Showing up here over a major summer holiday was like stepping into mass chaos. My first impression was that I wasn’t going to like it here but I’m glad we stayed. It has been surprisingly pleasant.

It was a great sail from Onset over to Martha’s Vineyard. It got a little crazy in the channel going from Buzzards Bay to Nantucket Sound but the rest of the sail was calm and it was a beautiful day.

We sailed through the cape cod canal and anchored just on the other side. We caught the current and made it through super quick.

We sailed from Boston, MA to Sandwich, MA. It was an absolutely beautiful day.

We left our safe haven in Portsmouth, NH to head to Boston, MA. The route we sailed was much farther out from shore than we had originally planned because even though the hurricane was past us the sea was still being affected. We saw massive waves crashing into the shoreline for most of this trip. The water was turbulent, and the wind was 20+ knots. It wasn’t the most comfortable trip, but we made it to Boston right after sunset.

We left the mooring ball at Portsmouth after swimming under the boat to check the bottom and propeller. The harbor was calm compared to the large, rolling waves we encountered which were remnants of Hurricane Erin. We motored into the wind until we reached the point at Gloucester and able to sail on a close haul/close reach to Boston. Saw several pods of dolphins and a sunfish along the way. We later learned of a sailboat thrown onto the rocks at York, ME in the same day and just North of our position.

We woke up extra early on this day to get the heck out of here. It wasn’t all that bad unless you were counting what should be an illegal amount of lobster pots in a perfectly good anchorage, but I digress. We thought this place would be a good spot to wait out hurricane Erin, but right after we pulled in the night before we knew that wasn’t going to be the case. So, before we had to start work for the day, we pulled up the anchor and headed to Portsmouth, NH in the hopes that it would be a more protected spot to wait for the hurricane to pass. Thankfully it was a great place, and the hurricane didn’t cause us any issues. What I learned from this experience was that even being this far north doesn’t mean you are in the clear for hurricane season, as I naively thought. It’s important to plan ahead, do your research, and trust your gut.

After showman the night on anchor at Stage Island, we decided it was not the place to shelter from the coming hurricane. We left early in the morning and headed to Portsmouth, NH which was much better protected.

Left Wood Island Harbor with a good wind on the beam. Sailed to Stage Island to wait out the passing Hurricane Erin. Lots of lobster pots and ultimately not comfortable with the anchorage.

As we were leaving Portland, ME I had to take several pictures and videos of the Portland Head Lighthouse on our way out. It was a beautiful day for it. When I was looking up the name of the lighthouse, I discovered it is considered the most photographed lighthouse in the WORLD! Why is this relevant? I think a big part of the draw to sail isn’t just about sailing. It is about constant learning, growth, and development. We are experiencing new things almost daily and a lot of that comes from going to new places, experiencing the culture, the food, the architecture and the history of each place. In my case on this particular day it was learning a random fact about a lighthouse that I may have never discovered, if not for being there.

Left Portland with light winds and had to motor most of the way. Arrived at sunset and set the anchor just before dark.

For some unknown reasons I became super nauseous about 6 hours into this sail. It was a beautiful day for a sail and good conditions. This almost never happens to me. I usually only get nauseous when I have been off the boat on land for several days and then get back on the boat and even then only about 50% of the time. I have learned to be prepared for this because being nauseous on a boat that you can’t get off of for hours on end may be one of the most miserable things I have experienced. Things I keep on the boat to help with nausea are: ginger ale, ginger tea, ginger chews, ginger gum, less drowsy and original Dramamine. I have nausea wristbands. I also have a couple different prescription medications that I keep around to help if all other methods fail and those are Scopolamine patches and Ondansetron.

Pulled up anchor and motored for half the trip without any wind. Circled around Egg Rock to look for Puffins, and saw one floating near the island. Wind picked up as we rounded Pemaquid Point and sailed the rest of the way to Portland. Set anchor just North of bouy #6.

After a night on anchor and visiting Turner Farm, we motored-sailed to Rockland. Saw a pod of short-nosed dolphins along the way. Set anchor in Rockland just South of the main mooring field.

We liked it so much the first time we came here we decided to stop here again on our way back down south. When we arrived we were having trouble getting our anchor to set. We have needed to add more chain, and the spot we were in was just a little too deep for the amount of chain we currently have so it wasn’t catching as we were trying to set it. We pulled it up and moved more towards shallow water and it set perfectly. Struggling to set anchor in deep water with too little chain drives home a simple but critical lesson: preparation matters. Anchoring isn’t just about where you dropped the hook. It’s about having the right gear for the conditions. Without enough scope, even the best anchor can’t do its job. It’s a reminder that cutting corners are hoping for the best doesn’t work at sea. Plan ahead no your depths and always carry enough rode. The ocean doesn’t forgive oversight it just keeps you drifting.

This was a short after work sail. It was perfectly clear all day until right when we started pulling up the anchor the fog rolled in. Most of the sail was in the fog which was a little disappointing because we wanted to see the beautiful landscape. There were patches where it would clear up for a few minutes and you could get a quick glimpse of some of the islands. Something I have learned from sailing in the fog is that it taught me patience, presence, and trust in our instruments, our instincts and each other. When visibility is stripped away, you’re forced to slow down and focus, navigating not by sight but by sound, feel, and intuition. It has been a powerful lesson in adapting to uncertainty, staying calm under pressure, and moving forward even when the path ahead isn’t clear.

A thick wall of fog blew in just as we picked up anchor. As if it would not be difficult enough to navigate the narrow passage between the islands while dodging lobster pots... Let's do practically blindfolded... We stay in our course as much as possible and dodger most of the lobster pots. The fog cleared up just as we reached out anchorage at North Haven Island.

Left Bar Harbor and motored straight into the wind. Lots of lobster pots to dodge and spotted a few short-nosed dolphins along the way. There is a shallow bar at Bass Harbor with a narrow channel close to shore and right next to the Bass Harbor Lighthouse. Anchored at Swan Island just after sunset. Beautiful anchorage with good protection.

We left Yarmouth in the evening with wind on the beam at 10 knots. Full moon have us plenty of light only small rolling waves through the night. We were greeted by a pod of Fin Whales after sunrise. We timed our passage to navigate through the insane number of lobster pots as we neared Bar Harbor. The main anchorages are filled with private mooring balls and had to find another location to anchor. Anchored around the other side of the sand bar at Bar Island. Good holding at 10 feet low tide and 10 foot tide difference.

We did a lunchtime Canoe trip around South Harbour. Located near Cape Breton Highlands National Park.