Need Boston advice (first timers)

does Boston have a ZTL?

No, but watch out for the falling ceiling pieces in the tunnels

Also is it ok to wear shorts in Boston?

You asking about yourself or your stunningly good looking wife?

I suspect a large amount of tongue in cheak from Roberto here.
My reply as a reminder to all those people who post ambiguous place-names, copied from Wikitravel (click here)):

The Stump - Boston's Parish Church of St Botolph has the tallest church tower in England at 272 feet and can be seen for many miles over the south Lincolnshire countryside and even from across the Wash. The church's foundation probably dates back to a monastery founded by St Botolph in 654. The present church building dates from 1309, though construction of the tower did not begin until 1450. A 17th century vicar of Boston, John Cotton, was one of the leaders of the Pilgrim Fathers who founded Boston, Massachusetts.

Don't miss the Freedom Trail, you can walk it yourself. The USS Constitution (Old Ironsides) is a 200 year old Frigate still in service in the US Navy. You can go on the ship.

Clam Chowder is great and lobster as well. Italian food is generally good, but I find much of the other food in New England to be bland. I don't think New Englanders care much for spicy food. My Grandchildren like a Mexican restaurant that has the most awful Mexican food I have ever eaten. It has virtually no chili powder or spices.

Salem is an interesting place to visit on a day trip. You can take the train from Boston. Also, consider a Boston Harbor cruise.

Boston had good public transportation and some excellent museums if you like that.

We've been to Boston more than a few times - we always drive but park the car at one of the parking spots where you can catch the T, or have stayed at airbnb's within walking distance to the T (our airbnb's have been out by the airport), or once stayed right downtown and parked the car and didn't move it for 3 nights (that was an expensive parking adventure). Luckily, my husband has a uni friend living there and he was our tour guide a few times.

Quincy Market area is always a fun touristy visit. After how many visits (5 or 6? I can't even rem how many times we've gone.) we finally did the Freedom Trail walk from start to finish in 2015. That was fun. We've popped over to Harvard for a visit - the Natural History Museum and we also visited the MIT museum in that area. The Aquarium is a must see if you like, uh, fish (and penguins!) - we've done that 2 or 3 times. Modern Arts museum didn't do much for us (they usually don't , but our 'free tour guide' took us there), but we did enjoy the Isabella Stewart Gardiner museum. USS Constitution (Old Ironsides) was fun, and I'm not big on old ships. And you have to visit Boston Commons/Public Gardens, even if you don't take a spin on the swan boats (which we haven't).

You have to go to some of the bakeries in Little Italy - we fell into the Mike's Pastry trap a few times, then visited Modern Pastry a few trips ago, and last trip went to Bova's on the recommendation of a few folks on this very forum. We don't really do fine food - we've eaten at the Black Rose (Irish pub type place) a few times and love visiting the food market at Faneuil Hall.

If you stay in the old historic downtown area, all the historic sights are walkable from there. We walked through Fannueil Hall (too lazy to check the spelling today) the old north end, to the Constitution, and all the way to Bunker Hill. Metro to Cambridge to see Harvard. We wished we had taken one of the ferry excursions to Cape Cod or Nantucket. Wear your moneybelt under your shorts edit -(humor attempt).

Good advice from the others. Would only add that, although staying anywhere near the city center will be pretty expensive that time of year, it might be worth it just for the comfort and convenience involved.

You really don't want to have a car in the Boston metro area - traffic is murder, ie some of the worst in the US and most of the drivers you'll encounter on the roads are certifiable. Public transportation (or on foot) is the way to go.

There's a local restaurant chain that you'll see all over the city called Legal Seafood - surprisingly good chowder, etc. at affordable prices.

Along with the other attractions previously mentioned, I'd suggest taking in a baseball game at Fenway if the Red Sox are in town during your stay - no better way to tap in to the beating heart of Boston ... of all of New England come to that.

Hi Roberto - I'm a local. Some thoughts:

Shorts - Absolutely fine. No need for a money belt, which someone mentioned. If you don't wear one in SF, you don't need one here.

Car - You won't need one, and you probably don't want to drive around here, anyway :) One of the best things about Boston is its walkability, and the T will get you everywhere you probably want to go (even from the airport).

Hotels - Anywhere in central Boston will be good (Back Bay, financial district, Seaport, Beacon Hill, etc); in Cambridge, Kendall Square is convenient. There are also some chain hotels walking distance from the Lechmere T stop in Cambridge.

Things to do - Two favorite places I like to take visitors are the Isabella Stewart Gardner Museum (do the free tour, too) and the observation deck at the Custom House (the clock tower by Quincy Market). The latter is, I believe, open twice a day except on Fridays; it is also a Marriott, so you can even stay there. Another idea is a day trip to Provincetown (tip of the Cape) via the fast ferry. P-town will be packed Labor Day weekend and then will be much quieter starting on that Monday, so that would be a good time to visit. If you can give some ideas of types of things you and your wife are interested in, I can try to think of non-touristy ideas.

Food - In the North End, I'm partial to Maria's Pastry (no relation!) for cannoli, etc. The Boston Public Market, near the North End, is a terrific place to check out local food vendors (akin to Pike's Market in Seattle). They also sell local beers, wine, and spirits, too. If there are certain types of food you're interested in, I can try to make some targeted suggestions.

We lived in a Boston suburb for two years after graduate school. When we go back we love to stay anywhere we can find a hotel or B&B along Back Bay. You are close to excellent public transportation and half way between a pleasant walk to all of the city center sites, Fenway Park and the Isabelle Stewart Gardner Museum, one of my favorites.

When we went 2 years ago I tried to have clam “chowda” or lobster something once a day. The lobster in particular is more plentiful and affordable than on the west coast. The North End Italian and city wide Greek restaurants are great too. Pizza is wonderful too, especially the thicker crust type.

For a first time of four days I would think that you wouldn't need a car. If you want to go further afield, like to Lexington-Concord, Salem or the Cape you could try a tour.

Labor Day weekend in Boston and Cambridge is when students are moving in and moving out of their off-campus apartments, so the in-city traffic tends to be horrible, with UHauls everywhere. And tons of trash and furniture at curbsides.

You can wear whatever you like, anywhere in Boston, except NY Yankees regalia.

We love Boston(but nowhere near as much as we love Florence) , and even better, Cape Cod (but probably not so good on Labor Day weekend-if you want to go there then, you'd better reserve now and be prepared to pay a lot!) If you like art, the Boston Museum of Fine Arts is wonderful(but Italian Renaissance is almost non-existent there) , is open until 8:30 some nights, and has good restaurant options. Paul Revere's house is interesting.

Boston is a GREAT city to visit in the summer. Make your hotel reservations as soon as possible because Labor Day weekend is not only very popular to be in New England, but college & university students will also be returning and hotel rooms will fill.

You do NOT need a car. Public transport by the MBTA is excellent.

Top tings to visit? It depends on what you like. Get out your Boston travel book to pick from the Isabella Stewart Gardner Museum, a Red Sox game, the Freedom Trail, whale watching, a lighthouse boat ride, Quincy Market, The Museum of Fine Arts, etc.

Great places to eat at reasonable prices? What is your budget for two people per meal including taxes and tip?

A car is a hindrance in Boston. I think it's not that important where you stay, the issue is comfort level and price of the hotel. You can use Google Maps to see how far it is to an MBTA stop. Although Boston is "walkable", like other big cities, you can't see all the attractions without using the subway-regardless of hotel location. I agree that Labor Day and the days after may be congested.

For the Italian Renaissance, you would go to the (unique) Isabella Stewart Gardner Museum which is walkable from the Museum of Fine Arts. Boston's modern/contemporary museum has just opened a second location (by boat from their main MCA location - which is a bit out of the way. But harbor-scenic.) Boston is a big music town, as well. The newly-unified Harvard museums might be worth a trip, if (as we are all assuming) you love art because of your Screen Name.

Thank you for the advice on what to do and how to act, and also on money bags. I don’t wear those in Naples, so I won’t either in Boston.

I’m glad both my wife and I can wear shorts in Boston, I heard the fashion attire is less informal than California. But now I wonder whether I can wear them also in churches being Boston a very catholic enclave. Should I make sure I’m not showing my knees?

As mentioned earlier, Labor Day is when the college kids return and move in. Crowded. There are a lot of colleges and univesities in aBoston and surrounding areas. Use the T to move around and walk.

---You really don't want to have a car in the Boston metro area - traffic is murder, ie some of the worst in the US and most of the drivers you'll encounter on the roads are certifiable.--- This brings back the memory of hubby's Boston friend/tour guides joke about Boston drivers - What's the definition of a millisecond? The time between the light turning green and the guy behind you hitting his horn. And that did happen to us - albeit, not in Boston, but on the outskirts - no mercy for someone with Nova Scotia license plate!

His other tip - if the subway cars are crammed (and some will be) just wait for the next one along - it won't take long to get there and chances are it'll be much less crowded (which was true for us more than once, not always though).

I second the idea to walk the Freedom Trail.
Take a Duck Boat tour

Another local here. There is an inexpensive hotel in Boston, relatively, the Charlesmark on Boylston Street. It is a European style hotel with small rooms, but it has all you need, across from the Boston Public Library. As I like the feel and the activity of the Back Bay, I would stay at Charlesmark (which I do when I'm researching even though I live less than 10 miles away) or the Copley Fairmont Hotel(have stayed here). My next choice would be to stay on the harbor at the Marriot (next to harbor and nice park, North end and Faneuil Hall Market Place) or, preferably, the Rowes Wharf Hotel(frequent here). The Bostonian Hotel is right next to Fanueil Hall Market Place, but I've never been inside...good location. I would not recommend staying in the Seaport District as it is new, bland, and less convenient, IMO.

Boston is a walkable city from the Back Bay, South End over Beacon Hill or down to the harbor, from the MFA to the harbor. We walk it even now. However, the subway (the 'T') makes anyplace a few minutes away as well. Definitely walk the Freedom Trail as it will give you a view of Boston's layout and history in colonial times. There are also historical houses in Boston from different eras if you like that type of thing. If you go to the North End, don't go to restaurants on Hanover Street, travel one block over, IMO. Bova's is also better and easier than Mike's Pastry or the Modern (a bit) and it doesn't get the tourists. The MFA is my favorite, but the Isabella Stuart Gardner Museum is unique and energetic. Harvard's Natural History Museum is really interesting (Cambridge). Modern art is down in the Seaport district. There will be plenty to do for 4 days without day trips. But if you need to day trip, I'd definitely recommend the ferry to Provincetown. Or just the ferry to the Harbor Islands...or stay on and just ride. Or you could do half a day and take the red line (the T) to Quincy to see the Adams Presidents' birthplaces, Temple & Crypt, and Peacefield, Dorothy Hancock's home (check to see it's open), but just a mention for John Hancock's birthplace...if you like that type of history and all doable on the trolley between sites. At that time of year there should also be a Ferry to Salem, which is interesting, too...but not my favorite. If you want beautiful beaches, take the train to Gloucester and taxi to Good Harbor Beach or Wingershaek, or just go to Stage Fort Park by foot for a dip.

You can find just about any ethnic food you want in Boston with or without spices. You just have to look.

I could go on and on, but I will stop. Please ask if you have any specific questions. Boston is my favorite city in the US...that's why I live here... LOL. San Francisco is a close second. Or at least was the last time I was there...which is a few decades now. Sigh.

PS. You can wear shorts into churches and most anywhere else during the day. At night, if you are dining upscale, then you might not be allowed in. Otherwise, you are fine.

hey roberto
don't forget some "baked beans" "cream pie" "afternoon tea party" "a beer with norm" CHEERS
aloha

No one has mentioned Chinatown. If you want dim sum, the locals go to Hei La Moon, 88 Beach Street. Go early, it will be crowded by 11:00-noon on the weekends. There are also several bakeries. Chinese cakes are less sweet.
As everyone has mentioned Boston is walkable. If it is a nice day, you can easily walk from Chinatown after your dim sum brunch to the Aquarium to the North End for Italian dessert. Or take a detour to Faneuil Hall and Quincy Market.
When you are looking at hotels, look for ones near the Red line or the Green line on the MBTA.

I've been to Boston many times. I wouldn't write off staying in Cambridge which is still very close by and where Harvard U is located. I like the local feel of the neighborhoods on the Red Line - either Porter, Davis, Harvard stops. Lots of young people and vibrant neighborhoods. Also, the Royal Sonesta Hotel (closest to Lechmere stop, end of the Green Line) is very nice, stayed there for work.
https://cdn.mbta.com/sites/default/files/maps/2018-04-map-rapid-transit-key-bus-v31a.pdf

Lots of highlights that stand out, but I'll just name two: Beacon Hill (lovely architecture) and North End (Italian food/bakeries).

Hi Roberto,

Walking around Boston, make sure your health & life insurance policies are updated...jk

Some favorites:

Perhaps you & your wife may like Newbury Street

http://www.newbury-st.com/

https://www.newburystboston.com/

https://en.wikipedia.org/wiki/Newbury_Street

https://www.trolleytours.com/boston/newbury-street

There's the Prudential Center - "The Pru"

http://www.prudentialcenter.com/

[The Prudential Center is located near several mass transit stations including: Back Bay Station – commuters can walk from Back Bay Station to the Prudential Center without going outside! Prudential stop on the E line on the green line of the T. Hynes & Copley stops on the B,C, D lines on the green line of the T.]

You may enjoy the "Skywalk" - http://skywalkboston.com/

The famous North End - not like it used to be - but, for someone who has never been, you wouldn't know. The North End was nicknamed "Little Italy." A lot of Italians & Sicilians who came over settled there. Maybe you find a "long lost cousin?" jk.

My family settled there as well as other surrounding neighborhoods. Restaurants, little markets & bakeries were plentiful; inexpensive & delicious. Over the decades, it's changed a lot!!

I favor Spinelli's - but they're in East Boston & Lynnfield - not convenient w/o car.

The Boston Pops - not sure if they'll play that weekend. Maybe there are other concerts at the "Hatch Shell on the Esplanade" - people line up in the early hours with picnic coolers, blankets, chairs to secure a "lawn seat."

Helpful stuff:

Visiting Labor Day Weekend, it'll be jam packed w/travelers, locals, festivities, college kids settling in, end of summer traffic.

Massachusetts Sales Tax is 6.25%.

A (metered) taxi - you can hail one - they'll practically screech up on the curb. I don't know the rates; I don't use cabs.

Crossing Boston streets - look 100 times in each direction....a car will come out of nowhere...Drivers don't always obey traffic signals, crosswalks or they try to pass a stopped bus.

No need for a money belt. As I tell people on the forum, just practice awareness & a big city awareness.

Trains & buses will be crowded. At train stations, make sure you stand "way back" from the yellow line...there have been instances where crazy people have pushed people. Just making you aware...You'll be competing with locals, travelers, musicians, & homeless people.

For train travel, there's the "Charlie Card" - https://en.m.wikipedia.org/wiki/CharlieCard

Past 8- or 9:00 PM, stay away from alleys (shortcuts), "The Boston Common" & "Downtown Crossing" near "The Financial District." Once businesses, banks, law firms & the like close, it becomes a little eerie.

Downtown Crossing shopping is nothing to see anymore. The "Jewelers' Building" was great in its heyday. The whole building housed many jewelers - eons go, when gold was dirt cheap/reasonable, you could bargain by comparing with competing businesses.

Back in the day, there was the famous Jordan Marsh - well known for its blueberry muffins - bakery shop was in store. As wee ones, we would get so excited when my family brought home a box. Can still smell the blueberries...

There was Filene's - (Both Jordan Marsh & Filene's were right across from each other & competitors. They also decorated their store windows at Christmas - magical. Filene's had a lovely restaurant.

Filene's also had "The Basement" as it was known back then. They would get surplus of "everything" & sell it at deep discounts. I got some beautiful Italian leather products - gloves, handbags, clothes - for almost nothing. Now it's a little super market (Summer St) similar to a small Coop.

Perhaps you may like to take a peek inside South Station which is right across from the Financial District.
https://www.south-station.net/ - A mini Termini.

Oh, and besides cars, buses and people not paying attention, look out for cyclists too. They come ripping around a corner (and don't always observe traffic signals either.)

Extra tips:

https://www.mbta.com/schedules/subway

https://www.mbta.com/schedules/commuter-rail < useful if you were to stay longer and venture to the outskirts of Boston - like Rockport, Gloucester or Newburyport - all quaint, picturesque little (beach) 'towns' to explore; lovely shops and eateries.

Keep in mind, the Commuter Trains do not have as frequent a schedule as the Boston trains.

Oh, and there is also Salem, MA
https://en.wikipedia.org/wiki/Salem,_Massachusetts

http://www.salem.org/

If you like Massachusetts after your visit, you can always plan another trip to see other parts of the Boston/Metropolitan area.

Another thought if you are inclined to explore:

Boston's Theater District -

http://www.touristsbook.com/boston/neighborhoods/theater-district-boston/

https://en.wikipedia.org/wiki/Boston_Theater_District

I don't know if theater doors are open all day except ticket windows. But, the lobbies and such to some of Boston's old theaters are really architecturally amazing and beautiful.

Don't care for Chinatown. If you are out and about in that area late at night - after about 11:00 PM, just keep aware.

"Should I make sure I’m not showing my knees?" It depends. If your knees are knobbly or infested with hairy warts then please have the decency to cover them up.

To add to the above. After the pleasure of visiting Princeton and UVA, Harvard is a bit of dump.

Spare day? Marblehead is a lovely place with lots of nice homes. Special time? Hop on the ferry to Provincetown for the day, it's a fantastic little place.

Oh yeah, how could I have forgotten about Marblehead.

If curious, take a look at this info: https://en.wikipedia.org/wiki/North_Shore_(Massachusetts)

In the summer, Nahant is beautiful. I had relatives who lived near the beach year round. Lovely.

So, if your travels during your stay in Massachusetts takes you out of Boston and on the "Commuter Rail," you'll pass by some of these towns - depending on your end route of course.

Also, if you plan to go to Cambridge and like Indian cuisine, I can give you the name of the restaurant that my friend goes to. She works in Cambridge and has tried a couple.

Since you live in San Francisco there is no reason to go to Boston’s Chinatown. If you want the ultimate Boston tourist attraction go to Durgin Park in Fanuiel Hall. For a good clam bake experience (including lobster), Woodman’s Shack in Essex, although Farnham’s across the street is less touristy. And believe it or not, Papa Gino’s does a pretty good lobster roll for a whole lot less money.

Oh, and if you want to look like you’re from Boston (and not from the west coast), tuck in your shirt and wear a belt. Yes, even when wearing shorts.

Adding additional info to my previous posts - (sometimes, you can forget the little things when you are so used to your own element)

https://www.hotels.com/de1741781/hotels-near-downtown-crossing-station-boston-united-states-of-america/

Downtown Crossing is a good place to access many things. - Trains - Macy's Store - Roche Bros. Market (where you can grab a sandwich, salad or pizza)

Sometimes, there are street musicians or particular groups playing in the center - near Macy's. A few times, a Native American group played there - absolutely stunning! When you can come upon something like that, it is a wonderful memory.

It is pedestrian friendly. Standing at Downtown Crossing, directionally, you can access a lot of 'districts' - a lot within walking distance - Tremont Street, Park Street, Boylston Street, Financial District, and so on.

The "Green Line and "Red Line" will take you to most anywhere in and around the immediate city. The Green Line will also take you toward Kenmore Sq. - Fenway Park if you want to tour the area.

It will be extra crowded with the college kids. The Red Line will take you toward North Cambridge area - all the way to Braintree

"Orange Line" goes to the "North" as well as to the "South" of Boston. "Blue Line" goes to Logan Airport, the beaches, Revere, Orient Heights

There is also the Seaport District - about 15 minutes from Logan Airport - https://www.trolleytours.com/boston/seaport-district - Boston's Waterfront

Someone mentioned "Durgin Park," (restaurant) - they closed their doors in January. But, there are other restaurants around Faneuil Hall - some cater to the tourist industry, of course. Expect higher prices.

Here's a map to give you an idea of the 'downtown' area:
https://www.google.com/maps/@42.3557853,-71.0644496,16z

So, with much of the information given, hopefully you will pick through, find places of interest and formulate a plan of sightseeing/travel.

Labor Day weekend in Boston and Cambridge is when students are moving in and moving out of their off-campus apartments, so the in-city traffic tends to be horrible, with UHauls everywhere. And tons of trash and furniture at curbsides.

Agreed. Many students' families would accompany them. Hotels, restaurants, and sight seeing locations would be jam packed.

OTOH, Allston Christmas is an experience not found anywhere else.

https://www.boston.com/news/local-news/2018/08/30/allston-christmas-boston-moving-permits-storrow

Moving day in Boston is August 31st, but unfortunately that falls on the Saturday of Labor Day Weekend. That being said I haven't found Boston proper to be as affected as it used to be by massive moves because the cost of living 'downtown' in an apartment is quite expensive now, compared with my college days. Allston/Brighton is an entirely different story, but you likely won't be headed out there. There also aren't as many long stay families in the hotels as school starts as compared to graduation day weekend, from my unscientific study. Parents are just dropping off. If you can avoid Saturday and Sunday of Labor day, even better, but the Boston rental shift shouldn't interfere with your reason for being in Boston. Just get a guide book. You'll probably enjoy Boston. However, as you are from Italy originally, I'm not sure you will get so much out of the North End and that's probably not why you are coming to Boston anyway.

They closed Durgin Park?? That makes me sad. First the Central Artery, then the Hilltop Steakhouse. And now Durgin Park. Nothing is sacred.

You do not want to have a car in Boston - it's a hassle and parking is expensive. If you can't walk to it or take the T (or it's just really late at night), then use Uber (in fact, make sure you have an Uber account before you visit and avoid using metered taxis as majority are smelly, dirty and have generally unpleasant drivers who can't drive their way out of a paper bag).

For first timers, I'd still recommend staying in Cambridge. For the life of me, I cannot understand the fascination with people always wanting to stay somewhere near Faneuil Hall/Quincy Market or Newbury Street. Especially if your goal is to "experience local culture and mingle with the locals and not do the typical touristy things". But if that's just lip service and your goal is to take your photo with life-sized cutouts of Norm, Carla and Diane from Cheers (oh yeah, they are all there since I had some of my boyfriend's out of state relatives jonesing to go to there despite my protests) or buy a t-shirt that says "Wicked Smaaahht" on it, then that's the place to be. Newbury Street is not at all what it used to be - with sky high rents, there's nothing unique about the stores there.

Define "reasonable prices" - do you have a specific budget you don't want to stray outside of for a sit-down white tablecloth kind of restaurant? In particular, since you are from Italy, and I lived in Italy years ago, I cannot recommend you waste your time in the North End waiting in a big line for an over-hyped cannoli or on the prowl for "Italian" food. Yes, we have some good Italian American restaurants (Trattoria di Monica on Prince Street has a really good homemade pappardelle with bolognese sauce), but there's very few that are probably going to live up to what you've had in Italy.

If you want some reasonable food where you rub elbows with the locals, have brunch over at North Street Grille, or swing by The Friendly Toast (there's a smaller one in Back Bay, but I'm partial to the bigger Cambridge location). Or go to SoWa Open Market on Sunday and in between shopping and checking out some galleries in the area, you can grab lunch at the food truck bazaar and stop for a drink at the beer & wine garden.

For activities, aside from the big tourist draws (MFA, Isabella Stewart Gardener Museum, NE Aquarium, Science Museum) definitely visit the museums affiliated w/ Harvard. Other activities to target would be a visit to the ICA if you like modern art and get yourself some tickets to a Red Sox game so you can experience Fenway Park. The Mapparium is also pretty unique and off the usual tourist track.

Is it OK to wear shorts in Boston? City ordinance prohibits anything that resembles what you'd wear to mow your lawn (cargo shorts, ratty basketball shorts, Daisy Dukes if that's your scene), but if you have a pair of perfectly ironed bermuda shorts with embroidered sailboats, lobsters, or whales on them, or your shorts are made out of seersucker or madras and said shorts are worn with Sperry Topsiders, then yes, you can wear them out in public between the hours of 8:00AM and 5:00PM. After 5:00PM as we enter cocktail hour and move on to dinner, we'd ask that you put on your big boy pants and not show off hairy knees.

Is it OK to wear shorts in Boston?

On a certain day, it's OK to wear no pants.

https://improveverywhere.com/2018/12/12/save-the-date-no-pants-subway-ride-2019/

I am from the New England/Boston area! Hence I unfortunately don't know where one can stay. The historic sites are all fairly close to each other, though. One can walk from Boston Common to North Church easily. Things to do in that area would be Old North Church tours (fun and low key!) the freedom trail, the Constitution (if it's up and running), the make way for ducklings statues in the Common. MFA Boston is great. The New England Aquarium is also excellent and offers whale watching in the spring and summer. For eats, anywhere Italian in the north end is a safe bet. Chinatown is also just across the common from the historic sites and is pretty good for New England!

I love Boston to death (I may be biased, though). Have fun!

City ordinance prohibits anything that resembles what you'd wear to
mow your lawn (cargo shorts, ratty basketball shorts, Daisy Dukes if
that's your scene), but if you have a pair of perfectly ironed bermuda
shorts with embroidered sailboats, lobsters, or whales on them, or
your shorts are made out of seersucker or madras and said shorts are
worn with Sperry Topsiders, then yes, you can wear them out in public
between the hours of 8:00AM and 5:00PM. After 5:00PM as we enter
cocktail hour and move on to dinner, we'd ask that you put on your big
boy pants and not show off hairy knees.

I hope the OP sees your sense of humor.

For now I booked the Midtown hotel in Back Bay next to the Symphony Station (T green line) but also very near the Mass. Ave. Station (Orange Line). Pretty reasonable prices compared to other hotels I checked.
If that area is a bad choice let me know and I’ll search more.
Thanks for the info you gave so far.

Roberto,

The hotel looks good. The area is pleasurable and very nice.

During the day, there will be a lot of hustle bustle with businesses, business people, locals, and travelers.

In the evening, people will still be out and about; especially on the weekend and a long summer weekend at that.

The Prudential Center has a mall inside with shops and restaurants. Retailers generally close by 9:00 PM, but restaurants should be open until much later.

If you are inclined, maybe you and your wife would enjoy the Skywalk Observatory.

The Pru http://www.prudentialcenter.com/dine_category.html and Copley Plaza https://www.simon.com/mall/copley-place/dining have their own restaurants inside their respective mall.

There's also the "Top of the Hub" restaurant. http://topofthehub.net/gallery/ It has a stunning view of the skyline since it's on the 52nd floor. The meals and lounge (drinks) have increased considerably over the years! There is a dress code. In the lounge, they have live music.

Within the distance of your hotel, you will be near Copley Place/Square, Back Bay, Newbury Street. There are a lot of good restaurants; some better than others; different price points. That part of Boston has many brownstone homes and shops; many reflecting European design elements.

Here's a link to spark your interest: http://www.newbury-st.com/Boston/6/Food_and_Dining

Restaurants along Newbury Street have outdoor seating as you walk up and down the neighborhood. People lounge, people watch, enjoy the scenery.

Some eateries are better than others. Some are very small, you have to walk up (or down) cement stairs for some. (I used to know someone who had a small Italian restaurant on Newbury Street years ago. It was small but busy. A patron had to walk down a bunch of stairs.)

A place may strike your fancy as you walk by. I think most of them you can check their menu before you go and sit down.

Maybe look at this link with some suggested restaurants: https://www.google.com/search?q=newbury+street+restaurants&rlz=1C1AOHY_enUS743US743&oq=newburyst&aqs=chrome.3.69i57j0l5.6292j0j4&sourceid=chrome&ie=UTF-8

A heads up if you buy an expensive 'luxury item': In Massachusetts, all clothing and footwear items at $175 or less are exempt from sales tax. Items above $175 are taxable at the statewide Massachusetts rate of 6.25%. That's why a lot of Mass people drive over the border to the New Hampshire malls, lol, no taxes at all for expensive electronics and other personal items. There are also benefits to those who own a 'second home' in NH as well.

Hopefully, this added info will be helpful to your making plans for your September holiday weekend.

Oh, and of course, Boston has a ton of churches. St. Anthony's Shrine on Arch Street up from Downtown Crossing.

St, Stephen's on Hanover Street in the North End. It is no longer a parish church. It holds a special memory for me since my Grandparents were married in that church.

Arlington Street Church (between Arlington and Boylston Streets in the Back Bay)

If interested, here's a link to browse some historical churches, buildings and places. https://en.wikipedia.org/wiki/National_Register_of_Historic_Places_listings_in_northern_Boston

Did anyone suggest the JFK museum? Accessible by mass transit, a very striking bit of architecture.

Did anyone suggest the JFK museum? Accessible by mass transit, a very
striking bit of architecture.

I've been to a few presidential libraries and found the JFK library lacking in comparison with the breadth of others which is why I don't recommend it.

The Midtown Hotel is in a very convenient location. Fun fact: the hotel makes a cameo in the movie "Ted" :)

Another attraction I recommend that's close to where you're staying is the Mapparium, which is a 3-story stained glass globe that you can walk through. It's at the Mary Baker Eddy Library; she was the founder of Christian Science.

Did anyone suggest the JFK museum?

There is another JFK building often missed by the Boston visitors. Easily accessible by public transportation, and a short walk through a town with good eateries and stores.

https://www.nps.gov/jofi/index.htm

Roberto,
If you're looking for a walking food tour of the North End, I've been on a tour with this company. Can highly recommend. Have fun!
https://www.bostonfoodtours.com/

Roberto, your advice and guidance I have used many times on trips to Italy.
I hope you have a wicked good time on your trip to Boston.
I support the recommendations given especially a Duck Boat Tour, Red Sox game, Freedom Trail, Boston Harbor tour to the Islands.
Boston is a very walk able city and you can enjoy the Public Gardens and the Boston Common.
People have already mentioned that clam chowdah and lobsta are wonderful.

I am also from Boston and lots of great advice on here from locals already. One piece of advice I did not see- Boston is a college town! 150,000 kids plus parents/families flock to Boston at the same time you are planning to visit. Lots of very cool energy but also higher prices for flights, hotels, airbnbs, and longer waits at restaurants. Mid August would be more affordable (but hot) Later September or even early October is beautiful (skipping Columbus day weekend of Oct 14 - again college kids flying home or parents flying in)

No dress codes for attractions - other than if you go fine dining somewhere. Boston is a very walkable city - much smaller than one would expect. So if your goal is to see the city and not travel throughout the state, skip the car. You'll just be paying $45 a night to park it and walking. But to answer about ZTL - no we don't have those. We do have a lot of one way streets though. And if you want to go somewhere in the city but don't want to walk there - Uber comes quick and Boston has a great public transportation (MBTA or known as the T) It is also very safe (of course normal precautions as anywhere else but don't need money belts etc). And easy to use credit cards everywhere so don't need to convert much cash.

If possible, stay in Boston, not Cambridge or the outskirts. You can come and go on foot or T so save money as well as time that way. (Back Bay, North End, South End, Seaport District, Beacon Hill are best bets and either hotel or airbnb is good)

Again, lots of great suggestions already. The P-Town option or even just a boat ride out is good. Don't think anyone mentioned the Museum of Fine Arts (jump on the subway) or the Architectural Tour of the Boston Public Library (only one hour - free - limited times - right in Copley Plaza and a great take for the day you are in the Back Bay. If you like history - In addition to the mentioned Freedom Trail (get tickets for the tour at ticket office by Park Street T as they will add a lot of great info vs walking yourself) you might add in a trip to the John F Kennedy Library - that is a stop on the red line, and if interested in government also has Ted Kennedy living museum there for a day in the Senate. Although that history part is better for Americans coming to Boston - of course Europeans have a very different reference point when visiting historical places.

You can download an App from the National Parks for the Freedom Trail, very helpful.
The “Charlie Card”, MTA transit card, was mentioned earlier. Google it to find out how it got it’s name!
Legal Seafood restaurants are all over Boston, even at Logan, good places for fresh local seafood, lobster rolls, etc.. There is one on the water out in the Seaport District.
Take the Red Line to Harvard Square and walk through this historic campus.
Harvard has a wonderful art museum, not too large, if you have time or it rains.
Take a walk down Marlborough Street in the Back Bay to see the historic townhomes, houses. Visit the nearby Boston Public Garden.
Newberry Street for shopping, eating.

A Fenway Park tour is good, since the building is 100+ years old, def purchase in advance on line, they do sell out.

Also, if you go to the Constitution, there's a WWII DD, the Cassin Young, that's a good tour, too.
Parts of the Navy yard are open and other parts aren't - we found that some buildings we couldn't get to (specifically those you can see off Chelsea street) are VERY fascinating from the outside.

If you like some innocuous history, you can go to Langone Park off Commercial street, there's the Plaque commemorating the Great Molasses Flood of 1919, the slab for the tank is under the baseball diamond.

Boston is a very walkable city and you can find things to do in many areas. Since you are visiting during the summer, I’d think that the Seaport/Waterfront would be a great choice, as you can take advantage of the Rose Kennedy Greenway, The Boston Harborwalk, Boston’s Aquarium, The North End, Faneuil Hall & Quincy Market, Boston Harbor Ferries, Bunker Hill Monument, Restaurants in the Seaport, and The Lawn on D. You can choose from a variety of tours, walk The Freedom Trail, take a Duck Boat Ride, or enjoy one of the hop-on-hop-off trolleys, but walking around Boston is really very enjoyable.

The Theatre District is more central and nearer to places like The Boston Common & Public Garden, Swan Boats, Newbury Street and Beacon Hill (for shopping), and The Esplanade (walking paths along the Charles River). Each of these spots is also quite walkable from the Seaport District, perhaps 15-20 minutes on foot or a quick uber ride.

Back Bay and the South End puts you in a more downtown setting near Prudential Center, Symphony Hall, and places like that, but most likely an Uber ride from the Seaport area. Also, the museum scene is somewhat spread out, so wherever you choose to stay, you’d probably either take public transportation or an uber.

In short, depending on your specific interests, anything in the Back Bay, Boston Common Area or Beacon Hill would also work. But, in your case, I’d recommend the seaport/waterfront area - as there is just so much to see and do, and many free things to do, especially when you are visiting.