TOP 20 Best Guided sailing excursions in Massachusetts

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.

Mad Max Sailing Adventures offers thrilling and unforgettable experiences on the water in Edgartown, Massachusetts. Our expert crew will take you on a high-speed sailing adventure, where you can feel the wind in your hair and the salt spray on your skin. Whether you're a seasoned sailor or a first-timer, our trips are perfect for anyone looking for a unique and exciting way to explore the beautiful waters of Martha's Vineyard. Join us at 25 Dock Street for an unforgettable sailing experience with Mad Max Sailing Adventures.

Island Girl Excursions is a premier travel agency located at 7 Great Plains Road in West Tisbury, Massachusetts. Specializing in curated experiences for adventurous travelers, Island Girl Excursions offers personalized itineraries and guided tours to explore the stunning natural beauty and cultural richness of Martha's Vineyard and beyond. With a team of experienced travel experts and a commitment to providing top-notch customer service, Island Girl Excursions is your go-to destination for unforgettable travel experiences. Book your next adventure with Island Girl Excursions and embark on a journey of a lifetime.

Sail Anejo is a premier travel agency located in Gloucester, Massachusetts, United States. Specializing in sailing adventures, they offer a wide range of services including private charters, sailing lessons, and guided tours of the beautiful coastal waters of New England. With a team of experienced captains and crew members, Sail Anejo ensures a safe and unforgettable experience for all their customers. Whether you are looking for a relaxing day on the water or an exciting sailing excursion, Sail Anejo is your go-to destination for all things nautical. Book your next sailing adventure with Sail Anejo and set sail for an unforgettable experience on the open sea.

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.

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.

Stage Harbor Excursions & Launch is a premier boating and excursion company located at 1533 Main Street in charming Chatham, Massachusetts. Offering a variety of boat tours and charters, including scenic harbor cruises, fishing trips, and private charters, Stage Harbor Excursions & Launch provides unforgettable experiences on the water for visitors and locals alike. With knowledgeable captains, top-of-the-line vessels, and a commitment to customer satisfaction, this institution is the perfect choice for those looking to explore the beauty of Stage Harbor and beyond. Whether you're seeking a relaxing cruise or an exciting fishing adventure, Stage Harbor Excursions & Launch has something for everyone.

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.

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.

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.

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.

Cape Ann Whale Watch is a premier tourist attraction and travel agency located at 415 Main Street in Gloucester, Massachusetts, United States. Embark on a thrilling adventure with experienced guides as you set sail to witness majestic whales in their natural habitat. Enjoy breathtaking views of the Atlantic Ocean while learning about these incredible creatures. Don't miss the opportunity to create unforgettable memories with Cape Ann Whale Watch.

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.

Albatross Fishing and Sunset Cruise is a long-standing institution located at 351 Sesuit Neck Road in Dennis, Massachusetts. For over 50 years, we have been providing exciting bottom fishing trips in Cape Cod Bay, where you can catch Winter Flounder, Black Sea Bass, Red Hake, and Tautog. Our trips depart from Sesuit Harbor and last approximately three hours, giving you plenty of time to reel in some impressive catches. In addition to fishing excursions, we also offer sunset cruises with live music during the summer months. Our boat, equipment, and crew are all inspected annually by the U.S. Coast Guard to ensure your safety and comfort during your trip. We recommend bringing a light jacket or windbreaker, as the bay can be chilly even on warm days.

Massachusetts Bay Lines is a popular tourist attraction and travel agency located at 60 Rowes Wharf in Boston, Massachusetts. Offering a variety of scenic cruises and tours on the beautiful waters of Massachusetts Bay, this institution provides visitors with a unique and unforgettable way to experience the city's stunning skyline and historic landmarks from the water. Whether you're looking for a relaxing sightseeing cruise, a romantic sunset sail, or a fun harbor tour, Massachusetts Bay Lines has something for everyone. With knowledgeable guides, comfortable vessels, and breathtaking views, this institution is a must-visit destination for anyone looking to explore Boston by sea.

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.

SV Dream Escapes LLC is a premier travel agency located at 6 Queen Circle in Dudley, Massachusetts, United States. We specialize in creating unforgettable travel experiences for our clients, helping them to escape the ordinary and discover the world's most beautiful destinations. Our team of expert travel planners is dedicated to crafting personalized itineraries that cater to every traveler's unique preferences and desires. Whether you're dreaming of a relaxing beach getaway, an adventurous safari, or a cultural exploration, SV Dream Escapes LLC is here to turn your travel dreams into reality. Contact us today to start planning your next dream escape.

Cape Cod Scenic Tours is a premier travel agency located on Center Street in Dennis, Massachusetts. We specialize in providing unforgettable scenic tours of the beautiful Cape Cod region. Our experienced guides will take you on a journey through charming seaside towns, picturesque beaches, and historic landmarks. Whether you're looking for a relaxing day trip or a week-long adventure, Cape Cod Scenic Tours has the perfect itinerary for you. Come explore the natural beauty and rich history of Cape Cod with us!

Cape Cod Boating Adventures is a premier travel agency located at 255 Commercial Street in Wellfleet, Massachusetts, United States. We specialize in providing unforgettable boating experiences along the picturesque Cape Cod coastline. Our expert guides will take you on a journey through the crystal-clear waters, pristine beaches, and charming coastal towns of Cape Cod. Whether you're looking for a relaxing sunset cruise, a thrilling fishing excursion, or a private charter for a special occasion, Cape Cod Boating Adventures has you covered. Come join us for a one-of-a-kind boating adventure on the beautiful waters of Cape Cod.

True Blue Waters is a reputable general contractor based in Sterling, Massachusetts. We specialize in providing top-quality construction services for residential and commercial projects. Our team of experienced professionals is dedicated to delivering exceptional results, on time and within budget. From remodeling and renovations to new construction and custom builds, we have the expertise to bring your vision to life. Contact us today at 14b Boutelle Road to discuss your project and see why True Blue Waters is the trusted choice for all your construction needs.

Welcome to Gay Head Lighthouse Nestled in the picturesque town of Chilmark, Massachusetts, the historic Gay Head Lighthouse stands as a beacon of maritime heritage and natural beauty. Located at the westernmost point of the island, this iconic lighthouse offers visitors a unique transit station experience, blending rich history with breathtaking views.

Island Time Charters is a premier charter service located at 19 Owen Park Way in Tisbury, Massachusetts. With a prime location on Martha's Vineyard, our experienced captains and crew are dedicated to providing guests with unforgettable experiences on the water. Whether you're looking to explore the beautiful coastline, fish for your dinner, or simply relax and enjoy the stunning views, Island Time Charters has a variety of options to suit your needs. Join us for a day of adventure and relaxation on the water with Island Time Charters.

Cruise One is a premier travel agency located at 124 Green Street in Weymouth, Massachusetts. Specializing in luxury cruise vacations, they offer a wide range of cruise packages to destinations around the world. With expert travel agents who are knowledgeable about various cruise lines and itineraries, they are dedicated to helping their clients plan the perfect cruise experience. Whether you are looking for a relaxing Caribbean getaway or an adventurous Alaskan expedition, Cruise One can help you find the ideal cruise vacation tailored to your preferences. Book your dream cruise today with Cruise One and set sail on an unforgettable journey.

Welcome to Steal Away Charters, your premier travel agency located in the heart of Newburyport, Massachusetts. Nestled at 346 Merrimac Street, our business is dedicated to crafting unforgettable maritime adventures for locals and visitors alike. At Steal Away Charters, we specialize in offering personalized and exhilarating charter experiences along the picturesque New England coastline. Whether you’re seeking a serene day of sailing, an exciting fishing expedition, or a customized private event on the water, our expert team is committed to making your nautical dreams come true.