The alarm clock rang way too early the morning after our wedding. But somehow, we managed to crawl out of bed and make it to the airport in plenty of time to get through security and grab an overpriced bagel and coffee before getting to our gate. For the first time in my life, I did not check a bag — we used carry-ons only, and let me tell you, I think that might be the secret to easier traveling. You don’t have to wait in line to check your bag, and then on the return home, you don’t have to wait for your luggage at the baggage claim. I’ve never been one to keep my checked bag under 50 lbs anyways, but I digress.

Activities/Things to do:

We didn’t really have many solid ‘plans’ when planning for this trip. We just knew there were places we wanted to visit, so our itinerary consisted of places to go instead of things to do. As far as planning excursions and day trips, the only activity we had booked in advance was the Lighthouse Bike Tour. We didn’t want it to sell out before making it to Portland, so we went ahead and booked tickets online before our trip. Everything else that we did came from the recommendations of locals.

Lodging: As far as lodging, we only booked the first 3 nights of AirBnBs and simply winged the rest once we were on our honeymoon. Since we didn’t have a solid plan, we didn’t want to book a bunch of hotels or Airbnbs in advance and then be stuck to those rooms/towns if our travels ended up taking us elsewhere. We used Airbnb and the HotelTonight app to book lodging. While having breakfast each morning, we would plan for the day and where we would be traveling to next and then book our room for that evening. I understand that not all travelers would like this kind of last-minute planning, but it worked for us. And since we did have a rental car, we had a bit more flexibility regarding lodging; if we needed to drive an extra 20-30 miles for a place to stay the night, that was an option.

Transportation: A couple weeks before our trip, we reserved an SUV from Budget. Since we were retrieving our rental car from one airport and returning it to another, we simply noted that in our reservation. And then confirmed this again with the rental car representative when we picked up the car.

A note on a rental car: we chose an SUV because we both prefer more oversized vehicles. And we weren’t really sure what the terrain was going to be during our travels, so we chose to be safe than sorry. However, if you prefer to save some dollars on a rental car, an SUV is definitely not required! A smaller car would work perfectly fine during the fall season.

Parking tip: when you’re parking in Portland, make sure to find a city-owned parking lot instead of a privately owned lot. The city-owned parking lots run about $15 for 24 hours, and the privately-owned lots start at $35 for only 3 hours.

All of the towns we visited offered the option to pay for parking by using the ParkMobile and PassportParking apps, both free apps in the Apple Appstore. You don’t have to use the apps. Still, I personally loved using them instead of having to find a kiosk, type in the license plate number, insert card, take the ticket back to the car, etc. Much quicker and streamlined to use the apps, in my opinion.

Day 01

We flew from Tulsa into Portland, Maine (left Tulsa at 8:15a, a short layover in Dallas, and landed in Portland at 3:45p), grabbed our rental car, and went about our way.

If you want to see more of Maine, consider flying into Bangor or Bar Harbor and hopping on over to Acadia National Park!

The Portland airport is small and super easy to navigate. Once we left the airport, we drove downtown to walk around and get a game plan/scope out where we needed to be on Sunday morning for our lighthouse bike tour. The drive from the airport to downtown Portland is only 4 miles! Portland could easily be a long weekend getaway, and all you’d need is an Uber to get you to downtown Portland and back to the airport. If you can snag a hotel/Airbnb downtown, everything is entirely walkable!

Saturday evening, we simply walked around, relaxed, shopped a little, and had an early dinner at ViA VECCHiA. Even if you only stop for a drink, this restaurant is beautiful with its ornate and speakeasy decor. The service was excellent, and the atmosphere was dreamy. For dinner, we shared the short rib ravioli and the central street pizza. I’m not typically ordering pizza out at restaurants. However, our waiter recommended it. I was also intrigued because it consisted of whipped ricotta cheese as the ‘sauce’ instead of marinara…so I had to try it. The pizza did not disappoint!

After dinner, we ended our first day with a walk over to Gross for dessert. This confection bar came highly recommended by our waiter at ViA VECCHiA.

Day 02

Started the morning with a cup of coffee and scones from Coffee by Design. We were trying to get amped up (caffeinated) for our 16-mile bike ride tour along the Portland coast. This lighthouse tour was undoubtedly one of our favorite things to do on the entire trip. The bike ride started at 9:30, and we biked until around noon, ate lunch, and headed back to the starting point. Lunch was provided with the cost of the bike tour, and of course, we had lobster rolls!

After our bike ride, we walked back to downtown Portland because there was so much we didn’t get to see on the first night. There is so much downtown to see and explore; you can walk it several times and still see something new and different each time. For the rest of the day, we walked, shopped, ate, drank, and people-watched. Portland is a dog-friendly community, so it was fun to see all the pups too.

Day 03

We woke up early, packed up from our Airbnb, and got on the road to Vermont. Along the way, we made a pit stop at the Polar Caves Park in Rumney, NH. The drive from Portland, ME to Burlington, VT, isn’t too long, but it was nice to get out and walk around/sightsee about halfway through the trip. The drive to Vermont during the fall season is so beautiful; not only will you see the ever-changing fall foliage but also old wooden bridges. After arriving in Burlington, we got checked into our Airbnb and walked around downtown. Our Airbnb was located downtown, so once we parked, we didn’t have to drive again until we left Burlington.

Vermont is a college town, and if you’re familiar with Lawrence, KS — it reminded me a lot of that same vibe. We simply ate and drank the night away.

Day 04

We woke up, packed, loaded the car up, and walked down the street for coffee & a snack to figure out what our next plan was. After finding out there was a ferry in the next town that could take us across Lake Champlain and into New York, we decided to do that. It was really cheap to take the ferry over, for 2 people and our vehicle it was less than $20. The ferry runs back and forth on the hour and is only a 25-minute ride.

The ferry took us to Essex, NY. This was a small and sleepy town; I don’t even recall seeing one single stoplight. Rather than waiting for the ferry to return and take us back to Vermont, we decided to just go ahead and get on the road and drive down New York state to Massachusetts. We were headed to Boston.

Initially, we had no intentions of staying in Boston— we were just going to drive through. But we had met a lovely couple at the lighthouse bike tour in Portland, who highly recommended a night in Boston. We were so glad we did. Boston is an elegant city; it felt like a smaller version of NYC. We stayed at the Godfrey Hotel downtown and were right in the middle of all the hustle and bustle of the financial district and several different colleges.

Fun fact: there are 35 different colleges, universities, and community colleges in Boston!

After checking into our room and getting cleaned up, we walked over to Sorellinas, an upscale Italian restaurant in Copley Square. We were lucky to get same-day reservations — all they had left was bar seating. But to be honest, we often prefer to be sat at the bar. Because it gives us better opportunities to chat with the waitstaff and hear about all of their and other locals’ favorite places to go and see.

One of the servers asked why we chose Sorellinas for dinner, and we told them it was just happenstance, and we had seen it had great reviews on the OverTable app. He then proceeds to tell us that we were in the right place because they had just been voted best restaurant in Boston!

We shared the tuna appetizer, and I had the lobster gnocchi, and Big had the filet. The food and service were outstanding! One of the bar-backs lived in a town near Salem and had grown up in the area his entire life, so he gave us great recommendations for Salem and Cape Cod.

We took an Uber back to the hotel. We were pleasantly surprised with a bottle of champagne waiting in our room with a note, thanking us for choosing the Godfrey Hotel and wishing us a happy honeymoon.

Day 05

The following day, we walked around downtown Boston, through the financial district, Chinatown, and some residential neighborhoods — there are some really charming brownstones! We ate breakfast at Tatte Bakery & Cafe — another local favorite. If you ever go to Boston, you must try Tatte’s!

Before leaving Boston, we wanted to see the Boston Harbor, so we headed there and had another light snack at Joe’s Waterfront. The weather was so perfect for sitting outside and people/boat watching! There are lots of things to do at the Harbor; an aquarium, bike tours, cruises, The Institute of Contemporary Art, Boston Tea Party Museum, and a lot more.

After Joe’s, it was time to head to Salem. What is only a 28-mile trek when looking at a map is actually an hour’s drive! You’ll only be driving through small towns, so the commute takes quite a while, not to mention, the traffic was pretty heavy.

A note: If we were to make the trip again, we would probably just take the fast ferry over to Salem from Boston instead of making the drive!

We made it to Salem, checked into our Airbnb, and walked downtown. Our Airbnb was only a mile from downtown / all Salem activities, so once we parked, we didn’t have to drive again until we left Salem. We had tickets reserved for the Salem Witch Museum. Then after that, we walked over to Adriatic, a restaurant and bar on the main drag of Salem. We sat outside on the patio and had a fantastic dinner. We shared their ‘bag of munchkins’ (think of a hushpuppy but with lobster & shrimp and served with spicy sriracha mayo) for an appetizer. For dinner, I had the chicken parm on a bed of cavatelli. I don’t remember what Big had, but I remember us both being satisfied with our food choices.

After dinner, we walked over to Notch, a taproom tucked back in an alley. Enjoyed a locally brewed beer and then walked back to our room and called it a night.

Day 06

Woke up bright and early and headed to breakfast at the Ugly Mug Diner. We ordered way too much food and devoured almost every bit of it. Biscuits and gravy, eggs, bacon, French toast, pancakes. If it’s breakfast food, we ordered it. Also, their mimosas are excellent (order a glass of champagne with a shot of cranberry!). After our meal, we had tickets to tour the House of The Seven Gables, and we can’t recommend this tour enough. There is so much history in this home, definitely a must-see when visiting Salem.

After the 7 Gables tour, we hopped in the car and headed for Cape Cod. It was recommended by several different people along our trip to make sure and stay at the tip of Cape Cod, specifically Provincetown. Before getting to Provincetown, we stopped at the Lobster Shanty for a lobster roll and clam chowder.

We got checked in to our Airbnb, and again, it was within walking distance to the main drag, so once we parked, we didn’t have to drive again until we left town. We really love and appreciate towns like this when traveling!

We walked up and down the main drag sightseeing, did a little shopping, and stopped for happy hour at several different places. Then had dinner at the Crowne and Anchor. I probably sound like a broken record, but our dinner was so good. I had the linguini & clams, and Big had the pan-roasted ribeye. SO GOOD.

A note: Like many tropical/coastal destinations, some restaurants and shops close after the summer season. If you’re planning to go to Provincetown in October, be prepared to see a handful of places closed until the following May. Provincetown is a very eccentric and lively community, and we will definitely be going back!

Day 07

We started our morning with a trip to the post office. Since we only used carry-ons for this trip, we had planned on shipping back a box of dirty clothes to make room for anything new we would buy. Then we had mimosas and watched the waves roll in on the waterfront patio of Bayside Betsy’s.

After brunch, we were off to our final destination, Newport, Rhode Island.

We had heard such great things about this bustling but quaint town, and we were not disappointed. We people watched and ate a late lunch at Barcino and then walked around downtown and stopped at what seemed to be a hotspot for locals (I can’t remember the bar’s name). And finally, stumbled upon The Mooring Seafood Kitchen & Bar for a late-night snack and glass of Prosecco. We didn’t have reservations but were able to be seated at one of the bars. A few minutes later, another couple comes in and sits next to us, turns out they were from Tulsa (only about a 40-minute drive from us)! What a small world — they were so nice and had essentially traveled the same road trip as us!

Day 08

It’s time to go home! Our last couple of days were bittersweet. We love traveling, but we love being at home too. Plus, we were missing the pups. We made the drive to Windsor Locks, Connecticut — we had planned on making a stop and sightseeing. But honestly, I think we were both tired and just wanted to return the rental car, make it through security and get home.

This was a fantastic trip, and I highly recommend it to anyone who doesn’t mind short stints of driving.

Travel times for those interested in how many miles we drove and hours spent on the road (approximately 18 hours on the road over the span of 8 days):

✈️ Tulsa to Portland: 7.5h
🚗 Portland to Downtown Portland: 5 miles (14m)
🚗 Portland to Burlington: 208 miles (4h 16m)
🚗 Burlington to Charlotte: 13 miles (28m)
⛴ Charlotte to Essex: 5 miles (25min)
🚗 Essex to Boston: 301 miles (4h 35m)
🚗 Boston to Salem: 26 miles (53m)
🚗 Salem to Provincetown: 132 miles (3h 15m)
🚗 Provincetown to Newport: 120 miles (2h 22m)
🚗 Newport to Windsor Locks: 98 miles (1h 52m)
✈️ Windsor Locks to Tulsa: 6.5h

Quick Links to places mentioned above:

Lodging/Transportation/Parking:
Airbnb
HotelTonight 
Godfrey Hotel
Budget
ParkMobile 
PassportParking
Ferry

Places to go/things to do:
Acadia National Park
Lighthouse Bike Tour
Polar Caves Park
Ferry
Boston Chinatown
Boston Harbor Islands
Salem Witch Museum
House of The Seven Gables

Dining:
ViA VECCHiA
Gross, a confection bar
Coffee by Design
Liquid Riot
Sorellinas
Tatte Bakery & Cafe
Adriatic
Notch  
Ugly Mug Diner
Crowne and Anchor
Bayside Betsy’s
Barcino
The Mooring Seafood Kitchen & Bar

This is officially the long post I’ve ever written. I hope it was helpful for those interested in making a New England road trip.

Feel free to send a message or leave a comment below if you have any questions!

xx,
Riss