Itinerary suggestions

Hi I’m planning a trip next summer (that’s organised for me!). We’re a family of four so it needs to be not too hectic for any of us (ages 50 to 9). I want to fly to Boston, take a few days there, then take in Niagara Falls, Toronto and Montreal and back to a beach resort near Boston. I intend the trip to be a couple of weeks. Any suggestions for where we may need to stop in between, recommendations for hotels and resorts and how long we need in each place greatly appreciated. ☀️

It sounds like you’re planning an amazing and diverse trip! A family of four with ages ranging from 9 to 50 will need a balanced itinerary with some variety in activities, while avoiding too much rush. Here’s a detailed suggestion on how to plan your trip, including time in each destination, travel stops, and hotel/resort recommendations.

Day 1-3: Boston, Massachusetts

Start your trip in Boston, a city with a mix of history, culture, and family-friendly activities. Three days will be enough to explore the main attractions without feeling rushed.

  • Day 1: Arrive in Boston and check into a family-friendly hotel like The Godfrey Hotel or HI Boston Hostel (if on a budget). Spend the afternoon strolling around Boston Common and the Public Garden. Take a ride on the famous Swan Boats in the summer.
  • Day 2: Visit the Freedom Trail, which will take you through 16 historical sites. You can either join a guided tour or walk on your own using an app. Don’t miss the Old North Church and Paul Revere’s House.
  • Day 3: Spend your final day visiting the New England Aquarium or the Boston Museum of Science, both of which are excellent for kids. End the day by exploring the quirky shops on Newbury Street.

Day 4-6: Niagara Falls, Ontario

Drive or fly from Boston to Niagara Falls (approximately a 7-hour drive or 1.5-hour flight). Plan for two to three days here, as the falls are a must-see and there’s plenty to do for the whole family.

  • Day 4: Arrive in Niagara Falls and check into a hotel with a view of the falls, such as Niagara Falls Marriott Fallsview Hotel or The Oakes Hotel. Spend your evening exploring the falls and enjoying the Illumination of the Falls at night.
  • Day 5: Take a boat tour on the Maid of the Mist to get up close to the falls, and explore the surrounding parks and hiking trails. For a more interactive experience, visit the Butterfly Conservatory and the Cave of the Winds.
  • Day 6: Head to the nearby Niagara-on-the-Lake for some wine tasting (if the adults are interested), or explore the quaint town’s shops and waterfront. You can also check out the Skylon Tower for panoramic views of the falls.

Day 7-9: Toronto, Ontario

From Niagara Falls, Toronto is about a 1.5-hour drive. Toronto is a vibrant, multicultural city with plenty to see and do. Two to three days is ideal to get a feel for the city.

  • Day 7: Arrive in Toronto and stay at a family-friendly hotel like The Fairmont Royal York or The Ritz-Carlton. Explore the iconic CN Tower for incredible views of the city, or visit Ripley’s Aquarium of Canada for some family fun.
  • Day 8: Spend the day at the Royal Ontario Museum or take a ferry to Toronto Islands for a day of outdoor fun, picnic spots, and bike rentals. The islands are a peaceful escape from the city buzz.
  • Day 9: Head to the Distillery District for its charming cobblestone streets, galleries, and boutique shops. You can also visit Toronto Zoo if your family loves animals.

Day 10-12: Montreal, Quebec

Drive or fly to Montreal (approximately 5-6 hours by car or 1-hour flight). Three days in Montreal will give you a good mix of cultural exploration and family-friendly activities.

  • Day 10: Arrive in Montreal and check into a hotel like Hotel Le Saint-Sulpice or Le Square Phillips Hotel & Suites. Spend your first day exploring Old Montreal. Wander around Place Jacques-Cartier and enjoy the cobblestone streets and historical buildings.
  • Day 11: Visit the Montreal Biodome, where you can explore different ecosystems, or head to the Montreal Science Centre, which is interactive and great for kids. Later, take the family up to Mount Royal for panoramic views of the city.
  • Day 12: Explore Jean-Talon Market for a taste of local produce, or visit the Montreal Museum of Fine Arts if your family enjoys art. You could also take a boat ride along the St. Lawrence River.

Day 13-14: Boston Beach Resort

For the final leg of your trip, return to Boston and spend a few days unwinding at a beach resort. There are several beautiful spots close to the city:

  • Cape Cod: Just an hour's drive from Boston, Cape Cod offers plenty of family-friendly beaches. Stay at a resort like Chatham Bars Inn or The Ocean Edge Resort for a relaxing beach experience.
  • Revere Beach: Closer to the city, this beach is perfect for families looking for a quick, relaxing stop before heading back home.
  • Marblehead: A quiet coastal town with scenic views, a short drive from Boston.

These beach resorts will offer a relaxing finish to your trip, with easy access to Boston if you need to catch your return flight.

Summary Itinerary:

  • Day 1-3: Boston (History, parks, museums)
  • Day 4-6: Niagara Falls (Maid of the Mist, scenic views)
  • Day 7-9: Toronto (CN Tower, Royal Ontario Museum)
  • Day 10-12: Montreal (Old Montreal, Mount Royal, Biodome)
  • Day 13-14: Relax at a beach resort near Boston (Cape Cod or Revere Beach)

This itinerary balances historical, cultural, and outdoor activities while allowing for enough downtime, making it ideal for a family trip. Enjoy your adventure!


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