New England Fall Foliage and Coastal Getaway Self Drive Explorer

After arriving at Logan Airport, meet your private transfer for a relaxing ride to your downtown Boston hotel. Once checked in, stretch your legs with a scenic stroll through the Boston Public Garden and Boston Common, catching early fall colors. Wander the cobblestone streets of Beacon Hill, one of the city's most charming neighborhoods. As evening sets in, head toward Faneuil Hall and dine at the historic Union Oyster House—the oldest continuously operating restaurant in America—famous for its fresh seafood and colonial ambiance. A perfect welcome to Boston's rich history and autumn beauty.

Today, dive into Boston’s iconic sights with a choice of unforgettable experiences. Hop aboard a classic Duck Boat Tour for a fun and informative ride through the city’s historic streets before splashing into the Charles River for scenic skyline views. Prefer sports history? Head to Fenway Park for a behind-the-scenes tour of one of America’s oldest and most beloved ballparks. This evening, make your way to the North End—Boston’s Little Italy—where you can indulge in delicious handmade pasta, fresh cannoli, and the warm, welcoming atmosphere of one of the city’s most beloved dining neighborhoods.

After a leisurely breakfast, pick up your rental car and begin your scenic drive north to Portland, Maine. Your first stop is the picturesque town of Portsmouth, New Hampshire, perfect for a relaxing lunch and a stroll through its historic downtown. Continue along the coast and detour into Kennebunkport, a quintessential New England village known for its charming shops, waterfront views, and presidential history. Before reaching Portland, stop at the iconic Portland Head Light in Cape Elizabeth for panoramic ocean views. After checking into your centrally located hotel, enjoy a sunset walk in the vibrant downtown and Old Port districts. Tonight, savor a fresh seafood dinner in the bustling port area.

Start today with a peaceful escape into Casco Bay. Board the ferry from Portland and enjoy a short, scenic ride to Peaks Island, a laid-back coastal retreat known for its charming cottages, quiet lanes, and sweeping ocean views. Take a leisurely stroll or rent bikes to explore the island, then enjoy lunch at a local café with a view. Return to the mainland in the afternoon for some downtime or a bit of shopping. This evening, indulge in dinner at one of Portland’s renowned James Beard Award-winning restaurants—a true celebration of Maine’s culinary excellence.

Today offers two unforgettable options to explore more of Maine. Freeport: Head just north of Portland to Freeport, home of the iconic L.L. Bean flagship store and a charming, walkable downtown. Explore the wooded seaside trails of Wolfe’s Neck Woods State Park, rich with fall color and ocean views. Cap the day with a craft brew tour at local favorites like Maine Beer Company or Mast Landing, then return to Portland for a cozy final evening. Bar Harbor: If you're up for a longer drive, venture to Bar Harbor and Acadia National Park. Hike scenic coastal trails, admire sweeping autumn vistas from Cadillac Mountain, and enjoy fresh seafood in this picturesque seaside town. Return to Portland for your last night in the Vacation State, full of memories and Maine magic.

After breakfast, depart Portland and journey west toward New Hampshire’s picturesque Lakes Region. Your route takes you through Conway, where you’ll begin the iconic Kancamagus Highway—a 34-mile scenic byway renowned for its breathtaking fall foliage, mountain vistas, and serene forest glades. Be sure to stop at scenic pull-offs like Sabbaday Falls, Rocky Gorge, and CL Graham Wangan Overlook to fully experience the beauty of the season. Continuing south, arrive in Meredith, a charming town nestled on the shores of Lake Winnipesaukee. After checking into your hotel, enjoy a leisurely lakeside walk along the waterfront, taking in the vibrant autumn colors reflecting off the water. Don't miss the Meredith Sculpture Walk, a year-round, juried exhibition featuring over 30 works of public art displayed throughout the village. This self-guided tour offers a unique blend of art and nature, with sculptures set against the backdrop of the lake and town. Conclude your day with a relaxing dinner at one of Meredith's cozy restaurants, savoring local flavors and the serene lakeside atmosphere.

After breakfast, begin your journey south toward the coastal elegance of Newport, Rhode Island. Known for its Gilded Age splendor, Newport offers a dramatic contrast to the mountain landscapes you’ve just left behind. Upon arrival, explore the city's grandest attractions—The Breakers, Marble House, and other opulent mansions once owned by America’s wealthiest families. Stroll along the famous Cliff Walk, where crashing waves meet historic estates, or take a scenic drive along Ocean Drive for sweeping Atlantic views. As the sun sets, check into your hotel and settle in for a relaxing evening in this timeless seaside town.

Today, savor the best of Rhode Island, whether you stay local in Newport or venture farther afield. In Newport, continue exploring the city's Gilded Age splendor. Visit opulent mansions like The Breakers or Marble House, stroll along the famous Cliff Walk where crashing waves meet historic estates, or take a scenic drive along Ocean Drive for sweeping Atlantic views. For a delightful afternoon, consider visiting Newport Vineyards in nearby Middletown. This 100-acre estate offers wine and beer tastings, farm-to-table dining, and a variety of events throughout the year. Feeling adventurous? Take a scenic drive to Providence, the vibrant capital. Stroll down Benefit Street’s Mile of History, explore the RISD Museum, or dine in the lively Federal Hill neighborhood. Alternatively, ferry to Block Island—a peaceful haven with dramatic Mohegan Bluffs, charming shops, lighthouses, and uncrowded beaches. A hidden gem worth the trip.

Today, depart Newport and make your way to Cape Cod, Massachusetts, where golden fall foliage meets sweeping sand dunes and salty sea air. Head straight for the Cape Cod National Seashore, a protected stretch of shoreline dotted with scenic lookouts, historic lighthouses, and quiet beaches. Spend the afternoon walking or biking along the Cape Cod Rail Trail, a 25-mile path that winds through charming towns, cranberry bogs, and forested groves ablaze with autumn color. In the evening, settle into your coastal accommodations and enjoy a fabulous seafood dinner—perhaps lobster, clam chowder, or fresh oysters—Cape Cod style.

Today, board the Steamship Authority ferry from Woods Hole for a scenic ride to Martha’s Vineyard, a classic island retreat steeped in charm. Begin in Vineyard Haven, browsing local shops and cafés before continuing to Oak Bluffs, home to whimsical gingerbread cottages and a lively harbor. In Edgartown, admire stately whaling-era homes and enjoy waterfront views from the lighthouse. Stroll the quiet streets, savor fresh seafood, and soak in the island’s laid-back beauty—long favored by U.S. presidents and vacationers alike. In the evening, take the ferry back to Woods Hole and return to your hotel for your final night in New England.

After breakfast, it's time to say goodbye to the coast and begin your journey back to Boston. Enjoy the scenic drive as you reflect on your unforgettable adventure—from the golden leaves of the White Mountains to the windswept beaches of Cape Cod. Upon arrival, return your rental car and check in for your onward flight at Logan Airport. Take with you the memories of charming towns, crisp autumn air, and some of the most spectacular foliage in the country. New England’s beauty will be waiting to welcome you back again someday.