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Sailing is the simple joy of moving by wind. A sailing boat uses its sails to harness breeze and glide across the water. It is calm, quiet, and close to nature. Choose it if you want a relaxed pace, hands-on fun, and a true connection to the sea.Most sailing boats have a roomy cockpit for relaxing and a protected cabin below. You may find a small kitchen, called a galley, and a toilet, called a head. Monohulls lean under sail, while catamarans have two hulls for a stable ride. Deck space is open, with clear areas to sit, move, and enjoy the view.Sailing is great for day trips, sunset cruises, and weekend getaways. Crewed trips let you sit back while the skipper handles the helm, which is the steering station. Want to learn? Many crews will show you how to trim the sails and help with lines. You can anchor in a quiet cove, swim, snorkel, or just watch the wake drift by.This boat type suits beginners, families, and seasoned sailors. First-timers can book with a captain for easy guidance. Bring soft bags, sun protection, a light jacket, and non-marking shoes. Life jackets, also called PFDs, are normally on board. If you get motion sickness, plan ahead with your usual remedy.Before your trip, check local rules for Sailing. Some places require licenses, permits, or specific captain credentials. Know the capacity rating for your group, follow safety briefings, and avoid BUI, which means boating under the influence. Always follow local navigation marks and no-wake zones. When in doubt, ask your captain or operator about the latest rules.

Popular Sailing Boat Tours Charters in Gloucester  , United States. Good availability and great rates. Read unbiased reviews and choose the best deal for your trip.

Sailing Boat Tours in Gloucester, MA- BoatBooker

Gloucester

Gloucester, United States

gloucester

Discover Gloucester, Massachusetts, United States—an authentic New England harbor where working waterfronts meet dramatic Atlantic scenery. Known for its proud maritime heritage and easy access to Cape Ann's rugged coastline, Gloucester boating charters connect you with rocky headlands, pristine beaches, and wildlife-rich waters ideal for sightseeing and adventure.Launch from Gloucester Harbor to explore sheltered coves, classic lighthouses, and island-dotted passages perfect for leisurely cruising or photography. In season, charters often venture toward productive offshore grounds for memorable wildlife spotting, while inshore routes reveal calm bays suited to family-friendly outings and relaxed sunset trips.Anglers will find varied opportunities around reefs and rips, while sailing enthusiasts enjoy steady coastal breezes and panoramic views of historic shorelines. Kayak- and paddle-friendly inlets offer a slower pace, and flexible itineraries make it easy to combine harbor touring with beach landings or lighthouse viewing.With convenient marina facilities, knowledgeable local captains, and options ranging from private powerboats to classic sailboats, Gloucester boating charters make it simple to tailor your time on the water. Whether you're planning a half-day harbor cruise or a full-day coastal exploration, this Cape Ann destination delivers quintessential New England character, sea air, and unforgettable horizons.

Experience the charm of Gloucester, a picturesque coastal town in Massachusetts, with our exceptional Gloucester Boat Tours. Located on historic Cape Ann, Gloucester offers a blend of maritime heritage, stunning natural beauty, and vibrant culture. Whether you're interested in exploring the bustling harbor, witnessing majestic lighthouses, or enjoying the thrill of lobstering, Gloucester has something for everyone.

Choose from a variety of tours that cater to different interests. Take a Lighthouse Cruise to admire six iconic lighthouses, including those at Eastern Point, and enjoy the scenic views of Cape Ann's rugged coastline. Alternatively, join a Harbor Tour to discover the famous fishing fleet, historic landmarks like Stage Fort Park and Norman's Woe, and artistic hotspots like Rocky Neck Art Colony.

For a more leisurely experience, opt for a Sunset Cruise aboard unique boats like the Friki Tiki, offering an "island vibe" amidst Gloucester Harbor's stunning scenery. If you prefer a more traditional sailing experience, board the Schooner Thomas E. Lannon and enjoy a relaxing sail while absorbing the rich maritime history of the area.

No matter which tour you choose, you'll be surrounded by the beauty of Gloucester's shores, rich history, and vibrant community. Let your Gloucester boat tour be an unforgettable adventure amidst New England's most captivating coastal scenery.

Join Captains Rick and Deb aboard the beautiful yacht Artemis for a 3-hour sail in Gloucester and Massachusetts Bay. Let the wind guide the course, with the chance to visit charming New England ports like Salem, Beverly, Marblehead, and Manchester by the Sea. We welcome up to 6 guests, or you can enjoy an intimate experience with just 2! Every trip includes a delicious meal, offering a more personal and relaxed alternative to crowded vessels with 20-30 people. This is your private yacht experience!

United States

Artemis Sailing Charters

Set sail on an unforgettable journey with Artemis Sailing Charters aboard the beautifully restored 1994 Sundeer Pilothouse 64 Sailing vessel, based out of Gloucester. Perfect for up to 6 guests, we offer flexible trips ranging from 3-hour and 4-hour excur

Join Captains Rick and Deb aboard the beautiful yacht Artemis for a sunset sail in Gloucester and Massachusetts Bay. The wind will guide the journey, with the chance to pass by picturesque New England ports like Salem, Beverly, Marblehead, and Manchester by the Sea. We welcome up to 6 guests, or you can enjoy an intimate experience with just 2! Each trip includes a delicious meal, providing a more personal and relaxed experience than crowded vessels with 20-30 people. This is your private yacht!

3 Hour Sunset Sail with a meal.

Awesome experience

Thank you Pat. We will provide sandwiches for lunch. Once this trip is booked I will be provided with your contact information and I can send you details about how to get to  the boat.. Thanks so much. Kind regards, Captain Rick And Deb.

4 hour sailing  trip for Pat B

Amazing Experience!!!

Lyla Rose Charters

On this trip you will set out to see these magnificent creatures in all of their glory! You could possibly encounter several species of whale during your trip. Humpback, Finback, and Minke Whale are all known to frequent the areas off our shore. Enjoy a more private experience and comfortable setting while viewing the whales and taking photos and videos with family and friends. 

5 Hour Trip – Whale Watching (AM)

Wonderful experience! 

Sportfishing boats are built for chasing big, fast fish in open water. They blend power, range, and comfort, so you can run offshore, find the bite, and enjoy the ride. If you want a stable platform for trolling or a quick dash to the next hotspot, Sportfishing is a great choice.Most models range from about 26 to 60 feet. Layouts often include a roomy cockpit for fishing, a shaded helm, and tall rails for safety. Many have a flybridge, which is an upper driving station with better views. Expect rod holders, a livewell for bait, a fish box, and strong outriggers to spread lines. Deep-V hulls help soften the ride when seas pick up.These boats shine on offshore runs for tuna, mahi, or billfish, and they handle coastal trips well. Captains may troll, drift, or bottom fish, depending on season and conditions. Fast cruising speeds help you cover ground, while modern sonar and GPS make finding structure simpler.Sportfishing boats suit beginners, families, and seasoned anglers alike. Newer anglers enjoy clear deck space and guidance from the crew. Experienced guests appreciate the tackle setup and the ability to switch tactics quickly. Bring sun protection, non-marking shoes, snacks, and a light jacket. Pack any personal medications and a camera for the action.Before you cast off, check local rules. Confirm fishing license needs, size and bag limits, and any seasonal closures. Make sure life jackets, also called PFDs, are aboard and sized for everyone. Follow captain briefings on safety, seas, and weather. Local operating rules, including no-wake zones and alcohol limits, can vary. Review them ahead of your trip.

Sportfishing

Sportfishing boats are designed for those who seek the thrill of deep-sea fishing while enjoying the comforts of a well-equipped vessel. Known for their robust build and advanced features, these boats are perfect for tackling the challenges of open ocean fishing and accommodating multiple passengers on extended trips.

On BoatBooker.com, you can explore premier destinations for sportfishing boat tours, ranging from offshore adventures to tranquil coastal waters. These tours provide a mix of excitement and luxury, offering opportunities to catch big game fish like marlin, tuna, and wahoo, while also enjoying the yacht-like amenities on board.

Booking a sportfishing boat tour ensures a high-end experience with features tailored for serious anglers. These boats typically range from 26 to over 100 feet in length and come equipped with powerful engines (outboard, inboard, or sterndrive) designed for long-range travel. Key features include bait-prep and rigging stations, multiple rod holders, livewells, fish boxes, and sophisticated navigation systems. Many sportfishing boats also offer comfortable sleeping quarters, full kitchens, and lounging areas, making them suitable for multi-day trips and family outings.

Sportfishing boats are built to withstand rough sea conditions, with deep-V hulls providing stability and a smooth ride. Their large fuel tanks allow for extended voyages, and advanced construction materials like fiberglass and sometimes Kevlar ensure durability and performance. These boats often feature high-tech amenities such as air conditioning, ice makers, and advanced fishing electronics, enhancing both the fishing experience and overall comfort.

Discover the perfect sportfishing boat tour for your next adventure on BoatBooker.com, and enjoy the best of both worlds: thrilling fishing expeditions and luxurious living on the water.

sportfishing

A Walkaround is a versatile small yacht with safe side decks you can walk along. You can move from the cockpit to the bow with ease. This makes fishing, anchoring, and docking simple. It is a popular pick for guests who want comfort and fishability in one package.Most Walkaround boats are 20–35 feet long. They feature a compact cabin with a berth for resting and a head, which is a small bathroom. Many also include a basic galley for snacks and drinks. A raised helm, or driver’s station, gives clear views when you throttle up or dock.On the water, a Walkaround handles a wide range of trips. It works well for trolling, casting, and bottom fishing. The design stays stable at anchor and tracks straight at cruising speed. It also suits relaxed sightseeing and quick overnight escapes.This boat type fits beginners, families, and seasoned anglers. Side decks and high rails boost confidence when you move forward. The cabin offers shade, storage, and a dry place for kids to rest. Bring soft‑soled shoes, sun protection, layers, and any personal medications. If you feel motion sensitive, sit near the center for a smoother ride.Before you go, check local boating and fishing rules. Confirm if you need a license or permits for your target species. Review safety requirements such as life jackets, also called PFDs, and capacity limits. Follow your captain’s safety briefing and any posted no‑wake or restricted areas. Local rules vary by waterway, so plan ahead.

Walkaround

Walkaround boats are a versatile and practical choice for both fishing and family outings, offering a blend of comfort and functionality. These boats are designed with a small cabin and a walkaround deck, providing easy access to the bow and allowing for safe movement around the boat, making them ideal for a variety of activities on the water.

Walkaround boats typically range from 20 to 35 feet in length and are equipped with inboard or outboard engines that provide reliable power for both short trips and longer excursions. Key features include a raised helm station for improved visibility, ample storage for fishing gear and supplies, and comfortable seating arrangements. The small cabin usually includes a berth for overnight stays, a galley, and a head (bathroom), making these boats suitable for extended trips and weekend getaways.

When you book a walkaround boat tour, you can expect a comfortable and enjoyable experience. These boats are designed for versatility, allowing you to engage in activities such as fishing, cruising, and even watersports. The walkaround deck provides easy access to all areas of the boat, enhancing safety and convenience, especially when handling fishing rods or anchoring. The cabin space offers protection from the elements and a place to relax, making it perfect for families and groups.

Walkaround boats are equipped with advanced navigation and fish-finding electronics, ensuring a successful and enjoyable fishing experience. The stability and robust construction of these boats make them suitable for various water conditions, from calm lakes to choppy coastal waters. The combination of a spacious deck and comfortable cabin ensures that both anglers and leisure seekers can enjoy their time on the water.

Experience the versatility and comfort of a walkaround boat tour for your next adventure. Whether you're fishing, cruising, or simply enjoying a day out with family and friends, a walkaround boat provides the perfect platform for a memorable and enjoyable experience.

walkaround

Downeast is a classic powerboat style built for comfort and tough water. It blends a seaworthy hull with a cozy cabin, making it a smart choice for cruising and fishing. Book a Downeast trip if you want a smooth ride, steady handling, and timeless lines.Most Downeast boats run between 25 and 45 feet. They usually have a deep keel, which helps the boat track straight, and a semi-displacement hull for a stable ride. Expect a sheltered helm, a large cockpit, and a cabin with berths, a small galley, and a head, which is a marine toilet.This boat type shines on day cruises, sunset runs, and weekend getaways. Anglers like the roomy cockpit for trolling or bottom fishing, and the high gunwales for added security. The hull handles chop well, so you stay comfortable while underway.A Downeast suits first-time boaters, families, and seasoned guests. It is easy to move around thanks to wide side decks and a steady beam, the boat’s width. Bring soft-soled shoes, sun protection, a light jacket, and small bags. Most trips provide life jackets, also called PFDs, but ask your captain about sizes for kids.Before you cast off, check local rules where you plan to boat. Some places require fishing licenses or special permits. Follow safety guidelines, know the capacity rating, and never boat under the influence, known as BUI. Ask your captain about required gear, float plans, and any local operating or no-wake zones. Staying informed helps you enjoy your Downeast trip with confidence.

Downeast

Downeast boats are renowned for their classic design, sturdy construction, and exceptional seaworthiness, making them ideal for a variety of water activities, including cruising, fishing, and overnight trips. These boats are deeply rooted in New England's maritime heritage and are designed to handle the rough waters of the Northeast coast, providing a reliable and comfortable experience on the water.

Downeast boats typically range from 25 to 45 feet in length and feature a distinctive design characterized by a pronounced sheerline, a long and deep keel, and a semi-displacement hull. This hull design offers a smooth and stable ride, even in choppy conditions. The boats are often powered by inboard diesel engines, which provide excellent fuel efficiency and reliability for long-distance cruising.

When booking a Downeast boat tour, you can expect a blend of tradition and modern comfort. The boats are equipped with spacious cockpits, ideal for fishing or socializing, and a protected helm area that offers shelter from the elements. The interior cabins are designed for comfort and practicality, often featuring berths for sleeping, a small galley for meal preparation, and a head (bathroom). The craftsmanship of Downeast boats is typically top-notch, with high-quality wood finishes and attention to detail that adds to their charm and elegance.

Downeast boats are versatile and can be used for various activities such as fishing, day cruising, or extended trips. They often come with amenities like rod holders, fish boxes, and advanced navigation systems, making them suitable for serious anglers. The deep, secure cockpits and wide side decks enhance safety and ease of movement around the boat, while the enclosed cabin provides a cozy retreat for overnight stays.

Experience the timeless appeal and robust performance of a Downeast boat tour for your next adventure. Whether you're exploring coastal waters, enjoying a day of fishing, or embarking on a weekend getaway, a Downeast boat offers the perfect combination of classic style, comfort, and seaworthiness.

downeast

A Headboat, often called a party boat, is built for group fishing trips. It offers a simple, social way to get on the water. You share the rail, learn from the crew, and enjoy steady action together.Headboats are large and stable, with a wide beam for comfort. Most have shaded decks, restrooms, and indoor seating. Many feature a galley for snacks, plus fish boxes and rod holders along the gunwale.These boats handle a range of trips. Crews run bottom fishing over reefs and wrecks, and sometimes troll when conditions fit. Half-day and full-day outings are common, and some boats offer night trips for a fun change.A Headboat suits first-timers, families, and seasoned anglers alike. The crew helps with tackle, bait, and safe handling. Bring sun protection, a hat, soft-soled shoes, and layers for wind or spray. Pack a small cooler for drinks and for your fillets after the crew cleans your catch. If you get seasick, plan ahead and bring motion relief.Before you cast off, check local rules. Some places require a fishing license, while others cover guests under the vessel permit. Know catch limits, size limits, and open seasons. Follow the captain’s safety briefing and the posted capacity rating. USCG rules, life jackets, and basic safety gear should be on board. Arrive early for check-in, listen for the plan, and respect the crew and fellow anglers. Local regulations vary, so review them before your trip and ask questions on the dock.

Headboat

Headboats, also known as party boats, are designed for large group fishing excursions, accommodating several dozen passengers. These boats are perfect for novice and experienced anglers alike, offering an affordable and social way to experience saltwater fishing. Typically, a day on a headboat includes fishing equipment, bait, and the assistance of an experienced crew. Onboard amenities often include a galley serving hot food and drinks, ensuring a comfortable experience even for those new to fishing.

Booking a headboat tour through BoatBooker allows you to explore some of the best fishing destinations, from the vibrant waters of the Gulf of Mexico to the scenic coastal regions of the Atlantic. These tours provide a unique opportunity to catch a variety of species, such as snapper, grouper, and mackerel, while enjoying the camaraderie of fellow anglers.

When you book a headboat tour, you can expect a well-organized trip with all the necessary fishing gear provided. The crew is there to help with everything from setting up your tackle to cleaning your catch. The large, stable boats ensure a smooth ride, making it an ideal choice for families or groups looking to enjoy a day on the water without the need for prior fishing experience.

Discover the best fishing spots and make unforgettable memories aboard a headboat with BoatBooker. Whether you're looking for a thrilling fishing adventure or a relaxing day at sea, headboat tours offer a fun and accessible way to enjoy the ocean.

headboat

A Catamaran is a twin-hull vessel known for a smooth, stable ride. Its wide stance cuts down roll and pitch, so more guests feel comfortable. You get generous space to relax, move around, and take in the view. Many boaters choose a Catamaran for family time, easy handling, and steady performance in light chop.The layout is open and social. Two slim hulls support a wide deck with room to spread out. Most models have a cockpit at the stern for shaded seating and gear. You will often find a salon for lounging and a galley for simple meals. The helm, which is the steering station, offers great sightlines. A Catamaran’s beam, or width, is large for its length. Its shallow draft, meaning it does not sit deep in the water, helps it reach quiet bays.Catamarans work well for day cruising, snorkeling stops, and island hopping. Power cats plane quickly and cruise efficiently. Sailing cats glide along with steady speed and little heel. Anglers like the stable platform for casting or slow trolling. When it is time to swim, the low transom steps make getting in and out easy. Anchoring near shore is simple thanks to the shallow draft.This boat type suits first-time boaters, families, and groups. It also fits seasoned guests who want comfort and deck space. Pack soft bags, non-marking shoes, sun protection, and a light layer. Expect a safety briefing and life jackets, also called PFDs. Bring any snacks and drinks your crew prefers, plus a camera for those wide-angle views.Before your trip, check local rules. Some areas require licenses or permits for certain activities. Follow capacity ratings and all safety instructions from the captain. In the United States, know basic USCG rules and avoid BUI, or boating under the influence. Local laws vary, so review them ahead of time.

Catamaran

Catamarans are popular for their stability, spaciousness, and efficiency. These boats, with their twin-hull design, offer significant stability compared to monohull boats. Additionally, they provide ample deck and interior space, making them ideal for family outings, fishing, or extended cruises.

A key reason for their popularity is the comfort they offer. Catamarans are less likely to pitch and roll on waves, which reduces the likelihood of seasickness and makes the onboard experience more enjoyable. They are suitable for various activities, including day sailing, fishing, and even transoceanic voyages. Their twin-hull design allows for more deck space, enabling activities such as sunbathing, barbecuing, and other outdoor pursuits.

Catamarans are also known for their efficiency. Their hulls create less drag in the water, resulting in higher speeds and lower fuel consumption. Additionally, the twin engines provide excellent maneuverability, especially in tight spaces or when docking.

One of the advantages of catamarans is their shallow draft, allowing access to shallow waters and hidden coves that larger boats cannot reach. These boats are often equipped with modern navigation and communication systems, enhancing safety and comfort on longer trips.

Booking a catamaran tour through BoatBooker allows you to explore the best destinations worldwide, from tropical paradises to scenic coastal regions. Expect a smooth, stable ride with plenty of space for relaxation and activities. Whether you're looking for a day of adventure or a luxurious multi-day cruise, catamarans provide the perfect platform for an unforgettable experience.

Discover the best destinations and embark on an exciting journey with a catamaran tour through BoatBooker, enjoying unparalleled comfort and stability on the water.

catamaran

Sailing

Sailing boats offer a unique and exhilarating way to explore the water, combining the tranquility of wind-powered movement with the adventure of navigating open waters. These boats, driven by sails and guided by the wind, provide an immersive experience that connects you with nature and the elements. Sailing boats range from small dinghies suitable for day trips to larger yachts designed for extended voyages, catering to a wide variety of preferences and sailing skills.

When booking a sailing boat tour through BoatBooker, you can expect an unforgettable journey through some of the most picturesque destinations. Whether you are cruising along the stunning coastlines of the Mediterranean, exploring the Caribbean's turquoise waters, or navigating serene inland lakes, sailing offers a peaceful and eco-friendly way to travel. Tours often include the guidance of experienced skippers, ensuring both safety and a richer understanding of the local marine environment.

Sailing boat tours can be tailored to various interests, from leisurely cruises focused on relaxation and sightseeing to more hands-on experiences where you can learn the basics of sailing. The rhythmic sound of the waves against the hull, the gentle sway of the boat, and the sense of freedom that comes from harnessing the wind create a soothing and invigorating escape from everyday life.

Most sailing tours provide all necessary equipment and a briefing on sailing techniques and safety procedures. This makes them accessible to everyone, including families, couples, and solo travelers. The diverse range of sailing boats available means that whether you prefer a romantic getaway on a small sloop or a group adventure on a spacious catamaran, there is a sailing experience to suit your needs.

For those interested in exploring the top destinations for sailing and booking a tour, BoatBooker offers comprehensive information on options and what to expect. Embark on a sailing adventure to discover breathtaking coastal landscapes, hidden coves, and vibrant marine life, all while enjoying the timeless allure of travel by sail.

Sailing in Gloucester

Top Sailing in Gloucester

Top Sailing in Gloucester

Artemis Sailing Charters

What boaters said about Sailing

Awesome experience

Amazing Experience!!!

Wonderful experience!

Other great boat types in Gloucester