This post was originally published on September 29, 2024 and was most recently updated on October 10, 2025.
As I've previously mentioned, since I'm a self-employed freelancer I have the flexibility to workation, or combine my workdays with vacation activities when I'm away from home. Mike's annual team work weeks are the perfect opportunity to workation in Boston's Seaport District—accommodations and his expenses are already covered, so we only have to pay for my flight and meals.
The Seaport District is a redeveloped, formerly industrial area along the Boston waterfront, with sleek glass office and apartment towers, hotels, dozens of restaurants, and the Institute for Contemporary Art. It's connected to the rest of Boston via rapid transit buses, and it's within a 15-minue walk of downtown.
Since the Seaport District is home to various corporate headquarters and a federal courthouse, it's geared towards the needs of office workers, with lots of coffee shops and fast-casual lunch spots. It's also a relatively convenient base for sightseeing, with easy access to historic Boston sights, museums, and the nearby city of Cambridge.
Getting to the Boston Seaport District
The MBTA Silver Line, a rapid transit bus, connects Boston Logan Airport to the Boston Seaport District. Buses run frequently and are free from the airport to the Seaport District.
Ride share services like Uber and Lyft are also a decent option, especially if you have luggage. If traffic is light, the ride takes less than 10 minutes and typically costs around $20-$25.
If the weather is nice, a more scenic (and traffic-free) option is to take a water taxi. Take the free Route 66 On-Airport Shuttle to the Water Transportation Dock, and from there you can take a short (about 5 minute) ride across the harbor to the Seaport District. The views of the Boston skyline are excellent, and it's a fun way to start your time in Boston. This is the most expensive option if you're traveling as a couple or group, about $20 per person.
Although you can book water taxis online, we've found it easiest to simply call dispatch once we've arrived at the Water Transportation Dock. Currently, Boston Water Taxi is the sole provider—we've had a great experience with them, with speedy pick ups and friendly, helpful captains.
Best hotel for a Boston Seaport District workation: Hyatt Place Boston Seaport District
Mike's employer puts us up at the Hyatt Place Boston Seaport District due to its proximity to their office, but it's also a perfect base for my workations. The hotel caters primarily to business travelers and conferences, so the lobby has an expansive seating area with chairs and tables well-suited for working, with plenty of outlets. Guests also have access to a 12th floor rooftop lounge, which has a glass-walled indoor space with tables, chairs, and a bar with outlets, as well as a rooftop patio with views of the harbor.
Other amenities include a complimentary hot breakfast, with items including oatmeal, eggs, bacon, breakfast potatoes, bread, pastries, yogurt, and fresh fruit; and the rooftop-level gym, which had floor-to-ceiling windows and well-maintained equipment. The standard king rooms are quite spacious, with a corner sofa, work desk, mini fridge, and lots of storage. I liked the bright, modern feel and subtle nautical decor.
The only downsides of the Hyatt Place Boston Seaport District are the price tag ($260-$320 per night for weeknight stays), and the proximity to the Leader Bank Pavilion, an outdoor concert venue across the street. If you're visiting during concert season (typically June through September), there may be significant noise until 11 p.m. However, if you want to attend a show the convenient location is a definite plus.
Where to dine during a Boston Seaport District workation
There are dozens of restaurants in the Boston Seaport District, running the gamut from delis to fine dining. One of the most famous is Yankee Lobster Co., a counter-service seafood spot that was featured on Diners, Drive-ins, and Dives. The restaurant is owned by third-generation local lobster fisherman (they have a commercial distribution facility nearby), and it's a perfect place to eat fresh seafood. The lobster rolls are pricey (about $40, including fries) but worth the price. They're absolutely stuffed with lobster, to the point where you need to eat some off the top with a fork in order to fit the lobster roll in your mouth. There's a covered patio with fun murals, and the menu also includes fish, shrimp, oysters, and more. Mike is not a lobster fan and really enjoyed the fish and chips.
If the weather's nice, my go-to workation lunch spot is Frank Anthony's Seaport Market, which has a deli serving salads and cold sandwiches as well as extensive selection of beverages, snacks, and housemade baked goods. The salads are generously sized and budget-friendly ($10-$12). I enjoyed the Healthy Blend salad with apples, walnuts, and goat cheese and the taco salad with corn, black beans, and avocado. There's no indoor seating, but there are a couple of sidewalk tables and the market is only two blocks away from Fan Pier Park, which has plenty of waterfront tables and benches.
I have a minor obsession with Tatte Bakery, an Israeli-inspired, Boston-based bakery chain with locations throughout the East Coast. Their baked goods are exquisite—I especially love the halva sesame tea cake and pistashio cherry tart. In addition to pastries, the menu includes soups, salads, sandwiches, and shakshuka. I recommend the fattoush salad, which comes with a freshly-baked roll.
Flour Bakery & Cafe is another (much smaller) Boston-based bakery chain, with baked goods, breakfast items, and a lunch menu of salads and sandwiches. I love their seasonal roasted heirloom carrot and farro salad, as well as the brown butter pecan blondie and the seasonal apple cinnamon pop tart. Their espresso drinks are also quite good.
Other quick lunch spots in the Seaport District include Cardullo's Gourmet Shoppe, which has a deli counter, and J. Pace & Son, which specializes in Italian and European specialty groceries and also offers a deli and housemade baked goods (the peanut butter cup cookies are fabulous). The Seaport District also has a Trader Joe's if you want to stock up on breakfast food, snacks, or premade sandwiches and salads.
Sightseeing during a Boston workation
The relatively efficient mass transit system and plethora of sights make Boston a great workation destination—it's easy to fit in some sightseeing in the evenings or take an afternoon off to visit a museum.
If the Red Sox are in town, head to Fenway Park for a game. Even if you're not a baseball fan, watching a game at the oldest active ballpark in Major League Baseball (Fenway opened in 1912) is a special experience. I love sitting in seats from the 1930s and watching the manual scoreboard, which is operated by three people working behind the board. There are exhibits throughout the ballpark about Red Sox and Fenway Park history, including a display depicting the Red Sox logos through the years and a collection of posters for movies that were filmed at Fenway Park.
If you can't catch a game, or if you want to learn more, tours of Fenway Park are available daily year round.
Boston Public Garden is a lovely urban park (it was the first public botanical garden in America) with a picturesque pond and pathways. It's also home to the Make Way For Ducklings statue, which is an homage to Robert McCloskey's 1941 children's book. Mike and I both have fond memories of reading Make Way for Ducklings in school, and we re-read it before our visit. It's a charming tale of a duck family that makes its home in Boston Public Garden, and several Boston landmarks also have cameos.
The Boston Athenaeum might be the classiest place in town to work remotely. The private library, museum, and cultural center was founded in 1807, with the current building dating back to 1847. It reminds me of Belle's library in the Disney version of Beauty and the Beast, with shelves of antique books and elegant architecture. You can purchase admission for $11, which includes access to the rooms on the first floor (an art gallery, lounge overlooking the Granary Burying Grounds, and a reading room), or you can purchase a day membership for $40, which includes access to the entire building.
Faneuil Hall Marketplace is extremely touristy but also a lot of fun, with over 80 shops and restaurants plus a vibrant street performer scene. The marketplace encompasses several buildings, including Quincy Market, which was originally constructed in 1826 as a produce market and reimagined in the 1970s as a food hall. Today, the central colonnade is lined with dozens of stalls, selling everything from heaping containers of fresh pasta to vegan ice cream. Seafood is well-represented, especially lobster rolls and clam chowder—I recommend the Boston Chowda Co. for the quality of their clam chowder and the bread bowl.
Once you've gotten your food, head up to rotunda's second-level seating area. It's a bit less hectic than the main floor, and you can get a good look at the historic signs from 1800s-era market tenants.
The North End is Boston's oldest residential neighborhood, with narrow, picturesque streets and colonial-era sites including Paul Revere's house, the Old North Church, and Copp's Hill Burying Ground. In the 20th century, it saw an influx of Italian immigrants, and that character carries through to today. Most of the restaurants are intimate Italian spots, and there are also Italian bakeries and grocery stores. Mike's Pastry is extremely popular with tourists—I loved their pumpkin spice cannoli.
The Isabella Stewart Gardner Museum is a beautiful and deeply weird place. It was purpose-built by heiress Isabella Stewart Gardner to house her extensive and esoteric art collection. She arranged the installations herself to evoke an emotional response to the art, and per her will nothing can be moved or labelled.
Have you ever visited a small town historical society museum where the curatorial approach seems to be "Let's put a bunch of old stuff in a room?" This is that, but with an enormous budget—there's an exquisitely landscaped courtyard inspired by a Venetian palace, a room of medieval tapestries, works by Rembrandt, and antique furniture.
Since the Gardner Museum has a relatively small footprint, you can easily see it in a couple of hours—I took an afternoon off to experience it.
Cambridge is another fun half-day excursion—the nearby city is about 40 minutes from the Seaport District via mass transit. Walking around Harvard Yard is the default tourist activity, but I recommend venturing a bit further and touring the Longfellow House-Washington's Headquarters (open late May through late October). Admission and guided tours are free.
The takeaway: Boston's Seaport District is an ideal workation destination—in addition to having a productive week of work at the Hyatt Place Boston Seaport District, it was conveniently located to great dining options and stellar sightseeing.
Further reading: Workation guide: Palm Springs, CA
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