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29 Hours in Seaport

Boston, MA

Kirsten Alana
By Kirsten Alana

Following a conference I spoke at in the Back Bay in June 2019, I accepted an offer to extend my trip and spend a day and night in Boston's "new" [to me, since I last visited Boston] Seaport district. This is a visual diary of my stay.

Where I Stayed in Seaport

The Envoy is part of Marriott's Autograph Collection & is located at Sleeper Street and Seaport Boulevard. My suite was a 'Coveted Corner' room.

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Envoy has an entirely bespoke art collection and public areas make it feel as if it is a boutique hotel, which is the hallmark of Autograph Collection.

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Where I Ate in Seaport

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Tuscan Kitchen felt like a chain restaurant but their take on Eggs Benedict, served on rustic Italian bread with prosciutto & truffle hollandaise, tasted more original than a normal chain restaurant dish. I dined in for brunch and had to try the choose-your-own Bloody Mary [which is my brunch cocktail of choice, always].

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Tatte Bakery is run by its founder but Panera Bread has an ownership stake. Normally that would turn me off, the connection to big business. But as of my visit, Tatte still tasted like a discovery. Especially since I'm a Francophile who drools over superb design and a perfectly caramelized Kouign-Amann. Seaport is just one of their many locations on the Eastern Seaboard, each one different from the next. I adore the Tatte design Instagram.

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Being a fan of hotels that have a great bar and restaurant experience, I had to try Envoy's Outlook Kitchen and the Lookout Rooftop bar. With a female head chef and the best deviled eggs I've ever had in my life (I really wish I had asked for the full size and not the small), I could have returned more than once had I been staying for longer. And it was easy to see why Lookout allows non-hotel guests to make reservations. It's the kind of bar that I'd go to regularly if I was a Boston resident. For the views alone. But the cocktails were also dynamite. The fun light-up party bowl made me long for friends to share the night with.

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Options for on-the-go snacking in Seaport that I took full advantage of: Taiyaki NYC and Juice Press. Let's be honest, you don't have to visit Seaport to find these. But sometimes old favorites are nice when traveling. Especially on hot summer days where you can't think straight because you need to cool off so bad.

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Nantucket-based Cisco Brewers may no longer be a craft brewery but as a native New Englander, I've been drinking their beer since long before word spread all over the US. Their Shark Tracker Lager is my go-to since it benefits OCEARCH and gives back to Protect the Ocean and Fund Shark Research. I enjoyed their pop up beer garden in the Seaport that wasn't quite an afternoon on the beach... but felt awfully close to it. If I'd had friends to play cornhole with, that is.

What I Did For Fun in Seaport

spoiler alert: lots of art 

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Air Sea Land by Okuda San Miguel is seven sculptures that decorate Seaport Boulevard starting near the entrance to Martin's Park and Seaport Shrine. Okuda is a favorite artist of mine so I was so pleased to see this showcased as part of the neighborhood.

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Seaport has the potential to feel as if it's nothing more than chain stores and restaurants. The Current outdoor village infuses it with the presence of small business (not to mention great shopping) while nearby District Hall gives co-working a bold and innovative new face [that's free]. I loved the "radio tuning sculpture" outside the Seaport Boulevard entrance and can honestly say I'd never seen anything like it before.

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IcA Boston is terrific. Weeks later, I'm still thinking about the room with the screens and the song that never ends. When you visit, you'll see what I mean. I don't use the word unique lightly, but I think it might fit that room and its thoroughly modern take on performance art.

I'm glad I saw a sign for IcA Watershed. This satellite location is free with admission to IcA and the entire experience - from the included water taxi ride over to it to the exhibit itself and the community gardens I passed along the walk from the water taxi - superb. All of it.

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I enjoyed the chance to kayak around Seaport, offered by the LL Bean store on Seaport Boulevard.

Boston's Blue Bikes were offered in multiple places all around Seaport.

I was tempted to hire a sailboat for a day until I realized there just wasn't enough time.

And I was pleasantly surprised by just how close Seaport is to the airport. That ensured I could maximize my stay in the area and leave later than I would have had to, if I was staying elsewhere in the city of Boston before flying home.

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Adjacent to the Children's Museum and guarding what felt to me like "the entrance" to Seaport -- Martin's Park, is dedicated to the youngest victim of the Boston Marathon bombing. It was designed with special sensory and adaptive features ensuring it will always be accessible to kids of all abilities.

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This is by no means an endorsement of Seaport being the only neighborhood I believe people should visit while in Boston, it's simply a report on the experience I had during my stay.


© 2025 Kirsten Alana

Kirsten has been to all 50 states and worked in more than 60 countries on six continents for some of the most awarded campaigns in new media. Her clients have included brands in travel, fashion, and lifestyle ranging from Four Seasons and Visit Britain to Ted Baker and Amarula. Her work has been featured in Travel + Leisure, Grazia, Cosmopolitan, Harper's Bazaar, and more. She resides in Los Angeles when she is not traveling on assignment. Email: hello at kirstenalana dot com
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