Private and shared sailing experiences designed to showcase the best of St. Petersburg and Tampa Bay.
Every charter includes a licensed captain, first mate, fuel, refreshments, ice, light snacks, and onboard music. Simply step aboard and enjoy.
Unwind as the sun dips below the horizon on a private evening sail along Tampa Bay. Enjoy calm waters, coastal and city views, and a relaxed atmosphere ideal for couples, friends, or a peaceful escape. Includes: Captain & First Mate • Fuel • Drinks & Light Snacks • Music • Blankets
An extended sunset experience featuring the iconic Sunshine Skyway Bridge. Perfect for guests seeking dramatic views, photo opportunities, and a slightly longer evening on the water. Includes: Captain & First Mate • Fuel • Drinks & Light Snacks • Music • Blankets
A relaxed private cruise along the St. Pete waterfront and Tampa Bay. Ideal for casual sightseeing, first-time sailors, or a flexible daytime or evening outing. Includes: Captain & First Mate • Fuel • Drinks • Light Snacks • Music
Designed for guests who want more time on the water, our daytime adventures combine sailing, swimming, and exploration at some of the area’s most beautiful destinations. Spend your day anchoring at island spots, enjoying water activities, and relaxing onboard with the comfort and space of our luxury catamaran.
Your ideal balance of sailing, swimming, and relaxing at anchor. Visit scenic spots such as Fort De Soto or the Skyway Bridge viewpoint with time to enjoy the water at a comfortable pace. Includes: Captain & First Mate • Snorkel Gear • Towels • Sunscreen • Refreshments • Music
Explore top destinations like Fort De Soto, Tierra Verde, and the Skyway Bridge. Swim, snorkel, paddleboard, and relax at anchor with plenty of time to enjoy each stop. Includes: Captain & First Mate • Snorkel Gear • Paddleboards • Towels • Refreshments • Music
A complete day on the water visiting Egmont Key, Pass-A-Grille, Tierra Verde, Fort De Soto, and the Skyway Bridge viewpoint. Designed for guests who want it all. Includes: Captain & First Mate • Snorkel Gear • Paddleboards • Charcuterie Board • Floating Mat • Inflatable Water Toys • Towels • Full Crew Support
Want to enjoy one of these experiences from Anna Maria Island or another pickup location? Many of our private charters can be adapted to alternative departure points based on availability and logistics. Simply select your preferred charter and submit a request. We’ll coordinate the details and provide any applicable adjustments.
Spend the day island hopping and enjoying water activities, then close your charter with a private sunset sail. Includes everything in the Half-Day Adventure Package.
Our most immersive experience. Enjoy a full day of exploration, relaxation, and water activities, ending with a breathtaking sunset over Tampa Bay. Includes everything in the Full-Day Excursion Package.
Our social sails offer a shared luxury sailing experience aboard Sweet Escape for guests looking to enjoy the water in a relaxed, welcoming setting. Perfect for couples, solo travelers, and small groups, these charters feature scenic coastal views, curated music, and a laid-back atmosphere at a more accessible price point.
A shared luxury sailing experience aboard Sweet Escape. Perfect for couples, solo travelers, and small groups looking for a relaxed daytime sail at a more accessible price point.
Join fellow guests for a shared sunset sail featuring panoramic skyline views, calm waters, curated music, and a laid-back onboard atmosphere.
Designed for guests seeking something beyond our standard offerings, these specialty experiences are available by request and tailored to your vision. From extended sailing to unique itineraries, these options allow for a higher level of customization and flexibility, with details coordinated directly with our team.
A flexible bareboat experience available by request. Ideal for experienced guests seeking a more customized or extended sailing arrangement.
An overnight sailing experience for guests looking to extend their time on the water. Availability, itinerary, and details handled by inquiry.
Luxury, service, and memories that last.
What Sets Us Apart
Luxury Bali 4.2 catamaran with panoramic views
Fully private & customizable experiences
Tailored celebrations and premium upgrades
Licensed captain & first mate on every charter
Prime access to Tampa Bay & St. Petersburg waters
We’d love to hear from you. Whether you have questions about our packages, want to customize your charter, or need help with booking, we’re here to help. Reach out anytime and we’ll get back to you promptly.