To quote Robert Burns, “The best-laid schemes o’ mice an’ men, gang aft a-gley“. We had been planning for weeks to set out on a small adventure, taking Belle and The Beast from Portland, ME to Booth Bay and back for the long Labor Day weekend. We expected to anchor in Southport and dinghy into the Botanical Gardens (highly recommended, and they have visitor moorings) during the day and an early dinner in Booth Bay. Then, sail back south to portland Sunday/Monday. Unfortunately, a series of unfortunate events lead to having our coastal passage aborted.
The weather looked good, with rain coming on Monday. So, we planned to set sail early Friday and return Sunday night. Both Windy and Predict Wind forecast an strong offshore breeze (“Danger Will Robinson”) that would shift more westerly late in the day to help us sail into the harbor in Southport. Winds were predicted to be ~15kts on from both sources but clear weather. All these things proved to be true that Friday.
I had stayed up late Thursday night, as work responsibilities foiled my plans to make upgrades to Belle during the day. Rushing to get the new wiring installed in the mast for an anchor light (not sure why Belle didn’t come with one, one interpretation of the rules suggests it might not need one. See Page 30 of this USGC brochure), and spreader lights as well as a proper through-deck wire fitting as well as new switches and USB power outlets, I did not get a chance to pack up the boat Thursday night.
As such, Friday morning took far too long to get moving. After we were loaded and made the trip up to Bug Light Park, it was noontime when we set to motoring out of Portland harbor. We motored out to between Cushing and Peaks Islands and set sails in the lee of Cushing. The offshore breeze was strong so we set only the Jib and this was plenty of power to push us to hull speed.

The surf was fine as we sailed due east with the southerly wind. At about 1:00 pm we rounded Outer Green Island. The swells were fairly large, I would estimate 8-10′ with a long period, maybe 100’/5-6s. This was perfectly comfortable for me and the two deckhands. The First Officer seemed OK but visible concerned. We were making good time and things seemed off to a good start.
At about 1:45 PM, we decided the wind was a bit strong for two sails given our crew was uneasy and I was the only one with a quick whit about trimming. Diana climbed forward despite her stomach complaint and took the sail down allowing me to single hand the vessel from the tiller position with ease.
Averaging close to 4kts with only the main, we passed Half Way Rock lighthouse with the seas starting to get a bit uncomfortable. A chop was developing on the swells that were making for a bumpy ride and the 1st officers face turned from concerned to a bit green. So at about 2:45 pm we sailed close-hauled for a bit and the crew took a bathroom break as we headed a slightly more comfortable heading for a short run before resuming course. Knowing we would not make Southport by dark and with the seas growing increasingly harsh I pointed us toward Cape Small Harbor to take refuge for the night.

The seas at this point, while not imminently dangerous (thank goodness for picking a hull with a heavy, self-righting keel and plenty of freeboard) they had become far too rough for a factor of safety. Then, at about 2:55 PM, things took a turn for the worse. The Beast had been towing behind us on a short painter the whole time with little issue. But now we were running from the swell and The Beast was surfing down the swells toward Belle and then pulling taught as the swells rose again with a thud. The tow ring gave out with this beating and The Beast was blowing away from us. Losing the free boat was not all that big a deal, but losing the engine and our spare fuel was. So, we took down the main and started up Not So Big Johnson to try and fetch The Beast.
The surf at this point was now in the 10′ foot range, not in itself an issue. But, the period had shortened dramatically to maybe 30’/3-5s or so. This was disturbing while trying to manage a stiff wind and fetch our dinghy. We now see the value of davits.
For the next 15 excruciating minutes, we looped back and forth and made several attempts to snag The Beast with our boat hook. We finally caught the dinghy and secured a line to the two forward rings with an improvised bridle. Not wanting to drag The Beast with the swells any more, I chose to turn hard to port and ride nearly broadside to the swells and make for Cliff Island. It was nearly 50/50 distance but looked to provide better shelter from the current weather and would allow us to take the swells at and angle and reduce the pitch angle making life easier for The Beast.
For the next hour, we motored along, our youngest actually enjoying the rollercoaster ride. The swell and wind remaining the same. Harsh but manageable with only the occasional white cap smacking the hull and sending a spray into the cockpit. Still, with water well above us on each side in a trough, it was a bit nerve-wracking for this skipper.
At about 4:10 PM and 2 miles from shelter, The Beast was adrift yet again. The knot I had tied in the improvised bridle had let loose and the line pulled through the d-rings. Being under power already, it only took about 5 minutes and three passes to capture The Beast this time. Approaching the rocky shore and the white caps seeming to be a bit worse, I decided to risk a bit more time adrift to tie a steadfast bridle onto The Beast. This would be even more important as we would have to run with the swells again for the last leg into the islands.

It’s interesting to look at the track for this “MOB” exercise in hindsight. Even though the wind and swells are coming in from south-south-west, you can see The Beast was actually drifting south-south-east. I believe tide was falling but I’m surprised there would be this much effect this far out.
The next 45 Minutes were challenging as we had to run with the swell again. I tried to set a snubber with a bungie cord looped over the painter (cleated to rear starboard) and the rear port side cleat. It was not strong enough and The Beast was taking a beating again. Until we rounded Cliff Island Bouy “5”, I hand snubbed the painter with my right hand extended over the transom and held the tiller with my right seated port in the cockpit (ouch, but no blisters).

We made anchorage at Cliff Island at 6:00 PM on the dot. With a huge sigh of relief, we motored into the anchorage side of the rocks at near low-tide and set anchor with ease in the muddy bottom. The harbor was nearly flat and wind very light compared to the open water. Only one other sailboat was anchored on this side and a dozen powerboats at moorings on the other side. It was beautiful and peaceful to watch the sunset over the cliffs. One the crew’s proper color had returned, we enjoyed a leisurely dinner of cold pizza and watched the stars come out.

With only a little light pollution from Portland to the southwest, the stars were fantastic and the Milkyway a bright stripe across the clear sky. Another sailboat attempted anchor near us, but soon pulled up and moved to the mooring side (brave in the dark). It seems they left there too as they were not there in the morning. I had read that this anchorage was rolly at high tide as the water then covers the rocks dividing the harbor. This proved every bit the case. With high tide some time in the middle of the night we rolled from about 10:00 PM to 3:00 AM.

By sunrise, the harbor was flat again and serene. With hardly a breeze I sent the drone up for some photos. We managed to break the floats I had fashioned out of balsa and styrofoam balls at some point in the chaos the prior day so I had to land in the cockpit, with a hand grab (successfully). We had a leisurely breakfast of hot coffee/cocoa and muffins using our new butane stove (canisters stored in the fuel locker) and made plans for the day.
We should have made a small hike on Cliff in hindsight. It would have been fun. But we made for Portland and that was a good decision too. We motored out of the harbor and sailed southeast through the islands behind Cliff Island. After a short motor-sail between Long and Chebeague Islands we made a few long tacks down to Portland and sought anchorage.
We made Portland at noontime and went to the same location we had spent the night for our anniversary a few weeks earlier just off the southern end of Eastern Promenade Beach. It proved convenient and secure at that time. This time, it gave us a bit of a scare. Our first attempt at anchor started to drag. Fortunately, we sat in the boat for a while just to monitor the anchor hold. We pulled up anchor and re-set a little closer to shore and further from the mooring field. This set seemed to be holding this time, but now with a bit of scare in us and wanting to go ashore, I set a second anchor using The Beast parallel to our main anchor.
Having taken such a beating the day before, The Beast was showing fatigue. His starboard tube needed air in the morning and again by the time we made anchorage in Portland. I pumped him up yet again and we made for Fore Point Marina. I had been in contact with them via email in advance to see if parking our dinghy was possible to which they replied yes. For $20, they allow a days use of the marina including the showers and wifi. They give you a pair of codes for entering the marina and the docks. I was a little concerned as they are trying to cater to mega-yachts which we have seen berth here, that they might not be keen to transient small craft but we were greeted with great kindness and welcome.

We ventured down to the waterfront and had an early dinner/drinks at Boon’s upper-deck. Fantastic fried calamari and fries for the boys. After “linner” Diana and Nathan wandered back toward the marina and James and I made a quick detour to Starbucks to download the Mimo app for my new action camera since it would only allow 4 uses before requiring me to register via the app. That done we quickly joined the other half of our party at the marina.
We made our way back and were pleased to find Belle where we left her. We climbed aboard and stowed G.v.C for the night on the floor of The Beast. Diana turned on a little Disney music for the kids while I broke out the adult beverages and cookies and put our feet up. As dusk approached, so did the Harbor Master. He made a pass by and waved as he moved north. As he returned south, he approached near and asked if we intended to stay the night. We confirmed and he then asked us to move our boat stating we could not anchor in or near a mooring field (despite it being marked an anchorage on the Navionics charts). You can’t fight the law, so we agreed. He suggested we move “the other side of the (Pomroy) rocks, in deeper water”. We took that to mean the other spot marked as an anchorage beyond channel marker “6” where there was a catamaran from Key West anchored.

We had originally considered this spot on our approach but decided it to be a long dingy row if G.v.C. gave us trouble. After having moved, we were not unhappy about our new location. The sunset was wonderful and the water flat. It doesn’t seem that much different exposure from Pomroy rock area, but it was almost roll-free all night long. The fish were jumping like crazy too. Large ones. Some fish 1.5-2′ long were jumping clear of the water every few minutes. At twilight and bug-free it seemed that they must have been under chase from bigger fish. We saw no seals, which were plentiful in the daylight hours, so we assumed bigger fish.

The next morning was cool and calm with almost no wind. Our oldest was up with the sun and we again made coffee/cocoa and had breakfast. The crew of “No More Monday’s 2.0”, the catamaran from Key West, raised anchor and made off while we ate. We exchanged waves as they passed. Soon thereafter, a large cruise ship was spotted making way into the harbor. We thought they were spinning around to berth stern-to-shore, but it turned out they were so far out they were just turning around the islands and channel markers. The ship soon came close enough to identify with the binoculars as Royal Carribean’s Anthem of the Seas. I was surprised to see such a big ship in New England. We had sailed on Freedom of the Seas this past April, our first time on a cruise ship. Anthem is slightly larger than the older Freedom and part of a class of ships that are currently the 3rd largest on the seas. Portland’s population suddenly increased by about 4000 people.

With the wind not blowing and poor weather predicted for Monday, we decided to motor back to the ramp at Bug Light and make for home a little early. It was not the weekend adventure we had planned, but it was an adventure none-the-less.