Planning, Road, Tips

How to Plan a Progressive Road Trip

April 22, 2013 • By
Probably NOT the Best Car for a Looooong Road Trip - We're Actually Using our Small SUV

Probably NOT the Best Car for a Looooong Road Trip – We’re Actually Using our Small SUV

So my husband and I have decided to do a “progressive” road trip this year, with stops in as many US states as we can manage. We call it a progressive trip, because we’re doing it in stages – even leaving our small SUV parked in an airport satellite lot for a month while we manage some things back home, then we’ll fly back and start the next leg.  (No, we’re not using that teensy thing in the photo, but it is cute!)

Our goal is to see America in style — but that can mean many different things. Style is so dependent on its surroundings. (Imagine that cute South Beach bikini in a grocery store in Manhattan for instance.)

Here are my tips on how to plan your own stylish, progressive road trip:

1. Start with an idea, but don’t plan all the life out of it. Build the foundation of a plan, but stay open to the freedom the road brings with it. With all the apps and gadgets available now, you can plan some of your meals or overnight stays from the passenger seat on I-95.

2. Spend some time with great guidebooks and websites before you leave and organize your trip around some must-sees. It would be shame to find out about a great place, AFTER you’ve returned! I’ve enjoyed the “1,000 Places to See Before You Die” book series, especially.

3. Pick a few “landmark” stays and build your trip around them. Maybe there is a grand old historic hotel you’ve dreamt of staying at. Or a cutting-edge design hotel that has captivated you online. Or a special tourist attraction. Don’t miss your opportunity – plan your trip around those stays and fill in with freeway-friendly chain hotels when you have to.


A stylish apartment I rented through Airbnb

A stylish apartment I rented through Airbnb

4. Consider staying in apartments or bed and breakfast inns as well as hotels. I’ve used both Airbnb and One Fine Stay to find some amazing apartments – and I’ve used other sites to book villas overseas. Think outside the hotel room to see a more real slice of local life.

5. Here’s what we’re doing – because life won’t always stop for a road trip. Maybe for some folks, but not for us. So we’re tying our trips into our business plans. For instance, we wanted to be at the High Point Market in North Carolina to check out the latest design trends and we need to be in Washington, DC for a conference a week later. So this first leg of our trip will include North Carolina, Virginia, Washington and Maryland (at least).

6. Take back roads. Get a little lost. See what happens off the beaten path. Stop at a roadside fruit stand. See the quaint downtowns. Pop into a local antique shop. Try out a local diner.


Steak and Haricots Vert at Bistro du Coin in Washington, DC

Steak and Haricots Vert at Bistro du Coin in Washington, DC

Yes, we’ve seen several Civil War and Revolutionary War sites – that goes with this territory. But a real highlight, so far? We explored one of America’s oldest homes – a working farm founded in 1618 along the James River in Virginia, and still run by the eleventh generation of the same family.

Have you ever visited historic Shirley Plantation? It’s a beauty.

Shirley Plantation - James River

Shirley Plantation – James River

Looking for tips on how to plan a progressive road trip? Here you go! Travel Tips from Rover @ Home - road trip, roadtrip, progressive road trip.