TOP 30 Best Sailing packages in Massachusetts

Sunset Sail Salem is a premier travel agency located in the historic city of Salem, Massachusetts. Our agency is dedicated to providing unforgettable experiences on the water, offering scenic sunset sails along the picturesque coast of Salem. Our expert crew ensures a safe and enjoyable journey as you relax and take in the stunning views of the sunset over the Atlantic Ocean. Whether you're looking for a romantic evening out or a fun adventure with friends and family, Sunset Sail Salem is the perfect choice for your next nautical excursion. Book your sail today and create lasting memories on the water.

Frayed Knot Sailing Charters is a premier travel agency located at 15 Ashland Avenue in the picturesque coastal town of Manchester-by-the-Sea, Massachusetts. Specializing in unforgettable sailing experiences, our charter services offer unique and personalized excursions on the open waters of the Atlantic Ocean. Whether you're looking for a relaxing sunset cruise or an adventurous day trip, Frayed Knot Sailing Charters has something for everyone. Our experienced crew and luxurious vessels ensure a safe and enjoyable journey for all our guests. Come sail away with us and create memories that will last a lifetime.

Cape Cod Catamaran Sailing Charters is a travel agency located at 255 Commercial Street in Wellfleet, Massachusetts, United States. Offering morning and afternoon charters as well as sunset cruises from Wellfleet Harbor, this institution provides an authentic Cape Cod experience on their catamaran, Discovery. Escape the crowds and immerse yourself in the serene beauty of Cape Cod with a private daytime charter, where you can explore the bay, watch seals, or simply relax and enjoy the tranquility of the local waters. The experienced captain ensures a smooth and comfortable ride as you navigate Wellfleet Harbor and Cape Cod Bay.

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.

Moment Sailing Adventures is located at 16 MacMillan Pier in Provincetown, Massachusetts, offering deluxe private captained day sailing charters. With a strict US Coast Guard policy limiting groups to six guests, including children, Moment provides a personalized and intimate sailing experience. The 47-foot Moment, designed by Sparkman & Stephens, offers 2, 4, and 6-hour sails to explore the wildlife, beaches, lighthouses, and sunsets of outer Cape Cod. Recognized as one of the 5 Best Sailing Charters by Yankee Magazine and rated 5 stars on TripAdvisor, Moment Sailing Adventures promises a memorable and safe sailing experience. The vessel underwent an extensive refit in 2013-14 and is equipped with modern amenities such as a guest toilette, refrigeration for beverages, and a tender named "Tary" for shore excursions. Guests rave about their experiences aboard Moment, praising the skilled captain, Chris, for creating unforgettable moments on the water. Whether it's a romantic proposal, a birthday celebration, or a leisurely sail around Provincetown harbor, Moment Sailing Adventures ensures a unique and special experience for all guests.

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.

Endeavor Sailing Excursions is a premier sailing company located in Nantucket, Massachusetts. We offer a variety of sailing excursions for all levels of experience, from beginners to seasoned sailors. Our experienced captains will guide you through the beautiful waters surrounding Nantucket, providing a safe and enjoyable experience for all. Whether you're looking for a relaxing sunset cruise or an adventurous day on the water, Endeavor Sailing Excursions has something for everyone. Come join us for an unforgettable sailing experience in one of the most picturesque locations in the United States.

Halcyon Days Sailing Charters is a premier travel agency located in Gloucester, Massachusetts, United States. Specializing in unforgettable sailing experiences, Halcyon Days offers a variety of charter options for individuals and groups looking to explore the scenic waters of the New England coast. With expert captains and top-of-the-line vessels, guests can relax and enjoy a luxurious and personalized sailing adventure. Whether you're a seasoned sailor or a first-time explorer, Halcyon Days Sailing Charters promises an unforgettable journey on the open sea.

ACK Sail is a premier travel agency located at 34 Washington Street in the charming town of Nantucket, Massachusetts. Specializing in unique sailing adventures and excursions, ACK Sail offers a variety of services to help you explore the stunning waters surrounding Nantucket Island. Whether you're looking to charter a private boat for a romantic sunset cruise or join a group excursion to discover hidden coves and marine life, ACK Sail has something for every type of traveler. With experienced captains and a passion for providing unforgettable experiences on the water, ACK Sail is the perfect choice for your next maritime adventure.

Sailing Martha's Vineyard is located at the Menemsha jetty dinghy dock and Basin Road in Chilmark, Massachusetts, United States. The institution offers ultimate sailing experiences aboard a custom-built mega-yacht designed for island passage-making. With a variety of short, protected sails, guests can glide across Vineyard Sound and explore the remote Elizabeth Islands. For the more adventurous, longer ocean sails around the island and beyond are also available. The institution prides itself on providing a range of sailing options, from 1-hour sails to overnight trips, all at affordable prices. With a focus on direct communication and booking, guests can enjoy savings on repeat visits. The experienced crew, led by Captain Nick and first mate Charlie, ensures a safe and enjoyable sailing experience for all guests.

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.

Jetties Sailing Center is a premier sailing institution located at Bathing Beach Road in Nantucket, Massachusetts. Offering a wide range of sailing programs and lessons for all ages and skill levels, the center is the perfect place to learn and improve your sailing skills. With experienced instructors, top-notch equipment, and a beautiful location on the shores of Nantucket, Jetties Sailing Center is the ultimate destination for anyone looking to enjoy the thrill of sailing on the open water. Come join us and experience the joy of sailing in one of the most picturesque locations in the United States.

Cape Sail is a renowned sailing institution located on Stage Harbor Road in Chatham, Massachusetts, United States. With a rich maritime history and beautiful coastal surroundings, Cape Sail offers a variety of sailing courses for all skill levels. Whether you're a beginner looking to learn the basics or an experienced sailor seeking to improve your technique, Cape Sail provides expert instruction in a supportive and scenic environment. Join us at Cape Sail and set sail on an unforgettable nautical adventure along the picturesque shores of Massachusetts.

Sail Buzzards Bay is a premier sailing institution located at 101 Main Street in Fairhaven, Massachusetts. Our facility offers top-notch sailing programs for all skill levels, from beginners to advanced sailors. With a stunning location on Buzzards Bay, our experienced instructors provide expert guidance and instruction to help you navigate the waters with confidence and skill. Whether you're looking to learn how to sail, improve your technique, or simply enjoy a day on the water, Sail Buzzards Bay is the perfect place to explore the beauty of the bay and hone your sailing abilities. Join us for an unforgettable sailing experience!

Wild Harbor Sailing is a premier sailing institution located at 386 Grove Street in Falmouth, Massachusetts, United States. Offering a variety of sailing programs for all ages and skill levels, Wild Harbor Sailing provides an exceptional learning experience on the beautiful waters of Cape Cod. With experienced instructors, top-notch equipment, and a passion for the sport, students can expect to improve their sailing skills while enjoying the scenic views of Wild Harbor. Whether you are a beginner looking to learn the basics or an experienced sailor seeking to hone your techniques, Wild Harbor Sailing has something for everyone. Join us for an unforgettable sailing adventure!

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.

Witch of Endor Sailing Charters is a premier travel agency located at 99 Water Street in Tisbury, Massachusetts. We offer unforgettable sailing experiences along the beautiful coastline of Martha's Vineyard. Our expert crew and luxurious vessels ensure a safe and enjoyable journey as you explore the scenic waters of New England. Whether you're looking for a romantic sunset cruise or a thrilling adventure on the open sea, Witch of Endor Sailing Charters has the perfect excursion for you. Book your sailing adventure today and let us help you create memories that will last a lifetime.

Sail Ena is a renowned travel agency located at 350 Lake Street in Tisbury, Massachusetts, United States. Specializing in sailing adventures, Sail Ena offers a variety of exciting and unforgettable experiences for those looking to explore the open seas. Whether you're a seasoned sailor or a novice looking to try something new, Sail Ena has something for everyone. With expert guides and top-of-the-line equipment, you can trust that your sailing experience with Sail Ena will be safe, enjoyable, and truly memorable. Book your next sailing adventure with Sail Ena and set sail for an unforgettable journey on the waters of Massachusetts.

Sail The Vineyard is a unique travel agency located at 13 Marine Avenue in Wareham, Massachusetts. Led by an adventurous and accomplished female captain, our all-female crew offers sailing excursions in Martha's Vineyard and The Caribbean. Our captain is a US Coast Guard Master Mariner and a Certified instructor by the American Sailing Association, specializing in mentoring female sailors. Embark on a thrilling adventure aboard our classic sloop-rigged sailboat and explore the beauty and history of Martha's Vineyard by sea. Enjoy the picturesque coastline with lighthouses, historic homes, and beautiful beaches. Feel the wind in your hair, embrace your inner mermaid, and learn the art and science of sailing with us.

Sail Cape Cod is a renowned sailing school located at 135 South Street in Barnstable, Massachusetts, United States. Our institution offers a wide range of sailing courses for all skill levels, from beginners to advanced sailors. With experienced instructors and top-notch equipment, we provide a safe and enjoyable learning environment for all our students. Whether you are looking to learn the basics of sailing or improve your techniques, Sail Cape Cod is the perfect place to embark on your sailing journey. Join us and experience the thrill of sailing on the beautiful waters of Cape Cod!

Plan Sea Adventure Charters, located at 53 Dock Street in Edgartown, Massachusetts, is the premier boat tour and rental company in Martha’s Vineyard and Cape Cod. Offering a variety of private cruise packages for groups of up to 18 passengers, our boat tours are perfect for family outings, bachelorette parties, team building events, and more. Our experienced Captains, with U.S. Coast Guard Masters Licenses, ensure a safe and enjoyable experience as you cruise along the beautiful shoreline of Woods Hole and Oak Bluffs. With indoor and outdoor heated seating, a bathroom, and a wet bar on board, our classic New England motor vessels provide a luxurious and comfortable ride for all guests.

Catboat Charters is a premier travel agency located at 1 Dock Street in Edgartown, Massachusetts. Specializing in unique and unforgettable sailing experiences, Catboat Charters offers a variety of charter options for exploring the beautiful waters of Martha's Vineyard and beyond. Whether you're looking for a relaxing sunset cruise or an adventurous day of sailing, Catboat Charters has something for everyone. With experienced captains and top-notch service, Catboat Charters is the perfect choice for your next nautical adventure.

Cape Ann Cruises is a reputable travel agency located at 63 Rogers Street in Gloucester, Massachusetts. They specialize in offering a variety of exciting cruise experiences along the beautiful Cape Ann coastline. Whether you're looking for a relaxing harbor cruise, a whale watching excursion, or a sunset cruise, Cape Ann Cruises has something for everyone. Their knowledgeable staff is dedicated to providing top-notch customer service and ensuring that every guest has a memorable and enjoyable experience on the water. Visit Cape Ann Cruises for an unforgettable adventure on the scenic waters of Massachusetts.

Capt. Tom's Charters is a premier travel agency located on F Street in beautiful Nantucket, Massachusetts. Specializing in personalized charter experiences, Capt. Tom's offers a range of excursions for visitors looking to explore the stunning waters surrounding the island. Whether you're interested in deep sea fishing, sightseeing cruises, or sunset tours, Capt. Tom's Charters has something for everyone. With knowledgeable and experienced captains at the helm, you can trust that your adventure with Capt. Tom's will be unforgettable. Book your next nautical adventure with Capt. Tom's Charters and experience the beauty of Nantucket like never before.

Located at 10 MacMillan Pier in Provincetown, Massachusetts, the Schooner Hindu and the Cutter Bloodhound travel agency offers unique and exciting sailing experiences. Step aboard these historic vessels and set sail on the waters of Cape Cod Bay for a memorable adventure. Whether you're looking for a relaxing cruise or a thrilling racing experience, the Schooner Hindu and the Cutter Bloodhound have something for everyone. Book your voyage today and discover the beauty of the Massachusetts coastline from a whole new perspective.

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.

LuxuryOnly Cruises is a premier travel agency located at 100 Quannapowitt Parkway in Wakefield, Massachusetts, United States. Specializing in luxury cruise vacations, we offer a wide range of exclusive cruise packages to some of the most exotic and breathtaking destinations around the world. Our experienced and knowledgeable travel advisors are dedicated to providing top-notch service and creating unforgettable experiences for our clients. Whether you're looking for a romantic getaway, a family vacation, or a solo adventure, LuxuryOnly Cruises has the perfect cruise package for you. Book your dream vacation with us today and set sail on a luxury cruise experience like no other.

Pirate Adventures Martha's Vineyard is a thrilling tourist attraction and travel agency located at 12 Circuit Avenue Extension in Oak Bluffs, Massachusetts, United States. Embark on a swashbuckling adventure as you set sail on a pirate ship and explore the beautiful waters surrounding Martha's Vineyard. With interactive storytelling, treasure hunts, and exciting activities, visitors of all ages will be captivated by the excitement of life on the high seas. Book your voyage today and create unforgettable memories with Pirate Adventures Martha's Vineyard. Arrr matey!

Cruises.com is a premier travel agency located at 100 Quannapowitt Parkway in Wakefield, Massachusetts. Specializing in cruises, this institution offers a wide range of vacation packages to exotic destinations around the world. With a team of experienced travel experts, Cruises.com is dedicated to helping customers find the perfect cruise experience tailored to their preferences and budget. Whether you're looking for a relaxing Caribbean getaway or an adventurous Alaskan expedition, Cruises.com has you covered. Book your dream cruise today and set sail for an unforgettable vacation experience.

CheapCruises.com is a leading travel agency located in Wakefield, Massachusetts, United States. As the name suggests, they specialize in offering affordable cruise packages to various destinations around the world. With a wide selection of cruise lines and itineraries to choose from, CheapCruises.com makes it easy for travelers to find the perfect vacation at a great price. Whether you're looking for a quick getaway or an extended adventure at sea, CheapCruises.com has something for everyone. Book your dream cruise today and set sail for an unforgettable experience!