New Chat
Download App
Ask me about your trip!
There are no messages for this conversation.
12-Day Family Road Trip from Boston to Toronto Itinerary
Last updated: 2024 Jul 01Exploring Boston's Historic Heart
Morning
Start your day with a visit to the iconic Freedom Trail. This 2.5-mile-long path through downtown Boston passes by 16 significant historical sites, offering a perfect introduction to the city's rich history. The trail will take you through various landmarks including Boston Common, the Massachusetts State House, and Paul Revere's House.
Afternoon
After lunch, dive deeper into Boston's revolutionary past with the Boston: Freedom Trail Small Group History Walking Tour. This guided tour provides detailed insights into the events that shaped America’s history. Following the tour, head over to Faneuil Hall Marketplace, a vibrant marketplace filled with shops, eateries, and street performers.
Evening
Conclude your day with a relaxing stroll through Boston Public Garden, America's first public botanical garden. Enjoy the serene atmosphere and perhaps take a swan boat ride on the lagoon. For dinner, head to Union Oyster House, one of America's oldest restaurants known for its seafood.
Bedtime
Find amazing hotels in Boston.
4.54Freedom Trail
Book Now
4.54Freedom Trail
Book Now
4.91Boston: Freedom Trail Small Group History Walking Tour
Book Now
4.91Boston: Freedom Trail Small Group History Walking Tour
Book Now
Cultural Immersion in Cambridge
Morning
Begin your second day with a visit to Massachusetts Institute of Technology (MIT). Explore its impressive campus and then join the Massachusetts Institute of Technology Public Tour for an insider’s look at one of the world’s leading research institutions.
Afternoon
Cross over to nearby Kendall Square for lunch at Glass House, known for its modern American cuisine. Afterward, explore Kendall Square, often referred to as 'the most innovative square mile on the planet.' Then make your way to MIT Museum where you can marvel at exhibits showcasing cutting-edge technology and innovation.
Evening
In the evening, enjoy a leisurely walk around Cambridge Common, a historic park that has witnessed many significant events in American history. For dinner, dine at The Red House, which offers delicious New England fare in a cozy setting.
Bedtime
Find amazing hotels in Boston.
4.33Massachusetts Institute of Technology (MIT)
Book Now
4.33Massachusetts Institute of Technology (MIT)
Book Now
4.57Massachusetts Institute of Technology Public Tour
Book Now
4.57Massachusetts Institute of Technology Public Tour
Book Now
Seaside Adventures and Scenic Views
Morning
Start your third day with an invigorating visit to Newport's famous cliffside walk - Newport Cliff Walk. This 3.5-mile scenic trail offers breathtaking views of both ocean waves crashing against rocky shores and grand Gilded Age mansions.
Afternoon
After enjoying some seaside air, head back towards Boston for an afternoon tour - join the popular Boston Duck Tour: The Original and World-Famous. This unique land-and-water adventure takes you through historic streets before splashing into the Charles River for stunning city views from water level.
4.46Newport Cliff Walk
Book Now
4.46Newport Cliff Walk
Book Now
4.65Boston Duck Tour: The Original and World-Famous
Book Now
4.65Boston Duck Tour: The Original and World-Famous
Book Now
Historic and Scenic Newport
Morning
Begin your day with a visit to the The Breakers, one of Newport's most famous mansions. This grand estate, once the summer home of the Vanderbilt family, offers a glimpse into the opulent lifestyle of America's Gilded Age elite. Take a guided tour to learn about its history and architecture.
Afternoon
After exploring The Breakers, head over to Bellevue Avenue for a leisurely stroll. This historic avenue is lined with stunning mansions and beautiful gardens. Stop by La Forge Casino Restaurant for lunch, where you can enjoy delicious American cuisine in a charming setting.
Evening
In the evening, visit Fort Adams State Park. This historic fort offers stunning views of Narragansett Bay and is a great spot for a sunset picnic. Afterward, head to The Mooring Seafood Kitchen & Bar for dinner, where you can enjoy fresh seafood with waterfront views.
Bedtime
Find amazing hotels in Newport.
4.34The Breakers
Book Now
4.34The Breakers
Book Now
4.59Bellevue Avenue
Book Now
4.59Bellevue Avenue
Book Now
Exploring Boston's Coastal Charm
Morning
Start your day with a visit to Ocean Drive, a scenic coastal route that offers breathtaking views of the Atlantic Ocean. Take your time driving along this picturesque road and stop at various lookout points to take in the scenery.
Afternoon
After enjoying the coastal views, head back to Boston for an afternoon tour - join the popular Boston: Whale Watching Catamaran Cruise. This exciting tour takes you out into the ocean where you can spot majestic whales in their natural habitat.
Evening
Conclude your day with a visit to Back Bay, one of Boston's most fashionable neighborhoods. Stroll along Newbury Street and explore its trendy boutiques and cafes. For dinner, dine at Atlantic Fish Company, known for its fresh seafood dishes.
Bedtime
Find amazing hotels in Boston.
4.73Ocean Drive
Book Now
4.73Ocean Drive
Book Now
4.58Boston: Whale Watching Catamaran Cruise
Book Now
4.58Boston: Whale Watching Catamaran Cruise
Book Now
Cultural Delights in Cambridge
Morning
Begin your day with a visit to Harvard University. Explore its historic campus and join the student-guided walking tour for an insider’s look at one of the world’s most prestigious universities.
Afternoon
After exploring Harvard, head over to nearby Harvard Square for lunch at Grendel's Den, known for its casual American fare. Afterward, explore Harvard Art Museums where you can marvel at exhibits showcasing art from around the world.
Evening
In the evening, enjoy a leisurely walk around Charles River, which offers beautiful views of both Cambridge and Boston skylines. For dinner, dine at Forage, which offers delicious farm-to-table cuisine in a cozy setting.
Bedtime
Find amazing hotels in Cambridge.
4.57Harvard University
Book Now
4.57Harvard University
Book Now
4.91Harvard Art Museums
Book Now
4.91Harvard Art Museums
Book Now
Journey to the Heart of History
Morning
Start your day with a visit to the Boston Old State House. This historic building, dating back to 1713, served as the seat of the Massachusetts General Court and is one of the oldest public buildings in the United States. Explore its exhibits and learn about its role in American history.
Afternoon
After exploring the Old State House, head over to Boston Massacre Site, located just outside. This site marks where British soldiers killed five colonists in 1770, an event that fueled anti-British sentiments leading up to the American Revolution. For lunch, dine at Union Oyster House, one of America's oldest restaurants known for its seafood.
Evening
In the evening, join the Boston: Ghosts and Gravestones Tour. This spooky tour takes you through some of Boston's most haunted sites and shares chilling tales from its dark past. Afterward, enjoy dinner at The Capital Grille, known for its upscale steakhouse fare.
Bedtime
Find amazing hotels in Boston.
4.48Boston Old State House
Book Now
4.48Boston Old State House
Book Now
4.64Boston Massacre Site
Book Now
4.64Boston Massacre Site
Book Now
Cultural Gems and Scenic Views
Morning
Begin your day with a visit to Isaac Bell House. This historic house, built in 1883, is a stunning example of Shingle Style architecture. Take a guided tour to learn about its history and architectural significance.
Afternoon
After exploring Isaac Bell House, head over to Charles W. Morgan Whaleship, located at Mystic Seaport Museum. This historic whaling ship offers a fascinating glimpse into America's maritime heritage. For lunch, dine at S&P Oyster Company, known for its fresh seafood dishes.
Evening
In the evening, visit Rosecliff, another grand mansion in Newport. This opulent estate has been featured in several films and offers beautiful views of Narragansett Bay. Afterward, enjoy dinner at The Black Pearl, known for its classic New England cuisine.
Bedtime
Find amazing hotels in Boston.
5.00Isaac Bell House
Book Now
5.00Isaac Bell House
Book Now
4.45Charles W. Morgan Whaleship
Book Now
4.45Charles W. Morgan Whaleship
Book Now
Exploring Toronto's Urban Wonders
Morning
Start your day with a visit to CN Tower. This iconic landmark offers breathtaking views of Toronto from its observation deck. Take an elevator ride up to enjoy panoramic vistas of the city skyline and Lake Ontario.
Afternoon
After visiting CN Tower, head over to nearby Ripley's Aquarium for an underwater adventure - join the popular Toronto: Ripley's Aquarium Admission Ticket. Explore various marine exhibits featuring colorful fish and other sea creatures from around the world.
Evening
Conclude your day with a visit to Toronto's vibrant Entertainment District - stroll along King Street West lined with theaters showcasing Broadway shows before dining at one renowned eateries like Jacobs & Co Steakhouse which offers delicious steaks cooked perfectly.
Bedtime
Find amazing hotels in Toronto.
4.44CN Tower
Book Now
4.44CN Tower
Book Now
4.55Toronto: Ripley's Aquarium Admission Ticket
Book Now
4.55Toronto: Ripley's Aquarium Admission Ticket
Book Now
Toronto's Natural and Cultural Treasures
Morning
Start your day with a visit to Toronto Islands. Take a ferry ride to these beautiful islands located just off the coast of downtown Toronto. Enjoy the scenic views, rent a bike, or simply relax on one of the beaches. The islands offer a peaceful escape from the bustling city.
Afternoon
After exploring the Toronto Islands, head back to the mainland for lunch at The Rec Room, known for its diverse menu and entertainment options. Following lunch, visit Royal Ontario Museum (ROM), one of Canada's largest museums. Explore its extensive collections ranging from natural history to world cultures.
Evening
In the evening, join the Toronto: Distillery District Historic Walking Tour. This guided tour takes you through one of Toronto's most charming neighborhoods filled with Victorian-era buildings, art galleries, and unique shops. For dinner, dine at Cluny Bistro & Boulangerie, offering French-inspired cuisine in a stylish setting.
Bedtime
Find amazing hotels in Toronto.
4.83Toronto Islands
Book Now
4.83Toronto Islands
Book Now
4.68Royal Ontario Museum (ROM)
Book Now
4.68Royal Ontario Museum (ROM)
Book Now
Adventures in Niagara Falls
Morning
Begin your day with an exciting trip to Niagara Falls - join the popular From Toronto: Niagara Falls Day Tour with Boat Cruise. This full-day tour includes transportation from Toronto and offers breathtaking views of the falls from both land and water. Experience the power and beauty of this natural wonder up close.
Afternoon
After experiencing Niagara Falls, enjoy lunch at Queen Victoria Place Restaurant, which offers stunning views of the falls along with delicious Canadian cuisine. Afterward, explore nearby attractions such as Clifton Hill or take a stroll along the scenic Niagara Parkway.
Evening
Return to Toronto in the evening and unwind with a visit to Harbourfront Centre. This vibrant cultural hub offers various events and activities along Lake Ontario's waterfront. For dinner, dine at The Goodman Pub & Kitchen, known for its relaxed atmosphere and tasty pub fare.
Bedtime
Find amazing hotels in Niagara Falls.
4.55From Toronto: Niagara Falls Day Tour with Boat Cruise
Book Now
4.55From Toronto: Niagara Falls Day Tour with Boat Cruise
Book Now
4.88Harbourfront Centre
Book Now
4.88Harbourfront Centre
Book Now
Final Day in Toronto's Urban Jungle
Morning
Start your final day with a visit to St. Lawrence Market. This historic market is home to numerous vendors selling fresh produce, meats, cheeses, and baked goods. Enjoy breakfast here while exploring its bustling stalls.
Afternoon
After visiting St. Lawrence Market, head over to nearby Distillery Historic District for lunch at El Catrin Destileria, known for its modern Mexican cuisine. Following lunch, explore more of this charming neighborhood filled with art galleries and unique shops.
Evening
Conclude your trip with an evening visit to Casa Loma, a majestic castle offering stunning views of Toronto's skyline. Take a guided tour through its grand rooms and beautiful gardens before enjoying dinner at BlueBlood Steakhouse located within Casa Loma itself.
Bedtime
Find amazing hotels in Toronto.
4.40St. Lawrence Market
Book Now
4.40St. Lawrence Market
Book Now
3.77Casa Loma
Book Now
3.77Casa Loma
Book Now
Top Boston Travel Videos
Adjacent Cities
Find the right stay during your trip.