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Exploring Shorelines: Newport to Portland Maine Itinerary

The New England Coast is known for its rugged coastline and historic ports. When you sail the Newport-Portland, Maine itinerary, you will experience this beautiful area’s history, wildlife, and cuisine.

Newport to Portland Maine itinerary
Southeast Lighthouse, Block Island, Rhode Island.

Day 1 | Newport, Rhode Island

Meet your yacht in Newport. This town is home to the famed New York Yacht Club, which kept America’s Cup trophy safe for 132 years. Visit historic buildings, peruse the boutiques, and enjoy dinner at a waterfront restaurant.

Day 2 | Block Island

Block Island is a great first stop on your sailing vacation. Whether you enjoy outdoor activities, art, music, shopping, dining, or simply enjoying the scenic beauty, this island has it. Best of all, you won’t find any traffic lights or chain stores here.

Day 3 | Nantucket

Charming Nantucket awaits you with sandy beaches and cobblestone-paved streets. Visit Cisco Beach and the Jethro Coffin House (the oldest house on Nantucket). See the Sankaty Head Lighthouse, Great Point Lighthouse, Brant Point Lighthouse, and the Maria Mitchell Aquarium.

Day 4 | Martha’s Vineyard

Famous for being a summer colony, Martha’s Vineyard is an island just south of Cape Cod and accessible only by boat or air. This lovely island has quaint harbor towns and historic lighthouses. And, since Martha’s Vineyard is an island, it has many beaches to explore.

Day 5 | Elizabeth Islands

Sail north of Martha’s Vineyard to the chain of small islands known as the Elizabeth Islands. Only two of the islands are open to the public, and the Forbes family privately owns the others. These secluded islands are a beautiful environment for simply relaxing and enjoying the scenery.

Portland Head Lighthouse at Cape Elizabeth.
Photo by haveseen on Unsplash.
Portland Head Lighthouse at Cape Elizabeth.
Photo by has seen on Unsplash.

Day 6 | Hadley Harbor

Hadley Harbor is the anchorage for the night. This is a very protected anchorage and provides the perfect spot to kayak or swim.

Day 7 | Hyannis

Head towards Hyannis on Cape Cod, home of the private Kennedy Compound and the JFK Hyannis Museum on Main Street. Main Street is also a fantastic place to shop, dine, and enjoy live music. Other activities include golfing, fishing, and windsurfing.

Day 8 | Provincetown or Plymouth

Head towards Cape Cod Bay, where you can stop at Provincetown, located on the tip of Cape Cod and home to gorgeous beaches, excellent restaurants, art galleries, and shops. Or, if you choose, continue to Plymouth Bay. Here you can see the legendary Plymouth Rock, the historic landmark where Pilgrims are thought to have landed. In addition, tour the Mayflower II, a full-scale replica of the original ship that carried the Pilgrims.

Day 9 | Boston

Today, continue north for Boston, possibly stopping at Castle Island on the way to explore the historical site of Fort Independence. Dock at Rowes Wharf Marina is in the heart of downtown and very close to the city’s attractions. Walk along the Freedom Trail and see historical sites such as the Paul Revere House, the Bunker Hill Monument, and the USS Constitution. After exploring, enjoy lunch or dinner at one of Boston’s seafood restaurants or trendy food trucks.

Day 10 | Wentworth by the Sea

Wentworth by the Sea is a Marriott Hotel & Spa that overlooks the Atlantic Ocean from the island of New Castle. This is one of the few surviving Gilded Age grand hotels. Enjoy all the resort offers, including spa treatments, dining, and two swimming pools.

Day 11 | Kennebunkport, Maine

Arrive at Kennebunkport, Maine, the summer home of President George H. W. Bush and several generations of the Bush family. Soak up the sun on Goose Rocks Beach, or use your yacht’s water toys. This is a fantastic spot to explore the peaceful waters by kayak or paddleboard. Onshore, make your way to the downtown area. Here you will find boutiques, art galleries, and restaurants.

Day 12 | Portland, Maine

Take a trolly tour to overview the city and learn about the historic buildings, architecture, and waterfront. Or, explore on your own. Walk the cobblestone streets and check out the boutiques, bars, and restaurants. In the summer, visit one of the country’s oldest continuously running farmers’ markets. Embrace your inner foodie and take a Foodie Tour. Portland has countless restaurants, cafes, and pubs, and the Food Network named Portland one of its top five “Most Delicious Destinations.”

Enjoy fresh seafood in Portland. Photo by Viviana Rishe on Unsplash.
Enjoy fresh seafood in Portland. Photo by Viviana Rishe on Unsplash.

Day 13 | Boothbay, Maine

Dock at laid-back Boothbay. Here you can kayak through quiet coves, visit island lighthouses, and walk the 1,000-foot-long footbridge that connects the east and west sides of the Harbor. Visit the Coastal Maine Botanical Gardens, Boothbay Railway Village, or the Maine State Aquarium.

Day 14 | Camden, Maine

On the last full day of your Newport to Portland, Maine itinerary, visit Camden. Camden is full of activities for outdoor enthusiasts and nature lovers. Hike, fish, and visit Barret’s cove, a freshwater beach on Megunticook Lake. See lighthouses, explore Camden Hills State Park, and in the summer, see the annual Parade of the Tallships. The downtown area offers gourmet dining, art galleries, and boutiques.

Day 15 | Bar Harbor, Maine

End your Newport to Portland, Maine Itinerary in classic Bar Harbor.