5 Day Maine Road Trip: Steal Our Summer & Fall Itinerary!

Maine Road Trip

There is just something about Maine that makes it so special. If you’re reading this debating taking a Maine road trip, then know that we highly recommend it! We’re drawn to this area of the USA for the small towns, scenic coastal route, and beautiful nature. While you can visit year-round, the best time for a 5 day Maine road trip itinerary is in the summer or fall. Here’s our favorite driving route, fun food stops, and essential tips from our own experience.

How to Get to Maine

Not already in New England? Then you’ll probably be arriving by flight! Be sure to check Skyscanner and compare dates on Expedia to find the best deals. 

The easiest way to start your Maine road trip would be to fly into Portland International Jetport and rent a car. Here’s a few of our best tips for renting a car in Maine if you’re considering this. 

Another popular way to get to Maine is to fly into the city of Boston! Flights and rental cars can often be cheaper here than Portland depending on where you are coming from.

Just be aware you’ll need to drive the 2 extra hours to Portland to start your trip. If you’re planning more than a 5 day Maine itinerary, you could always rent a car in Boston and add this section on between the two cities.

One important thing to mention is time of year for your Maine road trip. When visiting in the summer or fall, you should book rental cars and hotels well in advance.

We’ve been using this company for the last few years with awesome results. Specifically, we love having the free cancellation option in case our Maine itinerary changes. 

Maine Road Trip Itinerary 

Our Maine Road Trip Itinerary

This was the exact route we took on our last 5 day Maine itinerary! As you can tell, we much prefer the smaller towns, ocean views, and nature trails.

That’s the main reason why we decided to have just 1 night in Portland. If you’re more of a city slicker, know that Portland is super fun to explore.

You could easily add one more night in both Portland and Boothbay to make this a full one week Maine Road trip. When leaving Portland, you are able to drive the faster highway inland instead of the same coastal route both ways.

We liked the drive closer to the water, but it’s totally up to you! Here’s a quick breakdown of our 5 day Maine itinerary.

  • 1 Night Portland 
  • 2 Nights Bar Harbor 
  • 1 Night Boothbay
  • 1 Night Kennebunkport

5 Day Maine Itinerary

5 Day Maine Itinerary

1 Night in Portland Maine

We started our Maine road trip itinerary in the beautiful city of Portland Maine. This is not only is it the largest city in the state, but one of the most popular destinations in all of New England! 

Hopefully, you can check into your hotel and get out to explore quickly. We want to stress that Maine can be very expensive. Due to this, staying in downtown Portland won’t be cheap in the peak summer and fall season.

Two of the most highly rated accommodations are The Press Hotel and Canopy By Hilton Portland Waterfront. You could also look into an Airbnb if you’re traveling with a bigger group.

Spend most of your time wandering around the Old Port and Waterfront area which is our absolute favorites. There are so many shops, restaurants, and local breweries to check out here!

Two fun activities we recommend are the Portland Trolly Tour and a scenic harbor cruise. When it’s time to eat hit the Porthole Restaurant and Pub, or grab a pizza at Flatbread Company.

For something more unique, head over to Duckfat and try their Belgian poutine fries. We also love stopping by for happy hour at Eventide Oyster Co.

5 Day Maine Road Trip

2 Night Bar Harbor Maine Itinerary

This will be the longest section of our Maine road trip, so it was only fair to have two nights in Bar Harbor. From Portland, it’s about a three hour drive to the beautiful coastal town.

Bar Harbor is home to the world-famous Acadia National Park. It’s honestly somewhere you could spend a whole week out in nature if you have the time!

We recommend leaving Portland a little early if possible so you can have a nice afternoon in Bar Harbor. Some of the most popular places to stay are The Inn on Mount Desert and Atlantic Eyrie Lodge. After checking in, enjoy some dinner and a stroll around the cute town.

Try and wake up early the next day if you’re heading to the park. Only having one day at Acadia National isn’t ideal, but there is still plenty you’ll be able to see.

We loved driving the 27 mile loop road that circles the park. This way you can take your time stopping at scenic lookouts and hop out for some quick hiking trails. 

It’s best to pack whatever food and drinks you need for the day. There are so many beautiful places for a picnic inside Acadia National Park!

When you get back to town, stop into Thirsty Whale Tavern or Side Street Cafe for a relaxing dinner. Choc-Latte Cafe is also great for a quick coffee in the morning.

Ocean and Cliffs

1 Night in Boothbay Maine

Boothbay is quite simply one of our favorite small towns in New England! We enjoy it so much there, that it would be easy to spend an entire vacation instead of a full road trip.

Yet, with a 5 day Maine itinerary, you obviously have limited time. We recommend arriving as early as possible from Bar Harbor to make the most of it. 

It will take you between 2.5 and 3 hours to get to Boothbay. On your way into town stop at Bet’s Fish Fry for lunch. This popular street food stand makes a massive fried haddock sandwich fresh to order. 

We recommend staying right in the center of Boothbay Harbor. The Fisherman’s Wharf Inn and Boothbay Harbor Inn are both nice options. You can also check out our post about the best places to stay before your Maine road trip.

There are so many fun outdoor activities and things to do in Boothbay! Spend your time poking in and out of the colorful shops, walk across small harbor bridge, and visit the stunning botanical gardens. 

In the warm summer months, you’ll want to swim in the water or hop on a scenic boat tour. Getting out on the water is one of the best ways to experience this part of your 5 day Maine itinerary. Some of our favorite Boothbay cruises are the scenic schooner and this one as well.

Hold up! We have one more must-visit place before the last stop on your Maine road trip itinerary. Head over to Blue Moon for breakfast to get your fill of their mouthwatering blueberry pancakes.

Boothbay Maine

Maine 5 Day Itinerary

1 Night in Kennebunkport Maine

The final stop on our 5 day Maine itinerary was the charming village of Kennebunkport. This small town is picture perfect with it’s old style shops, beautiful river through town, and sandy beaches just a quick drive away!

The best rated hotel in the area is called AWOL Kennebunkport. Also, The Harbor Inn is a great option for those looking for a traditional Maine inn. 

The Clam Shack is a must for seafood lovers in Kennebunkport. The line may be long in the summer and fall, but it moves really quickly. 

Looking for more of a sit down restaurant with a view? Head over to The Boathouse Restaurant or Arundel Wharf. Additionally, Old Salt’s Pantry makes great take away sandwiches for the next part of this Maine itinerary!

Once you’ve explored the town center, it’s time to take a drive down to the beach. The short road which starts at Gooch’s Beach goes along the coast and is so gorgeous. Kennenbunkport is also popular for families and camping enthusiasts. 
Kennebunkport Sign
5 Days Maine Road Trip

Fall Maine Road Trip Advice

As we mentioned, this 5 Day Maine Itinerary is based on our visit during the summer season. This is when you’ll have the best and warmest weather throughout New England.

Nevertheless, one thing we really wanted to highlight is the fall! Every year, travelers come from around the world to see the fall foliage in New England. Along with Vermont, Massachusetts, and New Hampshire, Maine is one of the top places to go.

Hotels can book out as far as a year in advance for September and October, and the prices will fluctuate with the seasons. For this reason, you’ll want to plan out your trip out well in advance.

Have your larger items like a rental car (check prices), hotels, and tours booked before you go! For international travelers, it’s also a good idea to get a USA e-sim for your phone when you arrive. 

Fall Maine Road Trip

Have any questions about this article or want to share your own Maine road trip itinerary? Let us know in the comments below!

Safe Travels,
Brigitte & Jake



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  1. June
    April 18, 2024 / 4:46 am

    I haven’t had the chance to visit Maine yet and this is so helpful! Definitely going to consider this if I get to visit someday!

    • Brigitte & Jake
      April 18, 2024 / 5:08 am

      Maine is so beautiful! Thanks for reading (-:

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