Hello! That sounds like an exciting trip. Here are some travel tips for your visit to New York City, Boston, and Toronto.

Best Time to Visit:
The best time to visit these cities is in the fall (September to November) when the weather is milder. However, Spring (April to June) is also a good time to witness the cities in full bloom.

Route and Accessibility:
All three cities are well connected by road, rail, and air. From New York, you can travel to Boston by driving, taking a bus, train, or a short flight. Once done with Boston, you can either drive, take a train or fly to Toronto.

Accommodation and Booking:
These cities have a wide range of accommodations to suit various budgets. From luxury hotels to affordable hostels, you have multiple options. Booking in advance is highly suggested to get better rates and secure your spot.

Clothing and Essentials:
Pack lightweight yet warm clothing that can be layered easily, comfortable walking shoes, sun protection, rain gear (just in case), and all personal toiletries. These cities are hubs of fashion and culture so feel free to dress trendily!

Health and Safety:
Generally, these cities are safe for tourists. However, as with any large city, it's always smart to stay vigilant, especially in crowded areas. Also, remember to keep your travel insurance updated.

Local Etiquette and Respect:
People in these cities are generally open-minded. However, observing good manners, being polite and respecting local customs and regulations is always appreciated. Do remember that tipping is customary in restaurants, taxis, etc.