How To Plan An Epic Road Trip

Posted in Bucket List, Travel {Babymoons & Family Vacations}
on January 16, 2017

Have you ever dreamt of going on an epic road trip?  Just getting behind the wheel, hitting the open road, and discovering new adventures along the way?  Well, a couple of years ago, my hubby and I did just that.  We embarked on the road trip of a lifetime through New England, and made so many memories together.

Today on the blog, I’ll share with you the 5 simple…but very important…steps we took to plan our epic road trip.  So, buckle up and grab a pen and paper.  Let’s dream and plan your epic road trip together.

How To Plan An Epic Road Trip

Step #1: Decide Where You’re Going

I know, I know.  That sounds so simple, right?!  But, seriously.  Map out on a piece of paper where you would ultimately like to go.  For us, we pictured a New England Road Trip in the fall that took us through Vermont, New Hampshire, Maine, Rhode Island, Massachusetts, etc.  So, map out on paper where you’d like to visit.

To Plan An Epic Road Trip

Step #2: Figure Out How Long You Have To Explore

I scoured Pinterest for itineraries.  I saw trips through New England that were 7 days long to 3 weeks.  We had 13 days to drive through New England, so we couldn’t hit everything we wanted to see.  We had to cut some things off our itinerary, but it was still was an amazing trip regardless.  And, I feel like if we’d rushed ourselves even more to fit in other destinations, we wouldn’t have been able to relax and enjoy our trip.

Other things to consider when you’re figuring out your timeframe are…

Do you need to schedule some downtime?


How many hours a day are you willing to spend in the car? 

To Plan An Epic Road Trip

We (ahem…my husband ?) found an amazing deal on a waterfront hotel room in downtown Bar Harbor Maine, just minutes from the whale watching boats, lobster shacks, and Acadia National Park.  The room was gorgeous, and included our own balcony overlooking the Harbour!

{You can check out The West Street Hotel by clicking here….we highly recommend it}

He found a package that included a free 4th night stay, and free breakfasts every morning. We had to knock out a day in Boston (we’d already been there anyways) to take advantage of an extra day in Maine…I know right, rough life. ? The free breakfasts alone were worth a million bucks. As you’ll quickly realize on your road trip…you feel like you spend your life savings on food. ?

Well, little did we know, that this 4 night stay in Bar Harbor halfway through our epic road trip, would be a much-needed reprieve.  It was so nice to actually unpack our bags for a few days, not be stuck in the car for hours, and not feel the rush to checkout of the hotel every morning.  It was just the breather we never knew we’d want.

Plus, this amazing hotel, offered laundry services, which was a saving grace after several days hiking in a National Park.  And, every afternoon they’d set out freshly baked cookies in the little pantry on our hotel floor.  Yes….there was a small pantry stocked with goodies.  Everything from fresh fruit, coffee, hot chocolate, bottled water, and the before-mentioned cookies to help us refuel after a day of exploring.

To Plan An Epic Road Trip

So, when you’re planning your own road trip, factor in some rest days, or a rest period, where you really get to settle into a location and not have to spend hours in your car every day.  I’m telling you, it was necessary by day 6-10.

Which leads me to my next question.  How many hours a day are you willing to spend in your car? 

For me, I hate long days in the car. I almost was dreading our planned “drive days” cause I start to feel claustrophobic if I’m in the car too long.  Not to mention, if I’m behind the wheel too long, I have the tendency to get really tired!  Not a good combination.  ?

So, know you’re limits.  I think my hubby would’ve been fine driving 15+ hours a day….but not me!  No, thank you.  We built “drive days” into our itinerary, that were longer driving days.  That way I could psych myself up to not expect much.  However, I have to say, driving through various states, and seeing the mountains and the beautiful foliage (our trip was in October), made the driving days some of my favorite days on the trip.

To Plan An Epic Road Trip

When we planned our trip, we added in a stop to Niagara Falls USA, and then a stop in Hershey PA so that we never had to spend more than 8 hours in the car a day.  Planning our trip this way allowed us to…

A. See 2 more places that were on our travel bucket lists &

B. Have time on our “drive days” to get out and explore.

We stopped at maple syrup stands, and explored monuments. We took photos at waterfalls, and went on mini hikes during our driving day through Vermont. If we’d packed too many miles into that day, we would’ve felt rushed, and not been able to get out of the car and explore.  And, that’s what road trips are about, right?!

To Plan An Epic Road Trip

Step #3: Create a Road Trip Bucket List

You’ve already mapped out your destinations on paper; figured out how long a trip you’ll have to explore; factored in rest days; and hopefully, calculated out your miles between each destination.  So, now that you have a rough draft of where you’re going, let’s talk about what you want to do when you get there.

During this part of the planning process, my hubster and I spent hours on Pinterest and social media, looking for the best activities to do in each location.  We also searched for great places to stay and eat.

We started a list featuring every idea that we found interesting, and it turned into our trips Bucket List.

Here’s a few things that made it on our New England Road Trip Bucket List…

As you can see, we had a lot on our bucket list, and a lot more was added before it was all said and done.  But, this was certainly the fun part.

We researched different activities, restaurants, and national treasures in each of the areas we planned to travel to.  We then decided on which activities we would splurge on, and which ones to knock off the list.   Pinterest is an amazing resource when planning a road trip.  You’d be amazed at how many people have paved (no pun intended ?) the way before you, and already done the research.  Have fun dreaming and scheming, as you begin to pull this whole thing together.

To Plan An Epic Road Trip

Step #4: Decide On Where To Sleep

Sleep?!  Who has time to sleep when there’s so much to explore?  Well, let me tell ya.  You’ll want a nice place to rest for the night after all your Bucket List busting activities, believe me. Where to stay the night, is just as important as where you’ll spend your day.  And, if you’re anything like us (or me, really ?), I need somewhere decent that’s not screaming Bed Bugs!  You feel me?!

Once we had our itinerary nailed down, and our other activities planned out in our various locations, we then started searching for places to stay within a certain mile radius of our end destination.  We looked on popular websites like, trivago, airbnb, and so on.

We also chose to stay at some splurg-ey hotels, cause…that’s just how we roll. ? We looked for off-season deals, special activities offered through the hotel, and gorgeous spas…for me.

To Plan An Epic Road Trip

We stayed at The Omni, Mount Washington in New Hampshire, which looked like an amazing white mansion at the foot of snow-capped mountains.  This was the place where we went on a Moose Tour excursion, had breakfast in bed, & I enjoyed a very fancy spa day.  This place was a splurge location, but was definitely worth it.

Our ultimate splurge, though, was staying at The Ocean House in Rhode Island.  Adam introduced me to this glorious place through a picture he saw on Instagram.  It’s the kind of hotel that offers culinary classes in their 5 star restaurant, has their own private beach overlooking the Atlantic Ocean, dresses your bed with monogrammed sheets and pillow shams that coordinate with your last name, and offers a Mercedes-Benz for you to drive while you are their guest.  Yes, you read that right. ?

You could certainly RV your epic road trip, or stay in cabins in Kampgrounds of America. There’s also less expensive deals on airbnb where you can stay in someone’s time share for much less than a hotel.

But, for us, one thing led to another, and we ended up staying in a ski lodge in Vermont; a Culinary Resort in Essex Junction; & a French Inspired Chateau in the Pinehills of Massachusetts.

{Don’t worry!  I’ll be sharing all the details of our road trip itinerary with you soon!}

To Plan An Epic Road Trip

Step 5: Set a Budget & Stick To It

As my husband can clearly attest too, I’m horrible at sticking to a budget.  I start planning a trip, and I see fancy hotels, spas, and luxury…and I can’t help myself.  Good thing he’s always there to reign me back into reality. ?

So, when planning your epic road trip, set a budget and try your hardest to stick to it.  We did not do a great job with this.  We ended up spending double what we’d planned to.  Oops!

Decide what you’re willing to splurge on, and what you’re not. Are you going to pack granola bars and pop tarts to eat for breakfast so it’s one less meal to buy on the road? Are you the type of people who can “rough it” in rustic cabins along your journey, or are you willing to splurge on higher thread count sheets and turn down service?

What activities are you really wanting to splurge on, and what can wait for another time?  Are there restaurants you definitely want to dine at, or are you going to be frequenting drive thru’s more often than not?

We budgeted for everything….and I mean everything.  We knew exactly how much we could spend on gas, food, and souvenirs each day, and we kept a log on how we did.

We wrote every purchase down…and I do mean every!  We tracked how much we spent on gasoline and souvenirs, hotels and tickets.  We even kept track of tolls and tips.  Every penny was accounted for…even the pressed souvenir penny at the pit stop.

At the end of our adventure, we knew exactly how much we’d spent.  Gulp. ?

Now that you have a plan in place, and know where you’re heading, what you’d like to do while you’re there, and where you’d like to stay the night, nailing down a budget should hopefully be a little bit easier.

There you have it!  5 steps to help you plan your epic road trip!  I hope this helps!  Planning a road trip can be overwhelming, but I hope these steps will help you break down the process.  If you have any additional questions, please don’t hesitate to ask.

So, where are you going? Share your road trip with us in the comments.  We’d love to hear all about it.

To Plan An Epic Road Trip

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