Paul Revere, The Boston Tea Party, The American Revolution, Matt Damon and the Red Sox.
When you think about Boston, romance doesn’t necessarily come to mind. However, when you are way past due for a weekend away with your husband and you have to travel out of town for a conference, you make the most of the situation. This is how I found myself planning a romantic weekend getaway to Boston.
The reality is, you can have a romantic weekend getaway just about anywhere as long as you put in the effort. But I’ll give you a few suggestions of how to light the spark in Beantown.
Day 1:
We flew into Boston on a Saturday afternoon and didn’t arrive into the city until just before dinner time. We went to straight to the hotel from the airport. We chose to stay at The Fairmont Copley Plaza. This was an excellent location as the hotel sits in the Back Bay neighborhood of Boston. The Back Bay area is simply charming with its rows of Victorian brownstones and cultural institutions such as the Boston Public Library. It is also a shopping destination in Boston with top retail and great restaurants lining Newbury and Boylston Streets.
The Fairmont Copley Plaza is a beautiful and historic hotel. The lobby is lavishly decorated and the rooms were historic, large and had modern touches. The hotel was happening the whole weekend with a wedding and a conference, but it was not noisy at all. There was a Soul Cycle on the next block and shopping and dining options nearby. I was set.

That evening we went to Barbara Lynch’s Sportello. Barbara Lynch is the top restaurateur in Boston, and while I have been to the city several times, I have never eaten at a Barbara Lynch establishment. I chose Sportello because it’s a more casual spot and you get to sit at a counter while you eat. There are two “U”-shaped counters around the open kitchen where you watch the bustling staff prepare the food. It was so much fun. There were tons of couples all sitting two by two at the counters. This seating arrangement, and a few glasses of wine and delicious pasta, made for a very flirty atmosphere.
Day 2:
Since we had the entire day stretched out before us, we ate a late brunch on Newbury Street at Stephanie’s. So, how do you make brunch romantic? You share dishes! We ordered up their house Monkey Bread and their big cast iron skillet dish filled with eggs, bacon, sausage, and potatoes.

Then it was off to see the sights of Boston. Before we left for our trip, we decided we wanted to really tour Boston. There are many hop-on/hop-off bus tour options and even duck tours, but we wanted a walking tour because Boston is one of the most walkable cities in the country. We booked a two-hour, private walking tour through Tours By Locals. Our tour guide, David, met us at our hotel and customized the tour based on what we wanted to see. He sent me an email before our meeting and asked me questions so he could make sure he covered the right ground.
Our tour led us right to the North End, where David dropped us off at Bova’s Bakery, a family-owned bakery operating since 1932. For over three generations, Bova’s has made all their homemade products fresh daily and with a lot of love. We had cannoli and a chicken parmesan calzone. It was so delicious, we went back again the next night for more cannoli. Bova’s is open 24-hours a day.
After our tour, we walked over to Long Wharf and sat in the park and watched the water, boats, and people. It was a beautiful sunny day. We headed back to the hotel to get dressed and ready for the evening.

This night we went to one of the sexiest restaurants I have ever been. Yvonne’s is a playful supper club serving up small plates and sexy vibes. The restaurant is hidden away on Winter Place off Tremont Street in the pedestrian-only area of Boston. It’s a dark hideaway accented with marble, mahogany and beautiful crystal chandeliers. We sat in the main dining room and shared a few Mediterranean inspired small dishes and gorgeous craft cocktails. However, we were super impressed with the restaurant’s version of Baked Alaska – a vanilla semifreddo filled with nutty nougat, chocolate-covered almonds, and chocolate chips, all served on a fudgy chocolate cake. It’s topped with salted caramel and comes flaming to torch the meringue. Unfortunately, this dish is $45 and serves six people, so we opted for their Pumpkin Spice Latte cake. It was excellent. After dinner, we explored the dark and moody library and we were entertained by a portrait series of famous people dressed up like figures from the past.
Day 3:
Cambridge & Harvard
On Monday, Aaron had conference calls in the morning, so I slipped off to a Soul Cycle class, had a delicious breakfast at the juice bar next door and then headed to Dry Bar to get styled for the day. It’s always nice to get a blowout to make yourself feel glammed up. Then I met up with Aaron and we took the “T” to Cambridge.

Cambridge is a great college town! It’s a mix between artsy, independent establishments and places like Urban Outfitters. We ate a quick, affordable and delicious lunch at the Border Cafe then headed to Harvard to see if we could gain some knowledge. The Harvard campus is a classic, east coast campus. We parked ourselves on the steps of the library and watched the students, faculty, and tourists crisscross the quad.
Then we headed back to our hotel and it was time to pack up and head to a new hotel that was located closer to the conference we were attending for the rest of the week.
Reflecting on the weekend, it was the perfect combination of beautiful weather, exploring a new city together and finding a few flirty spots to spend some QT that had us leaving the weekend feeling closer and lovey-dovey.
Consider Boston the next time you’re planning a romantic weekend away. You will reconnect with your partner, learn great American history and be perfectly charmed by this adorable city.
Nothing better than exploring new places, especially on foot and local transportation. So glad you had a good time. Boston is a great town!