Osprey, Florida

St. Pete Coastal Cruises is an affordable luxury boat tour operation offering guided boat tours, private charters, sunset cruises, Skyway Bridge Light Show cruises, dolphin watching, shelling, sandbar parties, and booze cruises using their 50’ custom-built catamaran 'Escape' with capacity for up to 49 passengers.

StarLite Cruises is a family-owned business based in the Clearwater and St. Petersburg area of Florida, operating since 1986. With decades of experience, it has grown from a single vessel to Florida’s largest daily excursion fleet, serving over three million passengers. The company is known for its diverse offerings, including award-winning dining yachts, tropical cruises, and dolphin adventures, all set against the scenic backdrop of Florida’s inland and coastal waters. Its reputation for excellent service and variety makes it a standout choice for both locals and visitors seeking memorable water-based experiences. The fleet includes elegant dining yachts like the StarLite Majesty and StarLite Sapphire, which provide chef-prepared meals, live entertainment, and panoramic waterfront views ideal for special occasions or casual outings. For those seeking a more relaxed atmosphere, Calypso Tropical Cruises and Tiki Island Cruises offer casual buffet dining, tropical vibes, and social settings. Adventure seekers can enjoy the high-speed Dolphin Racer Adventure, featuring narrated tours with guaranteed dolphin sightings. The company also accommodates private events, group charters, and themed cruises, ensuring a tailored experience for birthdays, anniversaries, or corporate gatherings.

Totally Tiki Tours operates in Tampa Bay, Florida, offering a distinctive way to explore the area's scenic waterways aboard a spacious tiki boat. With locations at Rocky Point Island in Tampa, Downtown Tampa’s Riverwalk, and the St. Petersburg Pier, the company provides a unique blend of local charm and natural beauty. The tours are led by USCG-qualified captains, ensuring a safe and enjoyable experience for all passengers. What sets this business apart is its focus on private and public cruises that highlight Tampa Bay’s playful dolphins, manatees, and stunning Florida sunsets, all from the comfort of a well-equipped boat featuring Bluetooth speakers and onboard restrooms. The company specializes in two-hour private and public tours tailored for celebrations such as birthdays, anniversaries, graduations, and bachelor or bachelorette parties, accommodating up to 13 passengers on private charters. Guests can bring their own beverages and enjoy complimentary water, coolers filled with ice, and various water activities like floating mats and frisbees. Tours include stops at shallow sandbars for swimming and cruising through residential areas, offering a relaxed and customizable experience. Whether visitors are locals or tourists, these tours provide a memorable way to enjoy Tampa Bay’s natural attractions and festive atmosphere.

Founded in 1989 and headquartered in Sarasota, Florida, Freedom Boat Club is the world’s largest and oldest members-only boat club, operating over 400 locations worldwide including North America, Europe, and Australia. The club offers a unique alternative to traditional boat ownership by providing members with access to a diverse fleet of premium boats without the hassles of maintenance, storage, insurance, or repairs. With more than 35 years of experience, Freedom Boat Club emphasizes safety and convenience, offering unlimited training from certified captains to ensure members of all skill levels feel confident on the water. Its concierge-level dockside service and a robust reservation system allow members to enjoy seamless boating experiences at their home location or while traveling. Members can choose from a wide variety of boats such as pontoons, deck boats, center consoles, wake boats, and cruisers tailored to different recreational activities including fishing, water sports, and leisurely cruising. The club’s John’s Pass location on Florida’s Gulf Coast exemplifies the experience, situated in a charming fishing village known for its scenic shorelines, sandbars, and waterfront dining. Membership plans include unlimited boat usage with no hourly fees, and reciprocal access to all club locations worldwide. Complimentary training, premium fleet selection, and hassle-free boating make this club ideal for boating enthusiasts seeking flexibility, safety, and community without the burdens of boat ownership.

Kokomo Charters is a yacht charter brokerage based in Sarasota, Florida, specializing in arranging USCG-compliant bareboat charters across the Gulf Coast, including St. Petersburg, Anna Maria Island, and Tampa Bay. With a curated fleet of privately owned yachts ranging from 35 to 112 feet, the company offers a diverse selection of vessels to suit various group sizes and preferences. What sets this brokerage apart is its exclusive focus on bareboat charters, allowing primary charterers to assume control of the vessel while providing access to a vetted list of independent, licensed captains. This approach ensures a personalized and flexible boating experience tailored to the unique needs of each client. The company’s offerings include full-day, half-day, and sunset cruises, catering to both visitors and locals seeking a luxurious and stress-free day on the water. The fleet features yachts equipped for groups ranging from five to twelve guests, with options available in Sarasota, St. Petersburg, Anna Maria Island, and Tampa Bay. Clients can customize their charters with the assistance of Kokomo Charters, which also facilitates connections with approved captains and crews. The experience emphasizes comfort, luxury, and flexibility, making it ideal for special occasions, corporate events, or leisurely outings along Florida’s scenic Gulf Coast. Additionally, Kokomo Charters partners with Sarasota Motor Club to offer an enhanced luxury experience combining exotic car rentals with yacht charters.

Florida Tiki Tours, based in Florida, offers a unique boating experience with a fleet of four distinctive Tiki Boats designed to accommodate various group sizes. With options ranging from the Original Octagon Tiki Boat for up to six people to a large party boat that holds up to 18 guests and includes a restroom, the company caters to both intimate gatherings and larger celebrations. Their expertise in providing enjoyable and memorable water tours sets them apart, ensuring guests experience the scenic waterways in comfort and style. The company specializes in a variety of themed tours, including Island Adventure Tours and the Tipsy Tiki Pub Crawl, which combine sightseeing with social activities on the water. These offerings appeal to groups looking for a fun and relaxed atmosphere, whether for casual outings or special events. Equipped with well-maintained boats and staffed by experienced guides, the tours provide a safe and engaging way to explore Florida’s coastal areas while enjoying drinks and entertainment on board.

Florida Fishing Fleet is a premier fishing charter company based in Cortez, Florida, just minutes from Anna Maria Island. With over 18 years of experience led by Captain Lance, a United States Coast Guard certified captain, the fleet offers a unique blend of local expertise and professional service. The company operates a variety of vessels, including offshore party boats and smaller inshore boats, providing access to diverse fishing environments such as offshore reefs, nearshore waters, and inshore backwaters. Its location in the heart of the Cortez Fishing Village enhances the authentic Gulf Coast fishing experience. The fleet offers a range of fishing trips from four to ten hours, catering to all skill levels and group sizes. Options include private charters and split party boat trips aboard vessels like the 50-foot Kingpin and the 24-foot T-Craft, accommodating from six to twenty-four passengers. Specialty trips such as Full Moon Mangrove Snapper night fishing and targeted Red Grouper excursions are also available. All trips come fully equipped with fishing licenses, rods, bait, tackle, ice, and fish cleaning services, ensuring a convenient and enjoyable outing for families, groups, and avid anglers alike. The knowledgeable and personable crew emphasizes safety, fun, and memorable fishing experiences on the waters of the Gulf of Mexico.

Freedom Boat Club, established in 1989 and headquartered in Sarasota, Florida, is the world’s largest and oldest members-only boat club with over 400 locations worldwide. With more than 35 years of experience, the club offers a revolutionary alternative to traditional boat ownership by providing members access to a diverse fleet of premium boats without the hassles of maintenance, storage, insurance, or repairs. Members benefit from concierge-level dockside support and unlimited training from certified captains, ensuring safety and confidence on the water. The club’s extensive network spans North America, Europe, and Australia, allowing members to explore a variety of waterways with ease. At the St. Petersburg Skyway location, members enjoy access to Loggerhead Marina, a prime gateway to destinations such as Egmont Key, Fort De Soto, and the Skyway Bridge. The marina offers amenities including a clubhouse, boat supplies, restrooms, and complimentary parking. The fleet features a wide selection of boats suited for cruising, fishing, and watersports, including pontoons, center consoles, bowriders, and offshore fishing boats. Membership plans provide unlimited boating with no hourly fees, and members can reserve boats online or by phone. This location caters to boaters of all skill levels, offering free training and a seamless, walk-on, walk-off boating experience in one of Florida’s most scenic coastal areas.

Well Played Charters is a premier private yacht charter company based along Florida’s picturesque Gulf Coast, specializing in luxury experiences tailored to individual preferences. With a licensed captain and professional crew, the company ensures a safe and seamless journey aboard modern, spacious yachts equipped with contemporary amenities. Their personalized approach allows clients to design unique itineraries that range from lively celebrations to tranquil escapes, making each voyage distinct and memorable. Operating primarily in the St. Petersburg and St. Pete Beach areas, Well Played Charters stands out for its commitment to world-class hospitality and attention to detail. The company offers a diverse array of services including bachelor and bachelorette parties, private wedding ceremonies, corporate events, family vacations, and sunset cruises. Guests can explore hidden gems such as Pass-A-Grille, Shell Key Preserve, and Egmont Key, enjoying activities like snorkeling, dolphin spotting, and island hopping. Each charter is customizable, allowing clients to select routes, onboard amenities, and themes that suit their occasion and style. Whether seeking an energetic party atmosphere or a peaceful retreat, the experience aboard these luxury yachts combines comfort, elegance, and personalized service to create lasting memories on the water.

Located in Gulfport, Florida, this company is the oldest and largest provider of dolphin watching, snorkeling, and island adventure cruises in the Tampa Bay area. Operating four single-hull boats that accommodate up to 35 passengers each, the business offers unique dolphin encounters where wild dolphins jump and play in the boat’s wake—a feature not found on other tours. Their central location provides convenient access to notable attractions such as Egmont Key, Fort Dade, and John’s Pass Village, enhancing the sightseeing experience. With Coast Guard certified captains and experienced crews, the company emphasizes safety, comfort, and family-friendly service, welcoming guests of all ages. The company offers a variety of tours including four-hour dolphin snorkeling cruises to Egmont Key and three-hour dolphin and shelling cruises to Shell Island. Guests can explore historic sites, swim in clear, calm waters, and collect seashells on secluded beaches accessible only by boat. Snorkeling gear is provided, and all snorkelers are supervised to ensure a safe and enjoyable experience. Private charters are also available for groups up to 49 people, offering customizable trips such as sunset cruises, corporate events, and educational tours. Throughout each excursion, passengers enjoy close-up views of dolphins, opportunities for photography, and the chance to create lasting memories in a natural island paradise.

Discover Sarasota Tours is a locally owned tour company based in Sarasota, Florida, specializing in air-conditioned trolley tours that showcase the rich cultural history and vibrant communities of Sarasota and Venice. With extensive experience in providing engaging and informative excursions, the company offers a unique way to explore the region’s most notable landmarks, neighborhoods, and stories. Their fleet includes Dolly The Trolley, a 31-seat enclosed vehicle designed for comfort and convenience, allowing guests to enjoy the sights year-round. What sets this company apart is its diverse range of interactive and themed tours, combining entertainment with education to create memorable experiences for visitors and locals alike. The company’s offerings include a variety of specialized tours such as the Sarasota City Sightseeing Tour, the interactive Murder Mystery Trolley, and behind-the-scenes access to the Sarasota Opera House. Other popular experiences feature art crawls, wine tastings at local vineyards, historical explorations of circus heritage, and seasonal events like haunted tours and musical cabarets. These tours cater to a wide audience, including families, groups, and cultural enthusiasts, providing opportunities to learn about local history, architecture, and the arts in an engaging setting. Each tour is carefully curated to highlight the unique aspects of the area, often incorporating live performances, guided commentary, and exclusive access to venues, ensuring a rich and enjoyable outing for all participants.

MarineMax operates premier boating dealerships and marinas in Clearwater and St. Petersburg, Florida, serving the Tampa Bay area with over 30 years of experience. As the world’s largest lifestyle retailer of recreational boats and yachts, the company offers an extensive selection of premium brands including Boston Whaler, Sea Ray, Azimut, Bertram, and Galeon Yachts. MarineMax distinguishes itself through a comprehensive approach that combines boat sales, expert service, financing options, and educational programs, all designed to enhance the boating lifestyle. Their Clearwater and St. Petersburg locations provide access to high-quality vessels and boast full-service marinas equipped to accommodate a wide range of boats and yachts. MarineMax caters to boating enthusiasts of all levels, from beginners to seasoned captains, offering tailored services such as boat maintenance, repairs, winterization, and storage solutions performed by factory-certified technicians. Customers can explore a diverse inventory that includes sport catamarans, luxury day boats, offshore vessels, and superyachts, ensuring options for family leisure, watersports, fishing, and luxury cruising. Additionally, MarineMax hosts educational classes and exclusive events to build boating confidence and community engagement. With flexible financing and a dedicated team, the company provides a seamless ownership experience, supporting customers throughout their entire boating journey.