TWT Does Boston

Each year, we take a summer trip with our wives to one of the locations that Southwest Airlines flies to.  This year, we chose the City on the Hill… aka, Boston as our destination.  Along with Boston, we attempted to conquer Cape Cod and Martha’s Vineyard.  Here’s a little breakdown of our itinerary.

Day 1: Check-in
We landed in Boston pretty late at night, so it was already dark by the time we picked up our rental car.  Unfortunately, due my (Brian) poor navigation skills with the one way streets and lack of turn around spots, it provided us with some extra site-seeing.  We finally arrived at Park Plaza Hotel, which was built in 1927.  After checking in, we found one of the few places still serving food, called Parish Cafe located at 361 Boylston Street.  This place was a pleasant surprise.  I had the Parish Chicken Sandwich and it was great.  They also had a solid list of drafts on tap.

Day 2: Boston

Getting ready to conquer the Freedom Trail.

On this rainy morning, we started off by eating a quick breakfast at Au Bon Pain before heading out on Boston’s Freedom Trail.  With our ponchos on and coffees in hand, this day’s trek took us nearly 30,000 steps per Jeb’s Fit Bit.  Our hike included stops and photos at the Boston Common, Massachusetts State House, Park Street Church, Granary Burying Ground, King’s Chapel, King’s Chapel Burying Ground, Benjamin Franklin Statue & Boston Latin School, Old Corner Book Store, Old South Meeting House, Site of Boston Massacre, Faneuil Hall, Paul Revere House, Old North Church, Copp’s Hill Burying Ground, Bunker Hill Monument and USS Constitution. A few other adventures we had along the trail included short stops at Mike’s Pastry Shop (for some delicious Cannolis), North Market, Quincy Market and South Market.  We decided to stop at the famous Union Oyster House for a quick clam chowder soup.  We were not disappointed.

Granary Burying Ground. Final resting place to Paul Revere, Ben Franklin’s parents, John Hancock, Samuel Adams and nearly 5000 Bostonians.

The Union Oyster House – Serving people since 1826

Clam Chowder from Union Oyster House

Old State House and Boston Massacre site.

We then took a quick UBER ride to Fenway Park for a guided stadium tour!  The Green Monster was as big as you see it on television.  There was a true sense of history and spirit of baseball in the air.  We then UBERed to Newbury Street to check out some sweet shops and brands.  We then made our way back towards the hotel with a few stops including the iconic Boston landmarks Cheers Restaurant and Boston Common Park.  We decided to stop by the hotel to rest before dinner.  Dinner was served at Luke’s Lobster where we all had their highly coveted Lobster Roll.  I think we all fell in love.  On the way back to our hotel, we decided to stop by the Parish Cafe for a few drinks to bring an ending to a great, yet exhausting day.

Fenway Park and the Green Monster!

Fenway Park from behind home plate.

Paul Revere’s house from 1770-1800.

Day 3: Cape Cod
We walked to Mike & Patty’s for breakfast.  Due to their small space, we took our gourmet breakfast sandwiches to a small park area outside.  We then checked out of our hotel and headed to the Cape Cod.  It took us about 48 minutes to get to our first stop of Plymouth Rock.  Not a whole lot to see, but it was really cool to view the rock and to hear the history behind it. We then made a quick pit stop at Cape Cod Potato Chips headquarters in Hyannis, MA.  We did the short free tour, grabbed our complimentary bag of potato chips and headed back towards tip of Cape Cod.  Next stop was lunch at Young’s Fish Market housed in a little shack right by the docks at Rock Harbor in Orleans, MA.  This lobster meat was probably the freshest you could ever find.  We finally reached Provincetown at the very tip of the Cape Cod.  We walked around Commercial Street to check out the cool boutique shops, then headed over to Race Point Beach where we just enjoyed the view and the sounds of the water crashing against the beach.  This was a beautiful view out into the Atlantic Ocean.  One of the most exciting parts of the entire trip was when we got to see a seal right off the beach and a whale breaching out in the distance.

Finally, we headed back to Hyannis, where we checked into our hotel for the night.  We ended the night at the Roadhouse Cafe.  We chose this place due to their diverse offerings.  Their Lobster Bisque was spot on.

Plymouth Rock

Young’s Fish Market.

Day 4: Martha’s Vineyard


This day started off by a ferry ride departing from Falmouth, MA.  The ferry ride to Martha’s Vineyard was one of the highlights of

the trip.  The weather was wonderful and the ride was very relaxing.  The view of the sail boats along the way was a great change of pace from our neck of the woods in Frisco.  Our first stop landed us in the Oak Bluffs.  We looked around at a lot of the local boutique and souvenir shops. It was fun taking in the culture and local environment.  We then purchased day passes on their bus system before catching a bus to Vineyard Haven and then on to Aquinnah.  The amount of large homes along the shore and hidden within the trees really intrigued our curiosity by wondering which celebrity or politician owned that specific property. The trees were very dense, so it was completely different than the typical Caribbean islands we were used to. It was also crazy seeing the bus maneuvering around the bikers cruising on the narrow streets.  Aquinnah was a small, yet beautiful stop.  We were able to look out over the cliffs and a small private beach.  Truly breath taking scenery.  We looked around the shops and then at the Gay Head Lighthouse. To satisfy our hunger, we grabbed an ice cream cone before heading for another bus ride to Edgartown.  This was by far our favorite of the stops.  You could really feel and see the culture of Martha’s Vineyard that you always read about.  We looked at the shops including the original Vineyard Vines store.  We grabbed lunch at Kelley House where I enjoyed an Oyster Po-boy sandwich.  They also had a local beer selection to enjoy.  We walked around a little more before heading back to catch the ferry.  We ended our night by walking main street Hyannis, with a little ice cream treat at Katie’s Homemade Ice Cream.

Gay Head Lighthouse

Hydrangea flowers from Martha’s Vineyard.




The original Vineyard Vines at Edgartown.

Day 5: Cambridge
We started the day by checking out The Kennedy Compound and a private beach near their location.  The three houses, six acres and private Cape Cod waterfront property along Hyannis Port was just as luxurious as you would expect from American royalty.  We got back in our rental car and drove 1.5 hours to Cambridge.  We toured the Harvard campus, Harvard Book Store and the surrounding shops.  This was very rewarding to me since so many of our former students attended one of the many campuses in Cambridge.  We also sat at the park to look out across the river from the Harvard Campus.  We love the atmosphere on college campuses.  There is always a sense of pride, intellect and excitement, no matter what school you are at.  We walked over to Otto pizza (highly recommend) for lunch before heading out to the airport to end our trip.

The Kennedy Compound in Hyannis Port

We enjoyed Boston, Cape Cod and Martha’s Vineyard.  Although, we are stoked to be back in Texas.  There are so many memories that can be made, lessons that can be learned and cultures to experience while traveling.  We look forward to what adventure summer 2018 brings.

Drift & Explore

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