Pub crawls on Freedom Trail… walking tours in the Boston Common? Yawn. While life in Boston is already great, it’s definitely better when you do it our way. Take a ride on private seaplanes to Nantucket or go sunset sailing with local captains. Our version of Boston perfectly blends luxury with colonial history and cutting-edge innovation. And while there are so many activities to do in this city, we want to show you the best ones.

7 Ways to Live it in Boston:

At Overseas, we pride ourselves in finding the best of the best. So it should come to no surprise that we send out our very own team to find new activities and contacts for each destination. Boston’s no exception, Doers Marine and Tiffany successfully returned from their Boston trip with exclusive activities and insider information. Here are our favorites:

1. Seaplane to Nantucket Island for Lunch
Dramatic cliffs, sandy beaches, lighthouses, historical mansions, and more. Nantucket island is the perfect quick getaway from Boston to spend the day. Enjoy a farm to table lunch at Boarding House at the scenic patio or the cozy cellar dining room.

2. Take a Private Tour of Fenway Park
America’s Most Beloved Ballpark is nestled in the city of Boston. Fenway Park is a place where dreams are made, traditions are celebrated, and baseball is forever. See the home of Red Sox Legends, meet some of the players, stand on the field, and even throw a game-winning pitch on this VIP tour.

3. Fly a Biplane above Martha’s Vineyard
Discover Martha’s Vineyard on a bi-plane for the experience of a lifetime. Choose from different tour options that fly across Chappaquiddick, island towns, and state beaches. Pair with a seaside ‘all-white’ picnic to finish off the perfect Boston stay.

4. Lobstering in Boston
All roads may lead to Rome, but all lobsters lead to Boston. Experience the daily life of a Bostonian lobster fisherman in this authentic local experience. You’ll have the chance to join the fisherman’s daily routine on their very own boat where you can witness the captain hauling traps and catching the shellfish. Any legal lobsters you catch will be yours to keep (and eat)!

5. Dine at the Lighthouse
Drive North of Boston for a rare and luxurious experience for select visitors. Enjoy a private meal at the top of Newburyport’s lighthouse tower. A catered local meal will be paired with views of the bay and nearby harbor. If you’re looking to commemorate a special event, you will not be disappointed.

6. Sunset Sailing with Captain Seth
Captain Seth is an experienced sailor who has been taking visitors out sailing for over a decade. Take a journey on his 80ft historic “When and If” Schooner —a wooden yacht built in 1939 that has a long history in the Salem waters. On each trip, cCaptain Seth takes the best route on the water to see an awe-inspiring sunset while navigating across the wind for the best possible experience.

7. Smartphone Photo Tour with Saba
The days of carrying around a heavy DSLR camera are long gone. Take high quality pictures straight from your phone with our local contact Saba. With over 15+ years of experience and extreme passion as a guide and instructor, Saba will teach you how to take your photos to another level. Explore scenic views of the waterfront around Columbus Park and iconic Bostonian landmarks.

Doers Recommend:
Our Doers travel everywhere, but every now and then they’ll stumble across a city where the food has no match—Boston was one of these places. Marine and Tiffany took the locals recommendation and came back with happy stomachs and even happier souls. Here are some handpicked recommendations:

  • Neptune Oyster in Little Italy has a three hour wait, but eating the best lobster roll EVER makes everything worth it.
  • Visit Mike’s and/or Modern for cannolis that are out of this world, which one would be your favorite? That is THE conversation in town.
  • Champagne tasting at Bristol Four Seasons will relieve any stress.
  • You never went to Boston if you didn’t eat Boston chowda at Faneuil Hall. 

Meet our local Bostonian: Melody Z.
“I recommend starting your day in Back Bay and paying a visit to the Boston Public Library. It’s absolutely breathtaking, and the courtyard the perfect spot to relax before the rest of your day! Then walk through the Boston Common and Downtown towards the historic harbor. You can book a cruise or sail around the harbor, or have a drink by the water. Make sure you check out Quincy Market nearby! From there, you’re close to both the North End for a taste of Italy, or the Seaport for New England lobster!”