New England road trip itinerary: Where to go, what to see, and how to get there

Fresh lobster rolls. Craggy coastlines. Iconic lighthouses. Historic mansions. Diverse wildlife. Hike in the magical Berkshires or whale-watch in Rhode Island; sip a craft beer in Maine or relax on the beach in Cape Cod. A New England road trip is bursting with things to see and do.

Whether you decide to visit one or all of New England’s beautiful destinations, make it easy by renting a passenger van. Go where you want, when you want, and with whoever you want —  Greenvans will supply you with a secure, reliable vehicle to take you there. 

Take a look at our list of suggested three, four, and five-day itineraries to see the best of New England and, when you’re done, check out our favorite New England winter getaways for more ideas.

New England road trip: 5-day itinerary

A New England road trip of five days affords enough time to experience the region’s many personalities and landscapes. Start in the vibrant city of Boston before driving north along the Atlantic coast to Maine, uncovering the spectacular nature and scenery in this part of the world. 

In just five days you’ll visit small seaside towns, hike mountains, climb lighthouses, and dine on delicious, fresh seafood. Here’s how:

  • Day one: Boston, Massachusetts
    • What to do: Start your trip by exploring the historic Freedom Trail in Boston, a 2.5-mile walk through U.S. landmarks like the Massachusetts State House, and Paul Revere’s House. Check out Faneuil Hall Marketplace and enjoy an Italian meal in the North End, Boston’s Little Italy.
  • Day two: Portland, Maine
    • What to do: Wander the cobblestone streets and quaint fishing piers in the Old Port district. Visit the Portland Head Light, where you can take beautiful photos of the iconic lighthouse that sits above the rocky coast. If time permits, venture further up the coast to see other scenic towns like Kennebunkport or Ogunquit.
    • Road trip time: 1 hour 45 minutes
  • Day three: Bar Harbor, Maine
    • What to do: Drive along Park Loop Road directly to Acadia National Park, where you can spend the day discovering the park’s varied landscapes, hiking trails, pristine lakes, and abundant wildlife. Visit Bar Harbor and its bustling downtown brimming with boutique shops, delicious restaurants, and lively nightlife scene.
    • Road trip time: 2 hours 55 minutes
  • Day four: Portsmouth, New Hampshire
    • What to do: Head back south along the coast to Portsmouth to visit the Strawbery Banke Museum for a dive into the region’s past. Stroll the waterfront walking path or take a harbor cruise. The town is known for its cuisine, so enjoy an evening at one of the acclaimed farm-to-table restaurants or craft breweries.
    • Road trip time: 3 hours 45 minutes
  • Day five: Salem, Massachusetts
    • What to do: Witch hunts, ghost tours, ferry rides, and a downtown waterfront overflowing with galleries, shopping, and restaurants with fresh daily catches on the menu. What more can you ask for from a New England adventure? You’ll find plenty to keep you busy in Salem before returning home.
    • Road trip time: 55 minutes

This itinerary can be easily modified to a longer or shorter trip. Want to extend? Spend an extra night in Boston or tack on a visit to quaint Bangor, ME, where you might run into award-winning author Stephen King. If you need to shorten the trip, consider a half-day trip to Salem instead.

Starting your trip from Beantown? You’re in luck! We have plenty of Boston vans in stock and ready to roll.

Source: Acadia Magic

New England road trip: 4-day itinerary

We know that on a four-day New England road trip, you’ll want to keep the driving to a minimum. That’s why our suggested itinerary includes must-see places that are situated close together. 

This unique mix of New England destinations showcases a little bit of everything: small towns, rocky cliff views, expansive beaches, and urban hubs. 

  • Day one: Mystic, Connecticut
    • What to do: Mystic’s rich maritime history and abundance of water activities make it a great jumping-off point for your New England road trip. See historic ships at the Mystic Seaport Museum, visit a local winery, and go boating on the Mystic River. Dusk is a beautiful time to stroll the riverside trails before hitting the atmospheric downtown. 
  • Day two: Newport, Rhode Island
    • What to do: Meander along the dramatic Cliff Walk and its breathtaking views of the Atlantic Ocean. Visit the opulent Newport Mansions for a glimpse into life during the Gilded Age. Do a little boutique shopping on quaint Thames Street and when you’re ready for a seafood feast, head to the harbor for upscale waterfront dining.
    • Day one to day two road trip time: 1 hour
  • Day three: Cape Cod, Massachusetts
    • What to do: Known for its beautiful beaches, Cape Cod is an excellent place to relax in the sun. Take a stop in Chatham or Provincetown to discover the charming essence of local life in New England. For active travelers, the Cape Cod National Seashore is abundant with hiking and biking trails, historic lighthouses, and diverse wildlife. If time allows and the season is right, go on a whale-watching tour.
    • Road trip time: 1 hour 25 minutes
  • Day four: Providence, Rhode Island
    • What to do: Dive into Providence’s fascinating history with a walk along Benefit Street, where original houses from the 18th and 19th centuries still stand proud. Art lovers should check out the RISD Museum and Waterplace Park’s impressive outdoor installations that line the walking paths along the river. Visit Federal Hill to dine on classic Italian cuisine.
    • Road trip time: 1 hour 15 minutes

This itinerary works best when coming from the south, so if you’re renting a Richmond van it can be followed exactly as written. However, if you’re renting a van from our office in Providence, simply reverse the order! If you’ve got a week or more to explore, consider combining it with our five-day New England road trip.

Source: Travel and Leisure

New England road trip: 3-day itinerary

Why stay home on a long weekend when you can go on a family-friendly New England tour? Time is of the essence during a three-day road trip, which is why we suggest maximizing your hours on the road with a visit to Vermont. Not only are the destinations close in distance, but the scenery is spectacular. 

This trip works seamlessly with a van rental from any of our New England locations, like Boston or Providence.

  • Day one: Woodstock, Vermont
    • What to do: Start with a hike on the tranquil wooded trails in Marsh-Billings-Rockefeller National Historical Park. If you’re traveling with children, visit the Billings Farm & Museum to learn the workings of a dairy farm and perhaps milk a cow. Downtown Woodstock is great for souvenir shopping and dining at local restaurants.  
  • Day two: Stowe, Vermont
    • What to do: Take Route 100 for a lovely ride through the Vermont countryside to Stowe, a quaint village known for shops, art galleries, and many spas and breweries. Connect with nature on a gondola ride or a hike to the summit of Mount Mansfield, Vermont’s highest peak. For action-seekers, there are plenty of opportunities for mountain biking, zip-lining, and snow sports, depending on the season.
    • Day one to day two road trip time: 1 hour 15 minutes
  • Day three: Burlington, Vermont
    • What to do: Located on the shores of Lake Champlain, Vermont’s largest city boasts a beautiful waterfront with views of the Adirondack Mountains. Walk around Church Street Marketplace, Burlington’s lively center known for its street performers. End your trip with a memorable meal at one of Burlington’s eclectic farm-to-table restaurants.
    • Road trip time: 40 minutes

For those who’ve got more than a long weekend to spare, this three-day New England road trip itinerary pairs well with either, or both, of the road trips listed above.


Other excellent destinations to add include North Conway, NH, to visit the magnificent White Mountains, or Mount Washington, NH, where you can drive Mount Washington Auto Road to the top of the mountain itself, the highest peak in the Northeastern United States.

How to prepare for the ultimate New England road trip

As professional road trippers, we know the ins and outs of planning a journey by vehicle. There are simple things you can do to prepare and ensure your adventure is a seamless one. Here are our expert tips to guarantee an unforgettable vacation.

Do your research and plan ahead

First, read this list thoroughly and decide with whom you’ll travel and where you want to go. Leave some room for flexibility by choosing a few non-negotiable destinations and one or two places that you’re open to visiting if time allows. 

Using apps like Google Maps or Waze, map out your route. Remember to include any sites or detours that you’d like to hit along the way. Book overnight accommodations ahead of time on sites like or Airbnb, and consider reserving show, lift, or museum tickets before departure if you’re traveling during the high season. 

Additionally, book your rental van with Greenvans from the location most convenient to you. If you’re not sure which van is best, give us a call.

Pack for the season

Packing can feel more overwhelming than it has to. Make it easy by creating a list before departure and remember, whatever you forget, you can most likely buy a replacement on the road. 

Depending on the season that you’re traveling, you’ll want to bring specific things, so consider the following when packing your bags:

  • Spring: Layered outfits, a light jacket, hiking boots, a hat, sunglasses, a raincoat or an umbrella, and comfortable walking shoes.
  • Summer: Swimsuits, sandals, shorts or sundresses, sun protection, a hat, sunglasses, and a water bottle.
  • Fall: A light jacket, a scarf, comfortable boots or sneakers, hiking boots, and jeans or warm pants.
  • Winter: A warm jacket, hats and gloves, snow-sport clothes and gear, snow boots, and hand warmers.

In addition, include chargers, speakers, books, toiletries, and necessary medications in your bag. Remember that with a rental van, you can pack some extras you might not normally have space for, like beach chairs and blankets in the summer, skis and snowboards in the winter, picnic essentials, and a cooler for drinks and snacks in the spring and summer. Speaking of spring and summer, check out our East Coast weekend getaways for Memorial Day while planning your warm-weather road trip!

Rent the right ride

The most essential component of a successful road trip is the right ride. You want something safe, spacious, and convenient, where your loved ones can sit back, relax, and enjoy the views. 

That’s where we come in. With five locations and a fleet of modern vans to choose from, you’ll appreciate the ease of renting a passenger van with Greenvans for your New England road trip. Interested in learning more? Check out our guide to the best van for your needs.

Common questions about New England road trips

We know you have questions. Here is a list of the most common questions about New England road trips and responses from our local experts. 

How many days do you need to see New England?

You need at least three to five days to see New England. This is enough time to discover the beautiful coastline, the scenic mountains, the vibrant cities, and the quaint seaside villages.

Is a New England road trip worth it?

A New England road trip is definitely worth it! Since everything you want to see is pretty close together, driving will maximize what you get to see and do. Plus, you get to see the picture-perfect landscapes that make New England so popular.

What are the best months to visit New England?

The best months to visit New England are December and January for snow and holiday cheer, April for spring weather and hiking, July for beaches and festivals, and October for leaf-peeping.

Is it easy to drive around New England?

It is very easy to drive around New England. Destinations are situated close together, the landscapes are gorgeous, and drivers are friendly and alert. There are lots of roadside stops to make, like farmer’s markets and scenic overlooks. Just remember to stay on top of weather conditions in the winter to avoid road closures.

Hit the NE Coast with Greenvans

The best way to see New England is by taking a road trip in a 15-passenger van rental. The flexibility, comfort, and security are unmatched. With a rental van, you can hit as many towns as you want without worrying about departure times, security checks, and long periods of waiting around just to get where you want to go. 

Not to mention, the views. The varied scenery, from farmland to mountain peaks, seaside villages to lighthouses, is what makes a New England road trip so impressive. Any time of year is magical in New England, so rent a Greenvans 15-passenger van and start planning your road trip today!


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