By MEGHAN McEWEN

THIS city — named after the one in Italy because of its beautiful bay — is most widely known for its sugar-sand beaches, warm winter weather and sprawling, high-gated communities that attract older, well-off snowbirds who live to golf but go to bed early. (It has the nation's second highest number of golf holes per capita, just behind Myrtle Beach, S.C.). But now Naples is starting to draw a younger, more dynamic crowd attracted to outdoorsy pursuits off the course, high-end shopping and late-night noshing — all in a laid-back, upscale setting with enough cultural interest to support more than 130 art galleries and a symphony orchestra.

Friday

5 p.m.
1) Goodnight, Sun

Drop off your bags and head straight to Naples Pier in time for the sunset — an impressive show that beckons tourists and Neapolitans alike; some tote lawn chairs and coolers to the beach below. Last rebuilt in 1960 and strong enough to withstand Hurricane Wilma in October, the landmark extends 1,000 feet over the Gulf of Mexico, which teems with snapper, grouper and shark. (Note the signs warning fishermen not to clean their fish over the water.) As you wait for the applause-generating daily masterpiece and watch the pelicans dive for their dinner, keep an eye out for the occasional dolphin.

7 p.m.
2) Tiger Vision

"The wild is wilder after dark" is the tag line for the Naples Zoo's most unusual attraction: a nighttime tour using night-vision goggles. During the roughly two-hour tour, said to be the only one of its kind in the United States, the zoo director, David Tetzlaff, will personally guide you past African wild dogs, tigers, porcupine pens, lion dens, antelopes and monkeys. Do plan: tours are given on select nights during the winter, and tickets ($70 a person) tend to sell out (1590 Goodlette-Frank Road, 239-262-5409).

9 p.m.
3) Naples, as in Italian

While much of Naples's sprawling commercial development takes the form of the ubiquitous Florida strip mall, it's a rare gem like Naples Tomato (14700 Tamiami Trail North, 239-598-9800) that does something different inside. Opened by two New Hampshire transplants, Jack and Nadine Serfass, this new warehouse -inspired Italian-American restaurant prepares sweet, chunky sauce from heirloom tomatoes harvested locally. Never will you feast on better lasagna ($18.95), and the alder wood-plank Everglades tilapia ($29.95), topped with grilled tomato and truffled balsamic vinaigrette, is local seafood at its best.

Saturday

10 a.m.
4) Be One With Nature

Only three years old, Naples Botanical Garden (4820 Bayshore Drive, 239-643-7275) is in the opening stages of grand plans to develop its 160 acres into a plant paradise. The focus now is on botanicals along the 26th latitude (where Naples is), like reptilian-looking climbing oleander from West Africa and giant squill from Zanzibar. Grab a colorful butterfly identification guide at the entrance to the butterfly pavilion and try to find each wing design as you walk through the screened-in area. If you're comfortable with critters, proceed to the sections dedicated to geckos and to brightly colored chirpy honeycreepers and lorikeets, birds that aren't afraid to land on shoulders — especially Beeper, nicknamed for his ability to mimic cellphone rings.

1 p.m.
5) Under the Banyan Tree

With winter temperatures hovering from the mid-70's to the low 80's, alfresco dining is the thing among Naples's tanned socialites. There are dozens of places for it, often with heat lamps at tables for cooler evenings. But the best outdoor patio in town may be the rustic courtyard at Campiello (1177 Third Street South, 239-435-1166), with its giant banyan tree and a stone fountain. The lunch menu, featuring classic thin-crust pizzas fired to Neapolitan perfection in a wood oven ($12.50) as well as a muffuletta piled high with capicolla, mortadella, soppressata, salami and provolone ($12.50), won't disappoint.

3 p.m.
6) A Good Segue

Naples has its share of interesting historical tidbits, which you can encounter during Naples Water and Land Tours' new one-hour Segway Tour (1000 10th Avenue South at the Charter Club Resort, 239-793-7529; $50). You'll have a hoot zipping up and down the tree-lined streets while fascinated passersby honk and holler as the guide gives a general introduction to the downtown area. Starting near the City Docks and bypassing the main commercial avenues, you'll see "cracker houses" — the late-19th-century cottages of the area's first white settlers — and Tin City, an old maritime market that has grown into a touristy outpost peddling T-shirts, gator heads and coral necklaces. Don't be fooled by President Bush's Segway spill; the 15-minute introductory course beforehand has successfully trained participants ages 5 through 92.

4:30 p.m.
7) The Greenback District

Sure, there are brand-new Tiffany and Gucci stores at the Waterside Shops at Pelican Bay, and Hermès and Vuitton shops are on the way. But you may prefer to skip the chain stores for the boutiques and art galleries of Fifth Avenue South and Third Street South downtown. After all, Marissa Collections (1167 Third Street South, 239-263-4333) is a 10,000-square-foot bastion of luxury that sells an impeccable collection of Versace, Prada, Zac Posen, Derek Lam, Vera Wang, Miu Miu, you name it. Marissa Hartington, who opened the store 30 years ago with $500, still handpicks each piece, steadily expanding the "boutique" section of trendier, more affordable labels because of a younger clientele. If it's art you're interested in, Broad Avenue South goes by the moniker Gallery Row. Representing the likes of Milton Avery and Wolf Kahn, the Marianne Friedland Gallery (359 Broad Avenue South, 239-262-3484) stands out as a spare and serious modern and American contemporary gallery amid blocks of more ornate, decorative works and old masters.

8 p.m.
8) Not an Early Bird Special

If the late-night dinner crowds at trendy restaurants like Blu Sushi and Café & Bar Lurcat aren't convincing enough that there's a younger vibe in town, then make a reservation at Nektar (849 Seventh Avenue South, 239-435-1882). The ultrasleek bright-orange Mediterranean-style restaurant was opened last year by two Albanian brothers, Armand and Elton Alikaj, who moved from New York and London respectively. Start with the daily soup ($8) — a zesty lentil on one visit — or the watermelon salad ($12) sprinkled with red onions, fresh Greek feta and mint. Based on old family recipes (their mom is in the kitchen each day), the entrees range from a lusty pork stew over fresh vegetable couscous seasoned with Moroccan spices, raisins and sun-dried tomatoes ($22) to a slow-roasted lamb shank au jus with braised fennel and potato purée ($29).

Sunday

8 a.m.
9) Natural Habitat

The Naples area has nearly 20 miles of groomed beaches. But Delnor-Wiggins Pass State Park (11100 Gulfshore Drive, 239-597-6196) is different. It is one of the last remaining natural barrier-island beaches in Naples — a one-mile stretch from which you won't see any tall buildings, and where the ungroomed sand is strewn with shells and seaweed. Get there early (official opening, 8 a.m.) for flawless sand dollars, lightning whelks and cockle shells. You can rent a kayak at the concession stand, Hurricane Charlie's (239-314-0110), for a full ($30) or half day ($20). Paddle through the peaceful estuaries and mangroves — a haven for dolphins, sea turtles, shore and marsh birds, as well as manatee, often spotted feeding in the sea grass beds during winter.

Noon
10) Wacky Racers

Three weekends a year — the first was late last month, the next is March 4 and 5 and then Oct. 28 and 29 — scruffy racetrack regulars and V-neck-sweater-wearing Palm Beach types come together for some down-and-dirty fun at the Mile o' Mud at Florida Sports Park (8250 Collier Boulevard, 239-774-2701), the last legal place to watch swamp buggy races in the country. Loud, oversize and odd-looking buggies tear around a soupy track, spitting mud and dipping into mushy sink holes, while whooping fans, crowded onto rickety metal and wooden bleachers, go absolutely berserk. Every season, the lucky lass crowned Swamp Buggy Queen is dunked in the mud as part of the finale celebration.

Copyright 2006The New York Times Company