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Long weekend itinerary advice!

Ottawa, Canada
Level Contributor
56 posts
37 reviews
Long weekend itinerary advice!

Hello! My hubby and I are in our mid-30's and are coming to Boston for the Labour day long weekend - taking a trip for the first time without our kids in tow! Any advice on our itinerary would be appreciated!

My top question: I looked up fireworks for the long weekend and they are happening on Thursday night (??!) - will there be anymore on Sunday night? Do stores and restaurants close or have reduced hours or do they have extended hours because of the long weekend?

Also - are Faneuil Hall and Quincy Market the same?

Some notes:

We are planning on buying the 7-day MBTA pass but are aiming to walk most of the time

Not going to Fenway - my hubby wants to "save" it for any future boys trips. Unfortunately the Jays are playing the day we leave so we will just miss them!

Friday 6pm arrival at Logan - take Silver line to Renaissance Marriott

Dinner on harbourfront (seafood) – Legal Harborside, Yankee Lobster, The Daily Catch, The Barking Crab, James Hook and Co. 7-9pm - any favourites on these ones?

Walk along harborfront for dessert at Bova’s Bakery open 24 hours (cannoli) take bus back if tired


Breakfast 9:00 (Scali Café or Flour Bakery or Wheelhouse) en route to walking to Segway

Segway tour (2 hr) 10:30-1:00 (Freedom Trail) *Note: I have read the reviews about mostly travelling on the roads and we are ok with that. First time doing Segway but I think we will be ok.

Lunch at Faneuil Hall + walk around + see street performers (1-3)

Shopping and dinner (Cheesecake Factory) and shopping near Newbury/Boylston St and visit Copley Square and Khalil Gibran plaque near here


Breakfast (Flour Bakery or…??)

Harvard Square / Cambridge + canoe along Charles River (still researching more details on this)

Lunch - check out Alive and Kicking for a lobster roll or Legal Sea Foods

SOWA market and Newbury St and walk back up to Boston Common

Dinner (potentially sunset cruise on sailboat) - any recommendations? Pick dinner based on Friday's list


Boston Common / Boston Public Garden and walk around Beacon Hill

Go back along Freedom Trail for anything you want to re-visit (i.e.: Christopher Columbus Park)

Airport by 4:15

Thank you for looking this over!

Ottawa, Canada
Level Contributor
56 posts
37 reviews
1. Re: Long weekend itinerary advice!

Also - just realized that the MBTA pass includes the Inner Harbour Ferry - would this be a nice way to see the skyline without spending much on a cruise? If we do the trip from Christopher Columbus Park to Charlestown?

And another question - is the Skywalk Observatory open air (like Rockefeller in NYC) or are you looking from behind the windows?


Destination Expert
for New England
Level Contributor
7,278 posts
217 reviews
2. Re: Long weekend itinerary advice!

For your first night, I like the roof deck at Legal Harborside. Light bites and great views. On a warm evening it is a great place; even for a pre or post- dinner drink if you eat elsewhere.

Level Contributor
38 posts
3. Re: Long weekend itinerary advice!

SOWA Market is a great choice. Food trucks open at 11:00. Go early to browse the artisans and other vendors (open at 10:00) and be in line at the food trucks at 11:00. We were able to nibble at 7 out of 10 trucks and then resume browsing. Have one person hold a table under an umbrella and get food at one of the trucks. Rinse, repeat. Share food so you can taste more fun items! When we left at 1:00, the lines at the food trucks were about 20 people deep at each one - not fun in the hot sun!

4. Re: Long weekend itinerary advice!

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Removed on: 18 August 2017, 05:35
Level Contributor
6,761 posts
285 reviews
5. Re: Long weekend itinerary advice!

I don't think store hours should change b/c of labor day weekend. I'd pass on the Cheesecake factory. Itinerary looks good. Yeah, you will get some good views from the inner harbor ferry. It'd be a quick ride though as it's a commuter boat.

Level Contributor
2,601 posts
2 reviews
6. Re: Long weekend itinerary advice!

"And another question - is the Skywalk Observatory open air (like Rockefeller in NYC) or are you looking from behind the windows?"

The Skywalk is completely enclosed with windows - no open air. Terrific 360 degree views around Boston. We always bring out of town visitors there....


Level Contributor
77 posts
17 reviews
7. Re: Long weekend itinerary advice!

Unless you really really love Cheesecake Factory, I'd pick something local and not a chain restaurant.

Flour is fantastic for both breakfast and lunch.

Faneuil Hall and Quincy Market are two different buildings, but are in the same area.

South Windsor...
Level Contributor
119 posts
295 reviews
8. Re: Long weekend itinerary advice!

We love any Legal Seafood restaurant in the area but my favorite is the Harborside. Great views, nice ambiance. Yankee Lobster is nice - we've been there but not for ambiance. Like your plans and the suggestions you've received. Faneuil Hall is located within the Quincy Market area. Lots to see and do there. Walk to Copley Square thru the Public Gardens and ride the swan boats. Walking the esplanade along the Charles River is nice too. Hop on, Hop off trolley is another idea to see all there is to see and hear great history is what we do when we bring visitors. The North End restaurants have great food - many open to the outside - a nice place to walk and see the Old North Church, Paul Revere house and Bunker Hill. Enjoy your visit.

Level Contributor
79 posts
233 reviews
9. Re: Long weekend itinerary advice!

Your itinerary looks great and seems to be well thought out and researched. My one recommendation is to skip The Cheesecake Factory. If you give us some ideas for cuisine that you like we can make some recommendations for that neighborhood.

Lincoln, NH
Level Contributor
3,018 posts
11 reviews
10. Re: Long weekend itinerary advice!

The Segway tour concerns me. I walk around the Freedom Trail often and see these groups navigating the streets. You simply cannot be on a tour, looking around and driving the Segway. It is at least, a mediocre tour since you are driving and not looking, at worst, an accident. You also need to be at least 14 to ride one. (Guessing that a couple in their mid-thirties0 may not have two 14-year-olds.)

I would opt for a different activity.