Up to 6 Guests • 2 to 4 Hour Options • 47' Beneteau
Sail into the sunset aboard a serene 47-foot yacht off Naples’ stunning Gulf Coast. Perfect for couples and families seeking peace, panoramic views, and a memorable evening on the water.
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Difficulty
easy
Duration
2–4 hours
Fitness Level
No special fitness required; suitable for all ages and abilities
Wildlife
History
Naples has a rich maritime heritage dating back to its founding in the late 19th century as a fishing village along the Gulf Coast.
Conservation
Local operators emphasize no-discharge zones and wildlife protection efforts to preserve the Gulf marine ecosystem.
Island Sailing
Up to 6 Guests • 2 to 4 Hour Options • 47' Beneteau
Island Sailing is a Naples, Florida sailing company offering private charters and bareboat rentals along the Gulf Coast.
Island Sailing operates a fleet of sailing yachts for guided sunset sails, day sails, and bareboat charters that let licensed sailors take the helm. Trips include Island Dreams Sunset Sail, Island Dreams Bareboat Sail, Island Times Sunset Sail, and Island Times Day Sail, each designed for relaxation, scenic views, and opportunities to spot marine life such as dolphins.
Island Sailing focuses on safe, comfortable experiences with attention to local navigation, weather conditions, and guest comfort. Professional captains are available for guided charters; bareboat charters are offered to qualified sailors who meet local certification and insurance requirements. Reservations accommodate couples, families, small groups, and special occasions; private charters provide exclusive use of the vessel and personalized itineraries. Departure and return take place from Naples waterways, with routes that showcase the coastline, barrier islands, and Gulf sunsets unique to Southwest Florida. Island Sailing maintains transparent booking policies, clear trip descriptions, and safety briefings before each departure. Equipment and life jackets are provided according to local regulations. For travelers seeking a sunset cruise, a private day sail, or the freedom of a bareboat adventure, Island Sailing provides tailored options and local knowledge to make each trip memorable. Island Sailing is a feature on The Adventure Collective, reflecting a focus on outdoor, experience-driven travel in the Naples area. Bookings are available year-round, with schedules adjusted seasonally to match local weather, tides, and passenger demand.
Location
Naples, FL
Departures from Naples waterways
Tours Offered
4 Trip Options
Sunset, day, bareboat, private charters
Ideal For
Couples & Families
Relaxation and celebration on the water
Charter Type
Private & Bareboat
Captain-guided and captain-optional options
Book a sunset sail, private day charter, or bareboat rental to enjoy Naples' Gulf Coast scenery and dolphin sightings.
Bring Your Own Snacks and Drinks
There are no onboard food or beverage services, so bring your favorites or pick up something from local dockside eateries before boarding.
Arrive Early for Check-in
Plan to arrive 15-20 minutes early at Naples City Dock to ensure smooth boarding and settle in before the sail departs.
Dress in Layers
Evening temperatures on the water can drop quickly; lightweight layers help keep you comfortable as the sun sets.
Watch for Wildlife
Keep an eye out for dolphins and coastal birds that often accompany the yacht along the Gulf waters during sunset.
Light Jacket or Windbreaker
Protects against evening Gulf breezes during your sail.
spring
Sunscreen
Essential for sun protection during daylight sailing hours before sunset.
summer
Bug Spray
Helpful in late season to guard against mosquitoes near docks.
fall
Hat and Sunglasses
Shield your eyes and face from strong sunlight during the afternoon portion of the sail.
summer