Cape Cod
September 2020
3 Days
I had been to Cape Cod once when I was much younger, but don't remember much from then. From Portland, the drive is about 2.5 hours to the beginning of the peninsula and then another hour or so to get to Provincetown at the far end.
Contents
Daily Itinerary
Relive a witch trial in the town of Salem
Rooftop drinks at The Roof
Take the ferry to Martha's Vineyard
Seafood lunch at Seafood Shanty
Hike the cliffs and the beach at Aquinnah Cliffs
Dinner overlooking the harbor at Nancy's
Walk around the small town of Chatham
More beach time at the Cape Cod National Seashore
Visit the eclectic Provincetown
Martinis and dinner at Victor's
Flights
We drove from our first stop in Portland, Maine
Hotels
Courtyard Cape Cod Hyannis: 3 free night certificates
▸ A standard Courtyard located next to a strip mall. Not much nearby although it was a fine base location since we had a car. For a longer Cape Cod trip in the summer, I'd want to stay further up the Cape
Food
Union Oyster House - Recognized as the oldest restaurant in the US serving its famous clam chowder, oysters, and other seafood
Mike's Pastry - Famous Italian bakery that's been open since 1946. A perfect place to stop for dessert after some delicious pasta in the North End.
Full Itinerary
Day 1
Beacon Hill
Our Airbnb was in the Beacon Hill Neighborhood. As you may have guessed by the name, the neighborhood is located on a hill, so the streets are a bit steep and quite narrow making some streets very picturesque. Acorn Street is often called the most beautiful street in America, although this picture is of the street our Airbnb was on (not Acorn Street).
Beacon Hill - Boston, USA 2015
North End
Boston's North End is where you will find Little Italy. The narrow streets filled with Italian restaurants are fun to walk through day or night and grab a bite of pasta. After, head to Mike's Pastry for dessert. While the cannoli are the most famous item here, there are of course hundreds of other Italian desserts and bakery goods here.
Mike's Pastry - Boston, USA 2015
Day 2
Sam Adams
Typically, I don't find brewery and distillery tours that exciting since they are usually the same - a 10 minute talk about hops and then a small tasting. But Sam Adams is by far my favorite tour I have ever done. First off, the price is great - free! Second, there are no drink tickets like a lot of other brew tours.
Sam Adams Brewery - Boston, USA 2015
The tour of the actual brewery was pretty quick, but what came next took close to an hour. Notice Gwen has a pitcher to herself - this tour and tasting is definitely for beer lovers! We sampled a number of beers that are not available for resale, and we were guided through a description of what a cicerone would look for in a professional beer tasting.
Sam Adams Brewery - Boston, USA 2015
Doyle's
After you've drank as much of your pitcher of beer as possible, there is an optional party trolley which you can take to a bar called Doyle's. I say it's optional, but really this is a necessity. The party trolley was one our favorite and most memorable experiences in all of Boston!
Party Trolley to Doyle's - Boston, USA 2015
Gwen is obviously very excited for the lobster roll at Doyle's, and you should be too. It was an excellent roll at one of the best prices we saw! Doyle's also served supposed "secret" Sam Adams beers which are not available publicly. If you order one of them, you can take your glass home with you.
Doyle's - Boston, USA 2015
Fenway Park
Fenway Park is a must see for any baseball fan, even if there aren't any games going on, as was the case for our visit unfortunately.
Fenway Park - Boston, USA 2015
Freedom Trail
The Freedom Trail is a 2.5 mile route through Boston which goes past many of the most historic locations of American history. You will see markers and a red line throughout the city indicating the trail. If you are a history buff, this is a great self-guided tour you can walk on a nice day. The trail stretches from Boston Common to Bunker Hill.
Paul Revere's House - Boston, USA 2015
Union Oyster House
The Union Oyster House opened in 1826 and hasn't stopped since. This is the oldest, continually operating restaurant in the country. The interior is a mix of narrow stairs, hallways and small rooms with tables in them. Of course, you come here to get seafood. While I'm not going to say it's the best ever, it's still delicious and you can say you've eaten in the oldest, continually operating restaurant in the country.
Union Oyster House - Boston, USA 2015
Day 3
Haymarket
Faneuil Hall is an historic building serving as a marketplace and meeting hall since 1743. As one of the most popular stops on the Freedom Trail, it is now home to many shops and food vendors. It's a great place to stop for a quick bite to eat with lots of outdoor space to sit on a nice day.
Haymarket is a large outdoor market near Faneuil Hall that is only open Fridays and Saturdays. While a large portion is dedicated to fruits and vegetables, my favorite part is the freshly shucked oysters. Boston can be an expensive town, but 4 oysters for $5 can't be beat! This was our first stop of the day, and I couldn't resist indulging in some for breakfast.
Oysters at Haymerket - Boston, USA 2015
New England Aquarium
I don't think the aquarium is a must-see but it is a nice place to stop for a couple hours, especially if you need to get out of the sun for a bit.
New England Aquarium - Boston, USA 2015
Duck Tour
You will see the duck tour boats all over Boston. These are the bus-like vehicles which can also go on the water. Again, not a must do but a fun experience and also a good way to learn a bit more about the city.
Duck Tour Boat - Boston, USA 2015
Cambridge
Cambridge is home to what is probably the most famous and oldest University in America, Harvard. It's definitely worth it to take a quick visit to the campus, but also to stroll around the beautiful surrounding town of Cambridge. We stayed for dinner at PARK Restaurant and Bar.
Overall
I've been to Boston a couple times and always had a great experience. I love walking the Freedom Trail and visiting all the historic sites. This trip to Boston was the first trip Gwen and I ever took together, so it definitely was a special trip to us!
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