Fall Foliage and Coastal Charm: 7-Day Boston to Maine Journey Itinerary

Depart for Portsmouth, New Hampshire, and have a delightful breakfast at The Friendly Toast, a quirky spot with a creative menu. Explore the historic downtown area with its colonial architecture and boutique shops.

For lunch, head to Moxy, a restaurant that offers a modern take on New England cuisine. Afterward, take a relaxing harbor cruise to enjoy the coastal views and maybe spot some fall foliage.

Enjoy a cozy dinner at Ristorante Massimo, known for its authentic Italian dishes. Take a twilight walk along the waterfront and savor the peaceful atmosphere of this charming town.

Start your day with a scenic drive to Portland, Maine, and have a delicious breakfast at Becky's Diner, a local institution known for its seafood dishes. After breakfast, visit the iconic Portland Head Light and take in the breathtaking views of the rugged coastline.

For lunch, enjoy a lobster roll at Bite Into Maine, a food truck located near Fort Williams Park. Afterward, take a leisurely stroll through the charming streets of the Old Port district and explore the boutiques and art galleries.

Indulge in a memorable dining experience at Street & Co., a seafood restaurant housed in a historic building. After dinner, take a sunset cruise around Casco Bay and admire the fall foliage from the water.

Start your day with a gourmet breakfast at Figgy's, a cozy spot known for its creative dishes. After breakfast, take a guided foodie walking tour to sample a variety of local specialties and learn about the culinary scene in Portland.

After the tour, visit the Portland Museum of Art to admire its collection of fine and contemporary art. For lunch, try the innovative dishes at Central Provisions, a popular spot for small plates and craft cocktails.

Enjoy a farm-to-table dinner at Fore Street, a renowned restaurant that focuses on seasonal ingredients. After dinner, take a stroll along the Eastern Promenade and enjoy the city lights reflecting on the water.

Start your day with a hearty breakfast at The Sinful Kitchen, known for its indulgent brunch options. After breakfast, take a tour of the local breweries and distilleries, such as Rising Tide Brewing Company and New England Distilling.

For lunch, enjoy the food and beer pairings at Novare Res Bier Cafe, a popular spot for craft beer enthusiasts. Afterward, continue your tour of the city's vibrant craft beverage scene.

Have a casual dinner at Duckfat, a unique eatery known for its Belgian-style fries cooked in duck fat. After dinner, explore the lively nightlife in the Old Port district.

Start your day with a breakfast sandwich from Sisters Gourmet Deli, a cozy spot with a variety of options. After breakfast, rent a bike from Maine Coast Bicycle Rentals and explore the scenic coastal lighthouses on a self-guided tour.

For lunch, have a picnic at Fort Williams Park, overlooking the Portland Head Light. Afterward, visit a local farm or orchard to pick your own apples and enjoy the fresh air.

Enjoy a relaxed dinner at LFK, a neighborhood bistro known for its seasonal menu. After dinner, take a leisurely walk along the Western Promenade and enjoy the views of the city.

On your last day, have a leisurely breakfast at Tandem Coffee + Bakery, a popular spot for its pastries and coffee. Take a self-guided walking tour of the city, using the Downtown Portland In-App Audio Tour, and explore the hidden gems and historic sites.

For lunch, enjoy the vegetarian dishes at The Green Elephant Vegetarian Bistro, a local favorite for its Asian-inspired cuisine. Afterward, take a scenic drive along the coast and visit the charming town of Kennebunkport.

End your journey with a memorable dinner at Evo Kitchen + Bar, a restaurant that focuses on locally sourced ingredients. Raise a glass to your Maine adventure at a local brewery or wine bar.