New England, a region steeped in history and natural beauty, offers a unique blend of colonial charm and coastal allure. From the cobblestone streets of Boston to the picturesque shores of Portland, this area is a treasure trove of cultural and culinary delights. Known for its vibrant fall foliage, historic landmarks, and fresh seafood, New England is a destination that captivates travelers year-round.

Boston, the capital of Massachusetts, is a city where the past and present coexist harmoniously. As one of the oldest cities in the United States, Boston boasts a rich history that is evident in its well-preserved architecture and storied neighborhoods. Meanwhile, Portland, Maine, offers a more laid-back vibe with its scenic waterfront, artistic community, and renowned culinary scene. Together, these cities provide a perfect snapshot of New England's diverse offerings.

Whether you're a history buff, a foodie, or an outdoor enthusiast, New England has something for everyone. From exploring the Freedom Trail in Boston to savoring lobster rolls in Portland, this 7-day itinerary will guide you through the best that this enchanting region has to offer. Prepare to be charmed by the warmth of New England's hospitality and the beauty of its landscapes.

Boston

Boston, a city that played a pivotal role in American history, is a must-visit for any traveler to New England. Known for its prestigious universities, vibrant cultural scene, and historic sites, Boston offers a wealth of experiences for visitors. Walk the Freedom Trail to discover landmarks like the Boston Common, Paul Revere's House, and the Old North Church. Don't miss the chance to explore the bustling neighborhoods of Beacon Hill and the North End, where history and modernity blend seamlessly.

For accommodations, consider staying at a charming VRBO in the heart of the city or a comfortable hotel via Hotels.com. Both options offer easy access to Boston's top attractions and dining spots.

Travel to Boston is convenient with numerous flight options available through Trip.com and Kiwi.com. Once in the city, the efficient public transportation system makes getting around a breeze.

Day 1: Arrival in Boston

Afternoon: Arrive in Boston and check into your accommodation. Start your journey with a leisurely stroll through the Boston Common, the oldest public park in the United States. Enjoy the lush greenery and historic monuments as you unwind from your travels.

Evening: Head to the North End, Boston's Little Italy, for a delightful dinner at Giacomo's Ristorante. Known for its authentic Italian cuisine and cozy atmosphere, this local favorite is the perfect introduction to Boston's culinary scene. After dinner, indulge in a sweet treat at Mike's Pastry, famous for its cannoli.

Day 2: Exploring Historic Boston

Morning: Begin your day with a hearty breakfast at Tatte Bakery & Cafe, where you can savor freshly baked pastries and artisanal coffee. Then, embark on a journey along the Freedom Trail, a 2.5-mile route that takes you through 16 historically significant sites, including the Massachusetts State House and Faneuil Hall.

Afternoon: Visit the Boston Tea Party Ships & Museum to relive the pivotal event that sparked the American Revolution. Engage in interactive exhibits and witness a reenactment of the historic protest. For lunch, enjoy a classic New England clam chowder at Legal Sea Foods, a Boston institution.

Evening: Experience the vibrant nightlife of Boston's Seaport District. Dine at The Barking Crab, a lively seafood shack offering stunning waterfront views. Afterward, catch a live performance at the Blue Hills Bank Pavilion, an open-air venue hosting a variety of concerts and events.

Day 3: Cultural Immersion in Boston

Morning: Start your day with a visit to the Museum of Fine Arts, home to an extensive collection of art from around the world. Enjoy a leisurely breakfast at the museum's Garden Cafeteria, surrounded by beautiful sculptures and gardens.

Afternoon: Explore the vibrant neighborhood of Cambridge, home to Harvard University and MIT. Take a guided tour of Harvard's historic campus and visit the Harvard Art Museums. For lunch, try the innovative dishes at Alden & Harlow, known for its creative American cuisine.

Evening: Return to Boston and enjoy a dinner cruise on the Charles River. Savor a gourmet meal while taking in panoramic views of the city skyline. This relaxing experience is a perfect way to end your day of cultural exploration.

Portland

Portland, Maine, is a charming coastal city known for its picturesque waterfront, thriving arts scene, and delectable seafood. With its cobblestone streets and historic architecture, Portland offers a delightful blend of old-world charm and modern vibrancy. Explore the Old Port district, where you'll find an array of boutique shops, art galleries, and cozy cafes.

For accommodations, consider a cozy VRBO with ocean views or a stylish hotel via Hotels.com. Both options provide easy access to Portland's attractions and dining options.

Travel from Boston to Portland is a scenic journey, with options including a 2-hour drive or a relaxing train ride via Trip.com. The journey offers stunning views of the New England coastline.

Day 4: Arrival in Portland

Afternoon: Arrive in Portland and check into your accommodation. Begin your exploration with a visit to the Portland Head Light, one of the most photographed lighthouses in the United States. Enjoy the breathtaking views of the rugged coastline and the Atlantic Ocean.

Evening: Head to the Old Port district for dinner at Eventide Oyster Co., renowned for its fresh seafood and innovative dishes. Afterward, enjoy a leisurely stroll along the cobblestone streets, stopping by local boutiques and art galleries.

Day 5: Discovering Portland's Charm

Morning: Start your day with a delicious breakfast at The Holy Donut, famous for its potato-based donuts in a variety of unique flavors. Then, explore the Portland Museum of Art, which houses an impressive collection of American and European art.

Afternoon: Take a scenic cruise on Casco Bay with Viator, where you can admire the beauty of the surrounding islands and learn about the area's maritime history. For lunch, enjoy a classic lobster roll at The Highroller Lobster Co., a local favorite.

Evening: Experience Portland's vibrant food scene with a dinner at Fore Street, known for its farm-to-table approach and wood-fired dishes. After dinner, catch a live performance at the State Theatre, a historic venue hosting a variety of concerts and events.

Day 6: Outdoor Adventures in Portland

Morning: Begin your day with a visit to the Eastern Promenade, a scenic park offering stunning views of Casco Bay. Enjoy a leisurely walk or rent a bike to explore the trails. For breakfast, stop by Tandem Coffee Roasters for a freshly brewed coffee and a pastry.

Afternoon: Embark on a kayaking adventure with Portland Paddle, where you can explore the calm waters of Casco Bay and its surrounding islands. For lunch, head to Duckfat, known for its Belgian-style fries and gourmet sandwiches.

Evening: Enjoy a farewell dinner at Central Provisions, a popular spot offering a diverse menu of small plates and craft cocktails. After dinner, take a leisurely walk along the waterfront, soaking in the beauty of Portland's harbor at night.

Day 7: Departure from Portland

Morning: Spend your final morning in Portland with a visit to the Victoria Mansion, a beautifully preserved 19th-century home showcasing stunning architecture and period furnishings. Enjoy a leisurely breakfast at Becky’s Diner, a beloved local spot known for its hearty breakfast fare.

Afternoon: Before departing, take a final stroll through the Old Port district, picking up any last-minute souvenirs or enjoying a coffee at Bard Coffee. Depart from Portland in the afternoon, taking with you cherished memories of your New England adventure.

In summary, this 7-day journey through Boston and Portland offers a perfect blend of history, culture, and natural beauty. From exploring iconic landmarks to savoring local cuisine, you'll experience the best of New England's charm and hospitality. Whether you're a first-time visitor or a seasoned traveler, this itinerary promises an unforgettable adventure.