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5 Days of Coastal and Historical Exploration Itinerary

Last updated: 2024 Jun 14

Historical Boston Unveiled

Morning

Start your day with a visit to Freedom Trail, a 2.5-mile-long path through downtown Boston that passes by 16 locations significant to the history of the United States. This will give you a great overview of the city's rich history. Afterward, enjoy breakfast at Tatte Bakery & Cafe, known for its delicious pastries and coffee.

Afternoon

In the afternoon, head over to Boston Public Garden, America's first public botanical garden. Take a leisurely stroll through its beautifully landscaped grounds and perhaps enjoy a swan boat ride. For lunch, dine at Union Oyster House, one of America's oldest restaurants, famous for its seafood.

Evening

As evening approaches, explore Boston North End, Boston's Little Italy. Wander through its charming streets and indulge in an authentic Italian dinner at Giacomo's Ristorante. Cap off your night with a visit to Paul Revere House, which is beautifully illuminated at night.

Bedtime

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4.54
Freedom Trail
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4.52
Boston Public Garden
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Portland's Coastal Charm and Gardens

Morning

Begin your day with a visit to the iconic Portland Head Light in Cape Elizabeth, just a short drive from Portland. This historic lighthouse offers stunning views of the rugged Maine coastline. Enjoy breakfast at The Holy Donut, known for its unique potato donuts.

Afternoon

Head back into Portland and explore the serene beauty of the Portland Japanese Garden. This meticulously maintained garden offers a peaceful retreat from the hustle and bustle of city life. For lunch, try some local seafood at Eventide Oyster Co., renowned for its fresh oysters.

Evening

Spend your evening exploring the vibrant Portland Pearl District. This area is known for its art galleries, boutiques, and lively atmosphere. Enjoy dinner at Fore Street, which offers farm-to-table cuisine in an elegant setting.

Bedtime

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Portland Head Light
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Portland Japanese Garden
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Nature's Splendor in Bar Harbor & Acadia National Park

Morning

Start your day early with a visit to Acadia National Park. Begin with a sunrise hike up Cadillac Mountain for breathtaking views of the Atlantic Ocean. Enjoy breakfast at Jordan Pond House, famous for its popovers and tea.

Afternoon

Continue exploring Acadia National Park by taking part in the popular activity: Acadia National Park Small Group Guided Tour. This tour will take you through some of the park's most scenic spots including Thunder Hole and Sand Beach. For lunch, have a picnic within the park or dine at one of Bar Harbor’s quaint cafes like Cafe This Way.

Evening

In the evening, return to Bar Harbor and join the intriguing activity: Bar Harbor Haunted Ghost Walking Tour. Discover eerie tales as you walk through historic sites under moonlight. Finish your day with dinner at Side Street Cafe, known for its cozy atmosphere and delicious lobster dishes.

Bedtime

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Acadia National Park
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Acadia National Park Small Group Guided Tour
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Adventures in the White Mountains

Morning

Begin your day with a scenic drive through the White Mountains. Start at the Kancamagus Highway, known for its breathtaking views and numerous pull-off spots for photos. Enjoy breakfast at Polly's Pancake Parlor, a local favorite known for its delicious pancakes and maple syrup.

Afternoon

Spend your afternoon exploring Franconia Notch State Park. Take a hike to see the Flume Gorge, a natural granite gorge extending 800 feet at the base of Mount Liberty. For lunch, pack a picnic or dine at Cannon Mountain Aerial Tramway Cafe, offering stunning mountain views.

Evening

As evening falls, head to North Conway and explore its charming downtown area filled with shops and restaurants. Enjoy dinner at Delaney's Hole in the Wall, known for its hearty meals and cozy atmosphere. If time permits, take a short drive to Cathedral Ledge for sunset views.

Bedtime

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Charming Towns of Vermont

Morning

Start your day in Burlington with a visit to Church Street Marketplace, an outdoor pedestrian mall lined with shops and cafes. Have breakfast at Penny Cluse Cafe, famous for its hearty breakfasts and friendly atmosphere.

Afternoon

Drive to Stowe, where you can explore the picturesque town and take part in the activity: Stowe, Vermont Half-Day Local Brewery Tour. This tour will introduce you to some of Vermont's best craft beers. For lunch, stop by Harrison's Restaurant & Bar for some delicious local fare.

Evening

In the evening, enjoy more of Stowe’s natural beauty by taking a scenic drive along Smugglers' Notch. End your day with dinner at The Bench, known for its wood-fired pizzas and relaxed ambiance.

Bedtime

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