As the trees in Maine were starting to change colors, Zuzu and I took a quick New England Fall road trip from Boston to Acadia National Park. Follow along as we explore the Northeast on this fun 5 night trip which was almost free.
Day 1 in Massachusetts
Arriving on a Sunday night, we made it to the Hyatt Regency Boston Harbor. Even though it was a little overcast, we loved the views of Boston across the harbor, and we could also see the airport runway from our hotel. Pretty cool to see some planes landing out our hotel window.
After a free breakfast of Lobster Eggs Benedict and a Lobster Omelet (fyi, there’s a alot of lobster on this road trip), we took the Massachusetts back roads towards Plymouth Rock.
Zuzu & I stopped at a couple of beaches along the way, but we finally made it to Plymouth.
While the actual Plymouth Rock is not particularly impressive, there’s a small historical and tourist area built up around it.
There’s also a replica of the Mayflower that you can tour.
Our First Lobster Roll
After heading out of Plymouth, we stuck to the back roads and made a random stop at Bob O’Malley’s Whaleback Restaurant in Sandwich, MA. It was a really small bar along the side of the road with super friendly people.
More importantly, it was a really strong start to our lobster roll crawl of New England.
Lobster roll number one was really good. The Texas toast style bread was a stand out.
Our First Lighthouse
After heading south to get a view of Martha’s Vineyard, we got up close and personal with the beautiful Nobska lighthouse in Falmouth, MA.
Didn’t have time to take the ferry across the Vineyard sound to Martha’s Vineyard but we got some great pictures and memories.
Boston North End
In Boston’s North End, we had a nice late dinner at a Bricco‘s restaurant with a table on the sidewalk to enjoy the cool Boston weather.
After dinner, we popped in next-door at Modern Pastry to get their famous lobster tail.
It’s a huge cream filled pastry. Big enough for three or four people to gorge themselves on. The outer layer of our lobster tail was a little more done than we like on a pastry.
But even after picking off a layer, there was way too much for the two of us to finish.
Day 2: Salem and Essex Coastal Byway
For day number two of our New England trip, we checked out of our Boston hotel, spent some time in Salem, drove up the coast along the Essex Coastal Byway to Kennebunkport, and then checked in to our next hotel in Portland, Maine.
Leaving our Boston Hotel
After a free breakfast of French toast and the buffet bar, we checked out from our two night stay at Hyatt Regency in Boston in Harbor.
Quick Hyatt Regency Boston Harbor Review
We’ll share more in our full review of the Hyatt Regency Boston Harbor, but it was a perfectly nice place to stay. Fantastic location with views of both Boston harbor and an airport runway. Most of the staff were great. Pretty good food in the hotel restaurant. The only downside was that the hotel was just a little rundown.
If we had not stayed for free on Hyatt points, this would have been a $976 stay.
For a hotel that expensive, we would have expected a little nicer and newer furniture in our room. Another example of the hotel’s disappointing condition is that the main front door of the hotel was broken for the entire duration of our stay, from Sunday evening until Tuesday noon.
Since we used a pair of Hyatt Category 1-4 Free Night Awards, we saved over $950. Our total bill for this stay was $28. Some might claim that this wasn’t entirely free but a 98% discount off the regular cost is pretty good in my book.
Salem is a little less than an hour drive from Boston it would make a good day trip from Boston.
If you’re into witchcraft and other oddities, it would be easy to spend several days here. Since we only had a few hours, we mostly walked around to see the sights and did some window shopping, errr gawking.
Highlights for us were the Salem Witch Museum and the John Ward House.
OK, maybe it’s not the John Ward that I’m thinking about.
Leaving Salem, we picked up the Essex Scenic Byway, which went mostly along the coast and gave us some great views of the Atlantic as well as some quaint New England towns.
After crossing through New Hampshire and into Maine, our next stop was Kennebunkport.
Gorgeous scenery in and around this tiny tourist spot best known as the getaway for the Bush family. We picked up a couple of souvenirs and then made our way to the Clam Shack.
Lobster Roll Both Ways
The Clam Shack is famous for being Barbara Bush‘s favorite place to get a lobster roll as well as supposedly being the only place you can get a lobster roll with the traditional cold, mayo dressing, and hot butter at the same time.
Of course, we had to order our lobster boll both ways. And we got a sticker to prove it.
But Barbara, we’re kind of disappointed in you. This lobster roll was just on a plain hamburger bun.
While we still enjoyed it (I mean, how can you mess up a lobster roll, right?), it was the least favorite bread of any lobster rolls that we got on our five day New England itinerary.
Even though it was misting and light rain the entire time in Kennebunkport, we’d be happy to come back here and spend some more time as it looks like a wonderful little vacation spot.
Leaving Kennebunkport at dusk, we made our way in the dark to the Hyatt Place in Portland, ME. We we instantly impressed as soon as we arrived.
Only Hyatt in Maine
Since Hyatt is our favorite hotel brand, we have stayed in dozens of their entry-level Hyatt Place brand hotels. We’ll get into more details in our full Hyatt Place Old Port review, but there were three big standouts for this hotel.
First, they had a great location in the trendy part of downtown Portland in a beautiful old building. In that regard, it reminds me of another favorite: Hyatt Place in Knoxville Tennessee.
Second, we were greeted by a super friendly valet. Again, I can count on one hand, the number of Hyatt Place hotels that have valet service.
After checking in to our perfectly fine room, we went down to the front desk and asked where we could get the best late night lobster roll in Portland. Not only did we get a great recommendation, but they suggested we take their house car for free.
Yep. The Hyatt Place Portland has a Tesla as a house car which will shuttle guests in the nearby area for free. Our super friendly driver Mike dropped us off and then came to pick us up after our late dinner at Highroller Lobster Co in downtown Portland.
Lobster Rolls in Portland Maine
And speaking of lobster rolls, Highroller was probably our favorite of the trip! We got a flight of three small lobster rolls with different sauces, and they were all great.
Mike dropped us off at the Hyatt to end a fantastic day on our New England Fall road trip adventure.
Day 3 in Maine
After our stay in Portland, we headed towards Bar Harbor and Acadia National Park. The highlights of this day were:
- Lake St George State Park
- Bar Harbor
- Union River Lobster Pot
- Hampton Inn Ellsworth Bar Harbor
Day 4 Acadia National Park
Out 4th full day of our New England road trip was definitely our favorite. We finally got some good weather to enjoy Acadia and we enjoyed our last lobster roll of our trip.
- Cadillac Mountain
- Thunder Hole
- Hull’s Cove Visitor Center
- Jordan Pond House Restaurant
- Another Night at Hyatt Place Portland Old Port
We’ve got a truckload of Acadia National Park pictures that we’ll be adding to this blog post over the next few days. Make sure to check back for those plus more updates about our 5 day road trip to New England.
Day 5, Back to Boston
After another good night’s sleep at the Portland Hyatt Place, we headed back to Boston for our flight back to Nashville.
Chase Sapphire Lounge at Boston Airport
One of our favorite credit card perks is that we have free access to lounges at most airports. Thanks to having the Chase Sapphire Reserve® card, I was excited to experience the new Chase Sapphire Lounge in Boston Logan Airport.
In our opinion, this is the best airport lounge that we’ve ever experienced.
Everything’s free in the Chase Sapphire Lounge. Good food, good drinks, great views and Zuzu even got a massage! That’s a first for us in an airport lounge.
We’ll add all the details and dozens of photos in our upcoming Boston Chase Sapphire Lounge review.
New England Fall Road Trip Budget
While you could easily spend thousands of dollars on a New England road trip in the fall, Zuzu & I spent $614. We think it’s better to spend less on a vacation so you’re able to travel more often.
On this 5 day trip, we were able to save 86% on our vacation with the strategic use of credit card points and miles. Here’s how the math worked out.
What We Got For Free
Here’s what we would have paid on this road trip but got at no cost:
- Dinner at Nashville Airport Priority Pass Restaurant: $56
- Southwest Airlines 2 Roundtrip Flights: $990
- Nissan Armada Rental for 5 days: $387
- Hyatt Regency Boston Harbor for 2 nights: $976
- Hyatt Place Portland Old Port for 2 nights: $1014
- Hampton Inn Ellsworth Bar Harbor: $309
- Chase Lounge at Boston Airport: $100
That’s $3,832 of free travel that we got from credit card points and hotel status perks.
Points and Miles Spent
We used 2 Hyatt Free Night Awards, 46k Hyatt points, and 60k Hilton points to get our 5 hotel nights for free.
Out of Pocket Expenses
Our largest expenses for the entire trip were gas and 8 lobster rolls!
Not including souvenirs, our total out of pocket cost for this 5 day New England fall road trip was $614.
Our food bill (including $352 for lobster) came in at $412. Gas for that massive Nissan Armada SUV was $154. We also had a few expenses for Acadia Park access and parking over this 5 day trip.
In summary, this $4,446 trip only cost us $614 out of pocket. If we weren’t able to get $3,832 of free travel, we probably would not have been able to afford this trip.
How You Can Travel for Free
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Trip Reports: Luxury on a Budget
If you liked this recap of how we enjoyed a tremendous New England fall road trip on a budget of just over $100 per day, check out a few of our more memorable trips: