Sailing Maine: The Ultimate Guide

By Mike Sellers •  Updated: 04/13/22 •  14 min read

Maine is known for its beautiful, rocky coastline, its lighthouses, and its picturesque islands. If you think about it, Maine and sailing seems to go hand-in-hand.

So, if you’re looking for a fun get away with your family or friends that also involves water sports, hang on because I’m going to tell you everything you need to know when taking a sailing trip in Maine.

The Maine Coast

Maine coast is 3,500 miles long and includes 4,613 islands in all. About 1,400 of these islands are named. The largest island is Mount Desert Island (MDI), with an area of 108 square miles, located in southwest Maine on the Atlantic Ocean. The second largest island is Vinalhaven at 38 square miles with a population of 1,165 people (2000 census).

The state’s coastline extends into more than 400 harbors and bays that provide excellent opportunities for boating and sailing. Island towns include: Chebeague Island in Casco Bay; Islesford on Little Cranberry Island in Blue Hill Bay; Monhegan Island in the Gulf of Maine; North Haven on North Haven Island in Penobscot Bay; Peaks Island near Portland; Vinalhaven on Vinalhaven Island in Penobscot Bay; Matinicus Isle off Port Clyde.

Maine Sailing Winds

There are no bad sailing winds in Maine, just some that are better than others. The best sailing winds are from the northeast in the early summer (April to June) and south to southwest in the late summer (July through September).

The second-best sailing winds are from the southeast and northwest. These are great because they’ll keep your sails full but give you a bit of chop so you can enjoy a bumpy ride.

Southwest and northeast winds will provide you with a smooth, relaxed sail.

Rich History

The region has a rich history, with many historical sites to explore. You’ll find the remains of the first English colony in America at Popham Beach. The site was actually located in present-day Phippsburg and is situated along a beautiful stretch of beachfront property on the Kennebec River near Bath. It was established by the Plymouth Company colonists from England, who arrived in 1607 and named their settlement Fort St George. However, within one year nearly all its inhabitants returned to England due to harsh winter conditions and attacks by native tribes.

In 1614 Captain John Smith charted the coastline of what is now Maine and discovered many natural harbors as well as plentiful supplies of fish and seafood, which sparked renewed interest in colonization there.

In 1620 English separatist Puritans sailed from Europe aboard Mayflower to settle in present-day Plymouth Colony, Massachusetts. In 1621 Samoset, an Abenaki Indian chief whose tribe lived around Pemaquid Point (northeast end of Muscongus Bay), befriended William Bradford (1590–1657) who was then governor of Plymouth Colony—and became the first Native American known to have spoken English to Europeans.

Ocean Life: birds, seals, fish and shell fish

The Maine coast is teeming with fish, shellfish, and other ocean life. You’ll see large and small fish – including lots of lobster – seals, sea lions, whales, birds of all kinds, oysters and clams, mussels and scallops. Woah!

If you enjoy watching nature in action while you sail or kayak along the coast, be sure to keep an eye out for whales!

When to visit

Most years, the sailing season in Maine runs from mid-May through mid-October. However, there are a couple of caveats to that statement. The most important is that the sailing season depends on the weather (and since Maine’s weather is notoriously fickle, you can’t really always know what it will be).

Certainly, June through August is the prime time for sailing. During those months you can expect warm temperatures and consistent winds from the east. However, even then, summer storms with strong winds from any direction can make sailing uncomfortable or unsafe.

Cooler and more unsettled conditions prevail in May and October but with some luck they won’t prevent you from getting out on the water at least some of the time during those months as well.


There are two seasons in Maine: summer and winter. Summers are short and sweet—they’re about eight weeks long, starting at the end of June and going through most of August.

During these months, the weather is cool but pleasant, with temperatures averaging around 70°F (20°C) during the day. The sea temperature is also cool, so you’ll want to bring a wetsuit if you plan on doing any swimming.

The winters in Maine can be long and harsh. There’s lots of snow between November and April, but by May it has usually melted away to make room for springtime.

If you travel during the colder months, make sure that your sailing adventure is not one of the first things you do after getting off the plane! Instead, give yourself time to acclimate by spending a few days in Portland or another town before heading out onto the water.

Speaking of which—what time of year should you pay a visit? The best time to travel to Maine is in May or September when temperatures are milder than they are in July or August (in those peak-summer months it gets hot!).

You may also want to avoid visiting during local holidays such as Independence Day (July 4th), Labor Day weekend (the first Monday in September), and Columbus Day weekend (the second Monday in October).

Best Places to Sail in Maine

Bar Harbor

We don’t want to be the cheapest or second-cheapest place we could possibly be—we want to encourage visitors to stay with us and enjoy all of our Maine attractions. That’s why so many of our tourism resources are free. Be sure to check out our state parks, Acadia National Park, Mount Desert Island, Boothbay Harbor and especially Bar Harbor—the quintessential New England village just across town from us and a great place for tourists of all ages.

Sail Maine offers a variety of outdoor adventures for people who love the water from kayaking to mountain climbing to whale watching. But there’s more than just adventure: sailing can also be a great way for you, your family and friends alike, to experience Maine at its best without spending too much money on accommodations.

Monhegan Island

When sailing maine one of the best places to go is Monhegan Island. It’s only accessible by boat, but they have a ferry that leaves regularly from Port Clyde and it’s only $15. There are no cars on Monhegan, so you’ll need to plan ahead for how you want to get around the island. You can rent bikes for $20 for the day or you can walk around the whole island in about 4 hours. It’s beautiful with great hiking trails and cliffs that look out over the ocean.

Seguin Island

If you’ve never been to this lighthouse before, it’s worth a visit because of its history as one of Maine’s most important lighthouses. Built in 1795, it was an essential light for sailors navigating to avoid rocks and shoals when entering the Kennebec River from offshore in Casco Bay. This island is also home to numerous navy men who lived here in isolation while manning the lighthouse and later, guarding it during World War II.

Penobscot Bay

Penobscot Bay is a popular summer tourist destination, and for good reason. The rocky coastline features magnificent mountain views, historic lighthouses and plenty of opportunity for sailing and boating. Penobscot Bay is an inlet of the Gulf of Maine on the Atlantic Ocean that lies south of Blue Hill Bay and west of Eggemoggin Reach. This area is home to many coastal towns, including Camden and Rockport. Explore more than 30 islands between Mount Desert Island and the mainland—if you’re lucky you may spot bobcats, eagles or seals while you’re out there!

Boothbay harbor

Boothbay Harbor, Maine, is one of the best places in the world for sailing. With its deep harbor, warm summers, and great nautical traditions, it is a place to make memories for sailors of all ages. Whether you are planning on bringing your own boat or renting one from a local charter company, Boothbay Harbor offers you a chance to sail with the wind in your hair and water under your keel.

Booth Bay Harbor

With so many great options for sailing available in Boothbay Harbor, we’re sure you’ll find something that fits both your skill level and budget. We’ve compiled a list of seven easy ways to get out on the water this summer!

Blue Hill Bay

Blue Hill Bay is one of the best cruising grounds in Maine. From Bar Harbor, you can head to Blue Hill directly which is about 25 miles away, or stop over at Mount Desert Island and circumnavigate the island before sailing south to Blue Hill. Either way, it’s a great trip for families looking for a relaxed charter, or experienced sailors who are interested in an overnight passage. The entire coastline from Rockland to Blue Hill is dotted with islands and peninsulas offering many overnight stops along the way. If you stay on a mooring buoy in Blue Hill Bay’s outer islands instead of anchoring, you will experience the cooler water temperatures that provide a very comfortable sleeping temperature even on hot summer nights making it an ideal location for an extended charter or vacation.

Frenchman Bay

If you want to sail in a place that has it all, then Frenchman Bay is the place for you. From dramatic views of the surrounding ocean to peaceful days spent on the deck of your boat, there’s not much that this bay can’t offer.

Located just outside of Bar Harbor, Frenchman Bay will be an easy trip for most Maine sailors. Once you arrive, set up camp for a few days and enjoy all that the bay has to offer:

Mount Desert

If you’re looking for a place to sail in Maine, look no further than Mount Desert Island. It is the largest island off the coast of Maine, and one of its most popular tourist destinations. The rugged nature of its coastline and its accessibility via ferry from Southwest Harbor make it one of the best places to sail in all of New England.

Mount Desert Island is also known for other popular outdoor activities such as hiking, kayaking, fishing, and lobster catching. The only town on the island is Bar Harbor, which has a bustling downtown area full of restaurants and shops. One thing visitors will notice about this island is that there are many different types of restaurants to choose from regardless if you’re looking for pub fare or fine dining. For example, some popular places include Side Street Cafe and Jordan’s Restaurant which have a wide selection of seafood dishes.

Casco Bay

Casco bay’s southern shore is divided into a lower bay and an upper bay by Kennebec Point, site of Fort Preble in South Portland. The Upper Bay is home to Portland, Maine’s harbor and waterfront, as well as the Portland International Jetport. Its eastern end abuts the Fishing Banks and typical ocean swells make it too rough for safe boating. Numerous islands dot the smooth waters of Casco Bay in the central and northern areas; they are primarily residential except for Peaks Island (which includes a small village with shops).

Numerous municipalities border on Casco Bay, including Portland (the largest city in Maine), Freeport, Yarmouth, Falmouth, Cumberland, Cape Elizabeth, South Portland (largest municipality on the bay), Scarborough (smallest municipality on the bay), Westbrook, Long Island (with an island bridge connected to Peaks Island) and Chebeague Island.

What Else You Can’t Miss

Camden hills

The Camden Hills offer panoramic views of the islands. The mountains rise abruptly from the sea, and their slopes are heavily forested, except for open rocky areas near the summits. If your sailing trip takes you here (and you should make sure it does), don’t miss out on hiking these beauties.

Acadia National Park

Acadia National Park is a national park located in the U.S. state of Maine, southwest of Bar Harbor on Mount Desert Island. The park preserves about half of Mount Desert Island and its surrounding waters, as well as part of the Schoodic Peninsula on the coast.

Acadia offers hiking trails, bike paths and carriage roads to explore its rugged coastline and woodlands, along with ranger-led programs for kids. It has camping facilities but no lodging or food services–that’s all available in nearby towns, but you’ll need a car to get there if you’re sailing.

Maine sunset

Let’s get right to it. You’re probably wondering about the best time of day for sailing. The answer: sunset! While this may seem like an obvious choice, most people don’t consider it. Sunset is simply the best time to sail in Maine because…


There are many lighthouses in Maine, but let’s focus on three in particular: the Portland Head Light, the Spring Point Ledge Light and the Pemaquid Point Light. The Portland Head Lighthouse is considered one of the most picturesque lighthouses in America—and it’s not hard to see why. It has a historic brick tower that dates back to 1791 and has been used as the backdrop for many photographs over the years.

The Spring Point Ledge Light is closer to shore, so it can be seen easily from Fort Preble at Southern Maine Community College or Bug Light Park in South Portland. This lighthouse also serves as a reminder of dangerous ledges that boats should avoid. Last but not least, we have the Pemaquid Point Lighthouse which can be seen from an oceanfront park and museum in Bristol Mills, Maine (which happens to make for great viewing).

In addition to helping with navigation, these lighthouses also illustrate a few facts about the history of sailing: namely, how important safety is when navigating on open waters and how important lighting technology was when it came to guiding ships safely into ports.

Lobster boats

A lobster boat, or “lobstah” boat as we call them in Maine, is a key part of our state’s economic and cultural identity. Lobster fishing is the largest industry in Maine and the thousands of Mainers who participate in this industry are known as “lobstermen” (surprise! The women who do it are called “lobsterwomen”).

There are over 6,000 lobstermen currently licensed to fish for lobsters commercially in Maine, with most of their work taking place between Cape Elizabeth and Eastport. On average each Maine lobsterman works on his (and occasionally her) own boat and sets traps on the ocean floor by hand.

Each trap has a sign indicating who owns the trap along with a brightly-colored buoy that floats on top of the water so they can be found more easily.

Here’s something you may not know—Maine lobsters are sweeter than lobsters from other areas because they live where there’s plenty of cold water but not too much saltwater. The cold waters off Maine’s coast just happen to be perfect for raising sweet and delicious lobsters.

Most tourists only get to see them at restaurants, but here in Maine you have a chance to see them up close and personal when their catch arrives by boat at your hotel dock or harbor!

Wrap up

Maine is constantly ranked as one of the best destinations for sailing in the United States–and with good reason. It’s a stunning state with a rugged coast, breathtaking islands, and pristine lakes to explore from your sailboat.

Everything from the geography to the amenities is geared toward helping you enjoy your time on the water. Maine should definitely be on your sailing getaway list. It has something for everyone, no matter what type of sailor you are.

Mike Sellers

Hey there, my name is Mike Sellers. I’m the guy behind this website. I've been sailing for over a decade and I'm going to show you everything I know about how to sail better, cheaper, and smarter.