How to Plan a Road Trip from Boston to Miami

Moving from the U.S. to the U.K. has changed my perspective on road trips. It takes hours to leave London and make it to the coast, usually on cramped roads with tons of slow-moving traffic. I’ll never take either the open stretches of road in the U.S. or having the space to own a car for granted again.

Recently, I opted to drive with my brother-in-law from Boston to Miami in order to meet up with his girlfriend and my husband for New Year’s. They sensibly flew down to Florida, but the four of us did the long drive home in just two days. There were many things I learned, but I still definitely recommend this mode of transportation if you have the extra time. We were able to see some great destinations along the way.

First, let’s get you a car! A long trip is better with your own car, but there are options available for multi-state, unlimited miles or one-way trips.

Know Your Road Trip Timing

When I was younger, I could do the drive from top to bottom of the country in a day. For service trips or spring breaks, a whole caravan of us would drive from New York to Florida without losing a precious vacation day. However, for this most recent trip, we decided to take a solid three days for the journey down and two days for the way back. I was very thankful for the overnight breaks. If you have more willing drivers, you might not need as many days. Going slowly and steadily ensures you’re rested once you reach your destination.

miami beach road trip eileen cotter wright

Pit Stops for Days

Atlantic City, New Jersey, and Ocean City, Maryland

Our first stop was a little gambling and kitschy fun in Atlantic City, which was a new place for me. We stayed at Caesars Palace and had the place to ourselves because of the rain. You can easily take the car on a ferry down to Ocean City from there, or you can take the three-hour drive around to explore more fantastic hotels, restaurants, and gorgeous coastal views.

Charleston, South Carolina

A friend from college recently had a little girl, so I wanted to pop in to say hello. This was a little outside the regular route, but it was worth the detour for a quick visit and an overnight. A walk through the French Quarter and the old district is great for an afternoon to stretch your legs. If you dig interiors, take a tour inside the old Georgian Heyward-Washington House. Here are a few hotel options for Charleston, including the funky and upscale Vendue Hotel.

Savannah, Georgia

We hit this city on the way back from Miami after about eight hours of driving. An overnight was just what we needed to recharge for the long haul the next morning. Savannah is a beautiful place with old-school charm along the Savannah River and downtown. Have a look at our 48-hour guide to Savannah for some ideas. Or just book one of the taste of Savannah food tours and eat your way through the city.

What to Pack in the Car

It sounds silly, but pack cold weather emergency supplies like de-icer, blankets, flares, and high-protein foods just in case. We drove in the winter and didn’t hit the warm climates for a couple of days. For night driving, pack phone chargers that work in the car and extra batteries.

Besides normal vacation gear, I also made sure I had a warmer weather outfit easily accessible in a nearby bag or backpack. In fact, keep your road trip clothes separate from the rest of your belongings to avoid having to dig through tons of stuff.

Who Should Come Along?

If you’re yearning to have an adventure with friends or family but wondering if flights will be a hassle, then road tripping can be the best option. You set the pace and the pit stops, and you can pack as much or as little as you’d like. Some people will opt to rent a car to split the cost among passengers, while others will have a designated vehicle owned and driven by one person.

If you have a travel group of two to four, a regular economy-size car will work just fine, unless you have a large amount of luggage or supplies. For a group of four to eight people, it’s worth the investment to look ino passenger vans or even an RV, as long as you’re aware of the additional gas cost.

If you love road trips, have a look at our other itineraries for adventures worldwide on the road!

How far was your longest road trip? Do you prefer driving or flying?