A few weeks ago, Caleb and I took the boys on our first family (of four) trip. When deciding where we wanted to go, we had a few requirements: 1) neither of us had been there 2) easy walkability/getting around with two babies and 3) close to airport as we just had a few days to get away. Boston fit all of these and more – it was actually cold and felt like fall! We had the best time exploring the city on foot (and public transportation), the people in Boston are some of the friendliest we have ever met and we had the best view from our room at Four Seasons Boston.

STAY

• Four Seasons Boston: You can’t beat the location, the service or the beautiful rooms. We arrived late Friday evening and the bellmen greeted us by name when we arrived. Our suite was one of the best hotel rooms we have ever stayed in – it was larger than our first apartment! Cribs were set up for both boys, along with toiletries, diapers and wipes. The suite had windows that overlooked Boston Public Garden and William loved looking out the window and pointing out all the buses. The location is right in the heart of Boston and we could get anywhere quickly – whether walking, taking the bus or taking the T. The food was great and there is an indoor swimming pool. We almost didn’t want to leave our room!

EAT

• Bristol Bar: By the time the boys were asleep, we were starving! Caleb ran down to the Bristol Bar to grab a few late night snacks and drinks for us. The hot pockets and wings were delicious!
• Room Service: One morning we ordered in room service for breakfats. We loved waking up to a freezing cold day, ordering breakfast in and eating with amazing views of Boston Public Garden. William loved the pancakes and fruit skewers and Caleb and I had the egg white frittata and a traditional breakfast!
• Tatte Bakery: Our first morning in Boston we walked through Boston Public Garden to Beacon Hill and had brunch at Tatte. It was such a charming (and packed) coffee shop. The avocado toast was amazing and so were the pastries.
• Thinking Cup: This coffee shop is on Newbury Street and was a cozy spot to get coffee and breakfast on our last morning in Boston.
• North End: There are hundreds of amazing Italian restaurants in this area, you really can’t go wrong! We ended up going with the concierge recommendation of Antico Forno – for a kid friendly spot with brick oven pizza for William.
• Eventide: Near Fenway Park, one of our followers suggested this lunch spot for a brown butter lobster roll. You can’t go wrong with anything on the menu – they have some of the best brussel sprouts we’ve had!
• Select Oysters: We were in the mood for seafood one night, so we went to Select Oysters on the recommendation of the Four Seasons concierge. I had an amazing piece of sea bass and Caleb enjoyed oysters. The cocktail menu is incredible!
• Modern Pastry: We had to try a cannoli after our dinner in the North End! So delicious.

DO

• Boston Public Garden: Right across from the Four Seasons Boston is the first public garden in America. We loved having access to a park so close and William loved burning off his energy running through the leaves.
• Beacon Hill: One of my favorite parts of Boston was strolling around Beacon Hill. It is one of the most charming places I’ve ever explored. The shops are so quaint and the houses are so inviting. A great place to spend a few hours strolling around, grabbing a bite to eat and shopping. Don’t miss Acorn Street – the most photographed street in the country!
• Freedom Trail: This 2.5 mile walk is a great way to get a feel for the city, while also seeing so many historical spots. The boys loved strolling and we loved walking around!
• Newbury Street: The best shopping in Boston.
• Harvard: We had to – the campus is breathtaking!
• Fenway Park: Caleb says we will be back to take the boys to a Red Sox game in a few years.
• Plus, so much more. That’s all we had time to do, but there is so much to do in Boston. In the winter they have an ice rink, in the summer swan boats. We would have liked to do a duck boat tour, go to the Children’s museum and visit Boston Public Library, but there is only so much time!

WEAR

• Stia: I packed a few coats – this parka and this down coat, this sweater, this poncho and this cardigan, this scarf and my favorite over the knee boots – black and taupe. I threw on a pom pom hat each day to stay warm!
• William & Henry: I had the boys bundled because it was a high of 30 while we were there! William stayed warm in his pom pom hat, cords, his coat and thankfully, we purchased this footmuff before our trip! Henry stays very warm in his car seat, so I typically had him in a onesie, with this bunting suit, socks and a few blankets on top! Plus, he wore his pom pom hat that matches William’s!

Cheers,

Stia, Jean and Katherine

Thank you to Four Seasons Boston for collaborating on this post.