Olde Naples Hotel: A Charming Weekend EscapeSettle into a relaxing stay at Olde Naples Hotel, surrounded by the charm of historic Old Florida. Enjoy unhurried days exploring nearby boutiques and local dining, with waterfront strolls and sunsets over the Gulf.Authorsheydavina
DestinationsNaplesItinerary

Day 1

Olde Naples Hotel
A welcoming retreat in the heart of Old Naples, surrounded by leafy streets, neighborhood boutiques, and the relaxed rhythm of Florida’s Gulf Coast.
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Third Street South Farmers Market
Seasonal produce, fresh flowers, and local flavors bring a lively neighborhood feel to this open-air market in historic Old Naples.
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Banyan tree
Just a very short walk from the Olde Naples Hotel is this magnificent banyan tree. It’s incredible to see the size of this gargantuan tree with its roots above ground.
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Annie's Bistro
A leisurely bistro stop on the itinerary, setting the scene for good conversation and an unhurried meal between Old Naples outings.
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Day 2

Jane's Cafe on 3rd
The perfect spot to grab brunch on 3rd St in Naples. Dine next to the water fountain for a calm and peaceful ambiance while sipping on coffee and eating brunch.
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Naples Botanical Garden
Lush tropical landscapes, colorful blooms, and tranquil water features make this expansive garden a peaceful escape into Southwest Florida’s natural beauty. Go early to avoid the heat and crowds!
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Naples City Dock
Moored boats, bay breezes, and the daily activity of a working marina give Naples City Dock its distinctive waterfront charm.
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Tammy Fender Holistic Spa
Step through the Olde Naples Hotel's central courtyard and into Tammy Fender Holistic Spa, a quiet hideaway a block from the beach. Botanical skincare is the focus, whether you book the signature facial with oxygen therapy and foot reflexology or a massage with warm poultices of turmeric and lemongrass. Bring a friend or partner for a side-by-side treatment, then unwind in the relaxation lounge afterward.
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Naples Beach
White sand and calm water line Naples Beach, and getting there is as simple as walking to the end of almost any avenue in Old Naples. Spread out a towel, wade in, or hunt for shells along the shoreline. The beach faces west for great sunset views over the Gulf.
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Coast
Coast is the beachfront restaurant at Edgewater Beach Hotel, serving breakfast, lunch, and dinner every day. The menu features coastal dishes from around the world, with fresh seafood and prime steaks at dinner. Tables on the outdoor veranda look out over the hotel's pools to the Gulf.
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Day 3

Palm Cottage
Naples’ oldest house, Palm Cottage preserves a glimpse of the town’s early coastal life through historic rooms, period furnishings, and its intimate Old Naples setting.
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GLDN Hour Coffee
For all my matcha girlies, don’t skip this cafe! They have the BEST matcha (and coffee) in town, hands down! They just relocated to a new location - so make sure to visit their new place on 863 4th Ave S.
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5th Avenue South
Fifth Avenue South is the main street of downtown Naples, with boutiques, art galleries, and restaurants along several walkable blocks. Many of the restaurants have sidewalk tables, and the avenue is busiest in the evening when people come out for dinner. The Sugden Community Theatre, home of The Naples Players, is here too.
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Cambier Park
A leafy downtown oasis with open lawns, tennis and shuffleboard courts, and a community bandshell, Cambier Park brings a relaxed neighborhood feel to the center of Naples.
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Naples Pier
A historic symbol of Naples, the pier and its surrounding beachfront are closely tied to the city's seaside character, Gulf vistas, and sunset traditions. The pier is currently being rebuilt, with reopening expected as early as summer 2027.
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