Naples is one of the most sophisticated cities in Florida with the state’s highest per capita income, but behind such stature there’s a small town charm that makes visitors feel right at home. Skirting the Gulf Coast and the edge of the Everglades, the southwest seaside town is a hub of palatial homes to the rich, famous and not-so-famous (never mind that it’s home to Steven Spielberg and other celeb millionaires). Manicured neighborhoods surround the city’s fashionable Fifth Avenue South and Third Street South where stores and restaurant buzz non-stop during season. The arts are well supported here, with the Philharmonic Center for the Arts and the Naples Museum of Art presenting top-tier shows and exhibitions. Relaxation is always within walking distance. So head to the Naples Pier to cast a line with other fishermen, or spread your towel on its nearby beach, where volleyball players, sun seekers and sunset gazers congregate.
Fifth Avenue South boasts almost 70 stores, all tucked in a palm tree-studded five-block stretch. Pop into Jammin on 5th and be tempted by racks of funky women’s fashions range from jeans with bling to cool retro designs. Art collectors find a menagerie of ceramic frogs by sculptor Tim Cotterill at Gallery One. A 15-minute walk takes you through Old Naples past historic Palm Cottage (1895) to Third Street South, where fountains and flower beds lead to high-end stores like Marissa Collections for the ladies and John Craig Clothier for the gents.
At the family-owned Bellini on Fifth restaurant start with the signature Bellini (prosecco with peach nectar) before diving into a bowl of pasta, all served with the warm hospitality you’d expect from this Italian family. Dine at a sidewalk table and watch the pedestrian scene unfold. For sunset viewing grab a stool alongside one of the longest bars facing the Gulf: Sunset Beach Bar & Grill in the Naples Beach Hotel & Golf Club. Stay for dinner at HB on the Gulf where the Florida snapper layered with lump crabmeat and drizzled with lemon beurre blanc spoils taste buds.
Big-name resorts like the Ritz-Carlton (there are two) and the Waldorf Astoria provide waterfront rooms, golf and multiple-star amenities. But if you prefer something cozy and urban, the Inn on Fifth is right smack on Fifth Avenue South in the heart of the hustle and bustle—park your car and forget it.