Top St Petersburg Sightseeing Tours in 2026

Sail out from Bowden's Marina in Madeira Beach, through John's Pass and into the Gulf of Mexico as the sun goes down. This is a private charter, so the 45-foot sailboat is yours: bring friends, family or a date, plus your own food and drinks. Watch for dolphins along the Intracoastal and in the Gulf, take the helm if you want to learn, or just relax on deck. We leave about two hours before sunset, year round. Most of the captains are women and American Sailing Association instructors, and every trip runs with a USCG-licensed captain. Madeira Beach is about 30 minutes from downtown St. Petersburg, St. Pete Beach and Clearwater Beach.

Our fully customizable private tours make it effortless to get out on the water during your stay. Whether you're planning a laid-back shelling trip, celebrating a special occasion, or enjoying a romantic sunset cruise, we tailor the experience to you. Florida’s best spots are often only reachable by boat—let our local captains show you the hidden gems, with plenty of chances to spot dolphins along the way.

Spend a morning, an afternoon or a whole day on the water near St. Petersburg on your own private 45-foot sailboat. We sail from Bowden's Marina in Madeira Beach, out through John's Pass and along the Gulf coast. The 4-hour half day is all about the sail: cruise the Gulf beaches and the Intracoastal, watch for dolphins, and take the helm if you'd like to learn. On the 8-hour full day we also stop to anchor at Shell Key or Egmont Key, depending on wind and conditions, to swim, snorkel and walk the beach. The boat is private for your group of up to 6, so bring your own food and drinks and set your own pace. Take the helm and learn the basics, or relax on deck while the captain sails. Most of the captains are women and American Sailing Association instructors, and every trip runs with a USCG-licensed captain. Madeira Beach is about 30 minutes from downtown St. Petersburg and Clearwater Beach.

Your own private 42’ Bali 4.2 catamaran with no shared crowds — just your group, captain, and crew. Sweet Escape offers a premium all-inclusive charter experience from St. Petersburg with fuel, ice, bottled water, soft drinks, light snacks, Bluetooth music, paddleboards, floating mat, snorkel gear, towels, shaded seating, and spacious lounge areas included. Each trip is customized around your group’s priorities, whether you want scenic cruising, swimming, relaxing, sightseeing, sunset views, or a special celebration on the water.

Your own private 42’ Bali 4.2 catamaran with no shared crowds — just your group, captain, and crew. Sweet Escape offers a premium all-inclusive charter experience from St. Petersburg with fuel, ice, bottled water, soft drinks, light snacks, Bluetooth music, paddleboards, floating mat, snorkel gear, towels, shaded seating, and spacious lounge areas included. Each trip is customized around your group’s priorities, whether you want scenic cruising, swimming, relaxing, sightseeing, sunset views, or a special celebration on the water.

Your own private 42’ Bali 4.2 catamaran with no shared crowds — just your group, captain, and crew. Sweet Escape offers a premium all-inclusive charter experience from St. Petersburg with fuel, ice, bottled water, soft drinks, light snacks, Bluetooth music, paddleboards, floating mat, snorkel gear, towels, shaded seating, and spacious lounge areas included. Each trip is customized around your group’s priorities, whether you want scenic cruising, swimming, relaxing, sightseeing, sunset views, or a special celebration on the water.

We offer fully customizable party bus rentals—just tell us where you want to go, and we’ll get you there! Our package includes 4 hours of service, available in the morning, afternoon, or evening, with a limo bus that accommodates up to 26 passengers. We primarily serve St. Petersburg, Tampa, and Sarasota. Enjoy your ride as our party bus takes you to your destinations and stays with you for the full 4 hours. We specialize in bachelorette parties, birthdays, corporate events, concerts, sporting events, weddings, and group nights out. When booking, simply provide your preferred hours (e.g., Thursday 7-11 PM) and general service area (e.g., St. Petersburg to Tampa).

Welcome aboard Breaking Away, a beautifully maintained 48-foot Jeanneau Sun Odyssey monohull sailing yacht offering a true, wind-driven coastal experience. Graceful, responsive, and designed for performance cruising, Breaking Away delivers the timeless feel of classic sailing with modern comfort below deck. Unlike power catamarans and motor yachts, this monohull yacht heels gently under sail, connecting guests to the rhythm of the wind and water in an authentic and unforgettable way. Refined. Purposeful. True sailing. This yacht is ideally suited for guests who appreciate authentic sailing and a more intimate, refined experience. Sail Tampa Bay or Sarasota’s coastline, anchor near Shell Key, enjoy dolphin sightings, or simply cruise under canvas with the Gulf breeze filling the sails.

Your own private 42’ Bali 4.2 catamaran with no shared crowds — just your group, captain, and crew. Sweet Escape offers a premium all-inclusive charter experience from St. Petersburg with fuel, ice, bottled water, soft drinks, light snacks, Bluetooth music, paddleboards, floating mat, snorkel gear, towels, shaded seating, and spacious lounge areas included. Each trip is customized around your group’s priorities, whether you want scenic cruising, swimming, relaxing, sightseeing, sunset views, or a special celebration on the water.

Your own private 42’ Bali 4.2 catamaran with no shared crowds — just your group, captain, and crew. Sweet Escape offers a premium all-inclusive charter experience from St. Petersburg with fuel, ice, bottled water, soft drinks, light snacks, Bluetooth music, paddleboards, floating mat, snorkel gear, towels, shaded seating, and spacious lounge areas included. Each trip is customized around your group’s priorities, whether you want scenic cruising, swimming, relaxing, sightseeing, sunset views, or a special celebration on the water.

Welcome aboard Breaking Away, a beautifully maintained 48-foot Jeanneau Sun Odyssey monohull sailing yacht offering a true, wind-driven coastal experience. Graceful, responsive, and designed for performance cruising, Breaking Away delivers the timeless feel of classic sailing with modern comfort below deck. Unlike power catamarans and motor yachts, this monohull yacht heels gently under sail, connecting guests to the rhythm of the wind and water in an authentic and unforgettable way. Refined. Purposeful. True sailing. This yacht is ideally suited for guests who appreciate authentic sailing and a more intimate, refined experience. Sail Tampa Bay or Sarasota’s coastline, anchor near Shell Key, enjoy dolphin sightings, or simply cruise under canvas with the Gulf breeze filling the sails.

A 100% private, all‑inclusive Tampa Bay boat day with door‑to‑door transportation, your own local host, dolphin watching, snorkeling, shelling, island time, and a freshly grilled lunch with drinks included—zero logistics, just show up and enjoy.

This all‑inclusive private Weeki Wachee springs adventure is designed for travelers who want crystal‑clear water, good food, and zero logistics to worry about. You’ll have your own vehicle, guide, and kayaks, with round‑trip private transport from St. Pete, reserved boats, premium gear, and a riverside lunch with cold drinks so you never have to think about parking, timing, or what to pack. As a small local concierge team, we design the day around your group’s pace, time our launch to avoid the worst crowds, and share local tips and photos along the way, so it feels like spending the day at the springs with a knowledgeable friend who’s planned it all just for you.