Naples  nightlife is limited to bar-and-grill type places and sports-bar settings like the Foxboro Sports Tavern (4420 Thomason Dr., 239/530-2337, 10 a.m.–1 a.m. daily).
There are also a few spots like the Old Naples Pub (255 13th Ave. S., 239/649-8200, 11 a.m.–10 p.m. Mon.–Sat., noon–9 p.m. Sun.) and the waterfront Shane’s Cabana Bar (495 Bayfront Pl., 239/732-6633, 11 a.m.–2 a.m. daily) that serve decent pub grub but mainly function as drinking establishments.
Those determined to dress up and dance should head to Vision (11901 N. Tamiami Tr., 239/591-8383, 4 p.m.–2 a.m.)—a multiroom entertainment complex that features a large dance club, a swank ultralounge, and even a sushi bar—or to Snapper’s (2634 E. Tamiami Tr., 239/775-4114), which bills itself as Naples’s only gay bar.
Naples is famous for its high-end art scene, and the area in and around downtown is thick with galleries showcasing a wide variety of work. Along Gallery Row on Fifth Avenue, well-known galleries like New River Fine Art (600 5th Ave. S., 239/435-4515, 10 a.m.–5 p.m. Mon.–Sat., extended hours in winter) display masterworks from the likes of Dalí, Miró, Renoir, and more, alongside modern pieces from Frederick Hart, M. L. Snowden, Henry Asencio, and others. The Four Winds Gallery (658 5th Ave. S., 239/263-7555, 10 a.m.–5 p.m. Mon.–Sat., extended hours in winter) takes a different approach, with carvings, jewelry, pottery, and other examples of modern Native American art.
A block south of Fifth Avenue is the Von Liebig Art Center (585 Park St., 239/262-6517, 10 a.m.–4 p.m. Mon.–Sat., $5 adults, $2, children) at the Naples Art Center, which combines exhibitions and gallery displays of the work of more than 400 local and regional artists. The nearby Weatherburn Gallery (452 Bayfront Pl., 239/263-8008, 11 a.m.–5 p.m. Tues.–Sat.) has a 3,000-square-foot showroom displaying an array of impressionist and realist art.
A little farther south on Third Street between Broad and 12th Avenues is another concentration of galleries. Gallery Matisse (1170 3rd St. S., 239/649-7114, 10 a.m.–5 p.m. Mon.–Sat., extended hours in winter) has a handful of Matisse pieces on display alongside pieces by Picasso, Miró, Édouard Cortès, Dale Chihuly, and several high-profile Florida artists. Across the street is the Darvish Collection of Fine Art (1199 3rd St. S., 239/261-7581, 10 a.m.–5 p.m. Mon.–Sat., limited hours in summer), the second-oldest gallery in Naples; it focuses on 19th- and 20th-century artists.
For those interested in the performing arts, the Naples Players perform a mix of crowd-pleasing musicals, kid-friendly fare, and even some more modern pieces at the beautiful Sugden Community Theater (701 5th Ave. S., 239/263-7990, www.naplesplayers.com ). Ballet, classical music, and Broadway productions are performed at Philharmonic Center for the Arts (5833 Pelican Bay Blvd., 239/597-1900, www.thephil.org ).
Unsurprisingly, many of Naples ’s high-profile annual events are centered around art. Most occur during the peak snowbird season, like the Naples New Year’s Weekend Art Fair (Jan.), the Downtown Naples Festival of the Arts (Mar.), and the Naples Masters Art Festival (Mar.).
The twice-yearly Downtown Naples Craft Festival (Apr., Sept.) may be more interesting to those interested in creativity but without the bulging wallet to splurge on art; the events bring more than 100 crafts vendors to downtown, with all the food and activities that make craft fairs an appealing family function.
The trapped-in-amber vibe of the Old Florida Festival (1st weekend in Mar.), which takes place on the historic grounds of the Collier County Museum , is a must-see for history buffs. The grounds are divided into camps populated variously by Native American groups, Spanish settlers, British soldiers, Civil War fighters, pioneers, and more; the result is a look at the many different phases of history that Florida  has seen through the years.