Things to Do in Naples in May 2024

Hoffman Korff Group


Welcome to the vibrant city of Naples, Florida, where the sun-kissed shores meet cultural festivities and sublime relaxation. May 2024 is a special time to explore this Gulf Coast gem as the calendar brims with exciting events, unique attractions, and an atmosphere that can only be described as electric.

Whether you're yearning for soothing beach days, gourmet delights, or lively celebrations, Naples in May is the perfect canvas for your getaway masterpiece. Join us as we unveil the best things to do in Naples in May — a month that promises endless sunshine, enchanting songs, and a spirit of celebration. Pack your bags and get ready for an adventure filled with the allure and charm that only Naples can offer.

1. Rain - A Tribute to the Beatles

When: Thursday, May 2nd, 2024 from 8 pm – 10 pm
Where: Artis-Naples, 5833 Pelican Bay Blvd.

Step back in time and experience the magic of The Beatles with RAIN: A Tribute to the Beatles. This immersive concert experience brings the essence of one of the most influential bands in history to vivid life. Fans are transported through a musical voyage that spans the hits of Sgt. Pepper’s Lonely-Hearts Club Band and Magical Mystery Tour, along with other beloved Beatles anthems. Featuring meticulous attention to detail, RAIN performs the music with note-for-note perfection, accompanied by a vibrant fusion of costumes and psychedelic visuals.

Whether a lifelong fan or a newcomer to the timeless catalog of The Beatles, attendees at RAIN can expect an evening of sing-along melodies, nostalgia, and an invigorating showcase of a revolutionary era in music. This event is not just a concert; it's a lively homage to a band that changed the musical landscape forever. Don't miss this blend of historical artistry and nostalgic celebration, designed to enchant audiences of all ages.

Learn More:

2. Mercato Nights: The Beatlemaniax-USA

Thursday, May 2nd, 2024 from 6:30 pm – 8:30pm 
Where: Mercato, 9110 Strada Place, Naples, FL.

The Beatlemaniax-USA transports fans back to the height of Beatlemania with an exceptional tribute concert at the Mercato. Capturing the essence of the Beatles, the group delivers electrifying performances complete with authentic outfits and instruments.

Guests enjoy the open-air event among fellow enthusiasts, with drinks from The Pub's outdoor bar, and the comfort of your lawn chairs and blankets – pets in tow.

This free community gathering allows attendees to immerse themselves in the timeless tunes of the Beatles. External coolers and beverages are prohibited to maintain the provisioned amenities and atmosphere. Weather-dependent, this Beatles experience is a must-visit for locals and music lovers alike.

Learn More:

3. Comedian Bo Johnson Live in Naples!

When: Thursday, May 2nd, 7pm – 8:30 pm
Where: 2500 Vanderbilt Beach Rd. Naples, Florida 34109

Enjoy an evening of gut-busting humor with the talented Seattle-based comedian, Bo Johnson. Known for his appearances on Comedy Central and Just for Laughs, Bo brings his unique brand of comedy to stages all across North America. Expect a night of infectious laughter, sharp wit, and unforgettable jokes that have earned millions of views online. Don't miss the chance to see him live and be part of the hilarity!

Learn More:

4. Murder Mystery Play

When: May 1st – 19th | Wednesdays & Thursdays at 7:30 pm, Fridays & Saturdays at 8:00 pm, Sundays at 2:00 pm 
Where: 701 5th Ave S. Naples Florida 34102

Enjoy an evening of mystery at McSpadden Hall in Naples United Church of Christ, the audience will be treated to "The Murder at Haversham Manor," an amalgamation of comedy and mystery inspired by iconic board games and whodunit films. Set in 1954 during a stormy evening, the attendees at Mr. Boddy's dinner party are thrust into a chaotic investigation of their host's untimely death, leaving everyone to play the dual roles of suspect and detective.

The play features memorable mishaps and spontaneous humor, as actors comically navigate through misplaced lines and awkward pauses, while simultaneously engaging the audience to solve the unfolding enigma. Amidst the jovial blunders, such as an actress fainting and a 'corpse' struggling to remain still, the show is a delightful experience for all, highlighted by its accessible ticket prices of $49 for general admission and $39 for subscribers.

The evening promises to deliver a captivating theatrical event where the killer's identity remains a tantalizing mystery until the final curtain drops.

Learn More:  or (239) 434-7340

5. Garth Brooks & Brooks & Dunn- Legends Concert Series- May 3rd

When: Friday, May 3rd 6 pm – 10 pm
Where: 3940 City Gate Blvd S. Naples, Florida 34117

The Maxwell Mortgage Legends Concert Series presented an unforgettable tribute evening on May 3, 2024, from 6 pm to 10 pm, featuring the iconic music of country legends Brooks & Dunn and Garth Brooks.

Shawn Gerhard delivers "The Ultimate Garth Brooks Tribute," hailed by Johnny Garcia, Garth Brooks' lead guitarist, as the closest experience to the real deal. With a base in Nashville, Shawn’s fiery showmanship and top-notch musicianship captivate audiences of all ages, emulating the spirited essence of Brooks' legacy.

Meanwhile, "Dunn & Brooks" brings the 90s party back with their action-packed rendition of Brooks & Dunn's classics including hits like "Boot Scootin’ Boogie" and "My Maria." With a career spanning three decades and 20 #1 hit singles, their performance is a nostalgic trip down the red dirt road of country music lore, ensuring the duo’s influential music continues to resonate with fans old and new.

Learn More:

6. Wondrous Stories

When: Saturday, May 4th, 7 pm 
Where: Norris Center, 755 8th Avenue South Naples, FL 34102

Fee: $30 / $35 Premium Seats

"Wondrous Stories," an enchanting event featuring Carl Granieri, brought to life the most beloved musical tales on a night filled with song. With a mix of romance, humor, inspiration, and haunting melodies, attendees enjoyed a repertoire that included classics from Frank Sinatra to the Dubliners. Highlights such as "American Pie" and "Puff the Magic Dragon" invited vibrant sing-alongs, adding to the high-spirited fun of the memorable evening.

The event "Wondrous Stories" not only showcases the musical talents of Carl Granieri but also celebrates the timeless appeal of storytelling through music. Each song performed by Granieri holds a special story within it, captivating the audience and allowing them to become a part of the narrative.

As attendees sing along to popular tunes like "American Pie" and "Puff the Magic Dragon," they are reminded of the power of music to bring people together and create a sense of community. The event also highlights the importance of preserving and passing down traditional songs and their accompanying stories, ensuring that they continue to be cherished by future generations.

Learn More:

7. Hats & Horses: Kentucky Derby Watch Party

When: Saturday, May 4th from 5 pm – 8 pm  
Where: The Ritz-Carlton Naples, Tiburón, 2600 Tiburon Drive, Naples

Don your best hat and cheer on the horses in the Kentucky Derby at the Bella Vista Lounge.

Join the festivities at The Ritz-Carlton Naples, Tiburón for a stylish Kentucky Derby celebration! Experience the grandeur of the races with a live stream event on May 4th without traveling to Churchill Downs. Get into the spirit with your finest derby attire and participate in the Best Hat Contest, where creativity meets elegance.

Prizes await the top three hats, with judging at 6:00 p.m. and winners announced at 6:30 p.m. Enjoy the special Mint Julep presentation, and live music, and indulge in food and beverage specials. 
The excitement starts at 5:00 p.m. with preliminary races, leading up to the main event at approximately 6:50 p.m. RSVP now with a complimentary ticket for an exceptional derby day!

Learn More:

8. Thrifting Cinco de Mayo Bus Tour: Boarding in Naples, Bonita, and Ft. Myers

When: Saturday, May 4th from 8 am – 5 pm  
Where: BOARDING IN 3 locations #1 Naples 8 am Publix 5991 Pine Ridge Rd. & I-75, Naples, FL 34119, #2 Bonita 8:30 am Publix 12900 Trade Way Four, Bonita Springs, FL 34135, #3 NEW Ft. Myers 9 am Publix 13650 Fiddlesticks Blvd, Fort Myers, FL 33912, United States

Join in the fun, celebrating Cinco de Mayo in style! Party, shop for bargains, enjoy some margaritas, and have a blast!

The Cinco de Mayo Thrifting Bus Tour offers a wild adventure for treasure hunters and bargain shoppers. The event takes participants on a comfortable coach bus through North Port and Englewood, making stops at various thrift stores and bins while offering fun festivities to celebrate the day. Highlights of the tour include a luxury bus ride with onboard amenities, a catered lunch with multiple choices, and the excitement of securing unique finds at each stop.

Participants are encouraged to bring donations to earn an extra raffle ticket and potentially win prizes, supporting community giving through their thrifty escapades.

The event, while non-refundable, promises a day full of unique discoveries, delicious food, and festive fun. Participants will leave with not only thrifted gems but also a shared experience of celebration and shopping on this special Cinco de Mayo.

Learn More:

9. Cinco De Mayo

When: Sunday, May 5th from 5 pm – 8 pm  
Where: The Ritz-Carlton Naples, Tiburón, 2600 Tiburon Drive, Naples

Celebrate Cinco De Mayo in style with an authentic dinner experience designed by Chef Aldo Novoa Rodriguez

Enjoy an ethnic evening at Ria for an exquisite Cinco De Mayo celebration with a spectacular dinner, crafted by the renowned Chef Aldo Novoa Rodriguez. Your evening starts with live music and a unique welcome drink served upon your arrival. Indulge in a lavish buffet boasting authentic dishes like Arroz al Poblano, a Taque-Ria Cart featuring Al Pastor and Carne Asada, a fresh Ceviche Station, and delicious desserts like Tres Leches Cake and Cinnamon Churros. Don't miss out on the fun of the famous margarita bicycle as you savor culturally rich flavors and a night of festivity.

$95 for ages 13 and up | $50 for ages 2 to 12 | Complimentary for under 2 years
All tickets and packages will be charged an 18% service charge, taxes, & ticketing fees at checkout.


10. Cinco De Mayo Taco Fest All You Can Eat Taco Buffet

When: Sunday, May 5th from 11 am – 3 pm  
Where: 2740 Bayshore Dr #11, Naples, FL, United States

Celebrate Cinco de Mayo with a fiesta of flavors at this fun Taco Fest! Join in the festivities for an unforgettable All You Can Eat Indo-Mex Taco Buffet. Indulge in a variety of mouthwatering tacos, an inventive blend of Indian and Mexican cuisines that promise to tantalize your taste buds.

Don’t miss out on this spectacular feast of all-you-can-eat tacos and the festive spirit. Bring your appetite and get ready to savor an impressive spread of culinary delights. See you there!

Learn More:

11. Bouquets & Bubbly for Mom

When: 5-8 pm (May 10 & 11) | 11 am-1 pm (May 12)
Where: Mercato Central Piazza

Join in the fun with a luxurious Mother's Day weekend celebration with BUBBLES, BOUQUETS, BEJEWELED, and LIVE MUSIC! From May 10-12, where they will be honoring moms in style:

BUBBLES: Toast with a complimentary glass of prosecco* from our vintage bar.

BOUQUETS: Craft a custom bouquet for mom at Petals the Flower Truck.

BEJEWELED: Add sparkle with Summa Vita Linx's permanent jewelry.
LIVE MUSIC: Enjoy performances by West Wave Duo (May 10 & 12) and Wendell Ray (May 11).

Learn More:

12. Comedian Tim Meadows Live in Naples!

When: Thursday, May 9th thru 12th from 7 pm – 8:30pm
Where: 2500 Vanderbilt Beach Rd. Naples, Florida 34109

Join in the fun for an evening of laughter and stories, with the incredibly talented Tim Meadows! Known for his iconic decade-long stint on Saturday Night Live and his role in classic comedies such as Mean Girls and Grown Ups, Meadows brings his quick wit and captivating humor to the stage. Catch him live as he shares his experiences from The Goldbergs, Schooled, and Brooklyn Nine-Nine, and talks about voicing characters in hit shows like Bob's Burgers. Don't miss the chance to see this comedic legend in person – a night filled with entertainment guaranteed!

Learn More:

13. Naples Philharmonic w/ Patriotic Pops

When: Friday, May 24th from 8 pm – 10 pm
Where: Artis-Naples, 5833 Pelican Bay Blvd.

Enjoy an evening of stirring melodies and national pride with the Naples Philharmonic's Patriotic Pops concert. On Friday, May 24th, from 8 pm to 10 pm, immerse yourself in the sounds of liberty and tradition at the renowned Artis-Naples venue, located at 5833 Pelican Bay Blvd. Whether you're a lover of classical harmonies or searching for a musical way to celebrate the spirit of America, this is an event that promises to resonate with hearts and minds. Don't miss out on this captivating celebration of our nation's rich musical heritage!
Learn More:

14. Salsa Group Class Naples FL With Brian Oakes

When: Every Saturday, from 6:30 pm – 7:30 pm
Where: Brian Oakes Ballroom & Latin Lessons, 2367 Vanderbilt Beach Road Unit 812, Naples

Treat yourself every Saturday to an exciting Salsa Group Class in Naples, FL with the talented Brian Oakes! Heat up the dance floor from 6:30pm to 7:30pm as you learn the basics and more, all in a fun group setting. RSVP early limited spots available for just $15. To secure your place, text 561-287-0443 with the full names of attendees. Get ready to salsa the night away!

Learn More:

Whether you enjoy the melodies of the Naples Philharmonic, the infectious laughter from Tim Meadows' stand-up, the shared toasts over Bouquets & Bubbly, the vibrant celebrations of Cinco de Mayo, or an exhilarating Kentucky Derby watch party, Naples will have etched itself into your cache of memories.

With this tapestry of cultural festivities, each thread woven with unique flavors of joy shows that Naples is not just a sunny beach town on the map, but a vibrant stage for unforgettable experiences. 
If you're a local or a traveler, the richness of our city's offerings in May beckons you to immerse and participate in the communal revelry. Until the next adventure, Naples will hold these moments in time, waiting to unravel new ones when you return.


Insightful local knowledge and extensive expertise. We looks forward to earning your family’s trust and leveraging our success for your benefit for generations to come. We looks forward to earning your family’s trust and leveraging our success for your benefit for generations to come.

Contact Us

Follow Us on Instagram