Ultimate 7-Day Maine to Memphis Road Trip Adventure Itinerary

Wake up to the aroma of freshly brewed coffee and enjoy a hearty breakfast at Little Tap House. Fuel up for a morning of brewery exploration.

Join the Portland, Maine Local Brewery & Spirits Bus Tour for an afternoon of beer and spirits tasting. Visit renowned breweries and distilleries, learning about the craft and enjoying the flavors of Maine.

As the sun sets, take a leisurely walk along the Eastern Promenade. Enjoy the panoramic views of Casco Bay and the surrounding islands. For dinner, head to Five Fifty-Five for an elegant dining experience with a menu featuring local and seasonal ingredients.

Start your day with a visit to the Tate House Museum, where you can explore the historic home and learn about life in 18th-century Maine. Afterward, enjoy a delightful breakfast at Duckfat, known for its indulgent sandwiches and, of course, duck fat fries.

Spend your afternoon shopping at the Kittery Premium Outlets, where you can find great deals on a wide range of brands. Take a break and grab lunch at The Green Elephant Vegetarian Bistro, offering a refreshing vegetarian menu in a cozy setting.

For dinner, experience the culinary artistry at Union Restaurant, which focuses on locally sourced ingredients and creative dishes. End your evening with a stroll through the vibrant downtown area, perhaps enjoying a drink at a local bar or lounge.

Enjoy a leisurely morning with a self-guided audio tour using the Smartphone Old Port Portland, ME Audio Walking Tour APP/GPS. Explore the charming Old Port district at your own pace, taking in the architecture and waterfront views.

For lunch, head to Nosh Kitchen Bar for a casual yet gourmet experience. Their menu features a variety of comfort foods with a creative twist.

As the day winds down, visit the iconic Portland Head Light, Maine's oldest lighthouse. Take in the breathtaking coastal scenery and enjoy a peaceful evening by the sea. For dinner, return to Fore Street, a celebrated spot for its farm-to-table offerings in a rustic, elegant setting.

Begin your day in Boston with a visit to the historic Freedom Trail. Immerse yourself in the rich history of the city as you walk the trail and pass by 16 significant landmarks.

For lunch, indulge in the flavors of Boston's famous clam chowder at Neptune Oyster, a local favorite for seafood. Afterward, take a stroll through the charming North End, also known as "Little Italy," and explore the narrow streets and historic sites.

For a memorable dinner, head to Mike's Pastry in the North End and choose from a mouthwatering selection of Italian pastries and desserts. End your evening with a scenic Harbor Cruise, offering stunning views of the city skyline and waterfront landmarks.

Start your day with a delightful breakfast at The Friendly Toast, known for its quirky decor and creative menu. Fuel up for a morning of exploring Portsmouth.

Take a guided walking tour of the city with the Portsmouth, NH Self-Guided Historic Audio Tour. Discover the rich history and charming architecture as you visit historic sites and hidden gems.

For dinner, enjoy the vibrant atmosphere and contemporary American cuisine at Jumpin' Jay's Fish Cafe. Pair your meal with a selection from their impressive wine list. Afterward, take a leisurely stroll along the waterfront and enjoy the scenic views.

On your last morning in Portland, savor a delicious breakfast at Back Bay Grill, known for its upscale, yet welcoming, ambiance and a menu that features a fusion of flavors.

Spend your final afternoon in Portland on a self-guided tour, using the Portland Exploration Self-Guided Driving & Walking Tour. Visit any spots you may have missed and take in the scenic beauty of the city and its surroundings.

For a memorable farewell dinner, return to a favorite spot or try Grace Restaurant, where the elegant setting and refined menu will provide a fitting end to your Maine culinary journey. Raise a glass to a week of unforgettable experiences and flavors.