American Eagle, located in Rockland, offers various cruises of Penobscot Bay, including trips of 3, 4, 6, 10 & 14 days. The 92' Schooner American Eagle is a sailing vessel rich with history. This fishing schooner was built in Gloucester, Massachusetts in 1930 and initially launched as "Andrew & Rosalie". She took her first sail on June 26, 1930. On May 5, 1941, Andrew & Rosalie was renamed as the American Eagle by Capt. Ben Pine. In August 1983, after 53 years as a working member of the famed Gloucester fishing fleet, the American Eagle went on her last fishing trip and a month later arrived at Rockland, ME for rebuilding. On April 1986, the American Eagle was re-launched after she was completely rebuilt and restored and in the same year went sailing on the coast of Maine and other destinations. The American Eagle today is designated as a National Historic Landmark.

The Angelique, operating out of Camden Harbor, offers 3, 4, & 6 day cruises of Penobscot Bay. The 95' ketch-rigged Angelique was built in 1980 specifically for the Windjammer trade, mixing the elements of 19th century English Channel and North Sea Windjammers as well as the highest standards of marine safety for the 21st century. Patterned after the 19th century sailing ships that fished off the coast of England, the Angelique was built for safety and sea-worthiness, and offers many features typical of a modern day sailing yacht. When the Angelique was built, the shipwrights placed special emphasis on the comfort of passengers as part of the ship's design, making the Angelique one of the most comfortable and engaging sailing ships in the entire Windjammer fleet.

The Grace Bailey, operating out of Camden Harbor, offers weekend and 5 day cruises of Penobscot Bay. Built in Patchogue, New York in 1882, the Grace Bailey was engaged in the West Indian trade, and hauling timber and granite until 1940, when she started carrying passengers. Grace Bailey is a majestic windjammer. This 81' coaster was the flagship for the original Maine Windjammer Cruise fleet. She was restored in 1990. She measures 81 feet on deck and can easily accommodate 29 passengers. The Grace Bailey is listed as a National Landmark and holds a lot of history in her sails. Even though the Grace Bailey has been through restoration, her structure and history have been well-preserved while still providing maximum comfort for her passengers. This is very important as the Grace Bailey is a real, 19th century sailing ship – the very same ship that traveled the waters during the Fruit Trade and helped construct the Grand Central Station by carrying granite to New York City. Stepping onto the Grace Bailey instantly gives one the feeling of nostalgia, and a view of the main cabin with paneling carved by hand and a piano give guests a sense of the sailing history this ship has been in. The Grace Bailey effortlessly combines sailing nostalgia and luxury in a single vessel.

The 95' Heritage, operating out of Rockland Harbor, offers 3, 4, 5 & 6 day cruises of Penobscot Bay. The Heritage was built in 1983 by her owners, Captains Doug and Linda Lee, at the North End Shipyard in Rockland, Maine. Designed for the comfort of her passengers, the vessel was built in the tradition of a 19th century coasting schooner. The Heritage was launched on April 16, 1983 in front of a crowd of thousands of people, including news crews from TV networks and other national media. In the four years it took to construct the Heritage, construction was aimed primarily in providing the utmost comfort for the passengers, making the sailing experience truly a memorable one. Unlike most schooners, passengers can easily enter their cabins, enjoy a spacious place for meals, and not have a hard time going up and down because of stairs.

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The 65' Isaac H. Evans, operating out of Rockland Harbor, offers 1, 3, 4 & 6 day cruises of Penobscot Bay. The Isaac H. Evans was built in Mauricetown, New Jersey by George Vannamanin in 1886 and spent many years oystering on the Delaware Bay. In 1973 she was completely rebuilt for the Windjammer trade. The ship is a well-loved and well-cared for sailing vessel. The Isaac H Evans can easily and comfortably accommodate 22 guests, and measures 65’ on deck, has an overall length of 99’, and also has a beam that measures 19’. Today the vessel is designated as a National Historic Landmark.

The 90' J & E Riggin, operating out of Rockland Harbor, offers 3, 4, 5 & 6 day cruises of Penobscot Bay. The J. & E. Riggin is a beautiful old schooner that has been rebuilt to comfortably hold 24 passengers plus 6 crew. This schooner was named after the sons of Charles Riggin, namely Jacob and Edward, and was built in Dorchester back in 1927. The J. & E. Riggin was designated as a National Historic Monument in 1991 and is truly a monument that displays a rich history and sailing tradition. With GPS, a radio, and radar, the J. & E. Riggin is fully Coast Guard compliant and is certified to carry passengers. The schooner is also compliant in terms of safety, construction, stability, and water-tight integrity. Passengers and her crew are assured of arriving safely at their destination every time.

The Lewis R. French, operating out of Camden Harbor, offers 3, 4 & 6 day cruises of Penobscot Bay. The Schooner Lewis R. French was launched in April 1871 in Christmas Cove, Maine. The Lewis R. French is the oldest commercial schooner in the United States, and was recently designated a National Historic Landmark. This sailing vessel was built by the French brothers, who named the ship for their father. The Lewis R. French was a sailing vessel primarily used to transport freight and cargo until 1971. Three years later, the Lewis R. French was rebuilt but this time with the Windjammer passenger trade in mind. The rebuilding process used many quantities of timber, pine, fir, and oak. Today, the Lewis R. French still sails but with passengers in tow. She has two topsails and four lower sails which are all raised and trimmed by hand, and makes use of a yawlboat when there is not enough wind. She has also won the Great Schooner Race multiple times, and has taken part in many Tall Ship gatherings. The Lewis R. French undergoes an annual inspection from the US Coast Guard and makes use of GPS and radar. The 2010 season marks the schooner's 139th summer in Maine.

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The Mary Day, operating out of Camden Harbor, offers 3, 4 & 6 day cruises of Penobscot Bay. Launched in 1962, the 90' Mary Day was the first windjammer to be built specifically with comfort, safety, and performance in mind for the windjamming trade. Carrying on the Maine shipbuilding tradition, she is the first pure sailing schooner built in Maine since 1930. When she was launched in 1962, the Mary Day placed very high regard in the comfort and safety of passengers for cruising the Maine coast. Passengers will certainly find the Mary Day very comfortable, as she has plenty of comfortable seating areas and beautifully appointed cabins. Passengers will certainly find sailing in the Mary Day comfortable and relaxing at the same time. Speed was also one of the major factors that was considered in the construction of the Mary Day. She regularly participates in the yearly Great Schooner Race. The boat can comfortably hold 28 passengers and can tour shallow waters where other boats cannot. This windjammer is also certified and inspected by the US Coast Guard as well as the State of Maine, and is under the careful supervision of captains that have extensive sailing experience.

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The Mercantile, operating out of Camden Harbor, offers 3 and 4 day cruises of Penobscot Bay. The 80' Mercantile is often called the “Prettiest coaster on the Bay.” The Mercantile was built in 1916 in Little Deer Isle, Maine to carry salt fish, barrel staves, and firewood. The Mercantile became a cruise schooner in 1942 under the ownership of Frank Swift, the founder of the Maine Windjammer trade. The Mercantile underwent major restoration in 1989. When she was initially built, the Mercantile was intended to reach shallow areas which other vessels could not access. Even though the Mercantile was restored, the ship has still maintained her charm and character. The Mercantile comes with a big main cabin as well as a spacious dining area. She also has a private single cabin as well as 14 double cabins, ideal for those traveling with a special someone or even kids. These cabins are also very spacious and have either double or twin beds. What’s even better is that just because you’re out at sea doesn’t mean you’ll be deprived of certain amenities. The Mercantile offers fresh showers with hot water – the perfect complement to the crisp sea air.

The Mistress, located in Camden, offers various cruises of Penobscot Bay, including trips of 3, 4, & 5 days.The Mistress was built in 1960 on Deer Isle in Maine and uniquely blends the characteristics of a schooner and a private yacht in one. Although the Mistress may be fashioned after an old schooner, she comes with modern amenities that passengers will certainly find very useful. The Mistress was built with a loyalty to traditional lines and materials coupled with an attention to modern amenities. Forty-six feet long, with just three double cabins (each with private head), she offers an intimate sailing experience. The Mistress underwent restoration in 1992 but retained most of the unique qualities of the original boat. She can easily accommodate 6 passengers, and is the perfect solution for people who are in search of a true windjamming experience but also want to keep a level of privacy. Passengers who board the Mistress will find three private, double cabins complete with its own sink and companionway from the deck – it’s almost like having your own private yacht. Similar to other windjammers, delicious meals are served on the Mistress as well. Plus, the captain and the mate-cook are also there to help the passengers enjoy the trip and relax at the same time.

The 82' Nathaniel Bowditch, operating out of Rockland Harbor, offers 2, 4, 5 & 6 day cruises of Penobscot Bay. The Nathaniel Bowditch was designed by William Hand and was intended to be a private racing yacht. She was built in 1922 in East Boothbay, Maine and was initially named Ladona. A year after she was built, she was entered in the Bermuda Cup and won the race in 1927. She was later renamed the Jane Dore by her second owner and was even commissioned by the US Coast Guard to look for German submarines during World War II. In 1971, the Jane Dore was acquired by the American Practical Navigators Inc. The Jane Dore was rebuilt with the intention of making the schooner a passenger vessel for the Windjammer trade. The vessel was also renamed the "Nathaniel Bowditch" at that time, after the brilliant mathematician and author of The New American Practical Navigator.

The 68' Stephen Taber, operating out of Rockland Harbor, offers 3, 4 & 6 day cruises of Penobscot Bay. The Stephen Taber was built as a coasting schooner in 1871 on Long Island, New York. The 68' schooner is the oldest documented sailing vessel in continuous service in the United States, and she was recently designated as a National Historic Landmark. There are a lot of reasons why the Stephen Taber is very popular and is considered an easy favorite of tourists. People who have been aboard this sailing vessel often end up repeating the experience and referring others. The Stephen Taber provides passengers with the utmost comfort during sailing. With plenty of space to eat good food and relax, plus a library aft, and a large salon, this sailing vessel is certainly spacious. What’s even better is that if you choose to sail on the Stephen Taber, parking space is provided since the ship sails from its own wharf in Rockland. The Stephen Taber also provides its guests with the option to either enjoy quiet time at sea or join one of the many group activities available on-board. How you spend your time at sea aboard the Stephen Taber is truly your choice.

The Summertime, operating out of Rockland Harbor, offers 3 & 6 day cruises of Penobscot Bay. The Summertime is a schooner known for its ability to battle storms and its pink sterned hull, thus earning the name 'Pinky". She was launched in 1986 and used the traditional methods of construction. She was built by George Allen and Bill Brown, including many volunteers. The Summertime used various seasoned wood for different parts, like white pine for the Summertime’s deck, hackmatack was used for top timbers as well as deck beams, and other types of seasoned wood. She was built right in Maine and is under the care and guidance of its captain and owner Bill Brown. Capt. Bill Brown is a US Coast Guard licensed captain, not to mention that he is also a licensed Emergency Medical Technician. He has decades of experience in sailing other schooners as well as teaching. A trip aboard the Summertime will certainly fill passengers with the experience of sailing in a traditional schooner yet complete with modern amenities that makes the trip all the more fun and memorable.

The Timberwind sails from Rockport Harbor offering 3. 4. or 6 day sailing adventures along the sheltered waters and Islands of Penobscot Bay. The Timberwind was built in 1931 on Union Wharf in Portland, Maine. She was built to the highest standards to insure the comfort and safety of the men who sailed her. The schooner was built in Maine for Maine duty, and since her launching in 1931, she has never left Maine waters. Built to carry pilots to and from ships entering or leaving Portland harbor, she was constructed ruggedly using sturdy white oak frames and planks for seaworthiness through years of storms and icy Maine winters. As launched, she was bald-headed, had no bowsprit, and had her main cabin located aft with a large hold amidships. Timberwind's original name was the "Portland Pilot" and she served as the pilot boat for the harbor of Portland from 1931-1969. For thirty-eight years, twenty-four hours a day and in all weather conditions, Portland Pilot was on call. She was finally replaced with a steel power boat in 1969, but to this day she is fondly remembered by the men who worked on her out of Portland. They enjoy coming to Rockport to see her, and although they may chuckle at her fancier paint job and taller rig, they see that she is the same vessel underneath and are pleased to see how well she's cared for.

The Victory Chimes sails from Rockland Harbor offering 4 or 6 day cruises along the sheltered waters and Islands of Penobscot Bay. Built in 1900 in Bethel, Delaware to carry lumber up and down the shallow bays and rivers of the Chesapeake, the 132' schooner Victory Chimes is the last three masted schooner on the East coast, and the largest passenger sailing vessel under U.S. flag. A trip aboard the Victory Chimes is more than enough for any passenger to sit back, relax, and forget about the worries they left at home. Enjoy the peace and tranquil environment that will simply lure you to sit down and enjoy a good book or just sit back and enjoy what life on a tall sailing ship has to offer. The Victory Chimes offers plenty of activities for passengers to take part in. Choose from basking in the sun on deck, chatting with other passengers, swimming in the ocean, or help the crew in maneuvering the sails yourself. When the sun sets, passengers and crew gather on deck to share a toast for the successful day. Guests are welcome to bring their own food and drink, but of course, to make sure that everyone enjoys the trip, excessive alcohol intake is not allowed. Whether you are traveling alone, with a special someone, or with your family, the Victory Chimes has different cabins to suit different needs. So sit back, relax, and let the Victory Chimes take you on a memorable Maine Windjammer adventure.