Your Boston convention ends on Thursday afternoon or Friday morning. Instead of rushing back, why not extend your business trip and work remotely for a day? Staying in the city an extra day or two is a great way to explore local sights while getting work done, and Boston is one of the better cities for mixing productivity with sightseeing. Here’s how to make it work when you’ve got things to do and only a day or two to do them.
Where to Set Up Your Remote Office in Boston
Chances are, you’re staying in the Seaport District, Financial District, or Back Bay. Great news! There are plenty of places to spend a day working and enjoying Boston in these locations.
Seaport District: If you’re staying near the Boston Convention & Exposition Center, the Seaport is a remote worker’s dream. There are a multitude of local coffee spots with excellent WiFi, plenty of power outlets, and professional atmospheres where nobody bats an eye at video calls. The area is also known as the Innovation District, so expect weekday morning crowds of other business travelers and local tech workers. Notable spots:
- Flour Bakery and Cafe – Seaport @ 12 Farnsworth St.
- Cocorico – Seaport @ 450 Summer St.
- Caffè Nero – Seaport @ 368 Congress St.
Back Bay: Convention travelers staying near the Hynes Convention Center have even more options. Pavement Coffeehouse on Newbury Street strikes the right balance: serious enough for work but Boston enough to feel like a local. Fair warning, this place is usually packed. If you don’t mind a short wait for a table, the second floor is quieter for calls. If you need a more formal setup, Workbar Back Bay offers coworking day passes ($59+) with dedicated desks, private phone booths, and the kind of ergonomic setup your hotel desk definitely doesn’t have. (They have multiple locations across the metro area, btw.)
Financial District: For those extending trips downtown, Thinking Cup on Tremont Street is my go-to. The WiFi is fast, the coffee is legitimately good, and there’s a mix of tables and counter seating. Weekday afternoons (after 2 PM) are ideal. The lunch rush has cleared but it’s not yet packed with evening commuters. Plus, it’s across the street from Boston Common and only steps from the Freedom Trail, so you can get a nice walk in after you work.
Pro tip: Most Boston hotels will let you keep your room past checkout if you’ve stayed a few nights. Ask when you check in. Even if they don’t, many will store your luggage while you work from a nearby cafe.
The Essential Remote Work Setup for Hotel Rooms
Hotel desks are universally terrible, and many of the historic and boutique hotels don’t even offer desks. After years of working on the road, here’s what I use when working in-room: a portable laptop stand transforms any surface into a more ergonomic workspace and folds flat in your carry-on. Pair it with a compact wireless keyboard and you can sit comfortably during long work sessions, even if you’re working from a hotel bed.
Pro tip: Create a 30-minute hotel office setup to get the most out of your remote work time.
Boston hotel WiFi can be hit-or-miss, especially in older buildings. Bring a portable travel router as backup. It creates your own secure network and often speeds things up. I’ve had reliable connections with this one. I also carry a multi-device charging station because hunting for outlets in older Boston hotels is a special kind of frustration.
True story: I’ve stayed in more than one Boston hotel that had only two old-school outlets servicing the whole room. Small charging stations are a lifesaver in boutique hotels.
For video calls, a lightweight LED light makes a huge difference. Boston hotels built in the 1800s (and there are many) don’t have great lighting. Neither do most cafes. A small light is easy to pack and keeps you from looking like a zombie on calls.
Balancing Work and Exploring Boston
If you’ve only got one or two days to spare, here’s a schedule that makes the most of your time: Start your remote work day early (7-8 AM) while your West Coast colleagues are still asleep or your East Coast team hasn’t fully logged on. Work until 1-2 PM with real focus to hit any deadlines, and let your team know in advance you’ll be logging off early. At 1-2 PM, shut your laptop and actually explore.
This timing gives you 4-6 solid work hours and leaves your afternoon free for the Freedom Trail, walking through Beacon Hill, and checking out restaurants people told you about. Boston is compact. You can walk from Back Bay to the North End in 30 minutes and see half the city along the way.
This schedule has you working through lunch, but skip the room service. The Seaport has Sweetgreen and Flour Bakery within a five-minute walk of most hotels. Back Bay has Pret a Manger on nearly every corner, plus there’s a ton of restaurants in the Prudential Center (attached to the Hynes Convention Center). Grab some takeout, bring it back to your workspace, and save your dining budget for dinner.
Making Your Extended Trip Work
WiFi backup plan: Download any critical files before you leave the office or your hotel. Boston cafe WiFi is generally reliable, but don’t bet your deadline on it. Keep hotspot data available on your phone.
Time zone awareness: Boston is EST, so use the time difference to your advantage. Start at 6 AM local time and you’ll be ahead of the game by the time your North American colleagues log in.
Attention management: Boston history and travel guides can be distracting in the best way. Use your laptop’s focus mode or you’ll spend your whole work block reading about Freedom Trail history instead of finishing that presentation. Pro tip: use a physical travel guide for sightseeing to avoid falling into online rabbit holes when you should be working.
My picks?
- Fodor’s Guide to Boston – updated often, useful maps, and a solid restaurant focus
- Frommer’s Boston Day by Day – quick and easy itineraries you can do in a day
- Lonely Planet Pocket Boston Guide – compact and full of neighborhood-based walking guides
Expense tracking: Don’t forget to save receipts. Depending on your company’s policy and the nature of your work, some of your remote work activities may be deductible or reimbursable. Use a travel expense tracker or take photos with your phone.
The key to working remotely from Boston while extending a business trip is treating it like actual work, not a vacation with your laptop open. Put in focused hours, then close the computer and enjoy the city.
Your convention brought you to Boston. A remote work day or two lets you actually experience it.
Work Travel Getaways 