New England, USA 12-Day Trip Itinerary

Arrive at Boston Logan (BOS)

After your flight from Milan, arrive at Boston Logan International Airport.

Clear customs and collect your luggage.

Expect longer travel times during peak hours. Consider pre-booking a transfer for convenience.

Check into Boston Hotel

Check into your chosen hotel in a central Boston location, allowing you to easily explore the city on foot.

Consider hotels in areas like Back Bay, Beacon Hill, or the Seaport District for good access to attractions and dining.

Stroll Boston Common & Public Garden

Enjoy a leisurely walk through America's oldest public park, Boston Common, and the adjacent Public Garden with its famous Swan Boats and intricate landscaping.

A perfect way to unwind after your journey.

New England Holocaust Memorial

Visit the poignant New England Holocaust Memorial, featuring six glass towers representing millions lost.

A place for quiet reflection and remembrance.

The memorial is an outdoor, public space accessible at any time. It's close to Faneuil Hall and the North End.

Dinner in the North End

Experience authentic Italian cuisine in Boston's historic North End, known for its charming streets and delicious restaurants.

Reservations are recommended, especially on a Wednesday evening. Explore Hanover and Salem Streets for many options.

Walk the Freedom Trail

Embark on a self-guided walk along Boston's iconic Freedom Trail, visiting historical sites such as Paul Revere's House, Faneuil Hall, and the Old State House. This 2.5-mile red-lined path connects 16 historically significant locations.

Wear comfortable shoes. You can choose to walk the entire trail or just a segment. Guided tours are also available.

Lunch at Quincy Market

Enjoy a casual lunch at Quincy Market, part of Faneuil Hall Marketplace, offering a wide variety of food stalls and local eateries.

A bustling and popular spot for quick, diverse meal options.

Pick up Rental Car

Head to a convenient car rental location in Boston to pick up your vehicle for the scenic drive ahead.

A car is essential for exploring the New England coast.

Book your rental car well in advance, especially for summer travel. Ensure you have GPS or a reliable navigation app.

Scenic Drive to Salem, MA

Begin your coastal journey with a drive north to Salem, famous for its historic witch trials and maritime history.

Enjoy views of the Massachusetts coastline.

Explore Salem Waterfront

Wander around the historic Salem Maritime National Historic Site, see the Friendship of Salem tall ship, and enjoy the waterfront views.

Salem is walkable, with many shops and historical sites. If time permits, you could visit the Witch Museum (booking recommended).

Dinner in Salem

Dine at one of Salem's charming restaurants, offering a mix of seafood and international cuisine.

Explore Rockport's Bearskin Neck

Drive to Rockport and explore the picturesque Bearskin Neck, a narrow strip of land with art galleries, boutiques, and seafood shacks.

Don't miss the iconic Motif No. 1.

Gloucester Harbor & Fisherman's Memorial

Visit Gloucester, America's oldest seaport.

See the 'Man at the Wheel' Fisherman's Memorial and enjoy the bustling harbor views.

Scenic Drive to Southern Maine

Continue your scenic drive north, crossing into New Hampshire and then into Maine.

Take Route 1A or coastal roads through charming towns like Portsmouth, NH, and York, ME, stopping for photos.

Check into Ogunquit Accommodation

Arrive in the lovely coastal town of Ogunquit, Maine, and check into your accommodation.

Take some time to relax or explore the immediate area.

Walk the Marginal Way

Enjoy a breathtaking coastal walk along the Marginal Way, a paved cliff-walk path offering stunning ocean views, benches, and access to beautiful beaches.

Perfect for sunset views. The path is about 1.25 miles long and connects Ogunquit Beach to Perkins Cove.

Dinner in Perkins Cove

Dine at one of the picturesque restaurants in Perkins Cove, a charming fishing village at the end of Marginal Way, known for its fresh seafood.

Morning at Ogunquit Beach

Spend the morning relaxing on the expansive sandy shores of Ogunquit Beach, enjoying the ocean breeze and beautiful views. You can walk, swim, or simply soak up the sun.

July 4th will be busy, arrive early for parking if driving. Public restrooms and changing facilities are available.

Lunch in Kennebunkport

Drive a short distance north to Kennebunkport for lunch.

Explore Dock Square and enjoy a meal at one of its charming eateries.

Explore Kennebunkport & Harbor

Wander through the boutiques and art galleries of Dock Square, and take a stroll around the picturesque harbor. You might catch a glimpse of the Bush family compound at Walker's Point from a distance.

Independence Day Evening

Enjoy a relaxed evening.

Check local listings for Independence Day celebrations, which often include outdoor concerts, parades, and fireworks displays along the coast. Many towns will have their own unique festivities.

Be prepared for crowds and traffic. Reservations for dinner are essential tonight. Pack layers as evenings can be cool by the ocean.

Festive Dinner

Enjoy a festive dinner celebrating Independence Day.

Many restaurants will offer special menus.

Book your dinner reservation weeks in advance for July 4th.

Visit Nubble Lighthouse

Drive to York, ME, to see the iconic Cape Neddick 'Nubble' Lighthouse.

It's one of the most photographed lighthouses in Maine, perched on its own tiny island.

Drive to Portland, ME

Embark on a scenic drive further up the coast to Portland, Maine's largest city, known for its vibrant culinary scene and charming Old Port district.

Portland Head Light & Fort Williams Park

Visit Maine's oldest and most iconic lighthouse, Portland Head Light, located in Fort Williams Park.

Enjoy the stunning ocean views, explore the rocky coastline, and walk the park trails.

There's a small museum and gift shop. The park is excellent for photos and short walks.

Lunch in Portland's Old Port

Enjoy a delicious lunch in Portland's historic Old Port district, famous for its cobblestone streets, brick buildings, and fresh seafood restaurants.

Explore Old Port District

Wander through the charming streets of the Old Port, browsing unique boutiques, art galleries, and souvenir shops. Take in the bustling harbor activity.

Optional: Casco Bay Sunset Cruise

Consider an optional sunset cruise around Casco Bay, offering beautiful views of the Portland skyline, islands, and lighthouses from the water.

Book in advance, especially during summer. Pricing varies by operator. This is a great way to experience the coastal scenery.

Dinner in Portland

Enjoy Portland's renowned culinary scene.

From upscale dining to casual seafood shacks, there are options for every taste.

Portland is known for its James Beard award-winning chefs. Reservations are highly recommended for popular spots.

Scenic Drive to Camden

Enjoy a picturesque drive north along the Maine coast, transitioning from Southern Maine to the Mid-Coast region, arriving in the charming town of Camden.

Explore Camden Harbor

Wander through the quaint streets of Camden, known as the 'Jewel of the Maine Coast,' browse local shops, and admire the majestic schooners in the harbor.

Consider grabbing a coffee or a light snack at a local cafe.

Hike at Camden Hills State Park

Hike to the top of Mount Battie for panoramic views of Camden Harbor and Penobscot Bay.

There are various trails depending on your desired difficulty.

The drive up the auto road also offers stunning views if you prefer not to hike. Pack water and wear comfortable shoes.

Visit Rockport Village

Just south of Camden, Rockport is a quieter, equally beautiful harbor town, famous for its picturesque lighthouse and the statue of Andre the Seal.

Enjoy the art galleries and scenic views. Good photo opportunities here.

Classic Maine Lobster Dinner

Indulge in a fresh Maine lobster dinner at a local restaurant, savoring the regional specialty.

Drive to Pemaquid Point

Enjoy a scenic drive through picturesque towns and along the coastline to reach Pemaquid Point.

Visit Pemaquid Point Light

Explore the iconic Pemaquid Point Light, perched on a rocky promontory with crashing waves.

Climb to the top for spectacular views and visit the Fisherman's Museum.

Bring your camera! The unique layered rock formations are beautiful.

Coastal Maine Botanical Gardens

Immerse yourselves in the beauty of the Coastal Maine Botanical Gardens, featuring diverse themed gardens, walking trails, and impressive sculptures.

Allow plenty of time to explore this expansive and beautiful garden. Book tickets online in advance, especially during peak season.

Explore Boothbay Harbor

Wander through the lively Boothbay Harbor, known for its active fishing fleet, bustling waterfront, and charming shops.

Consider a short boat tour or a stroll along the footbridge.

Harborfront Seafood Dinner

Enjoy a delicious seafood dinner with views of Boothbay Harbor, perhaps trying some fresh scallops or clams.

Drive to White Mountains, NH

Embark on a scenic drive from Mid-Coast Maine west towards the majestic White Mountains of New Hampshire. Enjoy the changing landscapes from coast to mountains.

Lunch in North Conway

Stop for lunch in the charming village of North Conway, a hub for outdoor activities and quaint shops in the White Mountains.

Kancamagus Highway Scenic Drive

Drive a portion of the iconic Kancamagus Highway, a 34.

5-mile scenic byway designated an American Scenic Byway. Stop at overlooks for stunning mountain views.

There are many pull-offs and short walking trails to explore. The Russell-Colbath House offers a glimpse into local history.

Walk to Diana's Baths

Enjoy an easy, scenic walk to Diana's Baths, a series of beautiful waterfalls and cascades on Lucy Brook, perfect for relaxation and photos.

The path is relatively flat and well-maintained. Wear appropriate footwear for uneven terrain.

Mount Washington Cog Railway

Experience a historic journey to the summit of Mount Washington, the highest peak in the Northeastern United States, via the world's first mountain-climbing cog railway.

Enjoy breathtaking views.

The weather at the summit can be dramatically different from the base; bring layers! Book tickets well in advance, especially for summer.

Lunch near Bretton Woods

Grab a casual lunch near the base of Mount Washington or in the Bretton Woods area after your mountain adventure.

Explore Flume Gorge

Walk through the stunning Flume Gorge, a natural gorge extending 800 feet at the base of Mount Liberty.

Marvel at the granite walls, waterfalls, and covered bridges along the 2-mile loop trail.

The path can be steep in places with stairs; wear comfortable walking shoes. Book tickets online to ensure entry.

Franconia Notch Overlook

Enjoy a final scenic stop at one of the many overlooks in Franconia Notch State Park, capturing the beauty of the surrounding mountains and valleys.

Artists Bluff is a popular short hike with rewarding views, or simply enjoy a roadside pull-off.

Morning at Echo Lake State Park

Relax by the crystal-clear waters of Echo Lake, enjoying views of Cathedral Ledge and White Horse Ledge. You can swim, sunbathe, or walk around the lake.

Great spot for a picnic or simply enjoying the tranquil mountain scenery. Paid parking is available.

Drive up Cathedral Ledge

Drive to the top of Cathedral Ledge for breathtaking panoramic views of the Saco River Valley, Echo Lake, and the surrounding mountains.

The road to the summit is steep but paved. A great spot for photos and enjoying the expanse of the White Mountains.

Explore North Conway Village

Spend the afternoon exploring the shops, boutiques, and art galleries in downtown North Conway.

Enjoy the quintessential New England village atmosphere.

A good opportunity to pick up souvenirs or unique local crafts. There are also several casual dining options here.

Conway Scenic Railroad (optional)

Consider an optional scenic train ride from North Conway, offering picturesque views of the surrounding mountains and valleys, a leisurely way to see the landscape.

Various routes are available; check their schedule and book tickets in advance. This is an alternative to further driving.

Farewell Dinner in Intervale/North Conway

Enjoy a final dinner in the White Mountains, reflecting on your adventures in Maine and New Hampshire, and preparing for the next leg of your journey.

Drive into Vermont & Covered Bridges

Enjoy a scenic drive from the White Mountains region into Vermont, passing through picturesque landscapes.

Stop to admire one or two of Vermont's iconic covered bridges, such as the Taftsville Covered Bridge near Woodstock.

Routes 4 and 100 are renowned for their beauty. Take your time to stop at scenic overlooks.

Lunch in Woodstock, VT

Arrive in the charming village of Woodstock, often called 'the quintessential New England village'.

Enjoy a leisurely lunch at a local cafe or bistro.

Explore the village green and browse the unique shops after lunch.

Billings Farm & Museum

Visit this award-winning working dairy farm and museum, offering a glimpse into Vermont's agricultural heritage.

Explore the farm, historic farmhouse, and watch daily demonstrations.

A National Park site in partnership with the Marsh-Billings-Rockefeller National Historical Park. Great for understanding local history and nature.

Relax & Explore Woodstock

Check into your accommodation and take some time to relax.

Afterwards, enjoy a final stroll through the picturesque village of Woodstock, perhaps visiting some local art galleries or shops.

Dinner in Woodstock

Enjoy a delightful dinner at one of Woodstock's acclaimed restaurants, savoring local Vermont flavors.

Many restaurants feature farm-to-table menus. Reservations are recommended for popular spots on a Saturday evening.

Breakfast in Woodstock

Enjoy a final New England breakfast at your accommodation or a local cafe, savoring the peaceful start to your last day.

Scenic Drive to Boston Logan Airport

Begin your journey back towards Boston Logan International Airport (BOS) for your international flight.

Enjoy the changing landscapes as you drive from Vermont through New Hampshire and into Massachusetts.

Allow extra time for potential traffic, especially nearing Boston on a Sunday.

Lunch at Boston Logan Airport

Have lunch at one of the many dining options available at Boston Logan International Airport.

Airport Check-in & Security

Proceed with check-in for your international flight, clear security, and make your way to the departure gate.

Allow ample time for these procedures.

Departure from Boston to Milan

Board your flight from Boston Logan International Airport (BOS) back to Milan Malpensa Airport (MXP), concluding your memorable 12-day New England adventure.

Ensure all travel documents are in order.