TOP 30 Boston sailing vacations in Boston, Massachusetts

Classic Sail Boston is a premier travel agency located in the heart of Boston, Massachusetts. Specializing in classic sailboat tours and experiences, our knowledgeable staff are dedicated to providing an unforgettable and authentic maritime adventure. Whether you're looking to explore the historic Boston Harbor or cruise along the picturesque New England coastline, Classic Sail Boston offers a variety of tailored sailing experiences to suit every preference. Come aboard and immerse yourself in the beauty and tranquility of the open sea with Classic Sail Boston.

Come Sail Away Now is a premier travel agency located in the heart of Boston, Massachusetts. Specializing in luxury sailboat vacations, our experienced team of travel experts will help you plan the perfect sailing adventure. Whether you're looking to explore the picturesque New England coast or set sail to exotic destinations around the world, Come Sail Away Now has you covered. Let us take the stress out of vacation planning and help you create memories that will last a lifetime. Visit us at 1 8th Street in Boston and start planning your dream sailing vacation today.

Boston by Sea is a premier travel agency located at 60 Rowes Wharf in the vibrant city of Boston, Massachusetts. Specializing in unique and unforgettable sea expeditions, Boston by Sea offers a wide range of cruise options for travelers looking to explore the beautiful waters of New England. From whale watching tours to romantic sunset cruises, our experienced team is dedicated to providing exceptional service and creating memorable experiences for all our clients. Whether you are a seasoned sailor or a first-time cruiser, Boston by Sea is your gateway to discovering the wonders of the ocean.

Boston Sail Tours offers unforgettable sailing charters in the beautiful Boston Harbor. Our experienced captains will take you on a journey through the historic waters of Boston, showcasing iconic landmarks such as the USS Constitution and the Boston Tea Party Ships. Whether you are looking for a romantic sunset cruise or a fun-filled day out on the water with friends and family, Boston Sail Tours has the perfect charter for you. Come aboard our luxury sailing vessels and experience the thrill of sailing in one of America's most historic and picturesque harbors. Book your charter today at our location on 28 Constitution Road, Boston, Massachusetts, United States.

The Liberty Fleet of Tall Ships Boston/Bahamas is a travel agency located at 67 Long Wharf in Boston, Massachusetts, United States. Under new ownership and with a new location at Fan Pier, the institution offers day sail adventures in Boston Harbor aboard the classic schooner, the Liberty Star. Experience the beauty of Boston from the water during a sunset cruise on a classic tall ship. The friendly and knowledgeable crew is always available to help, ensuring a relaxing and unforgettable sail. Guests can participate in raising the sails and enjoy a unique sailing experience around the harbor. Whether it's a bachelorette party or a leisurely cruise, the Liberty Fleet of Tall Ships offers a memorable and enjoyable way to see Boston. Don't miss out on this incredible opportunity to explore the city from a different perspective. Visit the Boston Travel Guide for more travel inspiration.

Black Rock Sailing School is a premier institution located at 8 13th Street in Boston, Massachusetts, United States. As a top-rated sailing school, we offer a range of courses for beginners and experienced sailors alike. Our experienced instructors provide hands-on training in sailing techniques, navigation, and safety procedures. Whether you're looking to learn the basics or improve your skills, Black Rock Sailing School is the perfect place to embark on your sailing journey. Join us and discover the thrill of sailing on the open water.

The Harry McDonough Sailing Center is a premier sailing institution located in Boston, Massachusetts, United States. With a rich history and strong reputation for excellence, the center offers a wide range of sailing programs for sailors of all ages and skill levels. From beginner lessons to advanced racing clinics, the center provides top-notch instruction and access to state-of-the-art equipment. Whether you are looking to learn the basics of sailing or hone your skills in competitive racing, the Harry McDonough Sailing Center is the perfect place to embark on your sailing journey. Come experience the thrill of sailing on the beautiful waters of Boston Harbor with the expert guidance of the center's experienced instructors.

First Reef Sailing is a premier sailing institution located at 256 Marginal Street in Boston, Massachusetts. 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 skills, our team of professionals is here to help you achieve your goals. With a fleet of top-of-the-line sailboats and a picturesque location on the water, First Reef Sailing provides the perfect setting for an unforgettable sailing experience. Join us today and discover the joy of sailing with First Reef Sailing.

Boston Sailing Center is a premier sailing institution located at 54 Lewis Wharf in Boston, Massachusetts. Offering a wide range of sailing courses and programs for all skill levels, from beginners to experienced sailors, the center provides a unique opportunity to learn and master the art of sailing in the picturesque waters of Boston Harbor. With a fleet of top-of-the-line sailboats and experienced instructors, Boston Sailing Center is the perfect place to embark on your sailing journey. Whether you are looking to learn how to sail, improve your skills, or simply enjoy the thrill of being out on the water, Boston Sailing Center has something for everyone. Join us and experience the joy of sailing in one of the most beautiful and historic sailing destinations in the United States.

The Boston University Sailing Pavilion is a premier sailing facility located on the scenic Doctor Paul Dudley White Bike Path in Boston, Massachusetts. This state-of-the-art institution offers a wide range of sailing programs and classes for students and community members of all skill levels. With experienced instructors and top-of-the-line equipment, the Sailing Pavilion provides a safe and enjoyable environment for individuals to learn and improve their sailing abilities. Whether you're a beginner looking to try out sailing for the first time or an experienced sailor seeking to enhance your skills, the Boston University Sailing Pavilion is the perfect place to embark on your sailing journey.

Cataumet Boats Inc is a premier store located in Bourne, Massachusetts, United States. We specialize in offering a wide range of high-quality boats for sale, including sailboats, powerboats, and yachts. Our knowledgeable staff is dedicated to helping customers find the perfect vessel to suit their needs and preferences. Whether you are a seasoned sailor or a first-time boat buyer, Cataumet Boats Inc is the perfect place to find your dream boat. Visit us at 1280 Massachusetts 28A and let us help you set sail on your next adventure.

Cruise Planners is a reputable travel agency located at 400 Boston Post Road in Sudbury, Massachusetts, United States. Specializing in cruise vacations, the agency offers personalized trip planning services to help clients create unforgettable travel experiences. With a team of experienced travel advisors, Cruise Planners is dedicated to providing top-notch customer service and expert advice to ensure smooth sailing from start to finish. Whether you're looking to explore exotic destinations or relax on a luxurious cruise ship, Cruise Planners has the expertise and resources to make your travel dreams a reality. Contact them today to start planning your next adventure!

World Ocean School, located at 212 Northern Avenue in Boston, Massachusetts, is a unique travel agency that offers transformative education aboard their iconic tall ship, Schooner Roseway. The institution inspires students from all backgrounds to become courageous and compassionate changemakers for themselves, their communities, and the planet. With a focus on immersive, hands-on learning, World Ocean School provides education to over 600 students annually, with more than 23,000 students having participated in their programs since their founding in 2002. Students not only learn about ocean science and sailing while on board, but also develop important life and social emotional skills such as resilience, trust, and courage. The institution's innovative curriculum includes STEM-based learning and opportunities for personal growth. World Ocean School is a non-profit organization with a 501(c)(3) tax-exempt status, dedicated to empowering students to realize their full potential and make a positive impact on the world.

Welcome to Bakers Island Light Station Nestled off the coast of Salem, Massachusetts, on the picturesque Bakers Island, the Bakers Island Light Station stands as a beacon of history and natural beauty. Managed by the Essex National Heritage Commission (Essex Heritage), this historic site invites you to explore its rich heritage and breathtaking surroundings.