Qualified sailors may bare-boat charter our pristine, 30-foot O'Day mono-hull in an adventurous exploration of Penobscot Bay. Explore coastal towns, renowned parks & sanctuaries, remote islands ~ from a perspective few are ever able to experience!
As our friends & fellow sailors say, O'Happy Day may be the finest O'Day 30 in existence! Lovingly refurbished before our purchase, we maintain the highest standards of safety, cleanliness, and comfort for your (and our) sailing pleasure & adventure!
With O'HD in your capable hands, all that she offers is yours to enjoy. Cap'n Scotty's complete boat briefing includes all systems & equipment, while FM Kadee's tour highlights all supplies & amenities. Read our complete description to learn more, and contact us with any questions during your booking inquiry.
Interaction with Guests
We interact most during the booking inquiry, qualification process, and pre-sail planning, to best meet the expectations and needs of both owners and charterers. This may include itinerary planning (as needed) and other travel suggestions for before/after your sailing adventure. Following your welcome, boat briefing, and departure, you'll determine how much we communicate during your adventure. We're always just a cell call away, and will meet you at the dock for your return.
Penobscot Bay will be your "neighborhood" ... We suggest that you explore the possibilities in advance, online or by purchasing this wonderful resource (available aboard O'HD for your use): search for
"A Cruising Guide to the Maine Coast"
Depending upon the size of your crew, we'll offer our classic Puffin fiberglass dinghy (2-3 person), or our inflatable (3-6 person), to tow behind O'HD and allow shore & dinghy-dock access at your destinations.
Other Things to Note
Many details are available throughout our listing. Be sure to read every section!
We ask that you respect and upkeep our beautiful boat as we would ... and that you obey all Maine state laws and US Coast Guard regulations during your sailing adventure.
Really amazing trip! We had a blast with our two littles aboard. We covered a lot of Pen Bay and Blue Hill Bay and soaked in a great cruising experience. Like our previous sailing trip on OHD, the boat worked great and was wonderfully stocked with all necessary items. Our kids are hooked on sailing at ages 2 & 5 and we are so thankful to be able to provide this opportunity to them with the use of Scott & Kadee's boat. It's a gem!
Once, again, we SO appreciate the Morse family's skilled & respectful use of our li'l sailing vessel, O'Happy Day ... and we're thrilled to know that their girls are "hooked on sailing!" Way to start 'em early! We'll welcome Ehren, Lisa, and family, anytime, and highly recommend them as guests for other airbnb hosts. Beaucoup de bons voyages!
What an amazing experience! I have to admit that we didn’t set out to go on a sailing adventure, but just found this listing when exploring various coastal places to stay in Maine. Once I found it, though, I knew it would be the highlight of our trip. After chatting with Kadee about what we were looking for (touring some places from a beloved children’s book), she didn’t laugh and seemed to think it was a great idea. She and Captain Scotty planned our 3 day/2 night trip to hit up as many of the sights mentioned in the book as we could, as well as giving us time to go tidepooling, explore small islands, check out harbors big and small, and enjoy sailing. Kadee is a superb hostess and went above and beyond what we expected to prepare meals and attempt to satisfy a picky eater. She and Scotty were both great with our kids (ages 6y and 3y) and dealt with moodiness and one bad tantrum with kindness and compassion. Since this is such a tiny space, it requires flexible people who are easy to get along with, and I doubt many people would be more suitable than Kadee and Scotty. I hope they are able to continue to pursue this adventure in retirement, and I would definitely travel with them again (and if the kids were a little older, and my concentration a little better, I would love to learn more about sailing from them too)!
We had a fantastic experience on the O'Happy Day sailboat in Penobscot bay. The boat was beautiful, everything was clean and in perfect working order, and Karen and Scott made a terrific effort to make sure that we were comfortable and everything was ready for our trip. It really far exceeded our expectations.
Hosts were wonderful and received a very thorough briefing on the boats systems. Don't relie on the autopilot but all other systems worked well. Cruising grounds, Penobscot bay, has much more delightful areas to explore than you could visit in one entire season. Will seriously consider chartering with them again.
Three very O Happy Days out in the Penobscot with Captain Scotty and Kaddee were the highlight of our 4200 mile July odyssey. Our sons, Slapnuts and Grinder, so renamed by our skipper, stepped off the boat taller and with an experience they will never forget.
My wife and I could not have imagined a nicer, more considerate, outgoing, and supremely competent couple as our hosts. Within minutes we knew that our family was safe in their capable hands and that we were among friends.
We were all novices and Scott took it upon himself to make us sailors. He was a relaxed and patient teacher, especially with our boys, ages eight and five. What should I have expected? He flies giant airplanes filled with kerosene and is one squared away character, but not in the Sergeant from FULL METAL JACKET kind of way. He's a raconteur, historical tour guide, first class bartender, and grills a hell of a steak.
His greatest accomplishment was landing a wife like Kadee. You know what I'm talking about. Everybody loves being around a couple like them.
We had big wind, big seas, and big fun. They took us to seal habitats, pristine islands we had all to ourselves, charming harbors, and to gawk at the homes of people with much bigger boats.
Scott and Kaddee, you showed us all an adventure we'll never forget and your kindness towards our boys warmed our hearts. See you again!
Happy O'Day is a fantastic boat. Kadee and Scott have a very well maintained and outfitted boat. They also were extremely accommodating with our schedule and helped put together a detailed itinerary for us. If you want to the see the maine islands away from the crowds, I highly recommend sailing with them.
Karen and Scott were WONDERFUL!
These two went above and beyond in every way to make our sailing trip a success. My wife and I and our two kiddos (3 & 7months) and my folks were aboard during the day. The O'day was a wonderful cruising boat. It accomodated all quite well. The v-berth and large starboard setee were great for napping the kids and the onboard DVD was a great bonus! The boat was uber provisioned with necessary gear.. Karen & Scott also arranged the use of an inflatable dinghy to accomodate the large group. We can't thank you enough! This made transport very easy! Weather was outstanding and everything fell into place. We had a great trip...wish we had been out longer. Certainly will do this again in the future. Sailing Penob Bay was a treat!
My hubby and I crave & enjoy traveling, sailing, fine dining, films, music & "live" entertainment. Both originally from Maine, we've lived from NYC to TX to CO and back to coastal Maine, exploring wonderful destinations around our nation and the globe. We raised a fantastic son and daughter to adulthood and now enjoy the flexibility of our "empty nest" lifestyle ... living seasonally between our Maine lake-front cottage and our catamaran in the FL Keys. We look forward to sharing our spaces & places of respite with you!