Sixteen days + 2300 Miles + Four CA Provinces + Four New England States + Six Private Rentals + Three Hotels = Hundreds of Memories
In June 2019, my wife and I and our two youngest daughters took off on a sixteen-day road trip through Eastern Canada and New England as a high school graduation gift for the younger one.
I thought it would be fun to write a few stories of some of the people and places we encountered along the way.
Since this trip was different than anything we have done in the past, this first post will be about the planning process.
The Real Thing
When all our five kids were still at home, a “road trip” for us was a beeline back to South Carolina (the Beloved State) from wherever we were living at the time (IN, OK, OH). It did not require much planning.
In 2011, we moved back to South Carolina (finally). By that time, only our two youngest daughters were still at home.
It wasn’t until our last daughter graduated from High School in 2019 that we planned and took what I call a “real road trip” - Somewhere none of us had ever been before, with multiple stops in unique places, and a generous amount of time to enjoy the trip.
Even though there were some planned bed-down stops, this was the first time I felt that we could travel on a schedule not subject to a rush to get everything done.
Today’s post details the planning process - how we chose our destination, planned our route, and booked the travel and stops.
Choosing the Trip: Always have a Plan B
Plan A
Our original destination choice was France. We would fly to Paris or Toulouse, rent a car, and book stays in various interesting places we wanted to see. A road trip on our terms, not some tour guide.
As we began the research, two major things that we could not fit into “our terms” became apparent.
Travel time (to and from destination city)
Travel cost (roundtrip flights for four)
Even though I had a lot of vacation days available, my company had a limit of 15 days at a time. Anywhere close to affordable tickets required multiple stops over two days each way, leaving us with maybe 10 days for the road trip portion, not to mention recovery from jet lag.
Without taking advantage of the lower airfare schedule, we would not get near as much “bang for the buck” as we hoped.
So it was back to the drawing board.
Plan B
Susanna wanted Sarah, our next to youngest, to join us in whatever we ended up doing (I mean how boring it would be to travel alone with the parents, right). Sarah and her husband were living in Alaska, where he was based in the Air Force. So, the plan had to consider her travel costs as well.
Developing a Plan
When our kids were growing up, both these girls loved the Anne of Green Gables books and movies. So, naturally, we began looking at Prince Edward Island as a possibility. And, since France was the original plan, why not throw in the French Canadian Provinces as a consolation?
First things first - We used the research tools below to answer these four major questions when planning a Road Trip:
What Route?
What transportation?
How much time?
What will it cost?
Factors to Consider
Airfare for four
Trip Route
Rental Car
Accommodations
Food
Entertainment
Research Tools and Tips
Two things helped me with the planning here:
First, I’ve always been a budget guy.
Second, most of my career has involved information research and analysis. With the tools available today, these should not be an issue for anyone.
💡 Find a major bank or credit union travel card that fits your parameters. Some have no annual fee, but most fees range from $39-$75 annually. If you plan to travel a lot, it is worth it. Most offer a substantial amount of points for spending X # of dollars in the first 90 days.
Tools
One good thing about living in the Internet age is the ease of research. Here are the essential tools you’ll need for trip planning:
All-inclusive
The advantage of using an all-inclusive site for travel planning is that it’s, ta-da, All-Inclusive. Here are a few of the main ones:
Google Travel - Whatever your thoughts about Google, it is a very useful tool for researching airfare and accommodations. As far as I know, Google is not partial to any particular airline, hotel, or car rental company. You can conveniently book everything through this site or use it for comparative research before going to individual airline sites (recommended) as some deals or specials won’t show up on Google Travel).
AAA - An excellent service. While primarily for U.S. residents, they partner with many worldwide affiliates. They offer everything from booking flights, car rentals, accommodations, tour packages, and cruises. We joined AAA two decades ago, primarily for their roadside assistance service (which can quickly pay for itself. It wasn’t until this trip that we utilized their travel services.
Expedia Travel Group - Their website claims, “Whether it’s planning a family vacation, booking for business, or organizing the trip of a lifetime,
Expedia Group brands unlock the best possibilities for each individual traveler and each type of trip.” Their brands now include Expedia.com, Hotels.com, VRBO, Travelocity, Hotwire, ORBITZ, and Ebookers, so you can see how convenient this site would be.
Major Credit Unions or Banks - I am a member of Navy Federal Credit Union (the largest C.U. in the world). Whether you are on active duty, a veteran of any of the U.S. armed services, or even a family member you can join this credit union. They have a fantastic travel service and easily accommodate purchasing tickets, renting cars, or making hotel reservations with points or cash (debit/credit). I’m sure other major credit unions or banks have similar programs.
Airfare
💡All major airlines have travel reward loyalty memberships. You can sign up ahead of time for these without purchase or cost. Use this guide to get the links to major domestic and foreign airline rewards programs.
Timing is an important factor in finding the best airfare prices. Normally, the further in advance you book, the better the price. Also, the day of the week is important. Many times, off-season pricing can be a bargain.
Google Flights (a link on Google Travel) aggregates most airline flight schedules and pricing.
Going.com has become a popular site for finding low airfares worldwide. There are three membership levels: Limited (free), Premium ($49 annually), and Elite ($199 annually). Hat tip to
at for this information.Individual Airlines: Don’t forget to check Individual airline sites. All have travel hubs and areas of service. At certain times of the year, they will offer incentives and/or discount airfares to boost bookings.
💡 You can use airline reward points directly and link your airline loyalty account numbers with your travel card. This allows you to transfer credit card points to your airline rewards account. Use this handy guide from Going.com to walk you through the process.
Accommodations
VRBO - Vacation Rental By Owner (now a subgroup of Expedia Travel Group). offers stand-alone vacation properties only.
AirBnB - A broader selection of property types: stand-alone properties, shared spaces, hotel rooms, and campsites.
⭐ We used a combination. There was one (not typical) issue with Airbnb. I’ll get into that in one of the separate posts in this series. Which one you choose will probably be determined by location and length of stay.
There are many similar sites available.
Individual hotel chains: It’s always good to check directly with the major chains (Hilton, Hyatt, Sheridan) to see if there are deals. All have their own rewards programs.
Putting the Plan together
Here is the plan that came together after doing all the research:
I used a combination of the tools above: Flights and three hotels (one unexpectedly, which I will write about in another post) were booked through AAA. The rental car was booked using points from Navy Federal Credit Union. For our accommodation rentals, we used Airbnb for 1-2 night stays and VRBO for the longer stay on PEI.
The best roundtrip airfare to Toronto was from Charlotte (just 1.5 hours from where we lived). Our flight was non-stop and took less than two hours, which helped maximize our time.
Since weekends were not counted in my Personal Time Off (PTO), we booked our outgoing flight on a Saturday and return flight on a Sunday to add days.
As the map above indicates, our route to Prince Edward Island (PEI) would follow along Lake Ontario, the St. Lawrence River, and through New Brunswick Province with stops in Kingston, ON, Montreal, QC, Quebec City, QC, and Maramichi, NB. We then stayed five days on PEI before heading back to Montreal via New England.
Our return route would take us through Maine, New Hampshire, Vermont, and NY, reentering Canada at Niagara Falls. Stops included Southwest Harbor, ME, Lake George, NY, Niagara Falls, ON, and one overnight in Montreal.
Over the next few weeks, I will be writing a few stories about the places we saw, the people we met, and the things we did along the way.
I hope you will come along for the ride.
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While you’re here, check out my creative writing ‘Stack: The Talking Pen, where you’ll find fiction & non-fiction stories, poetry, art, and a short memoir.
My wife and I have traveled extensively, including living in Japan, England, and Vietnam for a total of eight years.
We've lived in Alaska, California, Idaho, Colorado, Ohio, Florida, North Carolina, Tennessee, upstate NY, and--for the last 8 years--in Virginia.
But she's never been to New England, so we were thinking about taking a similar trip next year for our anniversary. I'll be interested to hear your travel tips and suggestions, especially regarding lodging, in Maine, NH, Vermont, and the Atlantic provinces.