Best Early Entertainment in Naples

Get Your Party Started Early in Naples, Florida

With its reputation as a haven for rich retirees, Naples’ early entertainment scene comes as no surprise. Miami Beach this is not, so do not expect nightclubs that hit their stride in the after midnight hours. You are more likely, instead, to find folks partying in the middle of the day at beach and chickee bars such as the Snook Inn and others throughout the area.  In most cases, the music ends after the dinner hour, around 10 p.m. or earlier.

The area also has a reputation for live performance art at a variety of venues from Bonita Springs to Marco Island. Musicians, dancers and theater troupes from the community and across the nation make appearances at performance arts halls such as Sugden Community Theatre in downtown Naples and the Center for Performing Arts in Bonita Springs. Their performances typically end around 10 p.m.; furthermore, many of the venues host matinees on weekends.

This list directs you to the best of the Naples early live entertainment options. Those who like to plan their evenings for an early retreat back to home base will find everything from jazz quartets and  youth drama performances to indy films and opera. 


Dinner, live music and dancing: It all happens in one spot at The Stage in Bonita Springs. It features live performances by a number of different national tribute band acts. Tickets start at $25 and include a three-course dinner, the cover charge and dancing. The Stage opens at 5 p.m. for cocktails at the bar, and the first dinner seating starts at 5:45 p.m. The tribute band du jour takes the big stage at 7:30 p.m. and the kitchen serves dinner until 9:30. Those who do not wish to purchase dinner can enter for a cover charge that changes depending upon the popularity of the band.

Recommended for Early Entertainment because: The bar opens at 5 p.m. for pre-show cocktails, and entertainment begins at 7:30.

Chelle's expert tip: For the best seating, make reservations up to 60 days in advance. There's a $10 upcharge for preferred seating.

Read more about The Stage →

Wine Loft of Naples
Photo courtesy of Chelle Koster Walton

The gorgeous parlor setting at the Wine Loft Bar & Restaurant feels at once elegant and homey. It hosts live entertainment every Thursday, Friday and Saturday plus jazz musicians for its Sunday brunch each week. Of course fine wines are the tipple of choice, but the bar carries a full stock of beers and liquor. The restaurant serves meals until the bar closes, which is midnight on week days and 1 a.m. of Friday and Saturday nights. The menu keeps it light with appetizers, salads, sandwiches, flatbreads, small plates and desserts. Dishes such as crab and spinach dip, strawberry salad, fig and prosciutto flatbread, tenderloin medallions with blue cheese and turtle lava cake pair well with wines.

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Old Naples
Old Naples Pub
Photo courtesy of Chelle Koster Walton

The Old Naples Pub is located in the thick of one of Naples's leading shopping zones. Folks trying to avoid the sticker shock and relatively formal air of Third Street restaurants and bars head here for a casual setting indoor and out. The lunch and dinner menu strays a bit from traditional pub fare, offering everything from fish and chips and burgers to Caesar salads and bratwurst. The bar's extensive beer list makes a splash with brew-heads. This is a cool place to hang, and patrons are treated like long-lost friends. The shaded courtyard area holds tables that fill up on cool, sunny days. Inside has a typical pub feel. The happy hour prices are more than reasonable. Live entertainment includes regular performances on the 100-year-old tavern piano.

Recommended for Early Entertainment because: Solo live entertainers perform early evenings from Wednesday through Sunday.

Chelle's expert tip: The open-air courtyard provides the perfect place to enjoy Naples' warm weather

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Center for Performing Arts
Photo courtesy of Chelle Koster Walton

A newcomer to the Naples area live performance scene, it hosts a variety of entertainment in its Hinman Auditorium and Moe Auditorium & Film Center. Shows range from musical acts and improv to dance and performances by the center's youth groups. Part of the original Center for the Arts Bonita Springs, this facility opened in 2013 to expand upon the center's visual arts focus with theater programs for kids and adults. Besides its own community troupes, it welcomes entertainers from around the country and beyond. The center's film series shows a nice variety of foreign movies, family shows and indy productions.

Recommended for Early Entertainment because: Performances and films begin as early as 7 p.m., plus there are weekend matinees.

Chelle's expert tip: Ask about the dinner and film series in season.

Read more about Center for Performing Arts →

Sugden Community Theatre
Photo courtesy of Naples Players

Do not be fooled by the "community" in the theater's name - the Naples Players troupe that performs here is anything but amateur in quality. During its more than 50 years of performing, the company became so popular, it was able to raise funds to build its own modern theater in the late 1990s. And on post Fifth Avenue South, no less! The Naples Players mounts more than 220 performances each year. Besides its main stage and an experimental black box theater, the Sugden features an outdoor stage. In addition to the Naples Players, it plays host to the Naples Jazz Society, ballet, opera and other performance art.

Recommended for Early Entertainment because: Shows end early - around 10 p.m., plus there are Sunday matinees.

Chelle's expert tip: Buy tickets well in advance for Naples Players productions; the seats fill fast.

Read more about Sugden Community Theatre →

Bay House Restaurant
Photo courtesy of Chelle Koster Walton

Naples visitors looking for live jazz and other genres of music love the Bay House Restaurant not only for its musical selection, but also for its wonderful seafood dishes, polished decor and expansive views of the wild Cocohatchee River and its resident birds. Patrons can hear live music - often tasty blues and jazz licks - every night Wednesday through Saturday. The Tierney's Bar area boasts - as does the entire restaurant complex - tasteful nautical decor, and the tavern has a cozy brick fireplace ideal for a casual evening with friends, cocktails and mellow melodies.

Recommended for Early Entertainment because: Hear live music seven days a week from 6:30 to 9:30 p.m.

Chelle's expert tip: With its newest addition of a crab-obsessed bar, Bay House ups the "bar" on its seafood dining, so plan on dinner with your musical evening.

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H B's On the Gulf
Photo courtesy of Chelle Koster Walton

Part of the 100-plus-year-old Naples Beach Hotel, H B's draws fans from beyond the resort for drinking and dining with a fabulous view of the beach, gulf and sunset. For nearly 10 years, its wine list has earned the Award of Excellence from Wine Spectator magazine, plus the bartenders have a flair for tropical drinks. Have a seat at the bar with a clear view of the sea or get even closer at a row of chairs lined up outside the flung-open windows on the porch. Hungry? Lunch and dinner menus offer a variety of small plates, salads, sandwiches and entrees.

Recommended for Early Entertainment because: It hosts live musicians Wednesday through Sunday from 6 to 9 p.m.

Chelle's expert tip: It has the best seats in town for toasting the sunset. Get there early.

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M Waterfront Grille
Photo courtesy of peter sereno

Naples residents and visitors who love jazz head to M Waterfront Grille for its refined atmosphere, water views, fine cuisine and terrific live music. On Wednesday, patrons relax in the lounge or on the outdoor veranda for Wine on Wednesday from 4 to 7 p.m., which features smooth jazz music, wine and drink specials and discounted appetizer specials. The musicians perform from 5 to 8 p.m. The restaurant also hosts live jazz on Friday nights from 7 p.m. to 10 p.m. in season and at Sunday Brunch, 11 a.m. to 2 p.m. Guests can dine inside the restaurant or order something from the lounge menu.

Recommended for Early Entertainment because: Live entertainment takes place Wednesday from 6 to 9 p.m., Friday from 6:30 to 9:30 p.m. and during Sunday Brunch 11 a.m. to 2 p.m.

Chelle's expert tip: Call ahead for a live jazz calendar, which changes seasonally.

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Bayside Seafood Grill and Bar
Photo courtesy of Chelle Koster Walton

This bar's upstairs locale affords patrons incredible views of Venetian Village, the bay and its waterfront homes as they sip their favorite libations. The downstairs Cafe venue is perfect for an early or late supper, and diners have the pleasure of being serenaded by a pianist on Friday and Saturday nights. The Upper Deck Bar affords a casual, laid-back atmosphere in an open-air setting and also features live entertainment every day but Monday and Tuesday. Well-rounded menus both upstairs and downstairs cover all the culinary bases for nightlifers looking for sustenance. The clientele is mostly mature adults, so don't expect late-night revelry.

Recommended for Early Entertainment because: Entertainers perform starting at 6 p.m. (2 p.m. on Sundays) and play through the dinner hour.

Chelle's expert tip: Head to the Upper Deck when the weather permits.

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Snook Inn
Photo courtesy of Chelle Koster Walton

Chickee bars are a signature form of the Naples area party scene. Because of the destination's close proximity to Seminole and Miccosukee Indian tribes, many resorts and restaurants hire local tribesman to construct the open-air thatched structures for the best local color. The chickee at Snook Inn overlooks the Intracoastal Waterway and hosts live island music daily - what could be more purely Floridian? Whether a soloist or a small band, the music starts at 1:30 p.m. Lunchtime attracts an older crowd that comes for seafood with their rum punch and dancing. The music plays until 10 a.m., and the dinner-time crowd becomes younger and more local.

Recommended for Early Entertainment because: Live bands strike up starting with the afternoon lunch rush.

Chelle's expert tip: Get there early in the day on weekends, when the chickee bar fills early with drinkers and diners.

Read more about Snook Inn →


Meet Chelle Koster Walton

Chelle Koster Walton – the Local Expert for Naples, Florida and the Caribbean – has been covering the destination for 30 years. Her top-selling Sarasota, Sanibel Island, and...  More About Chelle