TOP 30 Best Customized sailing adventures in Florida

Pensacola Sailing Academy, located at 600 South Barracks Street in Pensacola, Florida, is the premier destination for sailing education on the Emerald Coast. Whether you are a beginner or looking to advance your skills, our award-winning instructors are here to help you sail with confidence. Since 2001, we have been dedicated to providing top-notch instruction in a fun and safe environment. Our students have raved about their experiences with us, praising our knowledgeable instructors, excellent customer service, and the overall joy of learning to sail. Whether you are looking to start your sailing journey or enhance your skills, Pensacola Sailing Academy is the place for you. Don't wait for someday, start your adventure today and experience the paradise of sailing in Pensacola with us.

Peace Sailing Charters is a premier travel agency located at 895 South Palafox Street in Pensacola, Florida. Specializing in unique and unforgettable sailing experiences, our institution offers a wide range of charter options for those seeking a peaceful and relaxing getaway on the water. Whether you are looking for a romantic sunset cruise, a family-friendly sailing adventure, or a corporate team-building excursion, Peace Sailing Charters has something for everyone. Let our experienced crew take you on a journey through the stunning waters of Pensacola Bay and beyond, and experience the serenity and beauty of sailing firsthand. Book your charter with Peace Sailing Charters today and set sail for a truly unforgettable experience.

Condor Sailing Adventures is a premier travel agency located at 655 Pensacola Beach Boulevard in Pensacola Beach, Florida. Specializing in unique sailing experiences, they offer a range of exciting and adventurous trips for those looking to explore the open waters. Whether you are a seasoned sailor or a novice looking to learn the ropes, Condor Sailing Adventures has something for everyone. Their knowledgeable and experienced staff are dedicated to providing top-notch customer service and ensuring that each trip is an unforgettable experience. Book your next sailing adventure with Condor Sailing Adventures and set sail for an unforgettable journey on the beautiful waters of Florida.

Sail Away - Destin Florida Sailing is a travel agency located at 404 Harbor Boulevard in Destin, Florida, United States. Join Captain Bryan Klein for an unforgettable experience on a luxurious and spacious 24-foot Tri-Hull private pontoon charter. The boat features plenty of lounge space in the sun and a large shaded area under a covered canopy. You are welcome to bring your own drinks and snacks (glass is acceptable), and the boat comes equipped with a cooler full of ice for your convenience. Enjoy the great sound system with Bluetooth capability and bring your own music to set the perfect mood for your cruise. The rate is $150 per hour for up to 6 people, with additional time available for booking. Watch the sunset over the beautiful white beaches and sparkling waters of Destin Harbor for a romantic evening or a fun family outing. Take a Fireworks Cruise along the harbor at Harborwalk for a spectacular end to your day in paradise, available from Memorial Day to Labor Day on Mondays and Thursdays at 9 PM.

Destin Sailing Adventures is a travel agency located at 1201 Miracle Strip Parkway Southeast in Okaloosa Island, Florida, United States. Step aboard the Stiletto 27 Special Edition Catamaran for an unforgettable experience on the majestic waters of the Emerald Coast. Our boat is designed for maximum sailing pleasure and performance, perfect for adventure and racing enthusiasts. With a 20hp motor on board, we can ensure that you have an amazing time even if the wind isn't blowing. Our private charters come with a local captain to guide you to all the best spots in Destin, Okaloosa Island, and Navarre Beach. Whether you're looking for a relaxing sunset cruise, a thrilling dolphin tour, or a romantic marriage proposal setting, we have something for everyone. Avoid the crowds and enjoy a personalized experience with just your group on board. Book early to secure your spot and beat the summer rush!

Gulf Islands Adventures is a premier travel agency located in Cortez, Florida, United States. We specialize in organizing exciting and unforgettable adventures to the stunning Gulf Islands. Our experienced team is dedicated to providing exceptional customer service and creating tailor-made itineraries that cater to all your travel needs. Whether you're looking for a relaxing beach getaway or an action-packed outdoor excursion, Gulf Islands Adventures has got you covered. Contact us today to start planning your next unforgettable vacation!

Spice Sailing Charters is a premier travel agency located at 840 South Bay Boulevard in Anna Maria, Florida, United States. Specializing in luxury sailing experiences, Spice Sailing Charters offers a range of customizable charter options for those looking to explore the beautiful waters of the Gulf Coast. Whether you're seeking a romantic sunset cruise, a day of snorkeling and swimming, or a multi-day sailing adventure, Spice Sailing Charters has the expertise and resources to make your nautical dreams a reality. With experienced captains, top-of-the-line vessels, and unparalleled customer service, Spice Sailing Charters is your ticket to an unforgettable sailing experience in the stunning waters of Florida.

Wind Star Sailing Dunedin is a premier travel agency located at 51 Main Street in Dunedin, Florida, United States. Specializing in sailing adventures, they offer a variety of unique and exciting experiences for those looking to explore the open seas. Whether you're a seasoned sailor or a first-time adventurer, Wind Star Sailing Dunedin has something for everyone. From day trips to week-long excursions, their knowledgeable staff will help you plan the perfect sailing getaway. With a commitment to excellence and customer satisfaction, Wind Star Sailing Dunedin is the go-to destination for all your sailing needs.

St. Pete Sailing Charters is a locally owned institution offering Day Sails and Sunset Cruises in Tampa Bay. Located at 1110 3rd Street South in St. Petersburg, Florida, United States, the institution specializes in Sailboat Photoshoots, Sailboat Proposals, and Onboard Weddings. Owners Nick and Kelly, who have sailed and explored the Caribbean Islands, operate the Morgan 44 foot Sailboat, Satori. This classic Florida-built yacht provides guests with privacy, comfort, and safety, making it a popular choice for special occasions and custom departures. The institution also offers services such as Sailboat Photography shoots, Express Photoshoots, and Ultimate Sailboat Proposal Packages. With a focus on quality and customer satisfaction, St. Pete Sailing Charters ensures a memorable and enjoyable experience on the water.

Key Largo Adventures is a top-rated travel agency located at 85501 Overseas Highway in Islamorada, Florida. Offering Multi-Activity Charters to the Sandbar, guests can enjoy snorkeling at the reef, stand-up paddle boarding at the Islamorada Sandbar, relaxing on floats, and dancing to bluetooth stereo. Visitors can bring their own lunch, snacks, and drinks or upgrade to a boat with a BBQ grill. Customize your Key Largo Adventure boat tour with amenities such as snorkeling, fishing, and exploring the flats. Full-day, half-day, and customized tours are available for an all-inclusive price. Captain Charlie Filpes and his crew provide five-star service aboard the TIKI TIKI, a 25-foot open fisherman. Guests can expect a fun-filled day on the water with paddle boarding, boat trips, snorkeling, and more. Customers rave about their experiences with Key Largo Adventures, praising Captain Charlie for his knowledge, service, and attention to detail. Don't miss out on the opportunity to book your own private, all-inclusive adventure with Key Largo Adventures in the beautiful Florida Keys.

Magic Wind Adventure Sailing is the #1 Sailing Charter on Fort Myers Beach, located at 2500 Main Street in Florida. Owned and operated by Captain Dan and Dianne since 2009, they invite you aboard their beautiful sailing vessel Orion's Child to experience the calm waters of the Gulf of Mexico. You can enjoy the wind in the sails as you search for dolphins, sea turtles, and other wildlife. With private and non-private sails available, it's the perfect experience for engagements, birthdays, anniversaries, and more. The vessel is licensed, insured, and Coast Guard compliant, with a maximum of 6 guests. Customers rave about the immaculate boat and the welcoming nature of Captain Dan and his wife. Unlike other charter operators, Magic Wind Adventure Sailing charges you only upon return to the dock, ensuring a high-quality experience every time. Visit them at Salty Sam's Marina for an unforgettable sailing adventure.

Follow That Dream Sailing is a premier travel agency located in the picturesque Fernandina Beach, Florida, United States. Specializing in unique and unforgettable sailing experiences, our team is dedicated to providing personalized and expert guidance to help you plan the perfect sailing adventure. Whether you're a seasoned sailor or new to the world of sailing, our knowledgeable staff will ensure that your trip is smooth sailing from start to finish. Embark on a journey with Follow That Dream Sailing and let us help you create memories that will last a lifetime.

Ocean Adventure Charters, located at 105 Lake Shore Drive in West Palm Beach, Florida, offers the best deals on boat rental services. Embark on thrilling maritime explorations with up-close encounters with aquatic creatures and access a new aspect of the stunning marine environment. Serving the Florida coast, including Miami, Fort Lauderdale, and Palm Beach, Ocean Adventure Charters arranges outings to breathtaking destinations where you can enjoy the wilderness of nature. With opulent boat tour packages at various price points, you can participate in a variety of thrilling activities while traveling. Book a private boat tour for a personalized and private boating experience, where you can customize your itinerary to your tastes. Enjoy exclusivity and seclusion on private boat cruises with Ocean Adventure Charters, ensuring a peaceful experience for everyone on board.

Welcome to Chadillac Adventures - Private Charter, your premier travel agency located in the heart of Clearwater, Florida. Situated at 445 East Shore Drive, our business specializes in creating unforgettable experiences on the stunning waters of the Gulf Coast. Whether you're seeking a serene sunset cruise, an adventurous day of island hopping, or a customized private charter tailored to your desires, Chadillac Adventures is your gateway to paradise. Our team of experienced and friendly professionals is dedicated to ensuring your journey is as enjoyable and seamless as possible. We offer a variety of bespoke packages that cater to families, couples, and groups looking to explore the natural beauty and vibrant marine life that Clearwater has to offer. With our top-of-the-line vessels, you can relax in comfort and style as you embark on your personalized adventure.

Suncoast Sailing is a premier tourist attraction and travel agency located at 11165 Gulf Boulevard in Treasure Island, Florida. Offering a variety of sailing excursions and services, Suncoast Sailing provides visitors with the opportunity to explore the beautiful waters of the Gulf Coast in style. Whether you're looking for a relaxing sunset cruise or an action-packed sailing adventure, Suncoast Sailing has something for everyone. With experienced captains and top-of-the-line vessels, you can trust that your sailing experience with Suncoast Sailing will be unforgettable. Book your next nautical adventure with Suncoast Sailing and set sail for an unforgettable experience on the open seas.

Sail La Vie Tiki Cruises is a unique travel agency located at 4903 Southeast Dixie Highway in Stuart, Florida. As the only private tiki boat around, they offer fun and exciting excursions on the pristine waters of Fort Pierce. With the crystal clear waters allowing for excellent wildlife viewing opportunities, guests can expect to see dolphin, manatee, osprey, pelicans, turtles, and more. The trips are private excursions, so parties are not mixed, ensuring a personalized and intimate experience. Captain Joe Tomasiello leads the tours, providing a professional and knowledgeable guide to the area. Whether you're looking for a relaxing sunset cruise, a fishing excursion, or a visit to the local sandbar or islands, Sail La Vie has a variety of tour packages to choose from.

Sailing Moby Adventures is a tourist attraction located in Destin, Florida, United States. This institution offers a variety of exciting activities such as sailing, snorkeling, fishing, and dolphin adventures. Guests can customize their own trips based on their preferences, whether it's exploring Crab Island, snorkeling in the crystal-clear waters, or watching dolphins play in the ocean. Sunset cruises are also available, allowing visitors to enjoy Florida's beautiful sunsets from the comfort of a private cruise. With options for up to six passengers, Sailing Moby creates personalized tours to ensure a memorable experience for everyone. The knowledgeable and friendly staff, including Capt. Ladd and Tracy, go above and beyond to make sure guests have an unforgettable time on the water. Whether you're looking for a relaxing day of sailing or an adventurous fishing expedition, Sailing Moby Adventures has something for everyone. Book your trip today and create memories that will last a lifetime!

Crab Island Luxury Adventures is a premier institution located at 174 Watercolor Way in Santa Rosa Beach, Florida, United States. Serving the 30A and Santa Rosa Beach areas, we offer the ultimate Crab Island boat rental and charter experience. Whether you're celebrating a bachelorette party, birthday, or any other special event, we specialize in curating bespoke adventures tailored exclusively for you. Imagine a day filled with radiant sun, pristine waters, and the freedom to embrace adventure. Our spacious Catamaran and luxury pontoons can comfortably host up to 13 guests per boat, along with our professional captain and crew. From snorkeling and beach hopping to exploring the vibrant coral reefs, every moment with Crab Island Luxury Adventures is a cherished memory against the backdrop of stunning scenery.

Reef Runner Sailing is a premier sailing institution located at 3151 West 10th Street in Panama City, Florida. Offering a wide range of sailing courses and experiences, Reef Runner Sailing is dedicated to providing top-notch instruction and unforgettable sailing adventures. Whether you're a beginner looking to learn the ropes or an experienced sailor seeking to hone your skills, Reef Runner Sailing has something for everyone. Come sail with us and experience the beauty of the open waters along the stunning coastline of Florida.

Located at 500 Harbor Boulevard in Destin, Florida, Flippers Snorkel Adventure Destin is the perfect travel agency to help you make the most of your vacation on the Emerald Coast. Specializing in snorkeling, dolphin cruises, and sunset tours, Flippers Adventures offers a wide range of options for groups of all sizes. Their well-appointed boats and top-of-the-line equipment ensure a safe and comfortable experience that you will remember for a lifetime. The friendly staff at Flippers Adventures are passionate about sharing the best that Destin has to offer, and their knowledgeable guides will make sure you have an unforgettable experience. Whether you're snorkeling in the crystal-clear waters, watching dolphins play in the sunset, or exploring the underwater wonders of the Gulf of Mexico, Flippers Adventures has something for everyone.

Adventure Cruise Inc is a premier travel agency located at 9610 Gulf Boulevard in Treasure Island, Florida. Specializing in exhilarating and unforgettable cruise experiences, we offer a wide range of cruise packages to suit every traveler's taste and budget. Whether you're looking for a relaxing tropical getaway or an action-packed adventure on the high seas, our team of expert travel consultants is dedicated to helping you plan the perfect cruise vacation. With a commitment to exceptional customer service and a passion for creating lifelong memories, Adventure Cruise Inc is your go-to destination for all your cruise travel needs. Book your dream cruise today and set sail on the adventure of a lifetime!

Sail Venice is a renowned travel agency located at 1968 Tarpon Center Drive in Venice, Florida, United States. Specializing in providing unique and unforgettable sailing experiences, Sail Venice offers a wide range of services including boat rentals, private charters, sunset cruises, and sailing lessons. With experienced captains and a fleet of well-maintained vessels, Sail Venice ensures a safe and enjoyable experience for all customers. Whether you're looking to explore the beautiful waters of Venice or simply relax and unwind on a leisurely cruise, Sail Venice has something for everyone. Book your sailing adventure today and discover the magic of Venice from the water.

Tropical Sailing is a tourist attraction and travel agency located at 401 Biscayne Boulevard, Miami, Florida, United States. They offer Catamaran Tours in Miami & Fort Lauderdale, Florida, providing a perfect way to end the day while taking in breathtaking views. Sunset cruises in both locations offer a relaxing experience with sun dresses, sandals, and chilled drinks. The institution offers various water sport activities for the whole family, including kayaking, stand up paddleboarding, and speedboat tours. The Everglades Day Safari is an in-depth exploration of the majestic Everglades, including an airboat ride, nature walk, mangrove wilderness boat ride, and a delicious lunch.

Sinbad Sail Ventures is a premier travel agency located at 997 South Palafox Street in Pensacola, Florida, United States. Specializing in unique and adventurous sailing vacations, our team of experts are dedicated to helping you plan the perfect getaway. Whether you're looking to explore hidden coves, snorkel in crystal-clear waters, or simply relax on deck with a cocktail in hand, Sinbad Sail Ventures has you covered. Let us turn your travel dreams into reality with our personalized service and attention to detail. Book your next sailing adventure with us today!

Smooth Sailing with V is a travel agency located at 7901 4th Street North in St. Petersburg, Florida. Specializing in unforgettable sailing experiences, we offer a fun and satisfying time at sea, particularly during the captivating sunset hours. Our trips typically last 2-3 hours between 4pm and 8pm, with pricing varying depending on the package chosen. For those looking to celebrate a special occasion such as a birthday, anniversary, or honeymoon, we offer customizable sailing experiences with hours tailored to the customer's preferences. Prices start at $200-$1,000 hourly for boat rental with a Captain, with rates varying based on boat size, type, and party size.

Bird Dog Custom Boat Charters Clearwater & St Pete is a premier travel agency located at 2848 Saint John Drive in Clearwater, Florida. Since 1997, we have been providing unforgettable experiences for those seeking adventure, nature enthusiasts, and couples looking for a romantic getaway. Our dedication to exceptional service and passion for the sea sets us apart from the rest. When you choose Bird Dog Custom Boat Charters Clearwater & St. Pete, you are not just booking a boat trip; you are opening the door to a world of unparalleled experiences. With over 20 years of experience, we are your trusted guides to the stunning coastal areas of Clearwater and St. Petersburg. Our goal is to create custom adventures that cater to your preferences, ensuring that each journey is unique and unforgettable.

Florida Sail in St. Petersburg, FL, offers exclusive private sail charters for those looking to experience the beauty of the water in a personalized way. Located at 400 Treasure Island Causeway in Treasure Island, Florida, this travel agency provides worry-free packages that include everything you need for a day of sailing and exploration. From snorkeling in crystal-clear waters to relaxing on pristine beaches, Florida Sail offers customizable day sails that cater to your preferences. With experienced captains, fuel, docking, snorkels, snacks, and beverages all included, you can enjoy a seamless sailing experience while taking in the sights of the bay and potentially spotting wild dolphins.

Cruise Planners - Top Sail Journeys is a premier travel agency located at 141 Willow Pond Lane in Ponte Vedra Beach, Florida, United States. Specializing in luxury cruises and personalized travel experiences, our team of experienced agents will help you plan the perfect getaway tailored to your preferences and budget. Whether you're looking for a romantic cruise for two, a family vacation, or an adventure-filled expedition, Cruise Planners - Top Sail Journeys will ensure a seamless and unforgettable travel experience. Contact us today to start planning your dream vacation!

Sail La Vie Tiki Cruises at Peanut Island is the ultimate destination for a unique and unforgettable experience on the water. Located at 105 Lake Shore Drive in West Palm Beach, Florida, this travel agency offers private Tiki boat cruises that are perfect for those looking for some fun in the sun. With the ONLY private Tiki boat around, Sail La Vie is the number one choice for a reason. Whether you're looking to relax and enjoy the stunning Florida sunset or want to explore the pristine waters of Fort Pierce, Sail La Vie has you covered. With opportunities to see wildlife such as dolphins, manatees, osprey, and more, this photographers paradise is sure to create lasting memories.

Sailing Port of Call Charters LLC is a premier sailing institution located at 13601 McGregor Boulevard in Fort Myers, Florida. Offering a 3 Hour Learn to Sail Experience and Sailing Charters, we provide a variety of sailing experiences on our Jeanneau Sun Odyssey 45′ yacht. Ideal for those looking to explore the Gulf of Mexico Southwest Florida waters, we also offer a try before you buy option for those dreaming of sailing off into the sunset or wanting to win the America’s Cup. Our diverse Ft. Myers Beach and Sanibel Island waters provide the perfect sub-tropical sailing environment, unmatched for training. Our ASA instructor ratings are excellent, thanks to our great coaches, outstanding training waters, and proper vessels for learning.