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Planning a Three-Week Road Trip

by Ashley
Published: Last Updated on 10 comments 444 views 13 minutes read

Months of research. Hours spent comparing flight prices. Countless nights debating destinations and routes, followed by whimsical dreams of far away cities and interesting people. The weeks and months leading up to a trip burst with expectation and possibility, your mind’s eye envisioning all the things that could go wrong and all of the things that could go delightfully right. And then, after how many months of planning and how many sleepless nights, you board that airplane or find your train seat, and arrive in a new place, and in a whirlwind of food and photos and feeling lost, you explore as much as you can, and then you make it home, exhausted, your head on your own pillow after all of that time away, and you exhale. The trip is over, just like that.

Did it live up to your anticipation?

Was it as much fun as planning it?

As a person who lives for planning (event, trips, imaginary school curriculums) this question crosses my mind often. After a party I’ve been planning all for months, or on our way home from a trip that took nearly a year to plan, I wonder: which was more satisfying? The event itself, or the planning period before hand, when everything was possible?


We’re in the midst of planning a big road trip right now, so I find myself worrying more than I should, not about logistics or cost but about enjoyment. Will all of this effort pay off?

As an optimist, I always think it will. I can’t think of any of our trips in which the effort of planning outweighed the enjoyment of the experience. We planned our European home exchange for over 10 months, so there was definite room for disappointment or regret, but we look back on those six weeks as a once-in-a-lifetime opportunity that was fun and challenging and worth every moment of planning.

Planning takes a lot of time and energy. At times it can require mental gymnastics and more flexibility than you might want to give. Budget traveling and home swapping both require a significant amount of thought, research, communication, and creativity. I totally get why some people cringe at the thought of getting into the nitty gritty details of trip planning.

But the planning period is also the dreaming period, when you don’t know what will be and can only anticipate what might be. This is my favorite part of any trip.


One of the many many honu we encountered in Hawaii.

Planning our honeymoon (2 weeks, San Francisco, Oahu, and the big Island) without spending an insane amount of money required creative airline points usage, relying on the generosity of friends, and spending one night in an airport. Everything came together, giving me major satisfaction, and all of our research led us on adventures we’ll never forget. A trip that could’ve cost eight or ten thousand, cost half that, thanks to diligent planning efforts.

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The first inquiries I sent out on HomeExchange.com

For our EU home exchange, I sent out over 50 inquiries and received a few dozen that we turned down. Those messages all took time to write, to read, to consider. Then figuring out how to use points to buy some of our flights, and which countries we’d visit, and if we’d stay in hotels or AirBNBs, and if we’d take the train or a bus or rent a car or fly, and what’s the most cost efficient way to go to all of these places….. planning that trip quickly became my hobby, and one that I enjoyed!

There’s satisfaction in checking things off a list, and blocking days off on a calendar. I get a small thrill each time an idea clicks and falls into place. When I was writing fiction in my spare time, the planning stages were my favorites. Plotting, imagining settings, detailing character sketches. I loved jotting down all of my ideas, quick little scene outlines, and mapping out the major story beats with color-coded notecards. Actually molding it all into a coherent story was the hard, and least enjoyable, part for me.


From a few days in Vermont to three weeks on the road…

This road trip originated as a mere, “What if?” that stemmed from a text conversation Justin had with a childhood friend of his who lives in Vermont. They were both lamenting the fact that their families, which live in and around the Sioux Falls area, rarely have the ability or opportunity to come visit them. “And we have all of this space!” said his friend. We jokingly said that WE wold come visit them if they were so desperate for guests, and he said, “Okay!”

Well, if we’re going all the way to Vermont, might as well make a few stops along the way. And hey, if we’re going to be in the Northeast, why not just hit all of those little states to help me on one of my #40Before40 goals? And, hey, while we’re at it, why not drop in to Eastern Canada? Neither of us have been there yet!

So, a quick jaunt to Vermont with Justin’s old friend has morphed into an epic three-week adventure.


So how do we do this exactly?

How do we make this trip happening without emptying our wallets, missing a lot of work, or driving each other crazy?


Maps and XLS and calendars, oh my!

The scheduling of this road trip has provided many challenges — and just the kind I like. The main issue comes down to not spending an exorbitant amount of money, and with 8 different cities on the route, accommodation costs can add up quickly. So we’re considering ALL options: staying with friends, using hotel points, renting cheap AirBNBs, and swapping homes.

Home exchange is an easy way to cut some costs (hello FREE!) but requires a ton of flexibility and pre-planning. Since we’ve been hoping for an exchange in DC or Boston (or both), we couldn’t make any hard decisions about the rest of the trip until arrangements for one of those cities were handled. I started sending requests in mid December. Two weeks ago, we solidified plans to do a reciprocal swap with a couple from DC, our first destination, so we’ve finally been able to move forward with plans in the other locations.

In the past, we’ve done reciprocal exchanges (simultaneous and non) and a passport exchange (where you earn a passport point for hosting a family, but don’t get hosted in return). We have yet to try a Hospitality Exchange, where you stay with your hosting family and they stay with you, in return. It’s like visiting friends you’ve never met before; definitely outside our comfort zone, but something we’re willing to try to make this road trip an affordable reality. We’re currently negotiating to stay with a lady in Toronto; if the dates work out, then she’ll be able to stay with us if/when she comes to Nashville. We’ve also lined up a Passport exchange with a couple in Portland, Maine.

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For the other locations, we’re going the AirBNB route, as per usual, and maxing out our loyalty and credit card point options. We’re taking advantage of the 60,000 point bonus with the IHG credit card. And we’re huge fans of the Chase Sapphire Ultimate Rewards program, usually using our points for Southwest or United, but will transfer a bunch to IHG so we can stay for free in at least one location. This kind of efficient use of resources makes me feel accomplished. (At this rate, it’s looking like we’ll only have to pay for AirBNBs for 4 out of 22 nights.)

As this three-week trip wouldn’t be possible without our amazing remote jobs, this will not be a vacation. We’ll be working part-time, putting in hours every work day, making ourselves as available to our co-workers and being as productive as we can from the road. I’ll make a calendar of availability, like I did for our six-week EU trip, and will work from the car as often as possible. Thank goodness for technology!

Handy apps and sites like Gas Buddy, Google Maps, and Budget Your Trip have been super useful in estimating daily costs. We don’t want to feel restricted, and by covering many of our accommodations with points or exchanges, our budget opens up a bit more for entertainment and dining out. Luckily, much of what we want to see in these places are historical monuments or free museums, so most of our costs will be food and drink related (and seeing a baseball game in Boston).


We even road trip with our cats!

There are still many unknowns, mostly surrounding what we’ll actually do in each of these locations. Oddly enough, THAT is the part of planning that I’m least concerned with. We usually arm ourselves with a handful of highlights, things we definitely want to see or eat, but we don’t book tours or make reservations ahead of time. We prefer to wing it, much of the time, asking bartenders for recommendations and going with whatever sounds most interesting when we wake up that morning. With accommodations nearly sorted, and our route mapped, we can now start figuring out what we want to see in each of these locations. If you have any specific recommendations for the following cities, please let me know! 

  • Washington DC
  • Boston
  • Portland, ME
  • Vergennes, VT
  • Montreal
  • Toronto

Planning Tips

I love road trips. I love traveling with my husband. I love visiting new cities. So this trip is going to be a blast. But I’m also having a blast right now, with the calendars and lists and maps. It’s all so exciting!  The sights we’ll see, the places we’ll stay, the efficiency of the route, maximizing our budget, the sheer possibility of what lies ahead — the planning of it all jazzes me up like a kid waiting for Santa.

But, I know not everyone gets excited by planning, and some in fact may dread it. So here are some things I’ve learned and find useful that might help with your planning efforts.

  • Create a budget range. What’s your max budget for the trip, and what’s your goal budget? You don’t want to disappoint yourself or stretch your funds too thin by working only with your all-in budget, but you don’t want to exceed your limits. Aim for the goal budget, but be flexible enough that going over it won’t break the bank.
  • Start early! I think part of the reason people get stressed out by planning is that they don’t give themselves adequate time, and get rushed into making more expensive decisions. To give some examples: we started planning this May/June road trip last November. Our two week Hawaiian/Californian honeymoon happened more than six months after our wedding. We went to Mexico in April 2017, and began conversations with our exchange partners the previous March.
  • Think outside the box. The costs of a family vacation can add up quickly, especially if you stick to traditional travel methods such as staying in hotels and eating out every night. Get creative. Rent a house or apartment. Experiment with loyalty programs and points. Bribe family and friends. Consider atypical travel methods such as home exchanges, couch surfing, hostels, etc.
  • Limit the number of apps you use. Pick a few, play with them, and only keep the ones you really like. Don’t try to use everything that’s out there. There are hundreds of sites and apps that can help but they aren’t ALL helpful ALL together.
  • Keep your research and notes in one place. Whether it’s Evernote, Google Docs, Google Keep, or a physical notebook, just use one “notebook” to detail information. You don’t want to be searching all over the place for what you need. I live in Google, so I created a Google Sheet with multiple tabs, one each to track a general outline of the trip, potential exchange partners in each city, a more detailed trip itinerary, and costs. I included links to my Google Map, for quick access, and links to AirBNBs and other research URLs.
  • If you have an office job, talk to your boss about temporary remote work. For traditional desk/computer jobs, many companies are opening up more remote opportunities for their employees, with flex hours and allowing people to work from home a day or two each week. Talk to your managers about the possibility of working remotely to give yourself more flexibility in terms of trip length, destinations, and when you can go.
  • Make a list of your Must Sees and Must Dos. You don’t want to wind up disappointed at the end of a trip, so what are your non-negotiables? Pick a few Biggies and a few Would Be Nice To Sees, but….
  • Don’t plan EVERYTHING. Leave room for spontaneity or things going unaccording to plan. Allow yourself ample time to explore a place, stumbling upon interesting streets and impromptu adventures. You don’t want your schedule overpacked so that you can’t stop to smell the roses, or taste the wine, or attend a random festival.

Are you a planner or a by-the-seat-of-your-pantser? How much do you plan before a trip? Do you or your partner do most of the planning? How do you handle plans falling through? What planning tips have you found to work for you and your family?


Kathy Poston February 28, 2018 - 3:02 am

You didn’t mention Buffalo, but it looks like you’re passing through there. You could see Uncle Mike’s ship, the Little Rock, docked at the Buffalo Naval & Military Park. And, there’s a very good pizza place across the street in the Courtyard hotel, Pizza Plant, which is owned by our own councilman, Jeff Syracuse’s, two uncles. If you come back through Lexington, the Makers Mark grounds are beautiful and there’s a nice tour.

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Danielle Owen July 7, 2022 - 9:38 am

I enjoyedd reading this

Ashley July 7, 2022 - 11:04 am

Thanks Danielle! Are you planning your own road trip? Would love to hear any tips or lessons learned!

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