A Perfect Winter Getaway to Naples, Florida

Short days and low temperatures have us dreaming of heading to warmer, sunnier places for some much-needed rest and relaxation. With its white sand beaches, warm gulf water, a lush tropical backdrop, and excellent shopping and dining options, Naples, Florida, is an ideal winter getaway destination.

To help us plan the perfect travel itinerary, we sought out recommendations from mother-and-daughter duo Martha Talton and Cullen Daane (shown above), co-owners of Pierre & Harry, a pearl and gemstone jewelry boutique in historic Old Naples that is a destination for out-of-towners and in-the-know locals. Featuring pieces that perfectly capture the organic beauty of tropical Naples with their luscious freshwater pearls and aquamarine and turquoise gemstones, the shop is ideal for visitors who come looking to purchase jewelry to commemorate their trip and Naples natives alike.

“My favorite gemstones to work with, of course, are pearls,” says Cullen, who designs and crafts bejeweled works of art available in her store. “After that, I love gemstones that remind me of the sky and the sea. Turquoise, aquamarines and amazonite are among my very favorite.”

With their local expertise (Martha has lived in town for 30 years, and Cullen was born and raised as a Neapolitan), the mother-and-daughter team was able to easily offer some must-see and –do tips for spending a long weekend in Naples. Here are their picks:


After arriving to town on Thursday afternoon, check into a vacation rental with The Holiday Life (239.349.2494). Spend the night at luxury properties that range from single-family homes in historic Old Naples (within walking distance to the beach and shops!) to estates with incredible amenities (think an infinity pool overlooking Naples Bay).

After checking in, casually get into the vacation mindset with a trip to the Naples Beach Brewery (4120 Enterprise Ave. Suite 116) for a local craft beer. Ask to sample Black Tulip Coffee cold brew, which the brewery keeps on tap. Cullen and her husband Andrew recently purchased the coffee company and are roasting organic, fair trade beans on site at the brewery.

Parked outside, food truck Porker BBQ (231.645.4025) serves up smoked meats — classic pulled pork sandwiches along with Mexican-meets-Southern tostadas and tacos. “Their chicken ’n’ waffles is the best I’ve had in my life,” Cullen gushes. “They make the waffles fresh and deep fry them.”


Grab breakfast at the hole-in-the-wall coffee shop tucked in the lobby of Cove Inn on Naples Bay (900 Broad Ave. S.) to energize yourself for a day of shopping on Third Street South. Cullen recommends the pancakes, French toast, and eggs. After breakfast, walk around the corner to the Naples City Dock (880 12th Ave. S.) to watch the boats depart for a day of fishing — an ideal way to see the heart of historic Naples.

Also, near the dock, visit Phil Fisher Gallery (810 12th Ave. S.) to view the namesake artist’s watercolor and oil paintings of the area. A majority of his work is plein air, highlighting the lush landscape of South Florida.

Start your shopping spree down the street from the Naples City Dock at the women’s boutique Brigadoon (719 12th Ave. S.), which has been a Naples gem for more than 30 years. “They have great selection of lightweight cashmere capes, toppers, and basics,” Cullen says.

Walk a half-mile down 12th Avenue to Third Street South, home to fabulous locally owned boutiques and bistros. One of Martha and Cullen’s favorite stops for high-fashion clothing and accessories is Marissa Collections (1167 3rd St. S.), which sells everything from casual washed-out denim by Stella McCartney to fabulous floor-length gowns by Monique Lhuillier. Buy a pair of Oliver Peoples sunglasses and a Eugenia Kim wide-brim straw hat for your walk downtown.

Pop into BRuno (1193 3rd St. S.) for gifts to bring home for friends and family. Finds include elegant home decor, along with personal accessories like jewelry and watches.

Swing by John Craig Clothier (1258 3rd St. S., featured above) to shop for the men in your life. The high-end boutique sells timeless clothing and accessories—brands like Salvatore Ferragamo and Peter Millar.

Judith Liegeois Designs (363 12th Ave. S., featured below, left) is an interior design shop where classic meets contemporary. “It’s a really funky place,” Cullen says. Organic pieces pulled from the sea (think driftwood and coral) intermingle with abstract artwork, upholstered furniture, and delicate china.

The next street up, Martha and Cullen’s boutique Pierre & Harry (374 13th Ave. S., featured below, right) sells opulent pearls and bejeweled pieces at a variety of price points. Perennial favorites include the Cote D’azur Crystal Lariat, a necklace of freshwater pearls and crystals, and the Florida Cuff, a freshwater pearl bracelet with a sterling-silver or gold vermeil bead starfish.

Nearby, at the stationery shop The Paper Merchant (340 13th Ave. S.), grab a journal to jot down your travel notes, or choose from an assortment of cards to write home about your Naples adventure.

Swing into Tickled Pink (1300 3rd St. S., Suite 202B) for tropical-inspired attire (brands like Alice & Trixie, Shoshanna, and Trina Turk) to wear during the rest of your stay.

Refuel with lunch at one of the fabulous restaurants downtown. Martha recommends lunching at Campiello (1177 3rd St. S.) for wood-fired pizza, Ridgway Bar & Grill (1300 3rd St S #101) for “the best burger in town,” or The Continental (1205 3rd St. S.) for American food and people watching. “The last time I was at The Continental, the Beach Boys were there!” Martha says.

Take an after-lunch stroll two blocks down to the Naples Pier (25 12th Ave. S.), a more than 1,000-foot-long wharf that extends into the Gulf of Mexico. The 120-year-old dock was just restored before the new year, and is the perfect place for bird watching, and if you’re lucky, dolphin watching, too.

Head back to your home away from home to get ready for dinner. Have Third Street South Concierge (239.434.6533) arrange a horse and carriage to pick you up from your rental and take you on a happy-hour ride (complete with Champagne!) to your dinner reservation at Bleu Provence (1234 8th St. S., featured below), which specializes in fare from the South of France. Cullen recommends getting the fresh catch of the day, and a glass of whatever you fancy. “They are really known for their wine selection,” says Cullen.


Start your day early at the Third Street South Farmers Market, where the entire street is shut down for local vendors to set up shop from 7:30 to 11:30 in the morning. Grab a cup of Black Tulip Coffee along with a bite to eat from one of the local vendors — sweet and savory crepes and delicious quiches from Chez Boet French Home Cooking, Acai Bowls from The Bowl, or beignets and pancakes from Dutchkinz food truck.

While at the market, stock up on food for a trip to Keewaydin Island later in the day—Maryland crab cakes from Mister Crab Cakes and gluten-free soups from Harvest Soups will fit the bill. And swing into Tony’s Off Third (1300 3rd St. S.) for wine, gourmet snacks, and pastries.

The Holiday Life will schedule a boat to ferry you to a secluded property on Keewaydin Island to spend a quiet evening. Enjoy a picnic on the deck as you watch the sun set, and later, if you’re feeling adventurous, take a moonlit dip in the gulf.


Spend your final morning in Naples relaxing paddling on the gulf. The Holiday Life will deliver stand-up paddle boards from Old Naples Surf Shop (1311 3rd St. S.), so you can enjoy soaking in the sun.

Before heading out of town, visit the Naples Botanical Garden (4820 Bayshore Dr.), home to 170 acres of manicured gardens with native plantings, along with flora from far-flung places like Asia and Brazil. The property is also home to a wildlife preserve for eagles, otters, and a host of amphibians and reptiles. (Insider tip: Check the calendar to see when they have tai chi and yoga in the garden.)

Text by MARISSA HERMANSON. For additional ideas on where to shop and what to do in the area, browse the print edition of TSG Naples HERE.

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