Herb steers and Doris does the heavy lifting. The couple built the Eastwind themselves, giving you the feeling that they really care for her. Great dynamic, watching this long time married couple who have circumnavigated the globe multiple times. Doris is very knowledgable about the area which makes for a sail with great area historical information. My wife and I... More

Elaine & I, visiting from England, booked the 10am trip for the morning after arriving in Boothbay Harbour. Next morning was a little breezy & cool, and we were the only people who actually turned up! Captain Sean allowed me to help put in a reef & raise the sails and we set off. We were delighted that the boat... More

We enjoyed out first sailing trip around the harbor but even more meeting Herb and Doris Smith. The made the sailing trip extra special by sharing their adventures of life and sailing around the world!

Smooth sailing on a sunny afternoon. Competent captain and crew regaled us with seafaring stories and information about the area. Sailed near the inn where we were staying. Loved the view of the property from the boat. An enjoyable way to spend a sunny afternoon in mid-coast Maine.

The 65 ft schooner Eastwind is a wood boat (cedar) and sails beautifully. The two hour harbor sail (which is actually done nearly entirely under sail rather than motor) is delightful. Bring a snack and a jacket and make sure all your gear is in a bag (no loose fill) so nothing slips overboard when the boat tacks. The big... More

This 2 hour trio around the bay was excellent. You can take food and drinks with you(yes wine and beer) for a very relaxing trip with lots of scenery and stories from the captain. Very interesting history about the schooner and if you want to help steer, raise the sails or honk the horn, they will let you participate. Well... More

The fact that the Smiths built this Schooner and sailed the world with their kids is reason enough to trust them with your time and money. Doris did all of the "work" - both as tour guide (pointing out light houses, homes, osprey nests , islands, etc) as well as moving the hugh sails around (don't know what the term... More

Went on the early afternoon sail, this is generally the best time as the temperature has warmed and is not declining on the return. Weather was fabulous and the crew was great. Bring cash though, the credit card machine was down due to rain the night before.

We went out today and the weather was beautiful. The staff were great! They knew a great deal of the bay's history and pointed out landmarks for everyone. They took great care of a special needs couple onboard and were genuinely nice people. The ship was in perfect condition and beautiful. This outfit lets customers bring their own food and... More