headlining acts for Disney Cruise Lines!! BNB has been featured twice with the Kansas City Symphony and is currently heading into their 14th Award Winning season in Branson, MO!
Regarded as a must see show for any evening out with the family! Their unexpected comedy, upbeat personalities and improvisational audience interaction make Buckets N Boards Comedy Percussion Show a theatrical experience you’ll remember for years to come!!
Tickets: $15 (Kids 12 and under FREE)
Buckets N Boards
Thursday, April 3, 2025 — — Coral Shores Performing Arts Center, Tavernier, FL
Buckets N Boards is a hilarious and high-energy show chock-full of amazing percussion, ridiculous songs, spectacular tap dancing, inventive instrumentation and an incredible variety of musical talents!
Matthew Levingston and Gareth Sever have hand crafted a fresh and unique clean comedy experience for the entire family to enjoy! The show was born from their shared passion for music, comedy, and rhythm, but it truly comes to life through the nonstop hilarious interaction between these two AND their audience.
Buckets N Boards have toured the world and are currently one of the top requested headlining acts for Disney Cruise Lines!! BNB has been featured twice with the Kansas City Symphony and is currently heading into their 14th Award Winning season in Branson, MO!
Regarded as a must see show for any evening out with the family! Their unexpected comedy, upbeat personalities and improvisational audience interaction make Buckets N Boards Comedy Percussion Show a theatrical experience you’ll remember for years to come!!
Tickets: $15 (Kids 12 and under FREE)
Love, The Journey, Acceptance
Keys Choral Arts presents…
Friday, April 11, 2025 — — St. Paul’s Episcopal Church
Join Keys Choral Arts, the Keys premier community chorus, for their spring concert presentation. The chorus presents "Love, The Journey, Acceptance", a beautifully constructed concert under the direction of Timothy Peterson, accompanied by Lou Ann Steely. In all of the chaos of life, it is time to embrace love, acceptance and the journey it takes to get there. The concert features several of Brahms Liebeslieder Waltzes to represent love, with Randall Thompson's Frostiana taking us on our journey. Several numbers deliver our acceptance, including a specially arranged piece from our own Michael Robinson. It is a true evening of beautiful music designed to touch the soul.
Tickets: $30
Circus of the Sea
Sunday, April 13, 2025 — — Southernmost Beach Resort
The Southernmost Beach Resort proudly presents Circus of the Sea! We could not be more thrilled with this talented family of acrobats joining our winning list of new and exciting events coming to Key West! This is a one hour pirate themed acrobatic and aerial show that will delight young and old.
Ariel stunts, trampolines, funny skits, drinks, snacks, face-painting and more… SO MUCH FUN! Seating is limited to 125 guests so please do not wait to book.
Admission price includes access to our Pineapple Pool for a pre-show pool party
Tickets: $30
Sandbar Series featuring
Anders Osborne
Wednesday, April 23, 2025 — — Little Palm Island
Be our guest on the evening of April 23 at 7:30 pm as we welcome back renowned singer, songwriter and virtuoso guitarist Anders Osborne to the storied Monkey Hut at Little Palm Island. This intimate and exclusive performance is only available to a limited number of guests.
Small plates and beverages will be available from the Monkey Hut Bar & Lounge during the performance and is not included in the ticket price. For dinner reservations please contact 305-422-4236 or email diningroom@littlepalmisland.com.
We are delighted to offer ferry transfer to Little Palm Island at 6:30 pm for this event.
Tickets: $80
Little Palm Island and the South Florida Symphony Orchestra present the next installment of the
ALLEGRO! Series
featuring the South Florida Symphony String Quartet
Tuesday, April 29, 2025 — — Little Palm Island
South Florida Symphony Orchestra's String Quartet returns to Little Palm Island for an unforgettable evening of music set against a breathtaking oceanfront backdrop. This exclusive, intimate concert features Mendelssohn’s passionate String Quartet No. 2, Ravel’s elegantly seductive String Quartet in F major, Gardel's beloved tango, Por Una Cabeza, and more.
Founded in 1997 in Key West by Music Director Sebrina María Alfonso, the now Fort Lauderdale-based South Florida Symphony Orchestra is celebrating its 27th season. Committed to delivering enriching cultural music experiences, SFSO serves residents and visitors across Monroe, Miami-Dade, and Broward counties.
South Florida Symphony String Quartet
Huifang Chen, Violin I
MeiMei Luo, Violin II
Brandon Wu, Viola
Claudio Jaffe, Cello
Ticket does not include dining reservations. Please make separate dining reservations to reserve a table.
Tickets: $75
The Florida Restaurant & Lodging Association Monroe Chapter presents
3nd Annual FRLA Monroe R.O.S.E Awards
Thursday, May 15, 2025 — — Hawks Cay Resort, 61 Hawks Cay Blvd, Duck Key
The ROSE (Recognition of Service Excellence) Awards recognizes Monroe County front line hospitality employees who demonstrate excellent customer service. These industry champions showcase the region’s commitment to creating an extraordinary visitor experience.
* Sponsorship opportunities available
Tickets: $100