Trip Report: 3 nights, family w/ young adults and teens

Question

My traveling party included 2 50-something parents and 3 “kids” (20,16,14). Parents have been to Boston several times but it was all new to the kids (and we all love your beautiful city). The Boston forum is very helpful and we appreciate all the advice given here.

Plane landed 3 pm on Tuesday 6/27; it was a quick Uber to Hotel Indigo Boston Garden. Don’t get confused (of course I wasn’t! Cough cough) and think the titular “garden” is the commons or public garden, lol. It’s the sport arena. It’s a good location, walkable to everything and across the street from the North Station.

Coming from a 106 degree Texas inferno and landing in a clear, gorgeous 75 degree afternoon, we were itching to explore. Walked from HIBG to Columbus park and picked up the Harborwalk, which we took to the Seaport. Ocean/harbor views on one side and the greenway/city views on the other. Took tons of photos and saw the seals, Tea party ship, etc. Then we crossed over to the Greenway and walked back to the historic north end. We probably spend 2-3 hours just enjoying the harborwalk and greenway, taking in the ocean views and the plants/flowers/art installations, etc. Highly recommend both! The greenway is a great place for little kids to burn off energy on the swings, playscapes, etc. There were also plenty of places to grab and drink and people watch.

Dinner was at Cantina Italiana (where I could make a reservation) in the North End and we all enjoyed it. Food was solid all around, but my youngest son surprised everyone and ordered some truffled gnocchi which we all tried to steal (it was the standout). Then, on to Mike’s for Boston cream pie, lobster tails and cannolis. The huge line moved fast; they are an efficient machine in there. We absolutely LOVED our pastries. The hype is legit!

Answer

Your trip report highlights a fantastic start to a family visit to Boston, with a mix of scenic walking, history, and delicious food that appeals to both adults and teens. Landing at 3 pm and taking an Uber to Hotel Indigo Boston Garden was a convenient choice, given its proximity to North Station and the arenas. The hotel’s location made walking to major attractions easy, which is ideal for a first-time family experience.

After arriving, your group took advantage of the beautiful weather and explored the Harborwalk and Greenway. This route is perfect for families, as it offers:

Scenic ocean and harbor views along the Harborwalk, with opportunities to see local wildlife such as seals.
Access to historical sites like the Tea Party Ship.
Greenway amenities like swings and playscapes for younger family members to expend energy.
Opportunities for casual people-watching and grabbing drinks along the route.

The North End dinner at Cantina Italiana was a smart choice for reservations, ensuring a smoother experience in a popular dining area. Key takeaways:

The restaurant provided solid Italian fare suitable for a range of tastes in your group.
Highlight dish: the truffled gnocchi ordered by the youngest son, which was memorable for the entire family.
Proximity to iconic North End pastry spots like Mike’s Pastry allowed for a dessert adventure afterward.

Mike’s Pastry experience was noteworthy for several reasons:

Despite the long line, it moved efficiently, making it manageable for families.
The pastries, including Boston cream pie, lobster tails, and cannolis, lived up to the hype and were a standout part of the day.
This stop adds a quintessential Boston experience, combining history, atmosphere, and food.

Overall, your first afternoon in Boston balanced sightseeing, physical activity, and culinary treats, making it both enjoyable and memorable for the whole family. For families with teens, the combination of walking routes, accessible parks, and iconic food experiences is ideal.