TOP 30 Best Sailing adventures in Wisconsin

Lakeshore Adventures Inc is a one-stop destination for all your outdoor needs. Located at 8113 Wisconsin 57 in Baileys Harbor, Wisconsin, this institution offers a wide range of products and services to enhance your outdoor experience. From high-quality outdoor clothing and gear to expert travel advice and guided tours, Lakeshore Adventures Inc has everything you need for your next adventure. Whether you're planning a hiking trip in the nearby woods or a kayaking excursion on Lake Michigan, this store and travel agency has you covered. Visit Lakeshore Adventures Inc today and gear up for your next outdoor escapade!

Bella Sailing Cruises, located at 9993 North Water Street in Ephraim, Wisconsin, is a travel agency offering unforgettable sailing experiences on the enchanting waters of Door County. Whether you're a first-time sailor or a seasoned seafarer, Captain Tom Schroeder welcomes visitors of all ages aboard Scuppers, a meticulously maintained traditional sailboat. Set sail from the historic South Shore Pier in downtown Ephraim and cruise through Eagle Harbor, taking in the stunning views of the surrounding bluffs, forests, and islands. Keep an eye out for wildlife such as soaring seagulls, terns, and maybe even a rare white pelican or eagle. Sail alongside Peninsula State Park, explore the Niagara Escarpment, and admire the unique Horseshoe Island. Captain Schroeder, with his years of experience and passion for sailing, ensures a safe and enjoyable journey for all passengers. Gift certificates are available for a variety of local businesses, making Bella Sailing Cruises the perfect choice for anyone looking to explore Door County in a unique and memorable way. Book your sail today and experience the beauty of Door County from the deck of Scuppers!

True North Sailing Charters is a premier travel agency located at 232 South 1st Street in Bayfield, Wisconsin, United States. Specializing in unforgettable sailing experiences, we offer a variety of charter options for exploring the beautiful waters of Lake Superior. Our expert crew and top-of-the-line vessels ensure a safe and enjoyable journey for all our guests. Whether you're looking for a relaxing day on the water or a multi-day sailing adventure, True North Sailing Charters has the perfect option for you. Book your next nautical excursion with us and set sail towards your true north.

All Hands Sailing is a travel agency located on Rittenhouse Avenue in Bayfield, Wisconsin, United States. Specializing in sailing adventures, they offer a variety of trips and experiences for those looking to explore the open waters. Whether you're a seasoned sailor or a beginner looking to learn the ropes, All Hands Sailing provides a unique and unforgettable experience on the water. Join them for a day trip, sunset cruise, or multi-day sailing excursion and let the wind guide you on your next adventure.

Sail Pepin is a premier sailing institution located at 303 1st Street in Pepin, Wisconsin, United States. Offering a variety of sailing courses and programs for all ages and skill levels, Sail Pepin provides a unique opportunity to experience the beauty of Lake Pepin while learning the art of sailing. Whether you are a beginner looking to try sailing for the first time or an experienced sailor seeking to improve your skills, Sail Pepin has something for everyone. Join us for an unforgettable sailing experience on the pristine waters of Lake Pepin.

Sail Door County is a premier travel agency located at 10707 North Bay Shore Drive in Sister Bay, Wisconsin, United States. Specializing in sailing adventures, they offer a wide range of services including boat rentals, sailing lessons, and guided tours of the beautiful Door County peninsula. Whether you're a seasoned sailor or a beginner looking to experience the thrill of the open water, Sail Door County has something for everyone. Come and explore the stunning coastline and crystal-clear waters of Lake Michigan with the experts at Sail Door County.

The Sail Training Foundation, located at 600 Nautical Drive in Sturgeon Bay, Wisconsin, is a non-profit organization dedicated to providing hands-on sailing experiences for individuals of all ages. Our programs offer a unique opportunity to learn the art of sailing while fostering teamwork, leadership skills, and a love for the open water. Whether you're a beginner looking to try sailing for the first time or an experienced sailor seeking to hone your skills, the Sail Training Foundation has something for everyone. Join us and embark on a thrilling adventure on the beautiful waters of Sturgeon Bay.

Sail Sturgeon Bay is a premier sailing institution located at 107 North 1st Avenue in Sturgeon Bay, Wisconsin, United States. Offering a variety of sailing programs and lessons for all skill levels, Sail Sturgeon Bay provides a unique opportunity to experience the beauty of sailing on the waters of Lake Michigan. With experienced instructors and top-of-the-line equipment, participants can learn the art of sailing in a safe and supportive environment. Whether you're a beginner looking to try something new or an experienced sailor looking to hone your skills, Sail Sturgeon Bay has something for everyone. Come and discover the joy of sailing with Sail Sturgeon Bay.

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Sea Dog Sailing is a premier travel agency located in Milwaukee, Wisconsin, United States. Specializing in sailing adventures, they offer a wide range of services including yacht charters, sailing lessons, and guided tours. Whether you are a seasoned sailor or a novice looking to learn the ropes, Sea Dog Sailing has something to offer for everyone. Immerse yourself in the beauty of the open sea and experience the thrill of sailing with Sea Dog Sailing. Book your next nautical adventure with them today!

The Sailing Club at UWM is a vibrant and exciting institution located on East Lagoon Drive in Milwaukee, Wisconsin. As a university night club, it offers students and sailing enthusiasts a unique and thrilling experience on the water. Whether you're a seasoned sailor or just looking to try something new, the Sailing Club at UWM provides a welcoming and inclusive environment for all skill levels. Join us for a night of fun, adventure, and camaraderie on the beautiful waters of Lake Michigan.

Breeze Sailing LLC is a premier travel agency located at 2 Christopher Columbus Blvd in Racine, Wisconsin. Specializing in sailing adventures, our experienced team can help you plan the perfect sailing trip, whether it's a relaxing cruise along the coast or an exhilarating racing experience. With our extensive knowledge of the best sailing destinations and top-notch customer service, Breeze Sailing LLC is your go-to agency for all your sailing needs. Contact us today to start planning your next unforgettable sailing adventure.

Green Bay Sail & Paddle Inc is a school located at 101 Bay Beach Road in Green Bay, Wisconsin, United States. This institution offers a variety of courses and programs focused on sailing and paddling, providing students with the knowledge and skills to confidently navigate the waters. Whether you are a beginner looking to learn the basics or an experienced sailor seeking to improve your techniques, Green Bay Sail & Paddle Inc has something to offer for everyone. Join us and embark on a new adventure on the beautiful waters of Green Bay.

At CR Adventure Travel, we understand that your life is full of responsibilities and you may not have the time to plan your next dream vacation. That's where we come in. We specialize in creating tailor-made travel experiences that are all about you and your interests, because details matter and experience is everything. You deserve the best.

The Kenosha Community Sailing Center is a charitable organization located in Kenosha, Wisconsin, dedicated to educating youth in the sport of sailing. Through collaboration with local organizations and schools, the center aims to integrate academic, leadership, and life skills into the sailing experience. By promoting awareness and access to the Kenosha Harbor and Lake Michigan, the KCSC offers sailing opportunities for people of all ages. Whether you're a beginner or an experienced sailor, come harness the wind, ride the waves, and experience the adventure with the Kenosha Community Sailing Center.

Ship & Shore Adventures LLC is a travel agency located at 2063 100th Avenue, Dresser, Wisconsin, United States. Whether you're planning a cruise, a Disney vacation, or just need plane tickets and accommodations, Ship & Shore Adventures has got you covered. Our team of specialists will work with you to customize the perfect adventure based on your preferences. We strive to provide the best deals by working directly with other companies in the travel industry. Ted, the founder of Ship & Shore Adventures, has personally sailed across the Gulf of Mexico and the Caribbean Sea, experiencing incredible adventures along the way. His passion for travel and creating unforgettable memories has inspired him to help others do the same.

Cruise Diver Sailing Adventures is a premier travel agency located at 1602 Cypress Trail in Middleton, Wisconsin, United States. Our agency specializes in organizing unique and unforgettable sailing adventures for those looking to explore the open seas. Whether you're a seasoned diver or a first-time cruiser, our experienced team will ensure that your trip is filled with excitement, relaxation, and breathtaking views. Join us for an unforgettable journey on the water with Cruise Diver Sailing Adventures.

Pewaukee Lake Sailing School is a premier educational institution located at N22W28024 Edgewater Drive in Pewaukee, Wisconsin, United States. As a school dedicated to the art of sailing, students of all ages can learn the skills and techniques needed to navigate the waters of Pewaukee Lake and beyond. With experienced instructors and a beautiful lakefront location, Pewaukee Lake Sailing School offers a unique and exciting learning experience for anyone interested in mastering the art of sailing. Join us and set sail on a new adventure today!

Sea Safaris Sailing School is a premier institution located at 9160 South 44th Street in Franklin, Wisconsin, United States. We also have locations in Sturgeon Bay, Milwaukee, and Port Washington, offering a variety of sailing classes, charters, and flotillas for all levels of experience. Our experienced instructors provide a safe and enjoyable learning environment for students of all ages. Join our email list to stay updated on upcoming classes and events, and start your sailing adventure with Sea Safaris Sailing School today!

Sea Safaris Sailing School, located in Milwaukee, Wisconsin, United States, is a premier institution offering top-quality sailing education and experiences. With a team of experienced instructors and state-of-the-art equipment, we provide a safe and enjoyable learning environment for students of all skill levels. Whether you are a beginner looking to learn the basics of sailing or an experienced sailor seeking advanced training, our school has a program tailored to meet your needs. Join us at Sea Safaris Sailing School and embark on a journey of discovery and adventure on the open waters.

Anchor's Away is a premier travel agency located at 830 Platt Avenue in Lake Geneva, Wisconsin. Escape from the hustle and bustle of everyday life and embark on a luxurious boat cruise with Anchor's Away. Leave your worries behind as you relax and soak in the beauty of Lake Geneva. With Anchor's Away, you can explore the stunning sights of Lake Geneva, from the crystal-clear waters to the charming shops and historic architecture. Take a private boat charter and experience Lake Geneva like never before. Whether you're planning a ladies outing, bachelorette party, family day, or corporate event, Anchor's Away has you covered.

The Inn At Timber Cove is a charming lodging institution located at 1319 Sanborn Avenue in Ashland, Wisconsin, United States. With over 20 years of experience, it has been a peaceful retreat for many guests seeking privacy and tranquility at the Cove. Just a few miles away from Bayfield and the Apostle Islands, guests have easy access to waterfalls, sailing, kayaking, and other outdoor activities. Situated on 40 acres of land, guests can explore groomed paths and trails while enjoying fresh berries, apples, and cherries grown on the property. The history of the property is also rich, with an original deed signed by Abraham Lincoln on display. Guests can also delve into the history of the Ashland area during their stay.

Superior Charters & Yacht Sales is a premier destination for sailing enthusiasts located at 34475 Port Superior Road in Bayfield, Wisconsin. As a combination school, store, and travel agency, we offer a unique experience for those looking to explore the stunning waters of Lake Superior. Whether you are a seasoned sailor or a beginner looking to learn the ropes, our experienced staff is dedicated to providing top-notch instruction and guidance. Visit us today to browse our selection of high-quality yachts for sale, book a charter for your next adventure, or sign up for one of our sailing courses. Embark on a journey with Superior Charters & Yacht Sales and discover the beauty of sailing on Lake Superior.

The Apostle Islands National Lakeshore, located at 415 Washington Avenue in Bayfield, Wisconsin, is a stunning tourist attraction that offers a unique blend of natural beauty, history, and outdoor adventure. Picture yourself standing on the rocky shoreline as the sun rises, casting a golden glow over the crystal-clear waters. The islands beckon you to explore, to discover their hidden treasures and to be inspired by their beauty. Whether you're visiting for a day trip or planning a longer stay, there is so much to see and do at Apostle Islands National Lakeshore. The park is open year-round, but it's important to check conditions before heading out to ensure you have a safe and enjoyable visit. Don't have a boat? No problem! There are plenty of ways to explore the islands, from guided kayak trips to boat tours and water taxis.

The Bayfield Maritime Museum, located at 131 South 1st Street in Bayfield, Wisconsin, is a fascinating institution dedicated to preserving and showcasing the rich nautical history of Bayfield and the Apostle Islands in Lake Superior. With over 15,000 guests entertained each season by dedicated volunteers, the museum offers a unique and educational experience for tourists and history enthusiasts alike. The museum is part of the Bayfield Heritage Association, which was established in 1974 and is committed to collecting, preserving, and sharing the history and culture of the Bayfield region through exhibits, programs, and research. Additionally, the Apostle Islands Historic Preservation Conservancy works to protect the culturally and historically significant resources in the Apostle Islands region.

Plowman's Marine Inc. is a premier marine store located in Woodruff, Wisconsin. We specialize in providing a wide range of boating and marine products to meet all your watercraft needs. Our store carries everything from boat accessories, maintenance supplies, safety equipment, and more. With a knowledgeable and friendly staff, we are dedicated to helping you find the perfect products for your boating adventures. Visit us at 382 U.S. 51 to explore our extensive selection and experience top-notch customer service at Plowman's Marine Inc.

Apostle Islands Cruises Boat Tour is located at 2 Front Street in Bayfield, Wisconsin, United States. Experience the beauty of Wisconsin's "Crown Jewels" - the 21 island archipelago - with a cruise on Lake Superior. Embark on a 2.5-hour, 55-mile journey with entertaining narration from the captain, showcasing iconic sights like historic lighthouses and intricate sea caves. Choose from a variety of tours, including the Michigan Island Lighthouse Tour, Raspberry Island Lighthouse Tour, Stockton Island Day Hiking shuttle, and Stockton Island and Oak Island overnight camping shuttles. Explore stunning natural scenery, historic landmarks, and marine wildlife at Apostle Islands National Lakeshore.

The Bayfield Chamber & Visitor Bureau, located at 42 South Broad Street in Bayfield, Wisconsin, is a renowned travel agency that has been named one of the "The 23 Best Places to Go in the U.S. in 2023" by Conde Nast Traveler. As the "Gateway to the Apostle Islands," Bayfield offers endless adventures and was voted among the 10 Best Coastal Small Towns and Best Midwestern Small Towns in 2023 by USA Today Top 10Best Readers' Choice. Known as Wisconsin’s Smallest City and the Berry Capital of Wisconsin, Bayfield is a picturesque destination on the shores of Lake Superior. Visitors can explore the mainland sea caves, hike scenic trails, sail on Lake Superior, enjoy concerts by the lake, and experience the beauty of changing seasons. From apple festivals to fine arts shows, Bayfield has something for everyone year-round. Shop local, dine at fine restaurants, and partake in winter activities like skiing and snowshoeing. Plan your getaway to Bayfield and discover the magic of this charming city and the Apostle Islands.

Betty Lou Cruises is a renowned travel agency located at 5339 Lighthouse Bay Drive in Madison, Wisconsin, United States. Specializing in providing unforgettable cruise experiences, Betty Lou Cruises offers a variety of cruise packages tailored to suit every traveler's preferences. Whether you're looking for a relaxing sunset cruise, a lively party cruise, or a romantic dinner cruise, Betty Lou Cruises has something for everyone. With top-notch amenities, excellent customer service, and a stunning backdrop of the Madison skyline, a cruise with Betty Lou Cruises is sure to be a memorable experience. Book your next adventure with Betty Lou Cruises and set sail on the journey of a lifetime.

The Kenosha Area Convention and Visitors Bureau is a travel agency located at 10519 120th Avenue in Pleasant Prairie, Wisconsin, United States. Picture a charming lakefront community with two iconic lighthouses, bustling downtown streets filled with museums, shops, and restaurants, and a vibrant arts scene with outdoor concerts and theatre performances. Explore scenic trails for biking, hiking, and skiing, as well as opportunities for fishing, golfing, and sailing. Discover a destination that goes beyond the expected in the heart of the Midwest - welcome to Kenosha. Visit the Bureau for information on upcoming events like the Dairy State Cheese & Beer Festival, Lakeside Players Production of Seussical the Musical, and the Kenosha Book Festival. Don't miss out on special activities and extended hours in Downtown Kenosha, or join in on Earth Week festivities at Hawthorn Hollow Nature Sanctuary and Arboretum. Whether you're a local or a visitor, the Bureau is your guide to all the exciting things to do in Kenosha.