We are quitting our jobs, saying goodbye to our friends and families, homeschooling our 3rd grader and heading South in the midst of hurricane season in 2.5 weeks.

And people thought we were out of our minds for wanting to winter in Maine on a boat!

What started as a joke, quickly turned into a viable plan to drastically change our lives – again. We decided that the money we would spend to get our boat ready for a Maine winter would be better spent using our boat as its meant to be used.

With little to no knowledge of the Southern coast, we had no exact destination in mind. We researched a few marinas on the coast, and ultimately decided to join some fellow Mainers in Beaufort, SC.

Leah and John have spent multiple winters aboard their Nor’West 33 ‘Brio‘ in Maine. Last year they added a tiny member, Zephyr, to the crew, and decided they were done with Maine winters aboard. I reached out to Leah to ask where they had landed for the winter.

After researching the marina where they had wintered last year, and making sure they had space for us this year, we had our Southern destination set. Lady’s Island Marina in Beaufort, SC will be our winter home.

We are leaving Sunday Sept 29th and plan to take about a month to make our way down the coast to South Carolina. We have the first 1/2 of the trip roughly planned out, with stops at Block Island and New York City as we attempt to make it to the Annapolis Boat Show by October 10th.

After the boat show, and a side trip (by car/train/bus) to DC, we plan to take it easy through the Intracoastal Waterway (ICW) watching the weather like a hawk to steer clear of any scary hurricanes that might be headed our way.

We will be having a send-off party of sorts on Saturday Sept. 28th. Not a formal affair – but if you are in Portland (or want to make the trip) we will be at our marina (Fore Points Marina) all day – working on last minute projects and giving tours of our home, and saying “see you later” to friends and family. Please stop by if you can!

Also – we created t-shirt and sweatshirts on customink.com if you want to get in on the first run of Jelanea Crew shirts. BUT YOU ONLY HAVE UNTIL FRIDAY to order them! We have to close the order on Friday so we can get them before we go. You can have them shipped to us for free if you plan to stop by the send-off party to pick them up (or if we will see you on our trip South we can bring them to you).

Get them here: https://www.customink.com/g/bbp0-00bz-51c6

This past weekend was blisteringly hot, 95 degrees and humid both days. We were dripping sweat the minute we stepped outside in the morning. The kids were miserable, Tristan really wanted to turn on the air conditioning.

*Note – while we do have an AC unit on board, we have never operated it. We suspect it will draw a LOT of power. Plus, we have never lived anywhere with AC before, and really don’t feel we need to use it. We live on the water, typically a nice sea-breeze is all you need to cool down.

We invited my sister and her family to come aboard for a sail to escape the heat of the land. They were happy to accept.

So we set off with 4 adults and 5 kids, outnumbered for the first time. The older kids (8, 8, and 6) are all pretty self sufficient, so it was only the younger ones (1 and 2) that needed constant supervision though.

There wasn’t much wind, but there was enough to push us along at a nice 3-4 knots. A beautiful, quiet, cooling sail down the bay. Despite the cooling effect of the sea-breeze, the kids still wanted to go swimming. Tristan would swim all day long if we let him, even though he gets cold easily and Maine waters are not known for their warmth.

We sailed on a beam reach down the bay all the way to Little Chebeague island, where we decided to try anchoring again. As we would be anchoring for just the afternoon this time we felt more comfortable trying it out.

After a few tries, the windlass finally grabbed the chain and let it down. We dropped the anchor in 30ft of water, but by the time we drifted back we were in 50ft. Since we are still learning our systems, we don’t know how much chain we let out, as it isn’t marked, but we did catch.

Using both the lobster pot in front of us, and the rocky ledge behind us, we made sure we weren’t dragging. Once the anchor was secure, I put the boom out to the side and attached the swing, as Tristan has been wanting to swing over the water (and so have I) since we moved aboard.

Ben jumped in first to check the current, and then Tristan not long after him. While I did spend some time in the swing the water was a bit frigid for my blood.

We sat and enjoyed the beautiful day for a couple hours, before heading toward home. We almost made it all the way home on one tack. There was a lot of wind when we got back by the marina, so we took the sails down and motored the last little bit, rather than tacking back and forth to get there.

Docking was a bit scary, as there were other boats around this time, but I did manage not to hit anything, with some friendly help from a group of people on the dock.

We did it, we bit the bullet and spent our first night away from the dock.

We had a beautiful 4.5 hour sail to a mooring we knew we could pick up for the night in Cundy’s Harbor, ME. Friends of our own the mooring and had told us we could use it for the night.

If was our first ‘off-shore’ sail, where we were in the open Atlantic Ocean, there was nothing between us and the Azores Island besides the Atlantic Ocean. The winds were 10-15 knots out of the East, which put us on a nice beam reach most of the way North-West.

There were quite a few swells in the open ocean, and two of our crew got sea sick! 🙁 Prior to this no one had had any problem with sea sickness, but the swells were too much for the male members of our crew. Being in the cockpit and able to see the horizon helped both of them and they tried to stay on deck after getting sick.

Trixie spent a good portion of the trip in her bunk, and she slept for a good portion of it as well. Often we leave the aft door to her cabin open to allow better air-flow, and this also allows for a quick peak in at her when she is snoozing. We spent most of the sail on a starboard tack, so her full lee cloth came in handy.

We arrived and picked up the mooring, and after Ben pulled off the algae and growth on the line, attached it to our bow. Just as we grabbed the line the skies opened up and we finished tidying up the boat during the following 10 minute rain shower.

After cleaning up the boat, dropping the mainsail and launching the dinghy we went ashore to say hi to our friends. The kids were eager to get in the water, and both of them got in. We did put Trixie in a full wet-suit, despite the fact that the water was 68 degrees, she was still turning purple after about 2 minutes in the water. Our children lack thermo-regulation skills, like their Mom.

After visiting with our friends we invited them aboard to see our boat. Just as we arrived at the boat, all of 50ft from the dock, the skies opened up again. Ben and I rushed about closing up the hatches and putting the full enclosure down on the cockpit while our kids gave the penny tour down below.

Our friends headed back to shore before the next squall hit, and we started the process of making dinner. Noodles with oil and garlic – a quintessential boat meal from my youth.

A few more squalls hit while we were eating dinner, and then the calm after the storm produced one of the most gorgeous sunsets we have ever seen. Each time we looked up it got prettier than it had been 10 seconds before. Ben and I braved the mosquito ridden deck a few times to capture it on camera. Our full enclosure did a decent job of keeping us mosquito free.

We had a windy night, and we swung on the mooring around and around. I woke up at 2am and the Captain in me needed to go on deck to make sure we were still secure on the mooring and in the cove. Everything was as it should be, and I was able to return to bed and sleep easy the rest of the night.

The next morning, after a breakfast of French Toast, we went ashore to visit our friends again. Trixie had been asking all morning if we could ‘go see Peppa’, Pepper being one of the dogs belonging to our friends.

Of course, as soon as we found Pepper, she shied away as Pepper tried to lick her face, but she soon found a wealth of toys to play with. After visiting with our friend for a bit, it was time to head home.

We said our goodbyes, dropped the mooring, and headed back toward home. There was very little wind, coming from directly behind us, so we sailed wing and wing, main and mizzen only, for a little while.

Our friends hiked out to a point on the land and we waved to them as we passed and they took some pictures of us sailing by. Soon after they faded out of view we lost most of our wind.

We sail/drifted down-wind, avoiding the famous Maine ledges that abound in this area and keeping a close eye on the charts and chart-plotter for ledges we didn’t know about. Once we finally made it out past all the ledges and islands the wind picked up again, but it was coming from the exact direction we wanted to go.

We had a great time tacking out in to the Atlantic, and then back toward shore a few times with 15 knots of wind pushing us along. With no large swells none of the crew got sea-sick on the sail home. We figured out how to fold back our bimini so we could stand in full sun at the helm. With the breeze it was a bit chilly in the shade, so we soaked in the sun while we could!

We did ‘rescue’ a tarp from the sea with the boat hook, saw one lone porpoise and a few seals along the way. Once we made it back down to Jewel Island, we did decide to motor-sail the rest of the way home. It was getting late in the day, and with the wind still not cooperating to take us home, it was the best way to get home in the quickest manner. There were also a few shallow spots to navigate, which we felt more comfortable doing under motor.

We made it home at 5:30, and once securing the boat to the dock, jumped ship to go find dinner as all of the crew were hungry after a long day at sea.

It was a beautiful day and we wanted to go sailing, it was time to jump the hurtle of sailing with just the 4 of us. The weather had predicted scattered thunderstorms, but we hadn’t seen any all day. As we had to clean up and organize the boat before leaving, we didn’t get off the dock until 4:30pm. We figured we would go out for a short sail to test the waters and see how it went.

We discussed maybe picking up a mooring somewhere for the night, or perhaps testing out our anchor for the first time, but we didn’t have any set in stone plans.

We sailed up Casco Bay again, headed in the same direction as our 7-hour sail from the week before. Chef Ben again whipped up a delicious meal of grilled chicken sandwiches while underway. Just before we were going to eat, we arrived at what we thought might be a good place to anchor for the night.

The back side of Little Chebeague island has a great little cove that Tristan and I stayed in 4 years ago aboard our friends Cape Dory Typhoon. There is just enough space on the Cape Dory Typhoon for an adult and a 4 year old to sleep, sort of. We had a very rolly night, and while we didn’t get much sleep, we had a great time. I thought it might be a good place to spend Jelanea’s first night out as well.

Unfortunately, we couldn’t find a good place to anchor that we felt comfortable with, so we decided to try another anchorage at nearby Cow Island. Cow island is a privately owned island by a local outdoor education company Rippleffect, but the West side is open to the public, and there is a small mooring field there, and anchoring among the moorings is allowed.

Our first attempt at finding a good spot gave us a quite the scare. As we slowly inched forward looking for a good place to drop the anchor the depth went from 9ft to 2.3 feet all of a sudden. I threw us into reverse and backed down and also turned out toward the bay. I think we went over a rock, that was mentioned on the chart.

Its important to note that our depth sounder is mounted on the bottom of our keel, so when it read 2.3 feet it was actually about 8ft deep there, so we didn’t run aground, but with only 2 ft of water under out keel I was pretty freaked out.

We left the rocky section behind and found another good looking place to anchor between some moornings. Having an audience of several boats wasn’t helping my nerves at all, but I tried to just pretend they weren’t there and concentrate on our boat.

We found a good spot, I gave Ben the go-ahead to drop the anchor, and the anchor wouldn’t go down. It went down about 4 ft and then the windlass was just spinning and no more chain was going out.

At this point it was getting pretty late, and I wasn’t interested in figuring out what was wrong with the windlass/anchor chain, or trusting our anchor at all, so we decided to just motor back to the marina where we could tie up in our slip and know we were safe and sound.

We hated to give up on our first over-night adventure, but the kids were tired, and we didn’t know what was wrong with the anchor chain, and it was time to do the responsible thing and think about trying again another time.

It was about a 30 minute motor back to the marina, and by the time we got to the outer attenuater we were pretty glad we had decided to return home. The rain had stared a few minutes before, and was coming down in droves as we turned into Fore Points. The nearby thunder was freaking the kids out, and we were so glad to be second from the safety of our slip.

The landing wasn’t the best I’ve ever done, and we actually had to back out and try again, but the second time it was very smooth. After securing the boat to the dock we left cleaning up the boat for later and got the kids into bed for the night.

It was good to know we made the right decision in returning home as we watched huge storms pass to the north east of us, right over the places we had thought about anchoring the the night. With reports of hail and 30 knot winds, the safety of our little slip was even more comforting for the night.

Our first overnight will simply have to wait for another time.

We had really hoped to get out for a sail the first weekend after moving aboard Jelanea. The weather didn’t cooperate with our plans however, but we did get out for a boat ride. We launched, outfitted and took a family trip on our dinghy, which the kids have named ‘Ducky’. We took a trip all the way down and back up Portland harbor and everyone had a blast. We figured out that we can get Ducky up on a plane with all 4 of us on board! We also learned that everyone loves riding in the dinghy, and the sides are just the right height to keep Trixie from falling in.

So the second weekend after we moved aboard we were determined to go sailing. We were a bit trepedicious about going out by ourselves, just us and the kids, so we invited a friend along. I’ve known Stef since high school, and took her on her first sail on my family’s old boat ‘Barefoot’ many years ago. She was also present for my first sail with Ben, aboard a friends Cape Dory Typhoon 4 years ago, so it seemed fitting that she would also join us for our maiden sail upon Jelanea.

She arrived around 12:15pm and we left the dock soon after. There was quite a bit of wind, about 15-20 knots, so we decided to play it safe and started with just out Yankee sail up. A Yankee is a very small head-sail. Both Ben and I were amazed as how small it actually was when we first saw it out. Its a good sail for high winds though, and we were cruising at about 4 knots with just the yankee out. We decided to raise the mizzen as well to balance the boat a bit more.

We didn’t raise another sail throughout the whole journey. We were making 4.5-6.5 knots the whole time and felt it was plenty of speed, especially since we weren’t going anywhere in particular, just out to enjoy the ride.

After the disaster that was the harness with Trixie on the trip to Dimillos, we didn’t hook it up to anything this time. Stef was a great help in corralling Trixie, and she did have her life jacket on when above deck always.

Ben was a fantastic first mate, clearing the deck of the dock-lines and fenders as soon as we left the dock, and pulling out the Yankee and raising the mizzen as well. Since there was a decent amount of wind I hand steered most of the time, but did allow the auto-pilot to have a turn as well.

We headed up Casco Bay, inside the islands and just went where the wind took us. We made it up past Falmouth and decided to go around Chebeague Island and then head back down on the Ocean side. The wind was mostly out of the northwest, and we were pointing pretty high most of the way up. On the way back down we were on mostly a beam reach, but with the wind still blowing 15-20 we were heeled over quite a bit.

Chef Ben made a delicious dinner of chicken and pasta, and really put the gimble on the stove to the test. Trixie spent about 3 hours in her bunk, but we aren’t sure if she did any sleeping. Tristan roamed from bow to stern to his bunk to read his book. I stayed behind the wheel for a majority of the sail, always keeping a watchful eye out.

We were out for 6.5 hours, arriving back at the dock at 7:00pm. A much longer sail than perhaps we had intended when we set out for the day, but a wonderful adventure.

We are constantly learning about our new home, and how she operates, and this trip was no exception. There were quite a few things below that were not stowed away as well as they should have been, including out block full of knives. Luckily no one was below when the knife block went crashing to the floor during a tack. The sheet pans under the stove joined the knives on the galley floor, and the saloon floor was also in the contest for being covered with stuff. Luckily nothing broke, and a little picking up once we returned to the dock put everything back in order.

It was a wonderful first sail, with fair winds, gorgeous weather, and good company. An experience we will not soon forget.

We have been living aboard for 1 week – at a marina that doesn’t have electricity or water at our slip yet. We have been living ‘off-grid’ in our first class marina. The marina is not technically open for the season yet, because there are no amenities, besides a dock to tie up at, available.

Onshore bathrooms are available, across the parking lot. On site bathrooms will be coming soon. There is no internet either. Its real ‘off-grid’ living. Needless to say we were running low on water and diesel (to run the generator to re-fill our batteries due to the lack of the ability to plug-into shore power.)

So we decided to take a short trip down the bay to another marina to fuel up, and fill up on water.

Since arriving on the dock a week ago, with the previous owner aboard and providing tips, we had not moved Jelanea. She had been tied up and nice and cozy on our dock, with no need to go anywhere. But we needed diesel and we needed water, and we needed to take the plunge and move her for the first time as well.

This was the kids first trip aboard Jelanea as well. So not only were we newbies on operating a 42’ boat on our own, but we had two small children to keep on board and safe as well. Luckily our 8 year old is a huge helper with his little sister, and can be given tasks to do. This proved very helpful.

The two year old, on the other hand, wasn’t too thrilled with the idea of being tethered to the boat. We had tested her harness earlier in the week, and discovered that our little Scallywag could easily remove herself from said harness. Since we were moving the boat, we put her life-jacket over top of the harness, which prevented her Houdini skill from being useful. But she was NOT pleased when we connected a tether and clipped her to anything, despite the fact that she was just sitting in the cockpit, with plenty of slack on the tether, she didn’t like it but would have to deal with it.

Tristan helped Ben get the lines off the dock, and we were off! I put Jelanea into reverse and back we went. In a moment of confusion, I couldn’t remember which way to turn the wheel to get the stern to go to starboard so we could exit our slip. I’m thankful that there were no other boats docked anywhere around us, as the stress of hitting another dock was plenty for my first trip as true captain of Jelanea.

So we backed out to port, because by the time I realized which way the stern was going, it was too late for corrections. We then did a 180 in between the docks until we were facing toward the exit of the marina. I was pretty proud that I didn’t hit anything on the way out of the slip.

The trip over to the fuel dock at Dimillos was slow and steady. We ended up having to wait for a few minutes while another boat cleared the dock, and then I executed a beautiful landing on the fuel dock.

We fueled up first, then filled our water tanks. The dock-hand said that while the water was technically potable, he didn’t fully trust the hose it was run through,so we pulled out the water filter (I knew right where it was after our exhaustive re-organizing of the boat) and ran all the water through the filter on the way to our tanks.

As we sat on the fuel dock and Dimillos, the famous Maine fog rolled in. When we were ready to cast off for home, we could only see about 50 ft in any direction. So our first return to our home slip was going to be flying mostly blind.

At this point I was pretty grateful we had decided to turn on the chart plotter for the 1/2 mile trip, as I was able to follow our track on the plotter and know it was a safe route.

We did see 2 other boats along the way, a small water taxi, which passed in front of us easily, and just as we were approaching the marina entrance, another sailboat that docks at our marina drifting outside the entrance.

We called for docking assistance on the radio, and seconds after we called the other boat called as well. They allowed us to go first and we crawled toward the entrance, barely able to see the split in the docks that we needed to go through.

The docking at our home-slip was not terrible, but also not great, I swung a little wide and the dock-hands had to pull us in a bit. Altogether it was a pretty good docking for my 2nd try as solo operator of Jelanea.

By the time we got back to our dock and settled in it was 8:30pm and the kids were hungry. I had tried to make dinner earlier, before we left the dock, so it would be ready when we arrived back, but couldn’t get the stove to light. Ben got it to light right away at 8:30, and heated up some leftover soup for the kids, who we then put right to bed and both of them were out in minutes.

We then made sure Jelanea was tied up the way we like her, cleaned up the deck and put away the water filter and deck plate tool. We then went to bed shortly after, exhausted after our first expedition aboard our new home.