Hello! It sounds like an exciting trip to Winnipeg, Regina, Saskatoon, and Edmonton. I'm happy to provide some useful travel tips for your journey.

Best Time to Visit:
The best time to visit these Canadian cities is during the summer months from June to August when the temperature is warm. The winter season from December to February is a great time for winter sports like snowboarding and skiing, but it can be extremely cold, especially for those not used to such temperatures.

Route and Accessibility:
All these cities are well-connected by air, rail, and road. You have the option to fly into Winnipeg International Airport, and from there you can either take flights, trains, or buses to visit Regina, Saskatoon, and Edmonton. Having a car could be beneficial for sightseeing at your own pace.

Accommodation and Booking:
These cities have a wide range of accommodations to choose from, including hotels, motels, and bed & breakfasts. You can book your accommodation in advance through various online platforms like Booking.com, Airbnb, and Agoda, to name a few. Early booking is recommended especially during the peak tourist season.

Clothing and Essentials:
Summer requires light clothing like T-shirts, shorts, sunglasses, and sunblock. Winters can be harsh, so heavy winter wear including a down jacket, gloves, scarves, and thermal layers are necessary. Don't forget a good pair of comfortable walking shoes for sightseeing.

Health and Safety:
Canada is generally a very safe country. However, it’s always advisable to have travel insurance for any unforeseen circumstances. Keep emergency numbers at hand. In winter, be careful of icy conditions and ensure you're well-equipped to handle the cold weather.

Local Etiquette and Respect:
Canadians are generally polite and respectful. It is customary to hold the door for the person behind you and to say sorry even if someone else bumps into you. Tipping is customary in restaurants, bars, and for services like taxi rides.