Enjoy Food, Fun and Fashion in the Historic Naples, Florida Downtown District

Exclusive shops, exquisite cuisine and exceptional entertainment – Naples’ historic downtown district delivers all of these and more!

Just a quick water shuttle or walk from Naples Bay Resort, the city’s famed Fifth Avenue South, Third Street South, Tin City and Bayfront are well-known by Southwest Florida locals and guests for their popular designer stores, quaint art galleries, gourmet restaurants and live entertainment.

Ready to get started? Grab your credit cards, walking shoes and our Naples shopping guide (below) and get going. A day of fun, food and fashion awaits you on Florida’s Paradise Coast!

Shopping in Naples, Florida
Lots of shops for every style in Naples

Explore Downtown Naples Shopping & Dining

8 – 10 a.m.: Fuel up for your day of Naples shopping with our Breakfast by the Bay served daily. Then stretch your spending muscles and awaken your fashion spirit with a power yoga class and steam bath in the Naples Bay Resort Fitness Center.

11 a.m.: Explore the resort’s promenade of shops located along the marina as you wait for the Naples Bay Water Shuttle.

12 p.m.: Hop on the water shuttle and travel to Bayfront to start your shopping and dining tour.

Located on Naples Bay at the foot of the famed Fifth Avenue South, Bayfront's colorful European architecture and brick pathways serve as the entrance to Old Naples. This upscale oasis features the rare galleries, specialty shops and impeccable cuisine that make the Paradise Coast a premier Florida vacation destination!

Continue your tour by foot or water shuttle as you make your way to Tin City.

Nestled among historic Third Street South’s courtyards, antique European fountains, and lush landscaping, Tin City was once a 1920s clam shelling and oyster processing plant. Today, its boutiques and cafés offer visitors an authentic glimpse into Naples’ rich nautical history.

While there, enjoy lunch overlooking the Gordon River at the Riverwalk Restaurant. A Naples staple since the 1940s, the restaurant is well-known for its fresh Gulf Coast fish, blue-ribbon fruits and vegetables and mouthwatering tropical cocktails.

As you leave Tin City to explore Third Street, stop in at the Naples Winery to sample their 37 award-winning Florida tropical fruit and berry wines.

Continue down Third Street where you will find more than 100 fine apparel shops, gift boutiques, restaurants and art galleries. Located between Naples Bay and the Gulf of Mexico, charming Third Street South is home to chic fashions, fine art, antique stores and unique boutiques. Upscale restaurants, relaxing cafes and pubs and ethnic delicatessens provide visitors countless opportunities to sample diverse flavors and fare.

Complete your shopping and dining tour on Naples’ famed Fifth Avenue South. Considered the downtown district’s Main Street, Fifth Avenue is home to designer fashion boutiques, European and American antique stores, traditional and contemporary art galleries, gift stores, jewelers, home furnishing and design showrooms, bookstores and many professional offices.

Charming, yet sophisticated, historical Fifth Avenue is Southwest Florida’s ultimate shoppers’ paradise! And if you have the urge to splurge on extraordinary cuisine, you can also find it on Fifth Avenue. Featuring more than 30 restaurants, Fifth Avenue delivers fresh Gulf Coast seafood, rustic farm-to-table specialties, seasonal hand-crafted cocktails and authentic fare ranging from Italian to French, Persian, Asian, Caribbean, American and everything in between. Add in the area’s quaint coffee shops, pubs, delicatessens and sweets shops and there’s truly something for everyone.

End your day with live music and dancing at one of the avenue’s many local entertainment venues or frequent community events.

8:30 p.m.: Return to Naples Bay Resort by water shuttle or on foot. Then enjoy a relaxing moonlit soak in our whirlpool as you recount your memories of a day filled with food, fun and fashion on the Paradise Coast!

Connect with our concierge team today to design the ultimate Southwest Florida shopping and dining excursion and discover what it means to Imagine More at Naples Bay Resort!