Maine - Oyster Yachts Insider Sailing Guide

Friday, 16th October 2020


From immaculate beaches to its impressive mountain backdrop, Maine is an area renowned for its wild, natural beauty. Yet there is one simple fact that stands out head and shoulders above the rest, Maine is big, really big.

With a coastline just shy of 3,500 miles, it is the fourth longest coastline in the States, bigger than those of Texas and California. Yet, the irony of such an expansive cruising ground is that once you are there, exploring this special region doesn’t mean that long days covering big distances are required. Instead, Maine can be enjoyed in bite sized chunks and cruised at your leisure.

So, while we have set out a suggested programme that will help you do just that, the following guide is less of an itinerary and more of an indication as to how to enjoy two weeks of leisurely cruising based on around half a day’s sailing at a time.

Furthermore, with this in mind and with so much to choose from, those that do want to stretch their legs a little more it is easy to extend your visit without turning the trip into a race against the clock.

Aside from its wildlife with seals, dolphins, whales and a wide variety of birds, Maine is also well known for its seafood restaurants ranging from local lobster shacks to five-star venues. And if this appeals, you should definitely plan to schedule in some time ashore.

The bottom line is that Maine is a special place and while getting there takes a little longer and will often require patience with weather that doesn’t always play ball thanks to its famous fog, as those that have become hooked will attest, this is a very special destination and well worth the effort.

Oyster Yachts News Maine Insider Sailing Guide Tips | Still Lake


For all these reasons and plenty more, the key tip is that Maine takes time.

With such a large area to explore and with so much to see, accepting that two weeks only scratches the surface will help to set the right pace.

Getting the boat to the area is a mini project in itself. The 157nm trip from the Cape Cod Canal to Camden will take around 24 hours, (30 hours from Newport). This can be broken down into two legs if you prefer by making the first stop after 100nm in Portland.

This city is popular with some who are joining their boats as it is close to the airport, there is a large marina and plenty of shopping and eating along with good music and nightlife. In the summer there’s a great fish market and plenty of farmers’ markets too.

 Oyster Yachts News Maine Insider Sailing Guide Tips | Camden Harbour


Start point – Camden

Camden in Maine is the hub for cruising in Penobscot Bay. The sailing here offers reasonable stretches in deep open water and is similar to the Scottish Hebrides.

Camden a classic Maine town. Although it is busy with tourists in summer it is still authentic Maine. It is important to reserve dockage/moorings in advance because they sell out and the anchorage isn’t great. Lyman Morse at Wayfarer Marina is a great marina and bar and is a short walk or dinghy across into town. As you would expect from such a hub, there is lots of shopping with several must visits that include:

Oyster Yachts News Maine Insider Sailing Guide Tips | Boat

Day 1 - Camden to Pulpit Harbor

Leave Camden to sail across Penobscot Bay and anchor in Pulpit Harbor, one of the most peaceful and protected anchorages in Maine, a quiet cove with Ospreys.

Day 2 - Pulpit Harbor to North Haven

From Pulpit Harbor head down to the southwest before turning northeast to head towards the Fox Island Thoroghfare and North Haven.

Day 3 - North Haven to McGlathery Island

In the morning, continue east through Fox Island Thorofare to Merchant’s Row, just south of Deer Isle.  There are many islands here with beautiful small coves in which to anchor for the evening. McGlathery Island is a must where you can anchor at the Eastern end. This is a protected uninhabited island which has a nice sandy beach and a path that goes around the island. This is a favourite island for those in the know.

Oyster Yachts News Maine Insider Sailing Guide Tips | Seals

Day 4 - McGlathery Island to Southwest Harbor

Head northeast for Mount Desert Island, the home of Acadia National Park. If you enjoy hiking there are miles of beautiful trails to explore. Another option is to sail into Somes Sound on the south side of the island. The only fijord on the east coast, Valley Cove is a great spot to anchor in for lunch. Spend the night on a mooring in Southwest Harbor.

Day 5 - Southwest Harbor to Northeast Harbor

Staying in this area, head to Northeast Harbor and visit the beautiful Cranberry island along the way.

Day 6 - Northeast Harbor to Swans Island

Heading back towards the south west, Swans Island feels remote and has the true flavour of the Penobscot. This island makes its living fishing for lobster and is virtually untouched by tourism. There is a totally protected harbour and rental moorings. You can sleep well and secure here. Good lobster is available and this is a great place to explore the town on foot, or with dinghy. A lovely Maine place.

Oyster Yachts News Maine Insider Sailing Guide Tips | Deer Island

Day 7 - Swans Island to Center Harbor

Heading northwest takes you through the Eggemoggin Reach to Center Harbor. This is an amazing sail with the right wind and clear sky. You will go under the Deer Island Bridge (clearance 85ft) and make your way to Center Harbor. The town of Brooklin offers a General Store, the cosy Morning Moon café and possibly the most charming public library on the planet. There are plenty of craft shops and galleries which are all an easy stroll from here down to the Reach.

Take in some local flavour at the Brooklin Inn where in the basement Pub you can chat with some of the local characters from the Wooden Boat School. The Brooklin Boatyard is a great place to check out the local marina life, opened in 1960 by Joel White and presently operated by his son Steve. They have the best craftsmen in the state and visitors are welcome. Ask for Steve, Frank or John to give you a tour.

For dinner, have a lobster bake at the Wooden Boat School Building.

Oyster Yachts News Maine Insider Sailing Guide Tips | Lobster Fishing Boat

Day 8 - Center Harbor to Castine

Castine is a small Maine town which is on the mainland. There are a few quaint stores and a decent market. This is where the Maine Maritime Academy is based, sometimes the huge research ship is on the dock. Denett’s Wharf is a nice place to eat.

The tide can rip in this harbour so docking can be tricky. You may want to get a mooring for a few hours and then tuck into Smith Cove for the night.

Day 9 - Castine to North Haven Island

A good long day sail to North Haven which is a small island with a few shops. There is a gallery with paintings by Eric Hopkins which are worth seeing. Anchor or pick up mooring in Fox Island Thorofare. The local market is about a 3 mile walk from town. You can get lobsters from Brown’s which is right off the dock.

Day 10 North Haven to Isle au Haut 

Anchor in Duck Brook and hike up to Duck Mountain for a view from the highest island in Penobscot Bay.  

Oyster Yachts News Maine Insider Sailing Guide Tips | Rockport

Day 11 - Isle au Haut to Vinalhaven.

Vinalhaven is Maine’s largest offshore island community. Carvers Harbor, on Vinalhaven’s southern end is home to one of the world’s largest lobster fishing fleets.

Day 12 - Vinalhaven to Rockport

Crossing the open stretches of the West Penbscot Bay, sail from Vinalhaven to Rockport. Here, one of the key places to visit is the Farnsworth museum which offers a nationally recognized collection of works from many of America’s greatest artists such as Andrew Wyeth.

Day 13 - Rockport to Camden

From here it’s a beautiful and straightforward sail along the coast back to Camden Harbor.

Day 14

After a relaxing morning depart for your journey home.

Oyster Yachts News Maine Insider Sailing Guide Tips | Cruising


While Maine is a beautiful part of the world, those that known it well say the best time to visit is during the last three weeks in August. The water is warm and the weather is usually settled.

However, it’s important to remember that this is still an exposed coastline that has a reputation for fog and will generally be colder than further south.

Just as those who are familiar with the west coast of Scotland take each and every sunny day as a bonus, so the same can be true of Maine. As a result, so long as you’re armed with realistic expectations and ready to take the weather as it comes it will always be a stunning place to visit.

So, while Maine may be big, it is easy to create a fascinating and easily managed cruise that can be adapted to suit the weather without having to face the consequences of a long passage to get back on schedule.

Oyster Yachts News Maine Insider Sailing Guide Tips | Maine Coast


Penobscot Bay — A Cruising Guide to the Maine Coast

This guide provides well written stories with hand drawn charts and beautiful pictures of the area that provide plenty of ideas and reasons to visit some of the special local areas. Coverage of every harbour and anchorage are included along with detailed suggestions for shoreside activities from hiking to dining.


In Maine you can’t navigate at night as there are too many lobster pots, even navigating during the day is tricky in certain places. Generally, it is best to get a mooring rather than anchor.

This cruise plan is based on notes from Molly Marston– Head of Oyster Charter who lives in the area and has both cruised this region for many years and provided plans for those who are chartering in the area.


Alan Parker - 82 Dama de Noche 

"We had an amazing summer in Maine on Dama de Noche, with all the family rotating in shifts.  It truly is a magical coastline, like Cornwall on steroids!  I really recommend it for the cruising experience of a lifetime, as long as you don't mind zig zagging through a million lobster pots.  p.s. the lobsters themselves are worth visiting for alone!"

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