14 Beautiful Places to Sail on the U.S. East Coast

Written by William Porter in Destinations

The East Coast of the United States has some of the more delightful and varied sailing grounds in the world. Whether you're looking for the secluded quiet of a remote anchorage or the bustle and hum of a popular summer destination, the variety is near endless and it all has its own beauty.

Starting from the north and working our way down the coast, here are eleven of the most beautiful spots to sail and cruise between Maine and Rhode Island.


The Maine sailing season starts late and ends early, and one short summer isn't enough time to do Maine justice. Although it can be cool and foggy, summer has plenty of warm days and pleasant evenings. The water is often chilly but bracing, beaches are popular, and the fishing is unmatched. Throughout the coast you'll find rugged shorelines, desolate lighthouses and unspoiled views.

Mt. Dessert Island, ME

Bass Harbor Lighthouse

With the Arcadia National Park centered on the island, Mt. Dessert Island has a wealth of natural beauty you can enjoy with miles of hiking and biking trails through the mountains, marshes, and lakes. Breathtaking views from the mountains are your reward, though even if you never leave the boat you'll see seals, seabirds, and other wildlife.

Bar Harbor, Maine

A free bus system links the entire island and takes you from Bar Harbor in the north to Bass Harbor at the sound and points between. Bar Harbor has commercial moorings and a few spots to anchor but is the largest town on the island and well worth a visit.

Southwest Harbor and Northeast Harbor are two of more popular harbors for moorings. Both have restaurants, groceries, access to the bus system, and lobster. Lots of lobster. From Northeast Harbor you can rent bikes with easy access to the extensive network of carriage roads and trails that cross the park. The views from the peaks of the twenty-six mountains are incomparable and worth the hike.

Penobscot Bay, ME

Penobscot Bay surrounds you with natural beauty and wildlife and easy access to lovely waterfront towns loaded with charm. With eleven large islands and countless small islets and harbors with a wide variety of terrain and shoreline.

From Rockland and Rockport to Castine and Northhaven you'll find plenty of pretty towns and villages to base your cruising. Near Castine you'll find Smith Cove, a typical anchorage for the area with tree lined shores, a wildlife preserve with walking trails, seals, porpoises, and birds. If you're lucky, you'll share the anchorage with a down-east schooner or tall ship.

For more remote and quiet, in Seal Bay on Vinalhaven is outside the reach of cell phones and electronic noise. You’ll be surrounded by trees and your company will be seals, birds, and other boats.

Penobscot Bay has a hundred anchorages like these to choose from, ranging from a busy town basin to the remote and wild spots where you'll hardly find another boat. Take care entering these remote harbors. Take caution, as the tides are quite large. It’s best to enter when the tide is rising but still low so most of the hazards and rocks that disappear at high tide will be visible as you pick your way through.

Portland and Casco Bay, ME

Portland Head lighthouse is the first of dozens of iconic and beautiful lights you'll see on your way through Casco Bay on the way to Portland. Maine's largest city has a rich cultural scene with excellent restaurants and a charming waterfront, yet as a small city it carries a small-town feel. Anchoring right in town is limited, but slips and moorings are available and there are anchorages nearby.

Caco Bay, Maine

Further into Casco Bay, you'll find scenic anchorages near picturesque seashores and lighthouses, while everything from lobster boats to classic schooners and ferries make their way around the bay. Hundreds of islands dot this archipelago - so many that it was once known as the "Calendar Islands" with one island for every day of the year.

Getting away from the city, you'll find rocky shores with dense forests and towns nestled in the middle of islands, pristine waters, and occasional fog. It's not a large bay, but it's broken up with coves and islands you could spend weeks exploring, looking for that spot of perfect beauty.


Massachusetts has some of the most accessible and varied destinations in New England. Marblehead, Buzzard's Bay, Salem and Boston Harbor are worth a visit even if we've not listed them here.

One of our favorite places to sail is Cape Cod Bay between Cape Ann and Provincetown. The rhumb line course between Gloucester to the Provincetown takes you through the Stellwagen Bank National Marine Sanctuary. This is a critical habitat for the endangered northern right whale and a summer feeding ground for humpbacks. In addition to whales, you may see dolphin and porpoise and countless seabirds.

Crossing these waters alone justifies the trip between two delightful places to visit if the prospect of seeing whales from your own boat excites you.

Cape Ann, MA

The "other cape" in Massachusetts, Cape Ann is home to Gloucester, Rockport, and some of the best kept secrets in New England.

Gloucester is a historic fishing town, but don't let the commercial nature put you off. The town has a distinct charm and isn't highly trafficked by visiting yachts. Near town are walks along the water past the famous Fisherman's Memorial, out to Stage Head, with lovely views of the harbor.

Nearby Rockport has New England charm mixed with art galleries, shops and tourist kitsch. Though the harbor is tight, moorings can be arranged or a nearby anchorage gives access in good weather.

A variety of beaches dot Cape Ann, from Gloucester all the way around the cape past Ipswich bay and up to the state line.

Provincetown, MA

The farthest point on Cape Cod hosts a distinctive culture amid the serene beauty and quiet of the remote cape. The town itself is filled with excellent restaurants, interesting shops, art galleries, a few museums and plenty of night life, while the harbor has constant turnover of visiting yachts and interesting traffic.

Completely surrounding Provincetown is the Cape Cod National Seashore. This preserve has forty miles of beaches, dunes, marshes and pristine natural habitats. Miles of bike and walking trails are accessible just outside of town. The ocean beaches and dunes are breathtaking.

Opposite town across from the harbor, Long Point is also part of the National Seashore. Anchoring there gives you quiet away from the bustle of town, where you can land your dinghy to explore the beach and lighthouse.

Nantucket, MA

The Grey Lady is a favorite vacation destination in southern New England. Waking up on the boat in the fog and watching it fade and lift as the boats and town come into view is a great way to enjoy your first cup of coffee. The variety and beauty of the boats and ships that pass, from sleek ferries to the famed "Rainbow Fleet" out on race night gives a non-stop panorama of things to see just sitting at anchor.

Upper Main St. Nantucket

Ashore, the town's cobblestone streets and old whaling-era buildings give an atmosphere like no other. In the quiet hours on a foggy morning you feel transported back to the age of wooden ships and iron men. Electric lights and cars feel out of place where it feels like the crew of the Pequod could step out of time and into the pub with you.

Bike and walking paths cross the islands, and many of the gorgeous beaches and smaller towns are easily reached by bicycle or bus. The island is low-lying and flat, with few serious hills to ride up so the cycling is not challenging.

Another favorite spot is Great Point, at the extreme tip of the island. You must rent a four-wheel-drive vehicle to get out there by land, but it's worth the trip for the remote, windswept beauty. Bring a camera, and a surf fishing pole if you can. Park on the sand with no one around, and for a little while all you will hear is the crash of the surf, the rustle of wind on the dune grass, and birds.

Martha's Vineyard - Edgartown, MA

Each major towns of Martha's Vineyard - Edgartown, Vineyard Haven, and Oak Bluffs - has its distinct character. And all are pretty in their own ways, from the quirky gingerbread houses in Oak Bluffs and the Bohemian touch of artsy Vineyard Haven, to the stately nineteenth-century buildings in Edgartown's historic district each town emphasizes something different.

Edgartown has a quiet anchorage off the lovely beach in Chappaquiddick, or reserve a mooring in the scenic inner harbor. Ashore, you'll find a variety shops and restaurants around the waterfront. Away from the commercial district, picket-fenced historic homes with lovely gardens lines the streets. From town, take the iconic Chappaquiddick ferry across the harbor or stroll out to Lighthouse beach to watch the boat traffic in and out of the harbor.

A walk up Main Street passes more shops in old buildings and the district court; turn right at the Old Whaling Church and you can catch a bus to other towns and beaches.

The Vineyard is known for its variety of gorgeous beaches. Most of the island is reachable via the bus system and bike trails, so no matter where you moor you can get around and see the best sights, though some of the more remote and private spots may need a car. Across from Edgartown you'll find Chappaquiddick Beach, just outside of town is the Joseph A. Sylvia State Beach, a calm family beach which runs over two miles from Edgartown to Oak Bluffs. For the more adventurous and surf minded, head south of town to Katama and South beach for a true ocean beach experience.

Martha's Vineyard - Menemsha, MA

Photo © Elkman (CC-BY-SA2.5)

Anchoring in a light southerly at Menemsha bight gives you easy access to the sleepy fishing village of Menemsha, with fantastic fish markets and seafood right on the dock. Far from the bustle of the larger towns and ferries you'll find a long, lovely beach, sweeping views of Vineyard Sound and the Elizabeth islands, and quiet.

Though Menemsha Pond is tricky to enter with a large boat, it is easy to explore in a dinghy. Recent dredging has opened it up to larger boats, but overnight anchoring is prohibited. Outside the village the Menemsha Hills Reservation Trails are open to walking and exploring.

West of Menemsha at the extreme end of the island is Gay Head, with breathtaking views of Cuttyhunk and the Elizabeth Islands, Vineyard Sound, and the open ocean. You may need to drive or take a bus to get there, but it's worth it. The sunsets are beyond description.

Cuttyhunk, MA

Across Vineyard Sound from Martha's Vineyard, Cuttyhunk is the opposite her larger, more crowded neighbors. You go there for the tranquility and the beauty and stay for the quiet. Instead of waterfront restaurants and bars, you have a single outdoor pizza restaurant, a taco or coffee cart, a fish market and an ice cream shop.

Hung on the west end of the Elizabeth islands, access to Cuttyhunk is only by seaplane, a small ferry, and private boat. Summer homes dot the island, but it never feels crowded.

Cutty is a walker's paradise, with trails, paths and roads stretching all over the small island. There are very few cars and truck, most summer residents use golf carts or bicycles and you can walk anywhere.

Moorings for boats up to fifty feet are available in Cuttyhunk Pond and outside the channel entrance during most weekdays, but they fill up on a first-come basis on the weekends, so get there early. No matter where you end up, you can't beat the mobile raw bar from the Cuttyhunk Shellfish Farm which will bring your order right to the boat while you wait for the sunset.

An early morning walk to the Cuttyhunk Fishing Club takes you to one of my favorite breakfast spots. The view overlooks Vineyard Sound and Gay Head light. It's a beautiful spot to catch a sunrise, even if someone wasn't bringing you breakfast and coffee. After breakfast with that view we never wanted to leave.

Rhode Island

The smallest state has a surprising number of pleasant cruising destinations. Narragansett Bay has beautiful and interesting places to sail from Beavertail Light all the way up towards Providence and Fall River. Though Newport is one of our favorites, you can spend a pleasant week or more exploring the bay further north.

Block Island, RI

Located eleven miles offshore from Point Judith, Block Island is a popular getaway spot for boaters from all around southern New England. Stunning beaches, charming vacation getaways, bike paths and walking trails, and great restaurants are some of the highlights. The main road in Old Harbor is a pleasant walk past shops, restaurants and old hotels, and the beach near town is a favorite with its beachfront bar and restaurant.

Come into the Great Salt Pond and anchor, pick up a rental mooring, stay in one of the three marinas. From there you can rent bikes, take a cab tour of the island or walk into town to rent a car or moped to explore. Two-mile long Crescent Beach is easily reached from the harbor with a short walk after beaching the dinghy, and several excellent restaurants and bars are right at the waterfront.

Southeast Light is a must-see spot, where you can tour the historic lighthouse and enjoy the magnificent view. At nearby Mohegan Bluffs you can follow steps down the cliffs to the water to a popular surfing beach. At the opposite end of the island, North Light sits on the beach at the end of a half-mile strip of sand where the waters converge around the island.

Newport, RI

Bowen's Wharf, Newport, RI

The original home of the America's Cup when it was taken from the British 1851, Newport lays its claim as the sailing capitol of North America to its roots in the 17th century as a valuable commercial port. Though the America's Cup is long gone, Newport is still a major recreational sailing center and you spend hours walking the docks or touring the harbor viewing classic 12 Meter cup yachts, J-Class legends, and countless other classic yachts.

Bowen's Wharf, Newport, RI

The town of has a wealth of historic buildings, from the oldest synagogue in North America, to massive Gilded Age mansions. The Cliff Walk passes the most of famous of these mansions, running from the west end of Easton Beach along the bluffs and rocks of the coast.

Just sailing out of Newport on a weekend day offers a continuous panorama of pretty boats of all shapes and sizes. With a regatta of some kind every weekend in the summer (and most week nights), colorful spinnakers will dot the horizon any time you’re on the water.

Across the bay from Newport is Conanicut Island and Jamestown, with bluff cliffs, waterfront parks and charming houses. A popular day trip is a circumnavigation around the island, ending with a sunset in Newport as the lights come up on the Claiborne Pell Bridge.

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