TOP 30 Sailing experiences in Annapolis, MD
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Annapolis Sailing Adventures
Annapolis Sailing Adventures is a premier travel agency located in Annapolis, Maryland, United States. We offer a variety of sailing experiences, including private charters, sunset cruises, and sailing lessons. Our experienced captains will take you on a memorable journey on the beautiful Chesapeake Bay. Whether you are a seasoned sailor or a beginner looking to learn the ropes, Annapolis Sailing Adventures has something for everyone. Come aboard and experience the thrill of sailing in one of the most scenic locations in the United States.
Seas the Bay Private Sailing Charters
Seas the Bay Private Sailing Charters is a premier travel agency located in Annapolis, Maryland, United States. Specializing in private sailing charters, they offer unforgettable experiences on the beautiful Chesapeake Bay. Whether you're looking for a romantic sunset cruise, a fun day out on the water with friends, or a corporate team-building event, Seas the Bay has you covered. Their experienced crew will ensure a safe and enjoyable journey as you take in the stunning views and relax on the open water. Book your private sailing charter today and make memories that will last a lifetime.
Chesapeake Sailing Tours
Chesapeake Sailing Tours is a premier travel agency located in Annapolis, Maryland. We offer unforgettable sailing experiences on the beautiful Chesapeake Bay, providing guests with the opportunity to explore the stunning waterways and historic landmarks of the area. Our knowledgeable captains and crew are dedicated to providing a safe and enjoyable sailing experience for all guests. Whether you are looking for a relaxing sunset cruise or a thrilling day of sailing, Chesapeake Sailing Tours has something for everyone. Join us at 1117 Skyway Drive for an unforgettable adventure on the water.
Schooner Woodwind Sailing Cruises
Schooner Woodwind Sailing Cruises offers an unforgettable experience for visitors looking to explore the waters of Annapolis, Maryland. Located at 80 Compromise Street, this tourist attraction and travel agency provides guests with the opportunity to sail on a beautiful schooner while taking in the stunning views of the Chesapeake Bay. Whether you're a seasoned sailor or a first-time cruiser, Schooner Woodwind Sailing Cruises offers a range of tours and experiences to suit every preference. Set sail with them for a memorable adventure on the water.
Granmar Sailing
Granmar Sailing is a premier travel agency located at #8 Randall Street in Annapolis, Maryland, United States. Specializing in sailing adventures, Granmar Sailing offers a variety of packages for individuals and groups looking to explore the open waters. Whether you are a seasoned sailor or a beginner looking to learn the ropes, Granmar Sailing has something for everyone. With experienced captains and top-of-the-line equipment, you can trust that your sailing experience with Granmar Sailing will be safe, enjoyable, and unforgettable. Book your next sailing adventure with Granmar Sailing and set sail for an experience of a lifetime.
Picture Perfect Sailing
Picture Perfect Sailing is a premier sailing institution located at 980 Awald Road in Annapolis, Maryland, United States. Escape the hustle and bustle of everyday life and enjoy quality time with family and friends on the beautiful Chesapeake Bay. Whether you are looking for a day sail or an overnight adventure, our experienced skippers will take you on a memorable journey. Choose from a variety of sailing charters, starting at $650 for 2 guests on weekdays. Your charter includes a skipper, snacks, and beverages. For a longer experience, opt for our all-day sailing or overnight options. Sail to destinations such as Baltimore or Saint Michaels and create memories that will last a lifetime.
Classic Sail Charters
Classic Sail Charters is a premier sailing school located in Annapolis, Maryland, offering private sailing adventures for up to six passengers. With world-class sailing yachts, experienced captains, and top-notch service, we ensure that your charter experience is truly unforgettable. Our charters are exclusively for private parties, allowing you to customize your adventure. Join us at 980 Awald Road for a unique and luxurious sailing experience on the beautiful Siena yacht. With Captain Nate, Payton, and Tony at the helm, you can relax, learn some sailing skills, and enjoy the stunning views of the West River. Whether you're looking for a romantic engagement shoot, a family outing, or a relaxing day on the water, Classic Sail Charters has something for everyone. Book your trip today and set sail for an unforgettable experience on the Chesapeake Bay.
Chronic Sailing
Chronic Sailing is a premier sailing school located at 7082 Bembe Beach Road in Annapolis, Maryland, United States. Our institution offers top-notch sailing instruction for all skill levels, from beginners to advanced sailors. Whether you're looking to learn the basics of sailing or improve your racing techniques, our experienced instructors are here to help you achieve your goals on the water. Join us at Chronic Sailing and experience the thrill of sailing in one of the most beautiful locations on the East Coast.
Annapolis Town Center Pavillion
Annapolis Town Center Pavilion is a vibrant tourist attraction located at 307 Sail Place in Annapolis, Maryland, United States. This bustling center offers a variety of shops, restaurants, and entertainment options for visitors to enjoy. From upscale boutiques to casual eateries, there is something for everyone at Annapolis Town Center Pavilion. The beautiful outdoor pavilion provides a charming setting for events and gatherings, making it a popular destination for both locals and tourists alike. Come and experience all that Annapolis Town Center Pavilion has to offer!
Annapolis Yacht Club Activity Center
The Annapolis Yacht Club Activity Center is a premier waterfront facility located at 314 6th Street in Annapolis, Maryland. This state-of-the-art institution offers a wide range of activities and amenities for members and guests to enjoy. From sailing and boating excursions to fitness classes and social events, the Annapolis Yacht Club Activity Center is the perfect destination for those looking to experience the best that the Chesapeake Bay has to offer. With stunning views of the water and a welcoming atmosphere, this institution is a must-visit for anyone looking to embrace the maritime culture of Annapolis.
SailTime Annapolis
SailTime Annapolis is a premier sailing school and store located at 105 Eastern Avenue in Annapolis, Maryland, United States. Offering a range of sailing courses for all skill levels, SailTime Annapolis provides hands-on instruction and certification for aspiring sailors. Additionally, the store offers a wide selection of sailing gear, equipment, and accessories for enthusiasts looking to enhance their sailing experience. With a knowledgeable staff and top-notch facilities, SailTime Annapolis is the perfect destination for anyone looking to learn how to sail or improve their skills on the water.
R&R Charters and Sail School
R&R Charters and Sail School, located in Chester, Maryland, United States, is a professional institution dedicated to sharing the joy of sailing with students. Our experienced educators provide personalized instruction to help students master the knowledge and skills needed to feel confident on the water. Whether you prefer individual instruction or learning in a small group setting with friends and family, our maximum of four students per boat ensures that each student receives ample hands-on experience. Captain Penny encourages students to "Learn to sail; you might want to go somewhere."
Annapolis Sailing School
Annapolis Sailing School is a premier sailing institution located at 7001 Bembe Beach Road in Annapolis, Maryland, United States. With a rich history and a reputation for excellence, the school offers a wide range of sailing courses for sailors of all levels. Whether you are a beginner looking to learn the basics or an experienced sailor looking to refine your skills, Annapolis Sailing School has a program for you. Their experienced instructors provide top-notch training in a safe and supportive environment, ensuring that students have a fun and rewarding experience on the water. Come sail with Annapolis Sailing School and discover the joy of sailing in one of the most beautiful locations in the United States.
J World Annapolis
J World Annapolis is a premier sailing school located in the heart of Annapolis, Maryland. Our experienced instructors offer a wide range of sailing courses for all skill levels, from beginners to advanced sailors. Whether you are looking to learn the basics of sailing or improve your racing techniques, our team is dedicated to helping you achieve your goals on the water. Situated at 213 Eastern Avenue, our facility is equipped with state-of-the-art sailboats and top-notch training equipment to ensure a safe and enjoyable learning experience. With a focus on hands-on instruction and personalized coaching, J World Annapolis is the perfect place to hone your sailing skills and build confidence on the water.
Smooth Sailing Sounds & Electronics
Smooth Sailing Sounds & Electronics is a one-stop destination for all your car repair and electronics needs. Conveniently located at 165 Gibralter Avenue in Annapolis, Maryland, this institution offers top-notch services and a wide selection of products to enhance your driving experience. Whether you need a tune-up for your vehicle or want to upgrade your car's sound system, the expert technicians at Smooth Sailing are here to help. Visit our store today and experience the smooth sailing difference.
Pirate Adventures on the Chesapeake
Pirate Adventures on the Chesapeake, located at 311 Third Street in Annapolis, Maryland, is a top tourist attraction and travel agency offering a unique and exciting experience for families. Guests rave about the high-energy and memorable adventures provided by the enthusiastic pirate crew. From searching for sunken treasure to firing water cannons, kids of all ages are sure to have a blast on this pirate cruise. The institution is highly recommended for parents of young children, as well as for school field trips. With activities like pirate dress up, face-painting, and interactive storytelling, Pirate Adventures on the Chesapeake is a must-visit destination for families looking for outdoor fun and entertainment. Don't miss out on this unforgettable experience – book your reservation today and set sail for a day filled with laughter and exploration!
Darling Charters
Darling Charters is a premier travel agency located at 1 Dock Street in Annapolis, Maryland. Specializing in luxury yacht charters and personalized travel experiences, our team of experienced professionals is dedicated to creating unforgettable vacations for our clients. Whether you're looking to explore the Chesapeake Bay or sail to exotic destinations around the world, Darling Charters is here to make your travel dreams a reality. Contact us today to start planning your next adventure!
Island Chill Yacht Charters
Island Chill Yacht Charters (ICYC) is a travel agency located at 1444 Shore Drive in Edgewater, Maryland, United States. We specialize in creating the 'Relaxing Excitement of the Islands' on private sail and powerboat cruises for families, friends, and couples. Conveniently situated in historic Londontowne, we are close to Washington D.C. and Baltimore, just 6 miles south of Annapolis - the 'Sailing Capital of America!' Our cruises are perfect for hot summer days and chill sunsets, making them ideal for birthdays, anniversaries, bachelorette parties, corporate retreats, national holidays, and special events. Choose from our 43-foot sailboat (Therapy), 34-foot powerboat (Irie Vibes), or 20-foot bow-rider powerboat (Tallawah) for captained cruises along the South and Rhode Rivers, Chesapeake Bay, and Thomas Point Shoal Lighthouse. Enjoy swimming, paddle boarding, floating lily pads, sunbathing, beaches, sandbars, islands, kayaking, and fishing options.
Ohana Charters
Ohana Charters is a travel agency located at 500 Piney Narrows Road in Chester, Maryland, United States. Specializing in Annapolis Charter, Catamaran Charter, Sailing Charter, and more, Ohana offers a luxurious and unique sailing experience on the Chesapeake Bay. Guests can enjoy stunning sunsets, delicious food, and the opportunity to enhance their sailing skills. Whether celebrating a special occasion like an anniversary, birthday, or graduation, or simply looking for a relaxing getaway, Ohana Charters provides a memorable and unforgettable experience on the water. With the option for overnight stays, intimate family reunions, or exclusive events, Ohana Charters offers a variety of packages to suit every need. Experience romance, relaxation, and adventure aboard Ohana Charters for an unparalleled sailing experience.
Schooner Woodwind Offsite Business Office
Schooner Woodwind Offsite Business Office is a travel agency located at 1930 Lincoln Drive in Annapolis, Maryland. Our office is dedicated to providing exceptional service and assistance to our clients in planning their travel adventures on the Schooner Woodwind sailboats. Whether you are looking to book a private charter, a team building event, or a unique corporate outing, our experienced team is here to help create a memorable and enjoyable experience for you and your group. Contact us today to start planning your next sailing adventure on the beautiful waters of Annapolis.
Liberte, The Schooner
Liberte, The Schooner is a renowned travel agency located at 222 Severn Avenue in Annapolis, Maryland, United States. Specializing in luxury sailing experiences, Liberte offers guests the opportunity to explore the stunning Chesapeake Bay aboard their beautiful schooner. With experienced crew members and top-notch amenities, guests can relax and enjoy the breathtaking views while sailing the waters of the East Coast. Whether you're looking for a romantic sunset cruise or a unique corporate event venue, Liberte, The Schooner is the perfect choice for a memorable and unforgettable sailing experience.
CBYRA
The Chesapeake Bay Yacht Racing Association (CBYRA) is a prestigious institution located at 821 Chesapeake Avenue in Annapolis, Maryland, United States. CBYRA is dedicated to promoting and supporting the sport of yacht racing in the Chesapeake Bay region. With a rich history and strong community of sailors, CBYRA organizes races, events, and educational programs to foster a love of sailing and competition. Join us at CBYRA and experience the thrill of racing on the beautiful waters of the Chesapeake Bay.
Chesapeake Boating Club
Chesapeake Boating Club, located at 213 Eastern Avenue in Annapolis, Maryland, is a unique institution that offers sail and power boat charters and rentals. Founded in 1992 in the Historic Eastport section of Annapolis, the club prides itself on providing flexible, fun, and affordable boating experiences. With a variety of boats ranging from 17' to 36' in length, members can choose the right vessel for any adventure on the Chesapeake Bay. In addition to boat rentals, the Chesapeake Boating Club also offers instruction in sailing and powerboating. The club's experienced J World coaches provide online educational seminars during the off-season to help members enhance their boating skills.
International Star Class Yacht
The International Star Class Yacht is a prestigious institution located at 914 Bay Ridge Road in Annapolis, Maryland, United States. This world-renowned yacht club is dedicated to promoting and supporting the sport of sailing, particularly in the competitive Star Class category. Members of this exclusive club have access to top-of-the-line facilities and equipment, as well as expert coaching and training programs. Whether you are a seasoned sailor or a beginner looking to improve your skills, the International Star Class Yacht offers a welcoming and supportive environment for all levels of experience. Join us and set sail towards your sailing dreams!
Sea Dog Pet Boutique
Sea Dog Pet Boutique is your local destination for small batch, ethically sourced pet products. Located at 172 Main Street in Annapolis, Maryland, our family-owned pet store offers a unique shopping experience for both pets and their owners. At Sea Dog Pet Boutique, we take pride in stocking a variety of products for your pet family, including toys, collars, treats, and more. We also offer a selection of human accessories, such as hats, clothing items, and cards. Our goal is to provide high-quality, ethically sourced products that you can trust.
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