Cruising towards August!

The Schooner Olad and Cutter Owl are cruising right along towards a busy August! July was filled with great sailing weather, lots of family charters and lobster bakes, and a recent heat wave that had folks eager to get out and enjoy a cooling sail on Penobscot Bay.

We are excited about some upcoming events, starting with the Camden Classics Cup this weekend! Join us aboard the Owl on Friday, July 29th and Saturday, July 30th to view the starting line and finish of the Camden Classics Cup races! You also don’t want to miss the CCC participants cruising through Camden’s inner harbor in the Parade of Sails on Saturday, July 30th at 10:00 a.m. Best viewing for this event is along the docks at the Public Landing.

On August 10th we are hosting a Full Moon Sail aboard the Schooner Olad! Watch the sun set behind the Camden Hills and the moon rise over the bay. Only a few tickets are left for this sail, which will also mark the last day this summer that the Schooner Olad will be departing at 7 p.m. After August 10th we’ll be changing schedules to four trips a day on the Schooner Olad and Cutter Owl, with our sunset sails departing at 6 p.m.

Our first and only public lobster bake of the season is fast-approaching. Join us on August 17th for an afternoon sail out to Warren Island where our crew will prepare a traditional Maine lobster meal over an open fire with all the fixings. Enjoy all the trails and beaches that Warren Island State Park has to offer, then take in the views of the sunset on your cruise back to Camden Harbor! (Trip schedule: 2:30 p.m. – 8:30 p.m., $235 per person).

As August is starting to fill up, be sure to schedule your day sail or private charter in advance. You don’t want to miss out on August sailing in Penobscot Bay!  

Cutter Owl Sails Again!

The Cutter Owl has just started her sailing season! Come aboard to enjoy all the sights and sounds of sailing in Maine this summer aboard our classic wooden yacht. The Owl is what's known as a "6 pack" vessel, and although she is ideal for a beer shared aboard with friends, this term actually refers to the maximum number of passengers she can hold. Perfect for small groups of 6 and under, The Cutter Owl excels at providing the privacy, freedom, and memories so many of us are looking for with our loved ones. All the special charters we offer on The Schooner Olad can be achieved sailing The Cutter Owl, with a much smaller budget. We don't call her "The most Versatile" for nothing!

The Schooner Olad and Cutter Owl have their sailing crew back!


It's been an amazing spring in Camden, Maine so far. April is finally here, and with it we get to see the smiling faces of our crew back in action. Fit out is in full force, with varnish already complete and a deep hull clean under way. Joining Captain Aaron, Devon, Matt, and Jeff this year are Captain Wilson and Captain Korina. Captain Wilson grew up on the coast of Maine and has been sailing for over 15 years. He has worked on such esteemed boats as the Victory Chimes, Heron, and the When and If, to name a few. Captain Korina has over 15 years of sailing experience working aboard the Stephen Taber,  Shearwater, and St. Laurence II. She has sailed extensively from New York harbor to Kingston bay, Ontario and many places in between, but now calls Maine home. We can’t wait for our passengers on Schooner Olad and Cutter Owl to experience both captains' knowledge of traditional boats and wisdom of the sea this sailing season. Penobscot Bay looks primed for the best summer sailing Maine has to offer, there is still room for you to book your passage today. Let us help you make your outdoor wedding or custom charter something they will never forget!

The First Days of Spring

As the first +40 degree days start to happen, we can’t wait to get back to sailing. Our day dreams turn from family ski trips, hot cocoa, and the Holidays to thoughts of long summer afternoons, playing in the sun, and a pleasant breeze filling the sails. We pack our sweaters away and bring out the sun hats and flip flops.

For the crew of Olad and Owl, it’s time to start spring maintenance and ready our boats for the hundreds of hours of sailing the season will bring. This job, like the great state of Maine, has its seasons. Everyone has their favorite, but for me, the variety that working on these boats offers each and every day is why I enjoy it so much. So thank you for making that possible by coming and enjoying aboard The Schooner Olad and Cutter Owl.

Already, people are planning their adventures with us. Full day charters sailing the Fox Island Through-fare, Destination Weddings with Lobster backs on Warren Island, Sunset that cameras just can’t capture. Experiencing all Penobscot Bay has to offer in a way few people ever get to. Making each trip a unique experience is why we love doing what we do. The schedule is filling up fast, especially with our new special event sails for The Great Schooner Race, The Camden Classic Cup, and Windjammer Weekend freshly up and available. So don’t let mud season get your down, or in our case, varnish season. Here’s to the possibilities of the year to come!

Give the Gift of Sailing

It's that wonderful time of the year ❄️  

Are you searching for the perfect gift for the sailing enthusiast in your life?  Well, search no further, we have the perfect gift for them!  Give the gift of a two hour sail or private charter on one of our beautiful wooden vessels this holiday season.  Your loved ones will be so happy you did.  Now, more than ever, something special to look forward to is it’s own gift. They’ll be dreaming of sailing all winter long.

We are available for the purchase Of Olad and Owl gift certificates for sailing by calling 207-236-2323, or our online store at  Our gift certificates never expire, and are good for up to 2 hours of sailing throughout our season.  You will also find a great selection of t-shirts, hats, sail maker bags, and other sailing oriented gifts on the Olad online store.  Orders typically ship next day, so you'll have your items well in hand before Christmas.  

We hope you enjoy a wonderful holiday season with family and loved ones.


Putting the Boats to Bed

Wrapping up the boats for winter is especially nice when you have a roof over your head. We’re lucky enough to be warm and dry as we put the Olad and Owl to bed for our off season.

Thank you all so much for helping make our 2021 sailing season such a success!  We’ve once again weathered these most difficult times with the help and support of the great community in which we live.  Our local community’s compassion and attention to keeping it’s local people safe and healthy was certainly acknowledged by the many folks coming to our area from away.  We were very lucky to be able to take many of our visitors and locals alike for a sail departing from beautiful Camden Harbor.

As we continue our in depth maintenance schedule on the boats, we’re also looking forward to some fun trips scheduled for our winter months. Lots of skiing is a surety and there may be a sail or two in warmer parts of the world to look forward to as well.  In the meantime, if you have a trip to Maine your planning for next season, a wedding or family event, please feel free to reach out to us to help you make it a fantastic sailing experience.  We are currently booking for our 2022 sailing season, and if this past year was any indicator, booking early is the best way to assure you get the day and time you’re considering for your event.  We’re always happy to talk about sailing, so please give us a call with any questions, etc. May 2022 couldn’t come soon enough.

Dreaming of sailing in Penobscot Bay! 

Fall breezes and foliage viewing on Penobscot Bay

One more month of sailing in our season remaining, and it's sure to be some of the best!

Fall in Maine is beautiful and breezy, lending to some picturesque scenery and some of the best sailing conditions of our season.  It may be a little cooler on the water, but bring a hot beverage, your woolie sweater, and your camera to capture the beautiful foliage.  We'll keep you entertained with our stories of the sea and the scenic views...and sailing, of course! 

The Cutter Owl is concluding her season of sailing this week, with just a few more days left to get out and enjoy a more private experience with our captain. Schooner Olad will end it's season closer to mid October with 3 available sailing excursions a day starting Friday October 1st.   Private charters as always will be available aboard Schooner Olad through the remainder of our sailing season.  Fall is a great time of year for a company event or a get together with a group of friends and family on the Schooner Olad. The bay is so pretty with the change of season, and the warm mulled cider you bring along with keep your fingers and belly warm while you get some great sailing in with us.  The perfect fall Maine experience.

The crowds are lighter this time of year, the kids are back in school, and the sailing is looking to be fantastic.  We hope you'll join us! 

We look forward to sailing with you out on Penobscot Bay!

Beautiful Fall Sailing Ahead

Question of the week: When will your last day of sailing be? 

We have just a little over a month of sailing left in our 2021 season!  Cutter Owl will be sailing through the end of September, and Schooner Olad's last day is scheduled for October 18th. 

We are looking forward to sailing some really fantastic conditions and fair winds through the rest of our season.  Fall breezes are some of the sailing season’s best out in Penobscot Bay, and the leaves are just starting to make their change to fall’s full splendor.  Wear your woolies and come out to see the beautiful views with our crew.  Our last special event of the season on Schooner Olad will be the full moon sail scheduled for September 19th at 5:15pm.  Come out to view the Harvest Moon rise with us.

We would like to send our gratitude out to everyone who has come sailing with us this season and in seasons past.  We are so fortunate to have such wonderful guests and to live in such a beautiful place for people to visit from near and far.  Thank you all for making it truly great.

We look forward to sailing with you through the rest of our 2021 season and beyond in beautiful Camden Harbor and Penobscot Bay. 

We’ll see you out there!

Hello Fall Sailing!

The sailing is truly fantastic in Penobscot Bay, and there's plenty of room to stretch out and enjoy the sea breeze aboard both Schooner Olad and Cutter Owl!

The end of August is upon us, and the warm weather continues to prevail for us sailing in Penobscot Bay.  There are lots of sailboats in the area to see, especially with Labor Day weekend just around the corner.  Enjoy a festive weekend in Camden and join us for a great sail out on the water to celebrate the end of summer and the beginning of our fall sailing season.  We’ll be offering many opportunities throughout the day to get out on the water with us aboard both the Olad and Owl throughout the month of September.  

Our sunset sails aboard both the Schooner Olad and the Cutter Owl will begin a little earlier in the evening to accommodate the sun setting sooner in our skies these days. Fall is right around the corner, so bring along your sweater, snacks and a bevie and prepare to watch a beautiful sunset with great friends. If a private sail is your thing, you are most welcome to charter our vessels out privately to enjoy a sail with close family and friends with just our crew to guide you.  It’ll be sure to be a lasting memory for all.

Happy almost fall sailing!

August Sailing in Maine

Enjoying this Weather!

There’s no hiding it, the weather has turned around this August in Camden, Maine and it has been beautiful! August has had some of the best weather this year and fingers crossed it continues into September. The sunshine and great breezes have made for excellent sailing during the day, and there’s been stunning sunsets in the evening. This is the best time of year to be on Penobscot Bay and the wildlife agrees. Guests have been seeing porpoise and seals daily! 


We will start to enjoy having both boats sailing at the same time in the evenings beginning tomorrow. They’re each doing 4 trips daily, including private charters and our 2-hour public sails. There are more people than ever wanting to get out on the water and Camden is a bustling downtown, so we recommend booking in advance to make sure your spot is saved. Come early to town and grab a snack and beverage from one of the local delis to bring along with you. There are all day lots to park in around town, just follow the blue P signs. Plan ahead to give yourself time. Camden is a great little town to check out while you’re in the area, and the harbor is the icing on the cake.


We hope to see you out sailing with us on the beautiful waters of Penobscot Bay!