Boston’s Seaport District: A Columbus Day Weekend Itinerary

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Boston’s Seaport District: A Columbus Day Weekend Itinerary

Boston Seaport District

With the promise of crisp, cool air, a Columbus Day weekend getaway is a favorite of many New Englanders, and no place offers more to do and see than the Seaport District. An easy drive from virtually anywhere in New England, Boston comes alive over the long holiday weekend as visitors flock to town and residents takes to the streets enjoying their beautiful city.

The Envoy’s roof-top bar.


With the recent growth in the Seaport, there are now ample hotels options, all of which offer swank digs and luxuriant service. Choices include the recently-opened YOTEL Boston, the Seaport Hotel and the Envoy Hotel, to name just a few. The Envoy has a prime waterfront location, and many of their sleek rooms have a water view. Whether or not you score a room with a view, a cocktail at Lookout Rooftop and Bar is an absolute must prior to heading out to explore.

After working all week, a laidback dinner is in order. LoLa 42 and Temazcal Tequila Cantina are two places where there’s no need to worry about putting your elbows on the table. For more dining possibilities, check out “Seeking Sustenance in the Seaport” on our website. After dinner, take a stroll along the Harborwalk or head to Lucky’s Lounge for a strong drink in a delightfully dark bar.


While room service breakfast is always a decadent treat, with a Flour Bakery right in the neighborhood, you may feel compelled to venture out for their renowned brioche au chocolat and coffee. After breakfast, head to the ICA for a dose of modern culture before moving on to Harpoon Brewery for a tour and tasting. Should you have tots in tow, Boston Children’s Museum may prove a more appropriate afternoon endeavor. Just across the channel, within a 15-minute walk, is the New England Aquarium.

If you’re planning on an indulgent Saturday evening dinner, a quick bite at Yankee Lobster Company should suffice for an afternoon snack, perhaps a shared lobster roll. A well-earned nap back at the hotel rounds out the day.

For couples looking for the ultimate date night, dinner at Menton, the celebrated Seaport restaurant of famed Boston chef Barbara Lynch, is a must, as are advance reservations (you’ve been warned). Should you opt to dine here, dinner itself – with multiple courses – will be the evening’s entertainment. This is something to be savored at Menton in every sense of the word. If you’d rather go with a more casual, and less time-consuming, dinner – not everyone wants to don a suit on a day off – take in the neighborhood’s outdoor art installations, such as Starry Night and the Channel Center Garage Installation afterward, and then enjoy a pre-bedtime aperitif back at your hotel.

Boston Harbor Islands

Boston Harbor Islands


Sundays are all about brunch, at least as far as we’re concerned. Sleep late – you’re on vacation – and then amble over to one of the many Seaport restaurants that make the most of this most precious Sunday ritual. The goal is to arrive no earlier than noon, when a mimosa or bloody is socially acceptable (and legal — we are in Massachusetts, after all).

Restrain yourself from over-imbibing so that you’ll feel up for a trip to the Harbor Islands. Choose your island, hop on a ferry, and spend the afternoon exploring. Arrive back on the mainland in time for a proper Sunday supper: on the early side and of hearty fare. Italian restaurant Strega Waterfront and French restaurant Bastille Kitchen both fit the bill perfectly.

After dinner, the mellower vacationer may choose an in-room movie and an early bedtime. The more adventurous traveler may opt to hit the town.  Should you fall on the adventurous end of the spectrum, you’ll find no lack of hot spots to hit within walking distance of your hotel.

Boston Public Garden

The Public Garden


We know there are some who will strongly disagree with this suggestion, but we’re making it anyway; before heading for home, act like a tourist. We won’t tell… promise.

There is a reason many of Boston’s ‘tourist attractions’ have been attracting people for decades. They’re fun and they’re quintessentially Boston. The Duck Tours are still running in October, the Public Garden and Common will be awash in fall colors and, if the Sox are still in it – and all indications are they will be – the Make Way for Ducklings bronze sculptures will be decked out in Sox gear. Although it is admittedly getting taken over by chain stores, Faneuil Hall continues to offer a thriving scene with street performers and hansom cab rides.