I’m back today with Part II of my Travel with Me post on our early October trip to New England. Read Part I here. In today’s post, I’ll describe what we did day-by-day on the trip, anything that I would change about the trip in hindsight, and any tips and tricks about exploring this area I have to share.

What We Did:

This trip was pretty short for all the places we were visiting. As a result, we didn’t necessarily do everything we would have wanted to do had we had more time. However, I do feel like we made a great use of our time to do the things that we wanted to do the most.

I’m going to use the same rating system as I did for restaurants in Part I. Thumbs Up! means I highly recommend that you take time during your trip to do the activity/ explore the area. Meh… for activities/areas that aren’t bad but that I wouldn’t recommend going out of your way to do/explore, and Thumbs Down for activities/areas that I believe you shouldn’t bother doing/going to at all during your trip. Keep in mind that many of the things that we do on our trips are based off of good reviews from friends or on TripAdvisor so Thumbs Down ratings will be rare and Meh… ratings won’t occur very often either.

Day 1:

Harvard University

Thumbs Up!

On our first day, we arrived at the Boston airport around noon, and then we went straight to our hotel to drop off our bags. Once we were settled, we took the T into Cambridge to explore Harvard University, something I’ve always wanted to do. We had wanted to do this tour, but the available tour times did not fit our schedule. So, instead, we did a self-tour via the Harvard University mobile app. This tour was very long, so we didn’t do everything or read all of the available material on the app, but it was very interesting and it guided us throughout the campus in way that allowed us to see areas and buildings that we might not have caught on our own. We very much enjoyed touring this beautiful campus — it was fun to pretend to be a student again.

After our campus tour, we visited The Coop, a giant student bookstore next to campus. It was a Barnes and Noble, but it had several floors with winding staircases, so it had a different feel than a basic Barnes and Noble. We love exploring bookstores, so we had a great time here.

Day 2:

Boston Common

Thumbs Up!

On our second day, we woke up fairly early for a long walk to brunch at The Paramount. Along the way, we explored Boston Common, the oldest park in the country. The leaves were just barely starting to change, but we got some decent pictures by a few colorful trees. We sat down and people-watched by the pond, drinking Starbucks coffees and enjoying the beautiful Fall weather. Throughout the whole city, there were pianos that had “Play Me. I’m Yours.” painted on them. Throughout the day, we say several people playing these pianos. I thought that this was a really neat thing for the community to do.

Beacon Hill

Thumbs Up!

Continuing on our walk to brunch, we explored the Beacon Hill area. This was such a cute neighborhood! Beautiful town homes lined the streets and the storefronts were all decorated for fall. This area remind me a lot of Georgetown in DC with a New England flair. Beacon Hill was definitely my favorite area of Boston.

Freedom Trail Guided Tour

Thumbs Up!

After brunch, we did a guided tour of parts of Boston’s Freedom Trail. Our guide was very informative and interesting. Some of the places he took us ncluded the Massachusetts State House, Park Street Church, the Granary Burying Ground, King’s Chapel and Burying Ground, the Old State House, the site of the Boston Massacre, and Faneuil Hall. Overall, we are really happy we took this tour because we learned some interesting facts about Boston’s history and saw places that we would not have thought to visit on our own.

Date Night

After touring around the city a little more on our own, we moved our suitcases from our downtown hotel to the airport hotel and then got dressed for our nice dinner back in downtown Boston. We took the water taxi back into the city which provided a really great view of the city at sunset. After our delicious dinner (see Part I of this post for details), we passed by the sites of the Boston Marathon bombings which were right next to our restaurant. While this reminded us of the very sad events that occurred here, we were glad to pass by and remember the people who were affected by the events of that terrible day.

Day 3:

Portland City & Lighthouse Tour

Thumbs Up!

We drove up to Southern Maine for the third day of our trip. It was only about an hour and a half drive, and we arrived in Portland right in time for our 11am City & Lighthouse Tour. Once we arrived, we checked in to our tour and loaded a van with three other couples. Our guide took us around the city of Portland providing us with interesting facts and history of the city. He then took us out to the Portland Head Light and let us loose for half an hour to explore and take pictures. I love lighthouses, so I was thrilled to be able to see this one up close and in person. Apparently, it is the most photographed lighthouse in North America. We really enjoyed this tour and would definitely recommend it to others who just have a short time to explore Portland, Maine.

Maine Beach

Thumbs Up!

We made a couple of stops on our way back to our Boston hotel. First, we stopped at a secluded beach that was right in the middle of a neighborhood. The views of the water and the surrounding beach homes were beautiful, and we had a great time walking up and down the beach taking pictures.

Kennebunkport

Thumbs Up!

Our second stop was Kennebunkport, Maine, a very cute little town on our way back to Boston. When we arrived, the sun was just setting, so most of our time there was spent exploring in the dark. We just walked around, peeking into pretty storefronts and going into a few shops that peaked our interest.

Day 4:

For our fourth and final full day, we drove south an hour and a half to Rhode Island. Our main stop in this state was the town of Newport. We had heard such wonderful things about this city from both friends and TripAdvisor reviews, so I was very excited to get to see it for myself.

The Breakers

Thumbs Up!

The first place we went to in Newport was The Breakers, a summer “cottage” that was built and owned by the Vanderbilt family for many years. We did the standard audio tour of the house for $19.50 apiece. I could not believe the beautiful detail of the home and the size. My favorite part was the giant terrace in the back overlooking the ocean. Newport has many mansions that the public can tour. If we had had more time, we would have toured a couple of the others.

The Cliff Walk

Thumbs Up!

After our Breakers tour, we walked about a mile to do the Cliff Walk, a pathway that runs along the ocean behind many of the Newport mansions. We really enjoyed taking this walk. The views of the water on the cliffs were very picturesque. It is definitely worth taking an hour or two to walk part or all of this path.

Watch Hill

Thumbs Up!

After the Cliff Walk, we took a very long walk back to our car and made about a 45 minute drive to Watch Hill, a very affluent neighborhood in Westerly, RI. It was a random decision to make this drive, but I’m so glad that we did. Once we arrived and parked our car, we took a walk through the neighborhood and came across a path to a small lighthouse. Once we followed the path out by the lighthouse and the water, we were suddenly surrounded by the most beautiful sunset I have ever seen. This spot was absolutely breath-taking. I felt like I had jumped right into a painting. Let the pictures below do the rest of the talking (although, they really don’t do it justice). We hope to come back to this area for a weekend at some point so that we can explore a little more.

In Hindsight…

There are a couple of things I would do differently if I had the chance to re-do this whole trip all over again.

I would go in mid- to late-October rather than early October. The leaves had just barely started changing colors when we were there.
I would explore the right area of Newport. We were slightly disappointed in the city of Newport as it just was not quite as cute as we had thought it would be (or so we thought). However, right when we were pulling away, we passed right by what was the actual city center, and it looked ADORABLE! Unfortunately, we were well on our way to Westerly and didn’t want to pay for parking again, so we didn’t get to tour that area. Next time!
I would move my car closer to the Cliff Walk entrance. We made the decision to walk one mile to the Cliff Walk entrance so that we didn’t have to move our car and pay for parking again, but I highly recommend moving your car and just paying again. The one mile walk to the entrance wasn’t bad, but after walking a couple more miles down the Cliff Walk, we had quite the hike left to do just to get back to our car. There were no cabs or bike trolleys waiting where we exited the Cliff Walk.

Tips & Tricks…

Public transportation from the airport to South Station (in city center of Boston) is free.
With a Charlie Card (Boston’s fare card), bus trips are $1.50 one-way and train trips are $2.00 one-way. A 7-Day Pass is $18, so if you are going to be using the public transportation system for more than a day, it’s worth it to get the 7-Day Pass. That’s what we did for our day and a half spent in Boston, and we definitely used public transportation enough for it to be worth the cost. Click here for more detailed information.
Book reservations at the nice seafood restaurants in Boston a couple weeks in advance. I booked our reservation at Atlantic Fish Co. two weeks early, and it was the last available option of the evening. Several other places were completely booked.
Parking by the water in Portland, Maine is difficult. The garages near where you first drive in are very expensive. In order to avoid paying the high cost of these garages, we drove around looking for another spot. We ended up in a Two Hour Only spot even though we knew we would probably be gone on the tour for over two hours. Later in the day, we found out that their were much cheaper parking garages just a little further down the street.

This concludes my first Travel with Me segment. I hope that it helps make planning a trip to New England a little easier for someone or that it encourages a few of you to explore this great area of the United States. Please let me know in the comments section below if you have any suggestions for future Travel with Me posts or if there is anything in this post or Part I that you particularly enjoyed. Also, feel free to comment with any questions.Thank you for reading and happy trip planning!