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10 Days of Exploration from Boston to Portland Itinerary

Last updated: 2024 Jun 14

Boston Beginnings and Coastal Drive

Morning

Start your journey in Boston with a visit to the iconic Freedom Trail. This 2.5-mile-long path through downtown Boston passes by 16 locations significant to the history of the United States. It's a great way to get acquainted with the city's rich past and vibrant culture. For breakfast, stop by Tatte Bakery & Cafe for some delicious pastries and coffee.

Afternoon

After exploring the Freedom Trail, head over to the Boston Public Garden for a relaxing stroll among beautiful flowers and swan boats. Enjoy lunch at Union Oyster House, one of America's oldest restaurants known for its seafood dishes. Post-lunch, make your way to the New England Aquarium where you can marvel at marine life from around the world.

Evening

As evening approaches, start your drive towards Portland, ME (approximately 2 hours). Upon arrival in Portland, check into your hotel and freshen up. For dinner, head over to Fore Street, a highly-rated restaurant known for its farm-to-table cuisine. End your day with a leisurely walk along the Old Port district's cobblestone streets.

Bedtime

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Portland’s Historical Charms

Morning

Begin your day with a hearty breakfast at The Holy Donut, famous for its potato donuts. Then embark on Portland Trolley City Tour with Portland Head Light Stop. This guided tour will take you through Portland's historical sites and includes a stop at the iconic Portland Head Light.

Afternoon

For lunch, visit Eventide Oyster Co for some fresh oysters and seafood delights. Afterward, explore Eastern Promenade, a scenic park offering stunning views of Casco Bay and ample opportunities for walking or picnicking.

Evening

In the evening, enjoy dinner at Duckfat, known for its Belgian fries and poutine. After dinner, unwind with a visit to one of Portland's local breweries such as Rising Tide Brewing Company where you can sample some craft beers.

Bedtime

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Lighthouses and Culinary Delights

Morning

Start your morning with breakfast at Arabica Coffee House before heading out on an adventure with Portland Best of Maine Lighthouse Scenic Cruise. This cruise offers breathtaking views of several lighthouses along Maine's rugged coastline.

Afternoon

After your cruise, have lunch at Central Provisions, offering small plates inspired by global flavors. Post-lunch activity includes visiting Tate House Museum, an 18th-century home that provides insight into colonial life in Maine.

Evening

For dinner, dine at Street & Co, renowned for its seafood dishes served in an intimate setting. Conclude your day with a relaxing evening walk along Commercial Street or perhaps join another local brewery tour if you're up for it.

Bedtime

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Cultural Immersion and Scenic Views

Morning

Begin your day with a delicious breakfast at Hot Suppa, known for its Southern-inspired dishes. Afterward, embark on Portland, Maine 2-Hour Guided History Tour. This tour will take you through the rich history of Portland, highlighting significant landmarks and stories from the past.

Afternoon

For lunch, head to The Honey Paw, a popular spot for Asian-inspired cuisine. Post-lunch, visit Fort Gorges, an abandoned military fort located on an island in Casco Bay. Accessible by kayak or private boat, this site offers a unique glimpse into Portland's military history and stunning views of the bay.

Evening

In the evening, enjoy dinner at Scales, a waterfront restaurant known for its fresh seafood. After dinner, unwind with a sunset cruise on Casco Bay by joining Portland Sunset Lighthouse Cruise in Casco Bay with Drinks. This cruise offers beautiful views of the coastline as the sun sets.

Bedtime

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Outdoor Adventures and Local Brews

Morning

Start your morning with breakfast at Bayside American Cafe, famous for its hearty brunch options. Then get ready for an active day with Portland Guided Foodie Walking Tour with Food and Drinks. This tour will take you through Portland's culinary scene, offering tastings from various local eateries.

Afternoon

For lunch, visit J’s Oyster, a local favorite known for its casual atmosphere and fresh seafood. Afterward, explore the scenic trails of Mackworth Island State Park where you can enjoy hiking and bird-watching along the coast.

Evening

In the evening, dine at The Thirsty Pig, which specializes in house-made sausages and craft beers. Conclude your day with a visit to New England Distilling where you can sample locally produced spirits and learn about the distillation process.

Bedtime

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Artistic Exploration and Coastal Beauty

Morning

Begin your day with breakfast at Tandem Coffee + Bakery, known for its excellent coffee and pastries. Then immerse yourself in Portland's art scene by visiting the Portland Museum of Art which houses an impressive collection of American and European works.

Afternoon

For lunch, head to Gilbert’s Chowder House to savor some classic New England clam chowder. Post-lunch activity includes joining Portland Schooner Tall Ship Cruise on Casco Bay. This sailing adventure offers a unique perspective of Portland's coastline aboard a traditional schooner.

Evening

In the evening, enjoy dinner at Five Fifty-Five, renowned for its fine dining experience featuring locally sourced ingredients. End your day with a leisurely stroll along East End Beach or perhaps join another local brewery tour if you're up for it.

Bedtime

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Hidden Histories and Waterfront Wonders

Morning

Start your day with a delightful breakfast at The Front Room, known for its hearty American breakfast options. Afterward, delve into the lesser-known stories of Portland with Portland, Maine Hidden Histories Guided Walking Tour. This tour will take you through the city's hidden gems and untold stories that shaped its history.

Afternoon

For lunch, visit Flatbread Company for some delicious wood-fired pizzas. Post-lunch, head to the waterfront to explore Portland Private Island Fort Tour. This private tour offers an exclusive look at one of Portland's historic forts located on a picturesque island in Casco Bay.

Evening

In the evening, enjoy dinner at The Grill Room & Bar, known for its steaks and seafood. Conclude your day with a relaxing evening walk along the Eastern Promenade or perhaps join another local brewery tour if you're up for it.

Bedtime

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Lighthouse Legends and Scenic Cruises

Morning

Begin your morning with breakfast at Scratch Baking Co, famous for its bagels and pastries. Then embark on an adventure with Portland Maine Lighthouses Sightseeing Cruise with Drinks. This cruise offers breathtaking views of several iconic lighthouses along Maine's rugged coastline.

Afternoon

For lunch, head to The Highroller Lobster Co to indulge in some of the best lobster rolls in town. Afterward, visit Tate House Museum, an 18th-century home that provides insight into colonial life in Maine.

Evening

In the evening, dine at Fore Street, renowned for its farm-to-table cuisine. End your day with a leisurely stroll along Commercial Street or perhaps join another local brewery tour if you're up for it.

Bedtime

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Culinary Delights and Sunset Views

Morning

Start your morning with breakfast at Bard Coffee, known for its excellent coffee and pastries. Then join Portland Old Port Culinary Walking Tour which will take you through Portland's culinary scene offering tastings from various local eateries.

Afternoon

For lunch, visit Duckfat, famous for its Belgian fries and poutine. Post-lunch activity includes exploring the scenic trails of Mackworth Island State Park where you can enjoy hiking and bird-watching along the coast.

Evening

In the evening, enjoy dinner at Street & Co, renowned for its seafood dishes served in an intimate setting. Conclude your day with a sunset cruise on Casco Bay by joining Portland Casco Bay Sunset and Lighthouse Cruise. This cruise offers beautiful views of the coastline as the sun sets.

Bedtime

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Farewell to Portland with Scenic Highlights

Morning

Begin your final day in Portland with a hearty breakfast at Becky's Diner, a beloved local spot known for its classic American breakfast options. Afterward, embark on Portland, Maine City and Lighthouse E Bike Tour. This guided e-bike tour will take you through the city's scenic routes and iconic lighthouses, offering a unique perspective of Portland's coastal beauty.

Afternoon

For lunch, visit Eventide Oyster Co to savor some fresh oysters and seafood delights. Post-lunch activity includes exploring the historic Old Port district on foot or by joining Portland Exploration Self-Guided Driving & Walking Tour. This self-guided tour allows you to explore at your own pace while learning about the area's rich history and vibrant culture.

Evening

In the evening, enjoy a farewell dinner at The Corner Room Kitchen & Bar, known for its Italian-inspired dishes made with locally sourced ingredients. Conclude your trip with a relaxing evening walk along the waterfront or perhaps join one last local brewery tour if you're up for it.

Bedtime

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