If you've read my last Boston post, you know I was just up there last month. Different trip, different reason. Same city.
This one was for the Celtics — which meant a completely different approach. No Seaport Hotel. No leisurely walk. No snow (well, a little snow). This was a fast trip: get in, see the game, get out, and spend as little money as possible doing it.
I've done this enough times now that it's almost a system. So here's the system.
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Step One: Find the Cheap Flight — Layover and All
The first thing I did was stop caring about a direct flight.
Direct Boston from where I am is fine, but it costs more. Book the one with a layover. If you've got flexibility with your travel dates and you're not on a tight schedule, the layover flight is almost always significantly cheaper, and on a trip like this where the whole point is the game, the money you save on the flight goes straight back into your pocket.
The layover adds time but not stress. You pack light — carry-on only, always — and you read, you eat airport food, you do what you were going to do anyway except now you're doing it in a terminal instead of at home. No big deal.
The savings are real. Do it.
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Step Two: No Hotel
This is the move most people don't think about: you don't need a hotel.
Boston is a city where people reflexively book a hotel because that's what you do when you travel. But if you're going for a Celtics game and flying back the next morning, a hotel room is money you spend to sleep four hours in a bed you'll never remember. Skip it.
Here's what you do instead.
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Step Three: Uber to Encore Boston Harbor
From the airport, you don't go to a hotel. You go to Encore Boston Harbor.
Encore is a luxury hotel and casino complex in Everett — about 15 minutes from Logan. The Uber fare is short and cheap. The property is clean, upscale, and well-run. And critically: they have a free shuttle to TD Garden.
That's the move. You Uber to Encore, you're on casino property with restaurants, bars, comfortable spaces to sit, and time to kill before tip-off. You clean up in the casino bathroom if you need to. You grab a drink or a bite. You walk the floor a little.
One thing worth knowing before you head over: TD Garden doesn't allow bags inside — no backpacks, no carry-ons, nothing. So before you get on the shuttle, drop your bag with the Encore concierge. They'll hold it for you at no charge, and you walk into the Garden empty-handed instead of getting turned away at security.
The shuttle runs both directions — to TD Garden before the game, and back to Encore after — so dropping your bag isn't a hassle, it's just part of the system. You get on the free shuttle to TD Garden — no parking, no MBTA scramble, no hassle — and you show up to the game relaxed instead of rushed.
A hotel charges you for a room to relax before a game. Encore lets you relax for free on the way there.
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The Game
TD Garden does what TD Garden does.
If you haven't been to a Celtics game there, the building has a good energy to it. The crowd is real — not a corporate crowd, not a half-empty arena where people are looking at their phones — the city actually cares about this team, and you feel that from the upper deck as much as the floor level.
I settled in with what turned out to be a first for me: Jack Daniel's and Ginger Ale in a premix can. I genuinely did not know they made those. Ready to go, no mixing required, right there at the concession stand. Had a blast. If that's what the kids are doing now, I'm not complaining.
Find your seat, get your drink, and let the game do the rest.
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Hidden Gem: Brattle Book Shop
If you've got a few hours to kill in the city before game time, go find Brattle Book Shop.
It's tucked into a side street in Downtown Crossing — 9 West Street — and it is exactly the kind of place that doesn't exist anymore in most cities. Three floors of used, rare, and out-of-print books. An outdoor lot with discount bins where you can pull a $5 hardcover out of a cart on the street and flip through it while the city moves around you. The kind of store where you walk in for ten minutes and come out 45 minutes later with four books you didn't know you needed.
The staff knows their inventory. The selection is real — not just paperback thrillers and discarded textbooks, but actual literature, history, science, philosophy, first editions. It's a working bookshop run by people who actually care about books.
Which raises an obvious question: what happened to all the bookstores?
There used to be one in every city worth visiting. Now most of the chains are gone, the independents are struggling, and the ones that survive are the ones that built something you can't replicate on a screen. Brattle is one of those. Knowledge is power, and there's something about a physical book — the weight of it, the marginalia from whoever owned it before — that a digital file never quite replicates.
I'll give Brattle its own post soon. It deserves more than a paragraph.
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Step Four: Shuttle Back to Encore — Grab Your Bag
After the final buzzer, don't just wander off toward North Station. Remember the shuttle runs both ways — so get back on it and ride back to Encore, where the concierge is holding your bag.
Once you're back at Encore, bag in hand, you decide the next move: Uber straight to Logan, or — if you've still got time before your flight — swing by Hyatt Regency Boston Harbor first (more on that below).
If you skipped the bag check entirely — no backpack, nothing to hold — the MBTA is still worth knowing. The North Station stop is literally attached to TD Garden — you walk from the arena straight into the station. Jump on the Green Line and connect to the Silver Line at South Station, or take the Orange Line to Back Bay and connect from there. Either way you get to Logan for a fraction of what a post-game Uber surge is going to cost you at midnight.
Navigating the MBTA has its own learning curve — enough that it warrants a dedicated post, which is coming. But getting from North Station to Logan is one of the simpler routes and it's well worth knowing.
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Hidden Gem: Hyatt Regency Boston Harbor
Before you settle in at the airport, there's one more stop worth knowing about: Hyatt Regency Boston Harbor.
It sits right on the waterfront, minutes from Logan — and it has been quietly one of my favorite spots in Boston for years. I've stayed there multiple times.
Harborside Grill, their waterfront restaurant. I stopped in for a Lobstah role and slaw.
A quiet lunch by myself, working through a few pages of a good book — landed on a line worth sitting with for a second: "A man does what he must — in spite of personal consequences, in spite of obstacles and dangers and pressures — and that is the basis of all human morality."
Afterwards I moved over to Midships Bar for a proper Old Fashioned. The bar has the right energy — not loud, not trying to be something it isn't. The service throughout, every visit I've made, has been excellent. The staff there are the kind of attentive without being intrusive — they've figured out the balance most places haven't.
If you're going to be near Logan with a few hours to spare and you want to eat well and sit somewhere comfortable before a red-eye or an early morning departure, the Hyatt Regency Boston Harbor is the answer. Most people don't know it's there. That's what makes it a hidden gem.
Bonus: The Water Taxi
That dock behind the hotel isn't just for the view — it's a real stop on Boston Harbor's water taxi network. From Rowes Wharf, right where the Hyatt sits, you can cross the harbor to a handful of downtown wharves in a few minutes flat.
Common drop-offs: Long Wharf, which puts you a two-minute walk from the New England Aquarium and Faneuil Hall, and the Seaport over at Fan Pier. There are a few other wharf stops along the way too.
It's a genuinely nice option if you've got a few hours to kill before the game or before a flight — faster than fighting Seaport/downtown traffic in an Uber, and a lot more scenic than the T. Cross the harbor by boat instead of sitting in it by car.
Most people staying near Logan have no idea there's an actual water transit system running right past their hotel. Worth knowing about even if you don't end up using it.
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Step Five: Sleep at the Airport
Logan International is not a five-star experience to sleep in, but it's not bad either. Terminal A and B have seating that's manageable for a few hours. You'll see other people doing the same thing.
The formula: find a quiet corner near your gate, set an alarm, put in earbuds, and sleep. Two or three hours is enough if you're used to running on not much. The airport wakes up early — people start moving around 4 AM and the energy shifts — and that's your cue anyway because the first morning flight boards early.
Bring a jacket or a layer. Airport terminals run cold.
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Step Six: First Morning Flight Home
First flight of the day is almost always on time. The cascading delays that knock out afternoon and evening flights haven't started yet. The crew is fresh. The plane is exactly where it's supposed to be.
You board, you sit down, and you're home before most people are at their desks.
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The Full Breakdown
If you're going to replicate this, here it is clean:
- • Book the layover flight. Save the money.
- • Pack carry-on only. No checked bag, no wait, no fees.
- • Uber from Logan to Encore Boston Harbor. Not your hotel — Encore.
- • Kill time at Encore. It's a casino. There are restaurants, bars, and plenty of room to exist comfortably before the game.
- • Drop your bag with the Encore concierge. TD Garden doesn't allow bags inside — no backpacks, no carry-ons. They'll hold it free of charge.
- • Take the free Encore shuttle to TD Garden. They run it regularly on game days and nights, both directions.
- • After the game, take the shuttle back to Encore. Grab your bag from the concierge, then Uber onward. (No bag to grab? The T works too — North Station is inside the Garden, and MBTA to Logan costs a fraction of a post-game Uber.)
- • Hidden Gem at Hyatt Regency Boston Harbor. Harborside Grill for a real meal, Midships Bar for a proper drink. Right near the airport. Hidden gem.
- • Brattle Book Shop if you have daylight hours. Downtown Crossing. Don't skip it.
- • Sleep at the airport. Gate area. Set an alarm. Two to three hours is enough.
- • Board the first morning flight. You're home early.
The game still happens. The experience doesn't suffer. You eat well, you drink well, you find a bookshop, and you spend far less than the standard hotel-and-direct-flight approach. You just stop paying for things you don't actually need.
Go see the Celtics. You don't need to spend like a tourist to do it.
— Dr. Scott