Best of Boston + feature recipe!

Hi everyone! Took some time off for an awesome family vacation to Boston and Cape Cod this summer. We had a wonderful time, and of course had delicious food adventures along the way. I am excited to share with you the first part of our trip, which was in Boston, where we enjoyed walking the city for 2 beautiful days. What a great city to visit in the summertime. Easily walkable, lots to see and do, and enjoyable for the whole family. Of course I made sure to do my research in advance and scout out the best places for Boston’s best food! Be sure to read to the end of my post for a great feature recipe inspired by my food adventures in Boston.

For our two days in Boston we stayed at the lovely W Boston at the corner of Stuart St. and Tremont (great rate found via hotwire). Super location by Boston Common, and easily walkable for us to all attractions (we are very lucky our kids are great walkers). It was also really close to the subway (aka the “T” in the Boston) for our trip over to Fenway.


We started our Boston adventures with walking down Tremont St. and seeing Boston Common, The State House, Park Street Church and the Granary Burying Ground which kicks off the Freedom Trail. Just a hop, skip and a jump from there was my first tagged hot spot. We stopped for our first food adventure at Sam LaGrassa’s for lunch, and WOW their sandwiches are awesome! We ordered two sandwiches to share – the Pastrami Corned Beef Combo and the Triple Club. Both were excellent and left us wanting more. The place was packed with the regular business lunch crowd but they moved us through quick and the service was friendly. If you are in Boston you must stop in, but note it is only open weekdays from 11-3:30 for lunch.


After some more sightseeing (Old South Meeting House, Old City Hall & King’s Chapel) we were stopped in our tracks next to the OMNI Parker House Hotel which is where the Boston Cream Pie was invented. Lucky for us they have a lovely little streetside coffee shop (Morsel’s) where they sell individual Boston Cream Pie’s for snacking : ) Well we couldn’t resist, so we snapped up a dessert and grabbed a cozy corner in the lobby for a few minutes to enjoy our treat!


After re-fuelling on Boston Cream Pie we headed back through Boston Common where my girls enjoyed some playing time on the Frog Pond Playground and enjoying the spray from the Frog Pond. We then headed over to the iconic Swan Boats for a lovely float around the Public Garden.


After a mid-afternoon refresh back at our hotel, we then headed out to the North End for some classic Boston American Italian food while enjoying more great landmarks along the way (Quincy Market, Faneuil Hall and Paul Revere’s House).


For our North End dinner, I booked a reservation at Gennaro’s 5 North Square after reading reviews and being intrigued by the Chef Marisa Iocco (Boston’s only Italian-born female chef). We were treated to an amazing and memorable dinner. We started with the Handcrafted Burrata & Proscitto with tomato and basil which was delicious, along with the house bread and olive oil they bring to the table. For mains I enjoyed the Eggplant Ravioli which was fresh and summery, my husband chose the Pappardelle Bolognese which he really liked, and my daughter chose the scrumptious Manicotti Italo Americani which was out of this world and quick frankly stole the show at our table!


Day 2 in Boston started with a quick breakfast across the street at the local Panera (easy, fast, and not expensive! . . .  I actually really liked their green smoothie). We then headed down to the New England Aquarium where we enjoyed a great few hours exploring. Afterwards, I walked my family over to James Hook & Co as the reviews for their lobster rolls were really, really good. What a gem, we lined up before it got really busy and my husband and I shared a large lobster roll which had the biggest chunks of lobster I have ever seen. It was awesome! We could have eaten more but we were headed over to my next destination  . . . .


Of course after a great lobster roll you need some dessert. I strategically scoped out our path from the Aquarium to James Hook to the closest Flour Bakery (which was founded by Joanne Chang). Over we headed to the lovely Fort Point location for some coffee and treats. We enjoyed brownies, a “Chunky Lola” cookie, a homemade oreo (one of my faves), and a yummy coconut macaroon. The bakery which also serves breakfast and lunch dishes is busy with the hustle and bustle of locals, but service is fast and well organized, I was really impressed. We liked it so much we made sure to pop into the location nearest our hotel (Back Bay) for our morning coffee and some more goodies before we left Boston. Stopping in at one of the four Flour Bakery locations is a must-do while in Boston!

Flour Bakery

After my pilgrimage to Flour Bakery we finished up our sightseeing route with stops at the Boston Tea Party Museum and walking up through Chinatown to our hotel.


The highlight of our Boston trip was a night at Fenway Park. Our baseball loving family enjoyed soaking up the atmosphere in the grandstands and exploring the history underneath. Before the game we grabbed some dinner and checked out the specialties of Fenway Park. Meatballs in a cup gives a nod to the North End, and was pretty good – nice meatballs in sauce with a big chunk of foccacia. My husband and I also grabbed a “Monster Dog” filled with yummy grilled pepper and onions to share (as it was a monster of a dog!). It was a perfect summer night, and we loved joining in the game traditions, especially belting out “Sweet Caroline” in the 8th inning.


Boston was such a great city to visit as a family. We really enjoyed our time and hope to go back again in the future.

However, to remind us of our fun, I have re-created the great ballpark dog we had at Fenway Park. Now you can make your own “Monster Dog” at home!

Kara’s “Monster Dog”

Recipe Serves 4.

Recreate this Fenway Park feast at home!



  • 4 All-Beef Weiners (I used VG Farms)
  • 4 of your favourite hot dog buns
  • 1 large green pepper
  • 1 large yellow cooking onion
  • 2 tsp canola oil
  • Coarse Salt and Freshly Ground Pepper


  1. Heat a large skillet to medium high heat.
  2. Add canola oil, then onions and peppers.
  3. Season with salt and pepper and fry until softened and you have some good grill marks.
  4. Set aside and prepare hot dogs on your grill or by boiling.
  5. Assemble your hot dog with your favourite toppings (mustard, ketchup, etc.) and the put a good helping of the onions and peppers on top.

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