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14 Days of Historical Exploration in Boston, Montreal, and Quebec City Itinerary
Last updated: 2024 Jun 14Historical Boston Beginnings
Morning
Start your day with a visit to 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 perfect introduction to the city’s rich historical tapestry.
Afternoon
After a morning of walking, enjoy lunch at Neptune Oyster, known for its fresh seafood and iconic lobster rolls. Post-lunch, head over to Boston Old State House, one of the oldest public buildings in the U.S., where you can learn about its pivotal role in American history.
Evening
For dinner, dine at Ostra, which offers a sophisticated seafood menu. Afterward, take an evening stroll through Quincy Market, a historic market complex that now houses an array of shops and eateries.
Bedtime
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Freedom Trail
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Boston Old State House
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Quincy Market
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Cambridge and Harvard Highlights
Morning
Begin your day with breakfast at a local café before heading to Harvard University. Explore the historic campus and visit landmarks like the John Harvard Statue and Harvard Yard.
Afternoon
Have lunch at Mamma Maria in North End, known for its Italian cuisine. Then visit MIT Museum to explore fascinating exhibits on science and technology.
Evening
Dine at Toro Boston, renowned for its Spanish tapas. End your evening with a walk around Kendall Square, known for its vibrant atmosphere and innovative spirit.
Bedtime
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Harvard University
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MIT Museum
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Kendall Square
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Colonial Charms and Modern Marvels
Morning
Kick off your day with breakfast before visiting Paul Revere House, the colonial home of American patriot Paul Revere. Then walk over to Boston North End to explore this historic neighborhood.
Afternoon
Enjoy lunch at Myers + Chang, offering Asian-inspired dishes. Post-lunch, head to the iconic Faneuil Hall Marketplace for some shopping and people-watching.
Evening
Have dinner at The Capital Grille, famous for its steaks. Conclude your day with a visit to the beautiful Boston Public Garden for an evening stroll.
Bedtime
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Paul Revere House
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Boston North End
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Faneuil Hall Marketplace
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Boston Public Garden
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Revolutionary Relics and Waterfront Wonders
Morning
Start your morning with breakfast before heading to the historic site of the Boston Tea Party Ships & Museum. Experience interactive exhibits that bring this pivotal event in American history to life.
Afternoon
Lunch will be at Oleana, celebrated for its Mediterranean cuisine. Afterward, explore more history at the impressive USS Constitution, also known as 'Old Ironsides.'
Evening
For dinner, savor seafood dishes at Island Creek Oyster Bar. Finish your day by visiting the serene waterfront area around Long Wharf.
Bedtime
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Boston Tea Party Ships & Museum
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Exploring Montreal's Historic Heart
Morning
Start your day with a visit to Old Montreal (Vieux-Montréal). This historic area is filled with cobblestone streets, charming boutiques, and beautiful architecture. It’s the perfect place to get a feel for the city’s rich history.
Afternoon
For lunch, head to Le Serpent, known for its contemporary Italian cuisine. Afterward, explore Notre-Dame Basilica of Montreal (Basilique Notre-Dame de Montréal), a stunning example of Gothic Revival architecture.
Evening
Dine at Moishes Steakhouse, one of Montreal’s most iconic restaurants. End your evening with a stroll through Jacques-Cartier Square (Place Jacques-Cartier), a lively public square that often hosts street performers and artists.
Bedtime
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Old Montreal (Vieux-Montréal)
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Notre-Dame Basilica of Montreal (Basilique Notre-Dame de Montréal)
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Jacques-Cartier Square (Place Jacques-Cartier)
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Markets and Museums in Montreal
Morning
Jean-Talon Market (Marché Jean-Talon) is the perfect place to start your day. This bustling market offers fresh produce, local delicacies, and vibrant atmosphere.
Afternoon
Le Serpent serves as an excellent lunch spot with its modern Italian dishes. Post-lunch, visit the Pointe-à-Callière, an archaeology and history museum that provides fascinating insights into Montreal’s past.
Evening
Moishes Steakhouse is ideal for dinner, offering classic steakhouse fare in an elegant setting. Conclude your day by exploring the vibrant nightlife around Crescent Street.
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Jean-Talon Market (Marché Jean-Talon)
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Pointe-à-Callière
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Nature and Culture in Montreal
Morning
Mount Royal offers stunning views of the city and is a great place for a morning hike or leisurely walk.
Afternoon
Le Serpent offers another delightful lunch experience. Afterward, head to the Montreal Museum of Fine Arts (Musée des Beaux-Arts) to explore its extensive collection of art from around the world.
Evening
Moishes Steakhouse provides another fantastic dining option. Finish your evening with a visit to Place des Arts, where you can catch a performance or simply enjoy the lively atmosphere.
Bedtime
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Mount Royal
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Montreal Museum of Fine Arts (Musée des Beaux-Arts)
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Place des Arts
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Exploring Montreal's Cultural Hub
Morning
Start your day at Montreal Underground City. This extensive network of underground complexes connects shopping centers, hotels, metro stations, and more – perfect for escaping any inclement weather while exploring.
Afternoon
For lunch, head to Le Serpent, known for its contemporary Italian cuisine. Post-lunch, explore more culture at the impressive Montreal Museum of Fine Arts (Musée des Beaux-Arts). The museum boasts an extensive collection ranging from classical to contemporary art.
Evening
Dine at Moishes Steakhouse, one of Montreal’s most iconic restaurants known for its classic steakhouse fare. End your evening by taking a leisurely stroll around Crescent Street to soak up Montreal’s vibrant nightlife atmosphere.
Bedtime
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Montreal Underground City
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Montreal Museum of Fine Arts (Musée des Beaux-Arts)
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Montreal's Historical and Cultural Finale
Morning
Begin your day with a visit to Saint Paul Street (Rue Saint-Paul). This historic street is one of the oldest in Montreal and is lined with charming boutiques, galleries, and cafes.
Afternoon
For lunch, head to Le Serpent, known for its contemporary Italian cuisine. Afterward, explore Montreal City Hall (Hotel de Ville de Montréal), an architectural gem that has played a significant role in the city's history.
Evening
Dine at Moishes Steakhouse, one of Montreal’s most iconic restaurants known for its classic steakhouse fare. End your evening with a visit to Place des Arts, where you can catch a performance or simply enjoy the lively atmosphere.
Bedtime
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NYC Admire Manhattan's Architecture on a 1920s Yacht Cruise
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Montreal City Hall (Hotel de Ville de Montréal)
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Place des Arts
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Historic Gems in Quebec City
Morning
Begin your exploration at Old Quebec (Vieux-Québec). This UNESCO World Heritage site is brimming with historic buildings, charming streets, and cultural landmarks.
Afternoon
Enjoy lunch at Restaurant Initiale, known for its refined French cuisine. Post-lunch, visit the impressive Citadel of Quebec (Citadelle de Quebec), which offers panoramic views of the city and river.
Evening
Dine at Le Saint-Amour, celebrated for its gourmet French dishes. Conclude your day with an evening stroll along Dufferin Terrace (Terrasse Dufferin), offering beautiful views over the St. Lawrence River.
Bedtime
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Old Quebec (Vieux-Québec)
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Citadel of Quebec (Citadelle de Quebec)
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Quebec City's Historical Treasures
Morning
Start your day with a visit to Plains of Abraham (Plaines d'Abraham). This historic site was the scene of a pivotal battle in the Seven Years' War and offers beautiful parkland and informative exhibits.
Afternoon
For lunch, head to Chez Muffy, known for its farm-to-table cuisine. Afterward, explore Quebec Museum of Civilization (Musée de la Civilisation), which provides fascinating insights into the history and culture of Quebec.
Evening
Dine at Légende, which offers innovative dishes inspired by Quebec's culinary traditions. End your evening with a walk through Upper Town (Haute-Ville), where you can enjoy the charming streets and historic buildings.
Bedtime
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Plains of Abraham (Plaines d'Abraham)
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Quebec Museum of Civilization (Musée de la Civilisation)
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Upper Town (Haute-Ville)
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Cultural Delights in Quebec City
Morning
Notre-Dame de Québec Basilica-Cathedral is a must-see for its stunning architecture and historical significance. Spend your morning exploring this beautiful cathedral.
Afternoon
Le Continental is perfect for lunch, offering classic French cuisine. Post-lunch, visit Fortifications of Quebec National Historic Site, where you can walk along the old city walls and learn about their history.
Evening
Laurie Raphaël offers an exquisite dining experience with its creative menu. Conclude your day with an evening stroll through Petit Champlain District (Quartier Petit Champlain), one of the oldest commercial districts in North America.
Bedtime
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Notre-Dame de Québec Basilica-Cathedral
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Fortifications of Quebec National Historic Site
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Petit Champlain District (Quartier Petit Champlain)
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Natural Wonders and Historic Sites
Morning
Montmorency Falls Park (Parc de la Chute-Montmorency) is a breathtaking natural attraction just outside the city. Spend your morning taking in the stunning views and exploring the park.
Afternoon
La Planque is ideal for lunch, offering modern French cuisine in a cozy setting. Afterward, visit Artillery Park Heritage Site, where you can learn about Quebec's military history.
Evening
Ciel! Bistro-Bar tournant provides a unique dining experience with its revolving restaurant offering panoramic views of the city. Finish your day by visiting Quebec Lower Town (Basse-Ville), known for its charming streets and historic buildings.
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Montmorency Falls Park (Parc de la Chute-Montmorency)
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Artillery Park Heritage Site
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Farewell to Quebec City's Rich Heritage
Morning
Start your day with a visit to Quebec Royal Square (Place-Royale). This historic square is considered the birthplace of French America and is surrounded by beautiful 17th- and 18th-century buildings.
Afternoon
For lunch, head to Restaurant Initiale, known for its refined French cuisine. Afterward, explore more history at the impressive Fort Museum (Musée du Fort), which offers engaging exhibits on Quebec's military history.
Evening
Dine at Le Saint-Amour, celebrated for its gourmet French dishes. Conclude your trip with an evening stroll along Dufferin Terrace (Terrasse Dufferin), offering beautiful views over the St. Lawrence River.
Bedtime
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Quebec Royal Square (Place-Royale)
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