Osprey, Florida

Siesta Key Watersports is the only full-service watersports company servicing Siesta Key, Sarasota, and Venice, with three locations. Voted #1 watersports company year after year, they offer parasailing with a 100% safety record, jet ski rentals for 1-3 riders up to 450 lbs max weight, dolphin tours (morning mimosas & dolphins, dolphin drinks & sandbar, sunset & dolphins) with complimentary drinks and bathroom on board, boat rentals with unlimited riding area including Gulf of Mexico, private charters, fishing charters, sunset charters, and custom charters. Over 28 years in business with USCG licensed captains, best maintained equipment, and free parking.

Located on Siesta Key, Florida, this established outfitter has been a prominent fixture in Sarasota’s outdoor recreation scene since 1959. Renowned as the largest bait and tackle shop on the water in the area, it offers a comprehensive range of services including boat rentals, fishing charters, parasailing, jet ski rentals, and golf cart rentals. The business stands out for its extensive experience and commitment to quality, providing access to premier equipment and leading outdoor sportswear brands for men, women, and children. Its long-standing presence and diverse offerings make it a go-to destination for both locals and visitors seeking water-based activities and island exploration. The outfitter caters to a wide variety of customers, from avid anglers to families looking for adventure on the water. Visitors can choose from half-day to weekly rental options for boats, jet skis, and golf carts, ensuring flexibility for different trip lengths and group sizes. Fishing enthusiasts benefit from expert-guided charters and a fully stocked bait and tackle shop, while thrill-seekers can enjoy parasailing and tiki boat tours. The experience is designed to be accessible and enjoyable, with knowledgeable staff ready to assist in planning memorable outings on Siesta Key’s scenic waters.

Mad Beach Party Charter is a locally owned private party boat rental company based in Madeira Beach, Florida, serving the greater St. Petersburg and Tampa Bay areas. Established in 2023, the company specializes in modern double-decker pontoon boats that accommodate up to 13 guests, offering a unique and comfortable way to explore Florida’s Gulf Coast waterways. What sets this service apart are its commercial-grade vessels equipped with water slides, premium sound systems, and spacious decks, providing an engaging and lively atmosphere for groups. With licensed and experienced captains available, guests can enjoy a safe and stress-free boating experience tailored to celebrations and casual outings alike. The charter offers a variety of packages ideal for bachelorette parties, birthdays, family gatherings, and mixed-age groups, focusing on private excursions to popular sandbar destinations such as the famous Johns Pass Sandbar, Fort Desoto Sandbar, Shell Key Preserve, and Clearwater Beach sandbars. Each trip includes opportunities for swimming, floating, music, and games, with optional add-ons like an 18-foot water mat and floating beer pong. The company emphasizes transparent pricing and easy online booking, ensuring a seamless experience from start to finish. Whether departing from Madeira Beach or exploring nearby hidden sandbars, guests can expect a memorable day on the water highlighted by fun, relaxation, and scenic coastal views.

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.

ECOmersion is a premier kayak tour and rental company located in St. Petersburg, Florida, specializing in guided excursions through the scenic Weedon Island Preserve. With over 80 years of combined kayaking experience among its staff, the company offers accessible adventures suitable for all skill levels, from beginners to seasoned paddlers. Recognized as a TripAdvisor Travelers' Choice award recipient for three consecutive years, ECOmersion distinguishes itself through its commitment to environmental stewardship and community involvement. Their knowledgeable guides provide insightful commentary on the local ecosystem, enhancing the natural experience while promoting conservation. The company offers a range of services including low-difficulty guided kayak tours lasting approximately 2.5 hours and flexible kayak rentals from one to four hours. These activities allow visitors to explore mangrove tunnels and observe native wildlife such as bottlenose dolphins, manatees, and migrating white pelicans. ECOmersion provides high-quality equipment and thorough instruction, ensuring a safe and enjoyable outing for participants aged eight to eighty-five. Beyond recreation, the company actively supports environmental initiatives in the Tampa Bay area, contributing a portion of proceeds to local non-profits and engaging in habitat restoration projects, making each excursion both an adventure and a contribution to preserving Florida’s natural beauty.

Located in St. Petersburg, Florida, Elite Watersports specializes in kiteboarding, wing foiling, eFoiling, hydrofoiling, wakeboarding, and surfing. Situated just five miles from both the Sunshine Skyway Bridge and St. Pete Beach, the shop offers convenient access to prime watersports locations. With certified instructors and a knowledgeable team, the business caters to all experience levels, from beginners to advanced riders. Their commitment to quality is reflected in their selection of top brands and well-maintained equipment, making them a trusted destination for watersports enthusiasts in the Tampa Bay area. Elite Watersports provides a range of services including lessons, equipment sales, repairs, and summer camps designed to enhance skills and enjoyment on the water. Customers can choose from kiteboarding and wing foil lessons, eFoil and hydrofoil training, wakeboarding charters, and surfing sessions. The shop also offers mix-and-match kite packages and discounted gear, allowing riders to find the perfect setup tailored to their needs. Whether seeking expert instruction or quality equipment, visitors experience a supportive environment focused on safety, skill development, and fun.

Located on Florida’s Gulf Coast, Madeira Beach is a vibrant barrier island community known for its scenic two-mile stretch of pristine sand and the historic John’s Pass Village, which offers a blend of shopping, dining, and nightlife. The city prides itself on providing exceptional services to residents, businesses, and visitors, emphasizing public trust, safety, and transparency. Madeira Beach combines a relaxed coastal atmosphere with a commitment to professionalism and community values, making it a unique destination for both leisure and local living. The Madeira Beach Municipal Marina serves as a central hub for boating and marine activities, offering a wide range of amenities including a floating fuel dock with ethanol-free gas and diesel, restrooms with showers, and a fully stocked ship store featuring live shrimp, frozen bait, and boating supplies. Open seven days a week with extended hours, the marina caters to boating enthusiasts seeking convenient access to the Gulf waters. Additional services such as 24-hour free pump-out, filleting tables, and coin-operated laundry facilities enhance the overall experience, making it an ideal location for both casual visitors and dedicated anglers.

Canoe Country Outfitters is a family-owned kayak, canoe, and paddleboard retailer located in St. Petersburg, Florida, serving the greater Tampa Bay area since 1986. With over three decades of experience, the shop offers an extensive selection of watercraft and accessories tailored to a wide range of paddling activities and skill levels. Their inventory includes canoes from Old Town and Wenonah, kayaks from leading brands such as Bonafide, Perception, and Wilderness Systems—the latter exclusively available in Pinellas County—and paddleboards from TAHE SUP. The store also specializes in Gheenoe micro-skiffs, known for their fiberglass hulls and high performance on Florida’s flats, providing customers with unique boating options beyond traditional paddling. The outfitter caters to both novices and seasoned paddlers by offering a variety of boats designed for fishing, touring, and recreational use, along with custom outfitting and repair services. Customers can find everything needed for a complete water experience, including motors, trailers, paddles, personal flotation devices, and storage solutions. The knowledgeable staff assists in selecting the right equipment to match individual needs and budgets, whether for casual paddling or serious angling. Additionally, Canoe Country Outfitters provides demo opportunities to ensure customers find the perfect fit before purchase, making it a comprehensive destination for water enthusiasts in the St. Petersburg region.

Marina Jack is a premier marina and waterfront dining destination in downtown Sarasota, Florida, since 1968, offering transient dockage, wet slips for vessels up to 228 feet, boat rentals, on-site charters including fishing and cruises, yacht services, fuel dock, and dining options overlooking Sarasota Bay. It provides boat rentals for 2, 4, or 8 hours equipped for fishing, beach hopping, swimming, and cruising, along with on-site charters like Tightlines Sportfishing for inshore and offshore fishing.

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.

Located in West Florida along the Gulf Coast, Thunder Marine is a reputable boat dealership and brokerage known for its extensive selection of new and pre-owned boats. Authorized to sell prominent brands such as Jeanneau, Regulator, Sportsman, and Monterey, the company offers a comprehensive range of vessels including center consoles, bowriders, cruisers, and bay boats. With a focus on customer service and long-term relationships, Thunder Marine combines knowledgeable sales staff with dedicated financing, service, and parts departments to ensure a seamless boating experience. Their commitment to quality and personalized attention distinguishes them in the competitive marine market. Thunder Marine caters to a diverse clientele, from first-time boat buyers to seasoned enthusiasts, providing services that extend beyond sales. Customers can access master service hubs for seasonal maintenance, repowering, and detailing, as well as a parts department featuring Load Master and Magic Tilt trailers. The dealership also hosts educational events like the Ladies at the Helm classes, designed to build confidence in boat operation and handling. With resources such as a boating blog, video gallery, and local boating forecasts, the experience at Thunder Marine is both informative and supportive, making it a trusted destination for boating needs in the region.

Located in Madeira Beach, Florida, this boat rental company offers a fleet of beautiful, late-model pontoon boats and golf carts, all maintained to high standards of safety and cleanliness. Situated at the Cambria Hotel Marina, the business benefits from a prime location between Clearwater and St. Pete Beaches, providing easy access to the scenic Pinellas County Gulf Coast. Customers appreciate the transparent pricing with no hidden fees and the company’s reputation for five-star service. The variety of boats available, including captained options and family-friendly pontoons, sets this rental service apart as a versatile choice for both novice and experienced boaters. The company provides a range of rental options, including self-drive pontoons that accommodate groups from six to twelve people, and a captained 22-foot Sport Slide Boat featuring a second-story water slide. Each boat is equipped with modern amenities such as GPS, Bluetooth stereo, coolers, and all required safety equipment. Rentals are available for four, six, or eight hours, catering to families, groups of friends, and fishing enthusiasts looking to explore local wildlife and waterfront attractions. Additionally, six-person Yamaha golf carts are offered for full-day rentals, allowing visitors to explore Madeira Beach and its surroundings in comfort and style. The knowledgeable staff assists customers in planning their outings to ensure a memorable experience on the water or around town.