Keep the Party Going: Celebrate Jimmy Buffett’s Legacy in Naples
Three days. Plenty of live music. One big party with a purpose.
This Labor Day weekend, grab your flip-flops and join us at Compass Hotel Naples for a celebration inspired by the music, generosity and laid-back spirit of Jimmy Buffett. From September 4–6, 2026, Compass Hotel Naples and 5 o’Clock Somewhere Bar & Grill will host an unforgettable Jimmy Buffett Day Weekend filled with live entertainment, island-inspired fun, special appearances and opportunities to give back.
Jimmy Buffett showed us that paradise is more than a place; it is a way of life. It means slowing down, appreciating the moment, caring for your community, and leaving the world a little brighter than you found it!
In honor of Jimmy Buffett Day, Compass Hotel Naples invites you to celebrate that legacy with the Keep the Party Going Package. This limited-time offer combines an easygoing Naples getaway with an opportunity to give back, so you can enjoy a little time in paradise while supporting a meaningful cause.
Friday, September 4: Jimmy Buffett Day
Ease into island time on Friday as the weekend-long celebration officially begins.
Starting at noon, guests can purchase tickets for the 50/50 raffle and begin supporting the Louisville Slugger Warriors. The evening continues with a special visit from Bird Gardens of Naples at 6 p.m., giving guests an opportunity to meet and take photos with colorful parrots.
Gypsy Blue will take the stage from 6–9 p.m., bringing the energy and live music needed to start Jimmy Buffett Day Weekend on the right note.
Friday’s schedule includes:
12 p.m. – 50/50 raffle ticket sales begin
6 p.m. – Special visit from Bird Gardens of Naples
6–9 p.m. – Live music by Gypsy Blue
Saturday, September 5th
Nonstop entertainment, special guests and fundraising activities planned throughout the day.
The island sounds begin at 11 a.m. with steel drum music by Orlando Phillips. Guests will also have the chance to meet former Major League Baseball player and author Curtis Pride during a special meet-and-greet and book signing.
The afternoon continues with live music from Wendell Ray, another visit from Bird Gardens of Naples and a charity cornhole tournament benefiting the Louisville Slugger Warriors. Brandon Allen will close out the evening with live music from 5–8 p.m.
Saturday’s schedule includes:
Silent auction and 50/50 raffle throughout the day
11 a.m.–2 p.m. – Live steel drum music by Orlando Phillips
11 a.m.–12 p.m. – Curtis Pride meet-and-greet and book signing
2–5 p.m. – Live music by Wendell Ray
3 p.m. – Special visit from Bird Gardens of Naples
3–4:30 p.m. – Charity cornhole tournament
5–8 p.m. – Live music by Brandon Allen
Sunday, September 6: One More Day in Paradise
We are keeping the party going for one more day with an afternoon of live music, fundraising and island-inspired fun.
Head Above Water will perform from 2–5 p.m., and Bird Gardens of Naples will return for another special appearance at 3 p.m. Guests will also have one final opportunity to place silent auction bids and purchase 50/50 raffle tickets before the winners are announced.
Sunday’s schedule includes:
Final day of the silent auction and 50/50 raffle
2–5 p.m. – Live music by Head Above Water
3 p.m. – Special visit from Bird Gardens of Naples
6 p.m. – Silent auction closes
6 p.m. – Final 50/50 raffle winner announced
Party with a Purpose
Jimmy Buffett Day Weekend is about more than live music and tropical fun. Throughout the celebration, Compass Hotel Naples will raise funds and awareness for the Louisville Slugger Warriors National Amputee Baseball Team.
The Louisville Slugger Warriors are a competitive nonprofit baseball team composed of athletes with amputations and limb differences. Its players include U.S. military veterans, active-duty service members, Wounded Warriors and current and former college baseball players.
Through competition, camaraderie and community, the organization gives athletes opportunities to continue playing the game they love while inspiring others to see what is possible when determination outweighs limitations.
Guests can support the Louisville Slugger Warriors throughout the weekend by participating in the silent auction, purchasing 50/50 raffle tickets, joining the charity cornhole tournament and exploring additional fundraising opportunities. Be sure to stop by the team’s information table to learn more about its mission and meet members of the organization.
Keep the Party Going with an Exclusive Naples Hotel Offer
Why celebrate for just one day when you can make an entire Naples getaway out of it?
With the Keep the Party Going Package, guests who book a stay of two nights or more can receive 20% off retail rates and two special-edition commemorative cups created for this annual Margaritaville tradition.
Compass Hotel Naples will also donate $5 to the Louisville Slugger Warriors for every night booked through the package, allowing your stay to make an even greater impact.
The offer is valid for stays between August 3 and September 27, 2026, making Jimmy Buffett Day Weekend the perfect opportunity to settle into an all-suite stay and enjoy everything Compass Hotel Naples has to offer.
Join the Jimmy Buffett Day Celebration in Naples
Spend Labor Day weekend enjoying live music, tropical drinks, special appearances and one more day—or three—in paradise. Most importantly, help us honor Jimmy Buffett’s legacy by celebrating community, supporting a meaningful cause and sharing the good times with the people around us.
Keep the Party—and Jimmy’s Spirit—Going
Jimmy Buffett’s music may have inspired us to escape to paradise, but his generosity reminded us to take care of one another along the way. The Keep the Party Going Package celebrates both sides of that legacy, inviting guests to unwind while helping make a difference.
The offer is valid for stays until September 27, 2026. Book a stay of two nights or more to enjoy 20% off retail rates, receive two special-edition commemorative cups and help support Louisville Slugger Warriors with every night of your visit.
Pack your flip-flops, gather your favorite travel companions, and join us in Naples as we raise a glass, give back, and Keep the Party Going.