Whether you're travelling to Boston for the first time or looking for new ways to discover Boston, you'll revert to Google. I guarantee these things will pop up: Union Oyster House, The Freedom Trail, Faneuil Hall, Cheers, Duck Tours. There are so many things to see and do besides the typical tourist traps. Some may be worth a visit or a look for you but here are my thoughts and suggestions.
Instead of Union Oyster House, try...
...Row 34. Just a short walk into the Seaport neighborhood of Boston, you'll find some of the freshest oysters and one of the tastiest raw bars around.
...Island Creek Oyster Bar. Right in Kenmore Square near Fenway Park, you'll find an upscale, ridiculously fresh oyster bar. Also don't miss their lobster roe noodles and fried oyster sliders.
...Neptune Oyster. Right in the heart of the North End in close proximity to Union Square Oyster House. If you can squeeze your way into this tiny non-reservation spot, do so. If not, it's worth the wait. Also, can't miss their lobster rolls.
...Select. New to Back Bay, this is a tiny yet fabulous addition and most definitely worth a visit.
Instead of Cheers, try...
Cheers is only good for the "history". The beer list is lame and the food is frozen. If you must go, make sure it's the one in Beacon Hill. (Why the one in Faneuil Hall exists, I'm really not sure.) I suggest just browsing then heading somewhere else to eat/drink. Below are two of my favorite local joints with a solid beer list and great pub food.
...Publick House. It is in Brookline, so a bit of a hike from downtown Boston, but directly accessible from the D line Washington Square stop.
...jmCurley. Downtown Crossing. Awesome hand-selected beers and crafted cocktails + amazing burgers and pub food.
Instead of a Duck Tour, try...
...kayaking the Charles River. You'll get the same views of the city and Cambridge, but with some exercise and the freedom to take it all in at your own pace! Renting a kayak could not be easier via Charles River Canoe & Kayak. Upon arrival, you take a quick written safety test, go over the important info and the crew is prepared to set you off! It is also a bit cheaper than a Duck Tour, which usually clock in around $35 pp.
PRICE: $20 double kayak / $15 single kayak first hour, pro-rated after. $1 for drybag.
DIRECTIONS: Charles River Canoe and Kayak has four rental locations in Boston, Cambridge & Newton. If you are traveling and don't have a car, the Cambridge location is less than a 5 minute walk from the Kendall/MIT Red Line stop on the MBTA.
Going from this location, you'll come out by the Museum of Science. Duck Boat launch close by. Paddle around the corner to head towards Back Bay and Copley for views of the Hancock and the Prudential Center. Enter the channels to kayak through the Esplanade for an absolutely peaceful and picturesque glide. From other locations, you are further from the downtown of Boston, so you'll have to paddle a distance to see the skyline. They do offer one-way rentals though, which is a cool option if you are coming from another area.
Instead of Faneuil Hall, try...
I say take a stroll for the visual on your way to other attractions or at dusk. It is a beautiful walk through the cobblestone, pedestrian only pathways, especially at night when the trees are lit up. That being said, Faneuil Hall tends to be very chain-oriented. If you're looking for a mediocre experience, welcome! Good spot if you need anything Boston or lobster branded, such as Ts, hats and shot glasses. If you're in the area and want a real dining experience, I recommend taking the short stroll to The North End or Seaport District. If you're looking for some unique shopping, try Harvard Square in Cambridge, Newbury Street in Back Bay or peruse the South End neighborhood. There you will find many local gems and much less of the chain-y places that you can find just about anywhere.
Instead of the Freedom Trail, try...
...the Harborwalk. No large groups of tourists in your way and it's along the water. If you do happen to do the Freedom Trail, use the trail as a guide and don't be afraid to venture off a bit! Boston is extremely walkable, so even if you get lost, you'll probably find something more unique. Which leads me to my next advice: take side streets when possible! There is always fun little nooks, cafes, bookstores and the likes to be explored. Bring your camera! Lastly, go early in the morning to avoid the major masses of peoplE.
PS: On the Harborwalk, drop into Sullivan's. Nothing fancy - it's a small shack, serving up some yummy, basic eats for cheap. Fried clams, soft serve cones, burgers, they've got it all. A great and fun way to take a break and enjoy Castle Island.
Instead of Mike's Pastry, try...
Ok, Mike's is STILL GOOD, but there are SO many other pastry shops to explore. Give Maria's in the North End a try.