Waypoints (formerly Sailing Florida) offers luxury sailing and motor yacht charters departing from The Vinoy Marina in St. Petersburg, Florida, exploring the beautiful seaside towns, secluded anchorages, fine marinas, and sparkling blue waters of Florida’s Gulf Coast. Guests can bring a camera to capture the unforgettable Sunshine Skyway Bridge (rated by The Travel Channel among the Top 10 Bridges in the World) and abundant wildlife, including ospreys, herons, egrets, pelicans, and dolphins.
Charter options include Daily, Weekend, and Week-Long trips, available Skippered, Bareboat, or through ASA Certification Charters, aboard newly appointed sailing and motor catamarans and monohulls equipped with air-conditioning and ice makers, plus provisioning and personal concierge services through a dedicated charter experience specialist.
Suggested itineraries range from a relaxing 1-day sail to the Resort & Club at Little Harbor (a Caribbean-style island resort with a beachfront Tiki Bar) or Egmont Key State Park (exploring the ruins of Fort Dade on a 126-acre island), up through multi-day adventures visiting Gulfport, Clearwater Beach, Tierra Verde, Longboat Key, Boca Grande (with its famous 1890 Lighthouse Museum), Cabbage Key (a boat-only restaurant with walls covered in autographed dollar bills), and Cayo Costa’s white sandy beaches. The most ambitious 10-day itinerary for experienced sailors travels the entire West Coast of Florida down to Key West and the remote Dry Tortugas, including Fort Jefferson — the largest masonry structure in the Western Hemisphere, built from more than 16 million bricks.
For sailors and groups near St. Petersburg, Florida looking for a genuinely luxurious, wide-ranging sailing charter — from a relaxing day trip to a 10-day Dry Tortugas expedition — Waypoints offers an exceptional, itinerary-rich operation out of The Vinoy Marina.
