Getaway Guide: Our Couples Trip To Boston

Planning a couples trip to Boston? Check out some of the sites my husband and I enjoyed on a recent trip to Boston!

The husband and I just returned from a 3-night stay in one of our nation’s oldest cities — Boston!

Established in 1630, there’s no shortage of U.S. history to learn while checking out beantown. If history, old taverns, lobster rolls and cannoli speak to you, this destination should be a must on your travel bucket list!

Flights from Detroit tend to be affordable during certain times of the year, and it’s a quick and easy 1.5 hour flight with no time change. The biggest budget hurdle for Boston is lodging. It’s an expensive place to stay, so plan on the bulk of your budget going toward your accommodations. We opted for an Airbnb, which was more affordable than many hotels, but still was one of the most expensive place we’ve ever stayed. We chose it because it had rooftop access, but we did need to climb 5 flights of stairs to get to it and there was no TV. We found this appealing, but that may not be for everyone 😉 {Here’s where we stayed.}

Speaking of climbing…While we ate great on this trip, we also walked a TON. To the equivalent of 9-10 miles each day. If walking isn’t your thing {at times on very uneven ground}, this is probably not the town for you. I wouldn’t bring young kids here either. However, the T Train can help you get around much more affordably than Uber/Lyft if you’re on a budget or you have kids in tow.

Here are the top things we did:

Explore the neighborhoods

Boston can be broken down into several sections. We stayed in the Back Bay, which was a great central location to most everything. Our other favorite areas were The North End {think Little Italy}, South Shore {gorgeous, newer, high-end along the bay} and Beacon Hill {think classic 1800’s Boston brownstones loaded with charm}.

Additionally, walking through the Boston Public Gardens is a real treat. We didn’t take a swan boat ride, but would definitely plan to stop next time. It was a beautiful, green part of the city!

Walk the Freedom Trail

Walking the Freedom Trail is a must for first-time visitors. Essentially this trail is a brick path that travels 2.5 miles of history, highlighting historic spots and key points that happened during our nation’s founding. We saw many people on official tours, but we opted to do it ourselves because we wanted the flexibility to stop along the way. Before our trip, we downloaded and printed information about each stop and also listened to a FREE podcast from Fodor’s Travel along the way to learn more.

You can learn more about the Freedom Trail here. There is no charge to walk the trail, but some stops do have fees to go inside. We did tour the Paul Revere house, and I would highly recommend checking it out. My favorite stop was the USS Constitution ship. It was really neat to explore!

We walked almost the entire trail in its entirety {Bunker Hill was closed during our visit} but opted for a Lyft ride home 😉

Take a tour

There were SO many to choose from while there; it felt overwhelming. But after several friends mentioned the Duck Tour as a must, that’s the one we chose. Our guide was absolutely hysterical and he re-enforced some of the things we had learned on the Freedom Trail. We also enjoyed seeing the city from the water. I would recommend taking a tour your first day and not your last like us 😉

Eat!

Isn’t eating the best reason to visit a new city? There are three things you should try while in Boston: New England Clam Chowder, a Lobster Roll, and the Italian pastry, cannoli.

After much debate over which spot has the best for all, we went with James Hook + Co. for the first two and Modern Pastry for the cannoli. We weren’t disappointed one bit. If we had traveled with more people, I would’ve loved to try ALLLLLL the cannolis and lobster rolls and compared them.

Drink!

Instead of a lot of formal and expensive meals, we opted to piece-meal apps while traveling to the various taverns and scenic spots in the city. Two historic taverns along the Freedom Trail are great stops — the Bell in Hand Tavern, America’s oldest continuously operating tavern, and The Green Dragon, where Paul Revere and his men planned the American Revolution.

For some more modern spots, we loved stopping by The Anchor, which was an outdoor spot across the river near the U.S.S. Constitution, and the Rooftop Lookout Bar, which was inside a hotel on the South Shore. The views were beautiful!

We also took a $5 tour of Harpoon Brewery, which was fun and was extremely generous with samples. We opted to leave off Sam Adams since it’s a bit of a hike outside the city, but would love to visit if we go again.

Overall, Boston was a big city that was so much easier to navigate than NYC. I loved how close everything was, all the history and the public art. We had a great time, and I hope to visit again when my kids are much older and can handle walking more than a few miles 😉

Have you been to Boston? What were your favorite sites to see?