TOP 10 Best Luxury sailing adventures 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.

Tiki Boat Boston offers a unique and unforgettable experience on the waters of Boston Harbor. Located at 60 Rowes Wharf in Massachusetts, our institution provides guests with the opportunity to cruise in style on a traditional Polynesian-inspired tiki boat. Whether you're looking to celebrate a special occasion, enjoy a relaxing sunset cruise, or simply have a fun day out on the water, Tiki Boat Boston has you covered. Our friendly and experienced staff are dedicated to ensuring your time on board is nothing short of amazing. Come aboard and experience the magic of Tiki Boat Boston for yourself.

Classic Harbor Line Boston is a premier travel agency located at 60 Rowes Wharf in Boston, Massachusetts. Step aboard one of our classic vessels and fall in love with Boston Harbor as you sail on a schooner or cruise on a motor yacht. Our fleet is historically inspired by turn-of-the-century style yachts, designed with classic elements to create an elegant atmosphere for hosting events such as Nautical Weddings, Corporate Outings, Graduations, and Team Building activities. Experience a fun and luxurious sailing excursion in Boston Harbor with Classic Harbor Line. Sail on the elegant schooner Adirondack III or relax on the motor vessel Northern Lights while taking in breathtaking views of the Boston skyline, historical sites, harbor islands, and wildlife such as harbor seals. Whether you're a first-time visitor or a local, our yachts offer a new perspective on the city of Boston. Kick back and relax as our hospitable crew takes care of everything for you.

Boston Harbor City Cruises offers a unique and unforgettable experience on the waterfront of Boston, Massachusetts. Located at 30 Shipyard Drive in Hingham, this institution provides a variety of cruise options including dinner cruises on the Odyssey and Spirit of Boston, brunch and lunch cruises, and fast ferries to Provincetown and Salem. Guests can also enjoy whale watch cruises, sunset sightseeing cruises, and thrill rides on the CODZILLA boat. With Boston's rich history and charming waterfront as the backdrop, Boston Harbor City Cruises is the perfect venue for weddings, bachelorette parties, and other special events. Couples can exchange vows with stunning views of the harbor, while bachelorette parties can enjoy a fun and memorable celebration on the water.

Welcome Aboard The Tall Ship Boston! Nestled at 1 East Pier Drive in the heart of East Boston, Massachusetts, The Tall Ship Boston is a unique and vibrant destination that promises an unforgettable experience. This extraordinary 245-foot vessel has been transformed into a floating oyster bar, offering a blend of bar, restaurant, and nightclub vibes, all set against the stunning backdrop of the Boston city skyline and harbor. Step aboard and discover three exquisite mahogany bars, thoughtfully positioned around the grand mast and at the fore and aft of the ship, creating the perfect setting for socializing and relaxation. Our galley kitchen serves up the freshest local oysters, shellfish, and delectable charcuterie boards, ensuring a delightful culinary journey.

Ptown Luxury Cruises offers an exclusive and luxurious experience for those looking to explore the beautiful waters of Provincetown, Massachusetts. Located at 9 MacMillan Pier, this travel agency provides a variety of options for sunset, sunrise, beach, and whale watching cruises. With charters available to destinations such as Boston, Cape Cod, Nantucket, and Martha's Vineyard, guests have the freedom to choose where they want to go. The cruise offers overnight accommodations for up to six guests, with private staterooms and full baths for added comfort. Unlike crowded cruises, Ptown Luxury Cruises provides a spacious and uncrowded environment where guests can relax, sunbathe, and enjoy delicious food and drinks.

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.

Local Tide Charters is a premier fishing and boating charter service located at 61 Crocker Drive in Edgartown, Massachusetts. Our experienced captains and crew are dedicated to providing unforgettable experiences on the water, whether you're looking to reel in a big catch or simply enjoy a relaxing cruise along the beautiful coastline. With a variety of charter options available, including deep sea fishing trips, sunset cruises, and private charters, Local Tide Charters is the perfect choice for both seasoned anglers and beginners alike. Join us for an adventure on the local tides and create memories that will last a lifetime.

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!