I have to start by saying how much both Amanda and I LOVE sailing Maine. We have only been cruising the coastline for three seasons, two of those offering trips aboard our Neel 45 trimaran, and we feel as we have barely scratched the surface. Maine has thousands of islands, hundreds of passageways, and a hand full of big inland bays, protected from the North Atlantic Ocean. Thus only a lifetime of cruising will yield a complete exploration. However, in our relatively short amount of time, I would like to share our Top 5 Go-To Anchorages.

Of the several large bays, or island grouped areas, we have focused our travels in the Penobscot region, basing our trips out of Rockland. From here, it is possible to sail to our top 5 anchorages aboard our quick trimaran.

Without sounding like a meandering online recipe, here are Amanda and I’s picks:

Valley Cove

Only anchorage in Maine (or really anywhere on the East coast) where you can anchor in a fjord and look out of your companionway to 500+ft granite peaks. The anchorage is surrounded Acadia National Park, so right from the beach where you can land your dinghy, you have access to 20+ miles of fantastic granite-peaky trails.

The anchorage is a little deep (~10m / 33ft) so plan accordingly with your ground tackle. But, the holding is fantastic and protection from storms is even better. Mind the Coast Guard bouy in the middle of the bay!

Holbrook reserve

Nestled at the top of Penobscot bay, just outside of Castine, lays this wonderful protected anchorage with Holbrook island on the West and Holbrook island sanctuary to the South. We love how remote feeling this anchorage is, coupled with easy hiking access. No need for beach landings here as there are not one, but TWO free docks to use. To boot, there are three guest moorning balls, orange, and denoted with ‘Guest’. Meandering the trails on Holbrook island is very pleasant, but a must is a hike up ‘The Summit Trail’, a quick but steep 0.9mi jaunt ending with exceptional views.

The anchorage is moderately deep in places, but shallower spots can be found just East of Holbrook island or off Indian Bar beach. Both entrances should be sailed with caution as there are various rocks and ledges which would come to a surprise if you weren’t checking your charts.

Hell’s Half Acre (Merchant Row Islands)

We could probably write a ‘Top 5’ just on the Merchant Row Islands (group of islands south of Stonington). However, condensing it down, our favorite has been this little secluded and super protected anchorage called Hells Half Acre. One big advantage is the protection, which when anywhere close to a big lobster town like Stonington, means you usually get the 4am ‘wake’ up call. You can access the little island of Hells Half Acre, which doesn’t offer much in terms of walking, but, it’s a great stop to stretch your legs, or even go for a summer swim off the granite beaches. The water there looks like you're in the Caribbean of the North!

Duck Harbor (Isle Au Haut)

Looking for one of of Acadia National Park’s best anchorage-to-hiking trail? Tuck into Duck Harbor on the South West corner of Isle Au Haut (translating to ‘high island’), and anchor between the two inlets. There is a public dock to tie your dinghy to (backside only, frontside is for a small ferry boat), and miles of incredible hiking trails are now at your disposal. The peak trail is probably the most scenic we have seen of all our hiking along this coast, so is absolutly worth the sweat to get there.

The anchorage can be a bit intimidating as it’s fairly deep and narrow. Shallower draft boats can tuck up next to the dock area, while deeper draft should stay a little further out. Also, there is some, but not a lot of protection from Atlantic swell, so best advised to visit when on the calmer side.

Seal Cove

Ah, an absolute Vinalhaven classic! Similar to Holbrook, this is a sort of ‘inland lake’, created by a collection of islands, passageways, and only one entrance. As you sail through, you’ll find lots of seals, granite islands, and in the summer, sailboats tucked away here and there. It is absolutely quiet and peaceful with no traffic, and no towns or harbors. If you are a fan of kayaking or paddleboarding (SUP), this is your spot!

We like to sail this passageway when we can as it offers a real challenge to a keen sailor. Enter the cove and turn left and sail up as far as you can, mind your ride though as it can really work against your progress. Our preferred anchorage is on the West side of Hay Island where you’ll find 3-5m / 8-15ft of solid mud holding.