My Parents Join us to Start Exploring Maine
It was the morning of Wednesday, August 6th, and Abby and I woke up early to get some final things done prior to welcoming my parents aboard. After changing the sheets in both bedrooms, we raised the anchor and set off for DiMillo’s Marina in downtown Portland, Maine. We hailed DiMillo’s Marina on the radio and they informed us that there was a mega-yacht taking up 75% of the fuel dock. After a little back and forth, they said that if we were comfortable trying to fit on the very edge of the dock, they would be able to accommodate us. We decided to do a drive-by to scope out how much dock space was available, and what the consequences would be if we screwed up. When we approached, it was clear they weren’t kidding when they said this mega-yacht was taking up most of the fuel dock – there was maybe 25 feet available right at the very edge, and we would have to be cognizant of all the mega-yacht’s bow lines as we approached. Now Salty Foxx is just a touch under 40-feet long, so docking on a 25-foot sliver of dock was going to be challenging. We had chosen DiMillo’s as they were the only marina in downtown Portland that had fuel, water, and pumpout services. They were also close enough to my parents’ hotel room that the Uber wouldn’t be crazy expensive. At this point I was pretty sure my parents were already in the Uber and on their way to Dimillo’s Marina, so we had to try. After doing another circle to look at the dock, we decided to go bow in so that our prop walk direction would bring the stern up to the dock and if we overshot, our forestay would hit the mega-yacht’s bow lines not our solar panels. After taking a deep breath, I slowly approached the dock and nailed the landing. What a relief! Now that we were safely on the dock, it was time to top off our fuel, fill up the water tanks, and empty our holding tanks. While I got to work, Abby headed down the pier to take Tots for a walk and pick up some coffee for my parents, as it was only 0900 Eastern time and they were still on Pacific time.
With everyone, including Salty Foxx, fueled up and ready to go, we cast off our lines and headed out the Portland Channel. We had a nice breeze to start the morning, so we almost immediately unfurled the sails and shut off the engine. Of course, the wind was coming from the wrong direction, so we set out on a deep tack out to sea. In the blink of an eye, we were almost 10 miles of the coast of Maine and still zig zagging through lobster pots. This was our first real taste of the lobster pot craziness that everyone had warned us about. We jibbed over and began heading back towards the coast. Almost immediately following our jibe, we lost the wind. Oh well, at least we got to show my parents some sailing on their first day. The wind never returned, so we slowly motored the remaining 20 nautical miles to our destination of Salter Island.
Salter Island is one of the less-traveled islands off the coast of Maine and is not mentioned in most guidebooks. We chose Salter Island mainly based off the location, and the southern protection the harbor offered. My parents planned to be with us for 5 nights and the goal was to make it all the way to Bar Harbor in that time. Bar Harbor is about 100 nautical miles as the crow flies away from Portland, so we needed to average 20-25 nautical miles a day without too many detours into deep inlets. Salter Island is off the tip of Georgetown Island and thus almost perfectly located on our path to Bar Harbor. Salter Island itself is a small, privately owned island but it offers a nice shoreline path to walk along. After doing a little exploration on land, we decided this would be the perfect night to grill the steaks we had purchased in Portland. As the smell of sizzling steak fat filled the air, the magic of the harbor came to life. It truly felt like we were living the dream – fresh grilled steaks, my parents visiting from the west coast, and exploring the beautiful coast of Maine on our own boat.
Unfortunately, our anchorage at Salter Island that night was one of the rolliest anchorages we had been at so far, and that meant a restless night for me. I think the rolling was caused because it was so calm that the boat floated aimlessly around the anchor, allowing the tiny bit of ocean swell to hit us broad side constantly throughout the night. Abby and I’s bed is orientated horizontally across the back of the boat, so any rolling is mighty uncomfortable. Luckily my parents berth lays forward to aft, just forward of the center of Salty Foxx, and thus the rolling is much less pronounced there, so they got a good night sleep. Waking up the next morning, I made a strong cup of tea and we set off towards Monhegan Island, praying that the anchorage there would be calm.
The wind was forecasted to pick up throughout the afternoon, so we started the morning with the engine running. Of course, the wind never picked up and we ended up motoring the entirety of the 20 nautical miles to Monhegan Island. We were excited to get to Monhegan as we were planning on meeting our friends Jamie and Tyler on SV Sasa there for our first official cruising meetup after years of dreaming of this journey together. Jamie and Tyler were a little bit ahead of us, so they sent us some advice on how to get mooring ball – hail the harbor master on VHF Channel 19 when 30 minutes away, give him your boat length, pay at the fish house when you arrive. This all seemed simple, but alas, we hailed the harbormaster on VHF Channel 19 and got no response. We had read online that the harbormaster didn’t always monitor the radio so if you got no response, pick up one of the unused mooring balls and head to shore to meet the harbormaster. We turned our radio back to VHF Channel 16 and continued into the harbor. The harbor was very tight and there were only a few unused mooring balls, so we were glad it was only 1400 and not any later. After slowly picking our way through the mooring field, we found a mooring that was unused and had enough room for Salty Foxx. We grabbed the pendant and attached the mooring lines only to see a sign saying “reserved for SV Osprey”. We had just passed Osprey on one of the further out moorings, and we figured they were too big to fit on this mooring and thus it was up for grabs. We planned to verify with the harbormaster on shore that this was okay. Right as we started to get comfortable, another sailing vessel (not Osprey) pulled in claiming they had reserved the mooring we were on. As we scrambled to get ready to move, a local lobsterman directed them to a different mooring right in front of us that was also available. We initially felt bad, but after talking to Tyler we realized that it was all just a misunderstanding. Tyler had been listening to VHF Channel 19 on Sasa and he heard the whole thing play out. First, we had hailed the harbormaster and got no response. 10 minutes later, this other sailboat had hailed the harbormaster and got a response instructing them to head to this specific mooring. While yes, this 2nd boat technically had reserved this mooring, it was after we had attempted to reserve the mooring. Oh well, no harm no foul. We both had a safe mooring to spend the night on. After speaking with the harbormaster, it seemed like this sort of kerfuffle was normal on Monhegan. We ended up chatting and apologizing to the other sailboat, and they were just as confused as we were and held no hard feelings. Now that this was over, it was time to explore the island!
Monhegan Island is one of 15 islands off the coast of Maine that maintains full time residents through the winter. Monhegan boasts only 40 residents in the winter, but the population swells to 400+ in the summers. It is known for its rugged hiking trails, historic lighthouse, the local brewery, and several vibrant art galleries. As it is accessible only by ferry or private boat, Monhegan has maintained its small island feel through the Maine summer tourist boom. After meeting up with Tyler, Jamie, and their 2-year-old son Baby Jamie, our first stop was, of course, Monhegan Brewing Company at the top of the hill. Sitting down with some cold IPAs (and a milk for Baby Jamie), Tyler, Jamie, Abby, and I couldn’t believe we had actually done it! We had all met while living in Hawaii in 2021 during a Halloween party on a catamaran anchored off the sandbar. We immediately hit it off, as we both had a shared dream of buying a boat and sailing the world. At this point, neither of us had any idea what this would actually look like, but as the years went on, our plans magically converged, and we ended up buying our respective boats only months apart with the same plan to spend the summer in Maine. After enjoying a few brewskis and regaling each other with our individual journeys so far, we made plans to meet up for dinner on Sasa. We went to go explore the D.T. Sheridan shipwreck while Jamie and Tyler went back to Sasa for Baby Jamie’s nap time.
The wreckage of the D.T. Sheridan
The D.T. Sheridan was a 110-foot diesel-propelled tugboat built in 1939 for the Sheridan Towing Company. On November 7th, 1948, the D.T. Sheridan was pulling two barges of soft coal from Norfolk, Virginia to Bangor, Maine when the crew became engulfed in dense fog. All a sudden, the crew heard a large bang as they ran aground on the rocks off Monhegan Island. A local lobsterman by the name of Raymond Pix jumped into action and was able to save all of the crew members from an almost certain death in the frigid northern Atlantic. In the 1970s a large storm moved the rusted carcass of the D.T. Sheridan a further 50 yards inland where it lays today. The rusty hull of the ship was impressive to walk around, although a little anxiety inducing, as rusty wreckage was everywhere you looked and more importantly, stepped. It’s hard to imagine what the crew of the D.T. Sheridan were going through on that fateful day in 1948. Today, we have modern marvels of navigation such as GPS, AIS, Radar, and digital charts, and navigating in dense fog is still a nerve-wracking experience. After taking several moments to admire the shipwreck and think deeply about all the past mariners who navigated these shores, we headed back to Salty Foxx to get ready for dinner.
Dinner on Sasa with our friends and my parents was incredible. We were having such a good time that we both audibled and decided to spend an extra day and night on Monhegan. The next morning, we awoke early to try and do the southern island hike before the morning ferry full of tourists stormed the island. Monhegan Island is about 12 nautical miles off the coast of mainland Maine and extremely exposed to the elements. It was clear the winters here were extremely rough by the barren and rocky shorelines, but there was something beautiful in the rugged look. We quickly could see why so many artists called Monhegan home. After walking around the southern tip of the island, we continued to the center of the island to explore the historic lighthouse. The actual tour of the lighthouse was a little pricey, so we settled for walking around the outskirts of the building and taking in the 360-degree view. We spent the mid-afternoon walking into each gallery and talking with the artists. It was clear that Monhegan meant a lot to all who called it home. During the day’s adventures, we popped into the local pizza shop for a look around. At long last, in this pizza shop, we found what he had been searching for - a beautiful wooden cribbage board with a topographical map of the island! All the games of cribbage we had played up to this point had been on a 12-dollar plastic travel cribbage board we had gotten years earlier. With the nice wooden cribbage board in hand, we finally felt like true seafarers.
My parents really wanted an authentic Maine experience, so we stopped by the local fish house and ordered six, 1-1/2lb lobsters to be picked up at sunset. We spent the late afternoon playing in the water at the beach with Baby Jamie. Soon enough the sun was setting, and it was time to pick up our lobsters. Never in my life have I seen such a feast! Jamie and Tyler came over and we thoroughly enjoyed local Maine Lobster and few bottles of wine. This was definitely a night of luxury. I do have to say, the lobster did create quite a mess in our cockpit, so we made the decision to use some of our precious freshwater to give the cockpit a thorough wash down. After we finished gorging ourselves with fresh lobster and cleaning up the boat, Jamie, Tyler, Baby Jamie, Abby, and I hiked back to the southern tip of the island where we had heard rumors of a full moon party. While there was a gathering going on, it was amongst the closeknit workers on the island so we continued walking along the shoreline basking in the full moon. We finally headed back to the boat and said goodbye to Jamie, Tyler, and Baby Jamie with plans to meet up again in a few weeks’ time.
The next morning, we awoke early knowing that we had a big day ahead of us. We didn’t have a specific destination picked out but knew we had to make it across Penobscot Bay at minimum, which was about 35 nautical miles. We had a little bit of wind to start the day so we unfurled the sails, hoping to avoid motoring for as long as possible. Sadly, after 30 minutes any hint of wind dissipated, and it was once again a day full of motoring. As the hours slowly passed, the density of lobster pots began to increase which meant the auto pilot had to be shut off and we had to hand steer all the way to our destination. It was a Saturday, so even though we wanted to spend the night in the Isle Au Haut Thorofare, there are only 2 moorings for guests with no room to anchor and if the moorings are taken, we would be SOL. Not wanting to risk making a long day even longer, we made the decision to go to a harbor between Merchant and Harbor Island on the north side of Isle Au Haut. This anchorage was extremely hard to research because there are probably 30 Harbor Islands in Maine and there is a whole group of islands called Merchants Row. With no mention of this anchorage in our guidebook, we relied on the few Navionics reviews and decided to test our luck. When we pulled in, there were 4 other boats on anchor, and we immediately knew that we had chosen correctly – it was absolutely stunning. We quickly dropped the anchor in 20 feet of water and headed off in Saltine towards Harbor Island.
Habor Island is a small island owned by a nature preserve that has partnered with the Maine Island Trail Association to allow public use. There are two public campgrounds that are open to private groups on a first come first serve basis with a maximum stay of two nights. The night we were there, the was a small group of young boys camping out on the far end of the island and living their best lives. We walked the entire island, picking wild raspberries as we went, just enjoying the smell of the pines and the natural beauty of the island. We soon realized that if we sat at the very tip of the island, we could watch the sunset over Penobscot Bay. With this realization, we quickly headed back to the Salty Foxx to fire up the grill with the hope that we could be done with dinner before sunset. Mission Success! The chicken and veggie skewers we made were delicious, and we had 30 minutes before sunset when my dad, the world’s slowest eater, cleaned off the last of the chicken. We grabbed a bottle of Soquel Vineyards wine (fun fact – this is the California vineyard where Abby and I had our rehearsal dinner) and headed back to the Island.
A Soquel Vineyard Pinot Noir
What a sunset it was! It was so nice to enjoy this peaceful night, sitting on the picturesque pink granite, watching the sunset over the water, with my wife and parents. Tots, however, sensed it was too peaceful and decided to start loudly barking at the children in the distance, causing me to spill my red wine all over my shirt. Thank you so much Tots. The sun had already set, so it was time to head back to Salty Foxx. My mom came to rescue and knew a trick to get red wine stains out utilizing rubbing alcohol and my shirt was back to being good as new. Even with the wine spillage, it was such a magical night and one that I will never forget. We all went to sleep that night with our hearts full.
The next day, there was finally good breeze in the forecast. We got up early, excited to finally be doing some real sailing! So far on this trip with my parents, we had unfortunately been forced to mostly motor. For once, the forecast matched reality and there was just enough wind to be sailing! The first bit of excitement occurred when a seagull landed on our solar panels. Luckily for us, Tots can be very scary and after a few barks the seagull was on their way. With Tots standing guard, we navigated around the various islands in Merchants Row and set our sights on the Casco Passage. The Casco Passage is the northern route along the ledges to northwest of Swan’s Island. It is supposedly easier to navigate than the York Narrows, which is the southern route along the ledges northwest of Swan’s Island. As we got closer, we realized that the wind angle would not support going through the Casco Passage and if we wanted to sail, we would have to brave the York Narrows. As this was our first real sailing day in a while, we really didn’t want to turn the motor on and so we decided to put our skills to the test and sail through the York Narrows. Man was that fun! It took all our attention as we had to constantly adjust sails each time we passed a navigational buoy and eventually we were staring at the last stretch. As we turned to line up the last green buoy, the wind shifted and the only way to keep sailing was to jibe the jib and go wing-on-wing. We had made it this far without issue, so we went for it. We jibbed the jib, set our sails wing-on-wing, and just like that we were through the York Narrows!
Tots guarding the boat
Excited to be through safely, we set our sights on the next major navigation feature, the dredged cut through the Bass Harbor Bar. In 1994, the army core of engineers excavated a 14-foot deep, 250-foot wide channel through the Bass Harbor Bar that you can navigate by lining up the white and red buoys that bookended each side. As we pushed on, the wind speed promptly turned to zero and we reluctantly fired the engine and motored through the cut. Soon enough, we rounded the corner and picked up a guest mooring ball off Little Cranberry Island and the town of Isleford. Little Cranberry is another one of the 15 islands off the coast of Maine that has year-round residents.
The town of Isleford provides two free guest mooring balls on a first come first serve basis so we were ecstatic about getting one, as the anchoring was difficult in this area. We quickly went ashore and walked through the little town. We stumbled upon another art gallery which showcased 15 or so local artists. This gallery really spoke to me due to the intersection of each artist’s style. The combination of contrasting styles, each stunning individually, created such an aura of beauty when laid together. We continued down to the pier, where there was a pottery studio and gallery, showcasing more incredible local artists. We almost bought several pieces of pottery but had to keep reminding ourselves that we lived on a sailboat which mixes very poorly with beautiful, breakable pottery. We finally sat down outside the local restaurant where we each got a nice cocktail to enjoy the afternoon sun. After looking at the menu, we made plans to come back for dinner and returned to Salty Foxx for a quick post-cocktail afternoon nap.
Coming back to town was a shock. This quiet little island town became packed with people as soon as the sun went down, and the restaurant had almost a 2 hour wait for a table. Undeterred by this, we took seats at some open bar stools and started reminiscing about my parents’ time aboard Salty Foxx, and the similarities between coastal Maine and the San Juan Islands where my parents spent most of their summers. Soon our table was ready, and we sat down ready to enjoy a nice meal together. I splurged and got scallops while Abby got lobster fried rice. My parents each ordered their own lobster. My dad specifically asked for the biggest lobster they had, and they came back with a 2 ½ pound behemoth of a lobster. After eating to our hearts content, we were one of the last tables to get up and leave. The almost full moon lit up the harbor which made for an easy dinghy ride back to Salty Foxx. As soon as we climbed aboard, we all immediately passed out with full bellies.
We slept in the next morning but when we all eventually woke up, we decided to do one more quick trip around Isleford. We went back to the pottery shop and debated more on if we could keep a handmade serving platter safe on Salty Foxx, and once again walked away empty handed. Besides the mosquitos that became overwhelming as soon as you walked to the forest edge, Isleford was a lovely town and is definitely on our list to visit again someday. The tide shifted to be in our favor around 1100, so we made our way back to Salty Foxx and prepared to depart for Bar Harbor. The plan was to sail to Bar Harbor where we would pick up Abby’s parents and then to sail around Ironbound Island with everyone on board. Our families get along really well, so we had deliberately planned to have a few days of overlap in Bar Harbor with everyone before my parents went back to the West Coast and Abby’s parents came aboard. The sail to Bar Harbor was a sail of confused wind. One minute we had 15 knots of wind blowing off the port beam and the next minute it would be perfectly calm. When the wind picked back up, it would have shifted 90 degrees to be directly off the bow. I think this crazy wind is caused by the proximity of Cadillac Mountain in Acadia National Park. Cadillac mountain is roughly 1500 feet tall with the peak only 2 miles from the shoreline which can create tremendous amounts of wind shear. After fighting the shifty winds all the way into Bar Harbor, we met Abby’s parents on the dock and headed back out to circle Ironbound Island. My dad especially wanted to go around Ironbound Island as his best friend’s son married the daughter of one of the original owners of the 900-acre island.
As soon as we exited Bar Harbor, 15 knots of wind hit us right off the bow, so we put up sails and hoped for a lift to get around the southern tip of Ironbound. As we continued, the wind did give us a lift but it also increased in wind speed to 25 knots. We were cruising at 7 knots SOG but the amount of heel made it hard, if not impossible, to eat lunch. Wanting to ensure that we passed the southern tip of Ironbound safely, we decided not to reef and to just ride the lift all the way out. Things were looking great until we heard the dreaded sound of a lobster pot banging against the hull. We looked around waiting for it to pop out from under the swim platform but when it didn’t, we knew we had caught it in the propellor. Soon our speed dropped from 7 knots all the way down to 1 knot and we were stuck with a lee shore. We tacked over to give us more distance to the lee shore with the hope that a change of direction would free the lobster pot. No luck, we were stuck solid. We started the engine and gave it a quick jerk in reverse followed by quick spurt of forward and magically the pot came off, and we were free! We turned off the engine, tacked back over, and rounded the southern point of Ironbound Island. Man did I feel embarrassed…. We had been dodging lobster pots continuously for the past week and hadn’t so much as grazed one. Now here we were, with all of our parents on board, stuck on a lobster pot. Thankfully, we didn’t have to jump in the water to cut it free, but it was still a very nerve-wracking experience with such strong wind and a lee shore. After we rounded the southern tip of the island, the wind promptly died, so we were forced to turn on the engine. This had its benefits though as the boat was now level and we could eat our sandwiches in peace. Once we passed the northern tip, the wind picked up again and we were able to sail all the way back into Bar Harbor. Even with catching the lobster pot, it was a nice day on the water with the whole family. We dinghied everyone to shore and made plans to meet for dinner.
It was bittersweet having my parents leave Salty Foxx, it had been really enjoyable to show them around my little piece of heaven the past week. From August 6th to August 11th, we covered a little bit over 130 nautical miles with a mix of coastal and offshore sailing. While I was sad to see them go, I was happy that they had a hotel room in Bar Harbor the following 2 nights and that their trip wasn’t over just yet.
