TOP 10 Best Sailing vacations maine in Portland, Maine

Sail Portland Maine, located at 1 Marina Way in Portland, Maine, offers the best boat charters in the city. Relax with friends and family aboard the Eleanor Hawkes or Calista Ann as you cruise through the tranquil waters of Portland Harbor and Casco Bay. Enjoy the sights of the Portland skyline, historic forts, and wildlife like seals swimming in the harbor. Experience the ultimate Flappy Hour celebration with a chartered cruise to Crown Jewel on Great Diamond Island. Choose from public or private charters, and bring your own food and beverages aboard. Private charters are perfect for special occasions, from romantic dinners to elopements.

Maine Coast Cruising, located at 14 Ocean Street in South Portland, Maine, is a travel agency specializing in casual cruising and custom excursions in beautiful Casco Bay. The Maine Cruising Club offers the flexibility to enjoy multiple trips on the water throughout the season at a discounted rate. With a commitment to just 3 trips, members can experience the luxury and comfort of a vessel in Casco Bay without the expense and maintenance of owning a boat. Whether you're looking for a relaxing day on the water or a custom excursion, Maine Coast Cruising has you covered.

Nautilus Sailing Company is a premier travel agency located at 1 Marina Way in Portland, Maine, United States. Specializing in sailing adventures, our experienced team of experts can help you plan the perfect sailing excursion. Whether you're a seasoned sailor or a beginner looking to learn the ropes, Nautilus Sailing Company offers a range of services to meet your needs. From private charters to group sailing trips, we are dedicated to providing unforgettable experiences on the open water. Contact us today to start planning your next sailing adventure with Nautilus Sailing Company.

Welcome to the White Sails Inn, a charming bed and breakfast located at 61 Fletcher Street in Kennebunk, Maine. Formerly known as the Elizabeth Rose House, this historic inn has undergone exciting changes under the ownership of Susanne Lillis. The property now features a cozy coastal Maine vibe with newly painted interiors, updated décor, and added amenities such as the Shipwreck Pub, outdoor fire pit, and a refreshed patio area. Wake up to the aroma of freshly brewed coffee and enjoy a homemade 3-course breakfast before exploring the nearby Kennebunk Beach, Wells Beach, and Ogunquit Beach. The inn provides beach towels, chairs, umbrellas, and parking passes for your convenience. Conveniently located just 40 minutes from Portland and 1.5 hours from Boston, the White Sails Inn is the perfect retreat for couples, families, or small corporate groups.

Portland Schooner Co. is a premier travel agency located at the Maine State Pier in Portland, Maine. Specializing in sailing adventures, they offer unique and unforgettable experiences aboard their historic schooners. Whether you're looking for a romantic sunset cruise or a fun-filled day trip with family and friends, Portland Schooner Co. has something for everyone. Set sail with them and explore the stunning coastline of Maine while enjoying top-notch service and hospitality. Book your next sailing excursion with Portland Schooner Co. for a truly memorable and exciting adventure on the water.

The Maine State Visitor Information Center in Kittery, located on U.S. 1, is the perfect starting point for anyone looking to explore all that Maine has to offer. From iconic lighthouses to award-winning restaurants, Maine has unique experiences year-round for every traveler. Whether you're seeking a peaceful retreat or a fun-filled family adventure, the Maine Tourism Association can provide you with the information and resources needed to plan an unforgettable trip. Maine is a state of vast natural beauty, with 90 percent of its land covered in forests and a coastline that stretches as far as California. With diverse wildlife, rich history, and deep cultural roots, Maine offers something for every history buff, art enthusiast, and foodie. From exploring historical landmarks to indulging in local cuisine at lobster shacks and fine dining restaurants, Maine has it all.

The Maine State Visitor Information Center in Yarmouth, located at 1100 U.S. 1, is a hub for travelers looking to explore the beauty and wonders of Maine. From iconic lighthouses to award-winning restaurants in Portland, Maine offers unique experiences year-round. Whether you're seeking a peaceful retreat or a fun-filled family adventure, the Maine Tourism Association provides all the information and resources you need to plan an unforgettable trip. With 90 percent of the state covered in forest and a coastline that stretches for miles, there is no shortage of things to see and do in Maine. Explore the rich history, cultural attractions, and diverse wildlife that make Maine a truly special destination. Indulge in Maine cuisine, shop for unique souvenirs, and experience the outdoor adventures that the state has to offer. Whether you're interested in hiking, fishing, sailing, or dog-sledding, Maine has something for everyone. Plan your trip with the Maine Tourism Association and discover all that this beautiful state has to offer.

Maine Tourism Associates is a travel agency located at 97 Main Street in Fryeburg, Maine, United States. From the iconic lighthouses to the cobblestone streets of Portland, Maine offers unique year-round experiences for everyone. Whether you're interested in world-class art museums, famous lobster shacks, fine dining, ski lodges, or spotting moose in the wilderness, the Maine Tourism Association has the information and resources to help you plan an unforgettable trip. Maine is 90% forest with a coastline that could stretch to California, offering endless opportunities for exploration. In addition to moose, the state is home to black bears, bobcats, and loons, making it a wildlife enthusiast's paradise. With a rich history and deep cultural roots, Maine also has plenty to offer history buffs and art enthusiasts alike.

Maine Sailing Adventures offers unforgettable sailing experiences along the beautiful coast of Maine. Located at 56 Commercial Street in Portland, our experienced captains and crew are dedicated to providing guests with a safe and enjoyable journey on the water. Whether you're looking for a relaxing sunset cruise, a hands-on sailing lesson, or a multi-day sailing expedition, we have a variety of options to suit your needs. Come aboard and discover the magic of sailing in Maine with Maine Sailing Adventures.

Portland Harbor Fleet is a renowned institution located at Chandlers Wharf in Portland, Maine, United States. With a long history of providing exceptional maritime services, Portland Harbor Fleet offers a wide range of boating and sailing experiences for enthusiasts of all levels. From boat rentals and charters to sailing lessons and regattas, this institution is dedicated to promoting a love for the sea and fostering a strong sense of community among sailors and seafarers. With a prime location on the beautiful Portland Harbor, visitors can enjoy stunning views of the water while experiencing the thrill of being out on the open sea. Whether you're a seasoned sailor or a novice looking to learn the ropes, Portland Harbor Fleet has something for everyone.

Casco Bay Custom Charters, located at 14 Ocean Street in South Portland, Maine, invites you to embark on an unforgettable journey through the splendor of Casco Bay. Our customizable private boat charters and tours offer a unique perspective of Maine's coastal beauty. For over a decade, we have been providing personalized experiences that showcase the region's landscapes, lighthouses, and culinary delights. Our experienced crews are passionate about sharing their knowledge and love for Maine, ensuring that each voyage is not only enjoyable but truly memorable. Whether you are looking for an intimate cruise for up to 6 guests on a vintage lobster boat or a larger gathering of up to 16, we offer exclusive charters tailored to your preferences.

Reel Action Charters is a premier charter service located at 1 Portland Street Pier in South Portland, Maine. Our goal is to provide our customers with an unforgettable fishing experience, whether you're looking for that "once in a lifetime catch" or a leisurely cruise along the coast. Our courteous and knowledgeable crew, top-notch equipment, and attention to detail ensure that every trip with Reel Action is enjoyable and productive. Our captains have Master licenses issued by the United States Coast Guard and over 20 years of experience, guaranteeing your safety while on the water. We pride ourselves on using the best tackle available and encourage you to bring your "lucky" rod to land a trophy fish. With a focus on customer satisfaction, Reel Action Charters goes above and beyond to exceed your expectations and keep you coming back for more.

Located at 88 Grandview Avenue in Boothbay Harbor, Maine, Spruce Point Inn Resort & Spa is a Conde Nast Top Resort that offers the epitome of a Maine retreat. Nestled "down east" from Portland, this historic gem provides an iconic coastal experience with its oceanfront setting, mature woodlands, and thoughtful amenities. Whether you're looking for a romantic escape or a family getaway, Spruce Point Inn has inviting lodge rooms and cozy cottages designed for your comfort. Indulge in dining excellence at the on-site restaurant, where Northeastern culinary mastery and coastal elegance come together. Relax and rejuvenate at The Spa, nestled in refreshing pines, offering massages, facials, and luxurious body rituals. Boothbay Harbor summer colonies have been a popular destination since the 1870s, embodying timeless coastal charm and maritime allure. Guests can also enjoy sailing on a fully restored classic Friendship sloop, the only wooden sailing lobster boat on the Maine coast, exclusively available from the Spruce Point Inn Dock. Additionally, Spruce Point Inn hosts events such as the Windjammer Days SPI Cup, a day of R/C sailboat racing, and offers a picturesque setting for weddings and meetings.

CruiseMaine is a premier travel agency located at 424 Fore Street in Portland, Maine. Specializing in cruises along the beautiful coast of Maine, CruiseMaine offers a wide range of cruise options to explore the stunning landscapes and charming towns of the region. Whether you're looking for a relaxing coastal getaway or an adventurous sailing experience, CruiseMaine can help you plan the perfect cruise vacation. With expert guidance and personalized service, CruiseMaine is your go-to agency for unforgettable cruise adventures in Maine.