Bucks Harbor to Cradle Cove, Isleboro

Today was a “mellow day” but that might be because the days have a routine-like feel to them. We wake up to blue skies and a light breeze, have some coffee and breakfast, and then go for a walk ashore followed by sailing for the rest of the day before dropping anchor in a new picturesque spot followed by dinner under a breathtaking sunset and finally relaxing onboard reading (or in Brandon’s case – optimizing OpenCPN and our navigational network devices.) 

We continue to be blessed with clear blue skies and a daily building sea breeze that maxes out around 15 knots every afternoon. We won’t even utter the “F word” onboard for fear it will hear us and appear. So “the-weather-phenomena-that-shall-not-be-named”, has yet to make its grey sea smokey presence known so far and for that, we are very grateful. 

The route from Buck’s Harbor to Cradle Cove

A mooring at Bucks Harbor comes with showers and trash removal – both key on a small boat. While we do have hot water and good water pressure on board via a cockpit shower, nothing quite beats a cascading shower nozzle you don’t have to hold. So our morning contained both a shower and another visit to the market. We heard about their fresh pastries and didn’t want to miss out. Turns out you have to get there early on a Saturday and 9am is too late! We still got some day old goodies that weren’t that bad either. 

By 11 we left the mooring and plotted a course for the west side of Isleboro, a 10 -mile-long island  in the middle of Penobscot Bay. We had a generous offer of a mooring on the east side but we wanted to take in the sights of sailing north around the island and had read there was some good hikes on the other side we wanted to try. (Thanks Ginny and Mike! Next time!) 

As the winds were light, we motored until the northern tip (Turtle Head) and then seabreeze came in nicely straight down the east passage of Penobscot Bay. Normally, going to windward back home in Narragansett Bay or Rhode Island Sound means trashing into waves making the ride uncomfortable, but here the waters are flat and our little C&C 34 loves it. She works to windward like it’s what she was built to do and our 135-jib is also made for these conditions making the sail relaxing and enjoyable.

Sailing up the west passage of Penobscot Bay

It still took us a few hours and quite a few tacks but was still sublime sailing. There were not as many lobster pots so we could relax a bit more and let the auto pilot do it’s thing. I was able to sit back and finally finish the book I started on the trip up. (Summer of ‘69 by Elin Hildebrand). 

When we turned past the Isleboro Ferry landing off Grindel Point we had to decide between two nearby anchorages: the space between Spruce and Warren Island or around the corner at Cradle Cove. As the winds were still up and more SE, we opted for Cradle Cove over the more exposed former. When we got around we found it actually very full of anchored boats and no one was using the moorings from Dark Harbor Marina. (Why pay when it’s good holding ground and you’ve got an anchor?) Once we settled, we questioned whether to move anchorages to avoid this crowd of a dozen or so boats, but we decide to stay.

Sunset in Cradle Cove

I noticed many of these boats were flying the same burgee (Yacht Club Insignia flag) from their side stays. It’s blue and yellow with a flying fish. So I google “flying fish burgee” and discover it’s the Ocean Cruising Club, and according to Wikipedia, you have to have skippered at least a 1,000 mile ocean passage to join. Most of the boats to appear to have older couples aboard 40-50 footers that looked like they had some sea stories to share. We heard them hail on the radio that there would be a “crab finding contest” in the morning followed by a “lobster bake by campfire.” Sounds like a good time.

We also saw a fleet of 15 or so boats racing by that had “DH” on the sail. So another google search rabbithole taught us that the Dark Harbor 20 was commissioned by the Isleboro-based yacht club, Tarratine Yacht Club, in 1930s designed by Sparkman & Stephens. They have raced every Saturday since.

We relaxed for the night watching the sunset and I started the latest Elin Hilsebrand novel (28 Summers). All in all the sense of adventure of Day 6 in Maine felt almost normal as we continued to just enjoy ourselves and the beauty around us.


  • Pre-Breakfast: Apple Turnover (Kate) and Cinnamon Bun (Brandon) from the Buck’s Market
  • Breakfast: Blueberry pancakes with Bacon 
  • Lunch: Chicken Salad in a hot dog bun
  • Snacks: Cheese and Crackers with Salami and a Cranberry Relish
  • Dinner: Chicken with Yellow Squash and Zucchini in a Butter Marsala with a little too much Sriracha added (whoops!))

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