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Trip List by TxAggieGirl

Best Long Weekend in Boston

25 Jun 2009  Recent trip to Boston
4.5 of 5 stars based on 14 votes

Boston for those who like to blow and go! Bring your walking shoes!

  • Explore locations featured in this Trip List: Boston
  • Category: Perfect weekend
  • 1. Hilton Boston Financial District
    Hilton Boston Downtown / Faneuil Hall, Boston, Massachusetts

    We had a king suite on the 9th floor -- it was a corner room so we could look out and see the water just 1/4 mile away or so. Not a lot of it, but our friends that stayed in a waterfront hotel said they could see less water from their hotel than we could!

    There were huge windows in the rooms with nice heavy curtains so we had the choice to let in a lot of light or none. The room was really nice and comfortable, and it was nice to be able to spread out in the bedroom and living area. The bathroom was smallish and we would have liked a small refrigerator for bottled water and such, but you can't have it all, right?

    They let us check-in early when we arrived at 1 pm, which was nice, and the concierge was great for giving directions and recommendations on the quickest way to get places. It was also nice to have an ATM in the lobby.

    This hotel is located in the Financial District, so it was very quiet on Friday and Sunday nights. Saturday picked up noticeably, but don't even think about finding anywhere for breakfast nearby on weekend mornings. The only main drawback. Is within walking distance to Boston Common, Freedom Trail, Faneuil Hall, the waterfront, etc. Great location!

    Nice comfortable hotel and I would definitely stay here again.

  • 2. Freedom Trail
    Freedom Trail, Boston, Massachusetts

    No visit to Boston (especially your first) would be complete without a trek on the Freedom Trail. They say it's 2.5 miles, but with stops for lunch, visits at the sites and a few detours, it took us all day. Many of the sites on the trail close to visitors at 5 pm, so it's wise to either start very early or break it up into two shorter days.

    You start at Boston Common, where there is a Visitor Center and you can buy all sorts of maps and trinkets. We just used the free map from our hotel. I'm sure the others would have given lots of helpful information, but we were determined to do this thing on the cheap.

    Along the way, you pass new and old government buildings, churches, meeting houses, burying grounds, Paul Revere's home, a war memorial and a ship. There's lots of variety, so everybody should find something (or many somethings) interesting along the way.

    There are also guided tours you can take, but we opted to go on our own at our own pace. Families might find these more fun with guides dressed in period costumes.

    Once you make your way through the North End and over the Charles River into Charlestown to see the Bunker Hill Monument and the U.S.S. Constitution, you probably won't feel like walking allllllllll the way back to your hotel. Save yourself the trouble and take the ferry (check ahead to see when the last one leaves -- it's around 6 pm or so, I think, and we almost missed it....eeek!) back to the waterfront. You can take some nice pictures of the city skyline from the water and they drop you right by the Aquarium. We hoofed it back to our hotel in the Financial District from there, but it would be an easy place to pick up a cab for the rest of the way if you wanted as well.

    However you do it, prepare yourself for a long but very interesting day, and be sure to bring good, comfortable walking shoes and a camera!

    ***A Word About the "T"*** : When we first started using the T on Friday, it was confusing, but as the weekend went on, we got used to the multiple entrances, options and stations. Just ask the folks working there if you have a question. For some reason, the fares are cheaper if you get a Charlie Card, a plastic card you load your fares on to, instead of just the regular paper one. Anyway, you have to get the card from the station attendant -- the machines don't dispense them (but of course nowhere does it say that). There aren't any stops in the Financial District, but we'd usually walk to the nearest station and go from there. It's just so much cheaper than taking a cab. Just grab a map of all the T stops and get going!

  • 3. Fenway Park
    Fenway Park, Boston, Massachusetts

    If you're in Boston during baseball season, you MUST MUST MUST get tickets to a Red Sox game. It's easy to get to the park from anywhere in Boston -- as our concierge told us, "just take the T and follow all the t-shirts to Fenway."

    The place reeks of history and it's neat to be there with all the folks that love their team. Great atmosphere and lots of good food and good beer. Plus, what other stadium gets the whole place to not only sing the national anthem and "Take Me Out to the Ballgame", but also "God Bless America", Neil Diamond's "Sweet Caroline" and Dropkick Murphy's "I'm Shipping Up to Boston"?

    It's an experience I'll never forget...and hope to repeat! And really....is there any better way to spend a Sunday afternoon?!?

  • 4. Boston Duck Tours
    Boston Duck Tours, Boston, Massachusetts

    So yes, it's very touristy, but it was actually a great way to start our trip. We took the tour from the Science Museum (easily reached by the T) after arriving in Boston on Friday afternoon. The great thing about it was that we got a quick overview of many of the sites around town so we could decide what we wanted to go back and see later in the weekend. Our driver also gave lots of history and fun, interesting tidbits about people, places and neighborhoods.

    Plus, who doesn't like to just drive right into a body of water? After driving around the city for about an hour, we spent 20-30 minutes tooling around the Charles River, checking out buildings and Cambridge on the other side.

    Definitely worth the money -- with taxes and such it came to $35 per person. Be sure to book your tickets online ahead of time, as they sell out in advance.

  • 5. New England Holocaust Memorial
    New England Holocaust Memorial, Boston, Massachusetts

    This is a small park just off the Freedom Trail, right across the street from the famous Union Oyster House and Bell in Hand Tavern. At first glance, the glass towers seem inconspicuous, but this Holocaust Memorial is very, very moving. Each tower is engraved with millions of I.D. numbers of those who were killed during the Holocaust, along with heartbreaking quotes from survivors. Please go see this place to pay your respects. You simply cannot walk away unmoved.

  • 6. Copley Square
    Copley Square, Boston, Massachusetts

    Copley Square is not on the Freedom Trail, but is not too far from Boston Common and is located in the Back Bay neighborhood. We saw it on the Duck Tour and returned on Monday morning before we flew home. The main three things to see are the Old South Church, Trinity Church and Boston Public Library.

    The two churches both are beautiful on the outside and inside -- if you like architecture in the least, these are worth a visit. To visit Old South Church is free -- Trinity is $6 per person for either a self-guided or guided tour. Both are gorgeous.
    We didn't have time to go inside Boston Public Library, but it is beautiful from the outside. According to our Duck Tour guide, it was the first truly free public library in the U.S. and holds millions and millions of titles.

    Copley Square has a nice green space between the library and Trinity Church with a park-like feel and fountains on one side. Would be a nice place to rest your feet or read a book.

  • 7. Boston Common
    Boston Common, Boston, Massachusetts

    You'll find that on a trip to Boston, there are many "U.S. firsts" in the city -- Boston Common was the first public park. A huge green space with lots of trees, Boston Common is not only the beginning of the Freedom Trail, but is an ideal way to spend a few hours just lounging and people watching.

  • 8. Faneuil Hall Marketplace
    Faneuil Hall Marketplace, Boston, Massachusetts

    A stop on the Freedom Trail, Faneuil Hall is one of the busiest, most touristy areas. When we were there, several celebrations and festivals were going on. There were street performers and stages set up outside with singers and dance groups, as well as a symphony playing on the 2nd floor in the main chamber. The first floor, which was historically a market, is still a place to check out, even if the vendors are mainly selling touristy items. There are tons of places to eat around here, and between Faneuil Hall and Quincy Market (just behind Faneuil), you'll have no problem picking up any souvenirs you might need for folks back home. The bar built to look like the Cheers set is also located here.

  • 9. Durgin Park
    Durgin Park, Boston, Massachusetts

    The nearly 200-year old Durgin Park is located in the Quincy Market building, just behind Faneuil Hall. We'd read about it somewhere and heard it had hearty, New England type food and decided to give it a try. It's touristy, but we had a nice lunch (shepherd's pie and corned beef sandwich) and it wasn't overly pricey. They are known for their grumpy waitstaff (part of the schtick, I suppose), but our waitress was friendly. Tables are available on a patio and upstairs in the dining room -- we ate upstairs as to avoid being stared at by the folks walking by just six inches away over the railing. Their dinner menu looks pricier, but by the looks of the meat case in the lobby, there would be some great cuts of steak to be had, as well as lamb, pork, chicken and seafood. Talk about a carnivore's paradise!

  • 10. Vintage Lounge
    Vintage Lounge, Boston, Massachusetts

    Vintage Lounge is a nice bar and tapas restaurant across the street from the Hilton Boston Financial District. The front bar area is nice and cozy with leather furniture and T.V.s behind the bar for watching the game. Drinks are pricey but well made. The food was fantastic -- we split steamed mussels, black truffle mac 'n cheese and a grilled goat cheese, bacon and tomato sandwich with potato salad, finished off with a creme brulee trio. Everything was delicious, except the coffee, which was made so strong we could hardly drink it. Other than that, things were great. Perfect choice in the Financial District (especially for Hilton guests) when you don't want to get room service but you don't want to go far either.

  • 11. Mr. Dooley's Boston Tavern
    Mr. Dooley's Boston Tavern, Boston, Massachusetts

    Next door to the Hilton, Mr. Dooley's is a great little Irish pub. There was live music (three-piece Irish groups) on both Friday and Saturday nights when we stopped in and they had several good beers on tap. Cover was $5. Great atmosphere and a fun place to spend a few hours.

  • 12. Beantown Pub
    Beantown Pub, Boston, Massachusetts

    Can't speak for this place at night, but we breakfasted here on Saturday. Great location, right across the street from the Granary Burying Grounds on the Freedom Trail. Prices were some of the best we saw all weekend, the food (three-egg omelet and eggs benedict) was pretty darn good, and it stuck with us all morning until our late lunch around 2 that afternoon.

  • 13. Union Oyster House
    Union Oyster House, Boston, Massachusetts

    Yes, it's a tourist trap, but it's the longest continually running restaurant in the U.S. It took a while to get seated, even at 2 pm, and then once we got seated it took a while for anybody to decide to wait on us. However, once we were noticed, everything was fine. The clam chowder was very good and our other dishes (crab, fish & lobster cake trio, crab cake sandwich and fried scallops) were good to very good. The booths and tables are made of dark wood and the ceilings are low, so the place has a unique atmosphere. We sat across from the booth with a plaque that said it was JFK's favorite booth when he ate there. The place is huge and is touristy, but if you're in Boston for a few days, squeeze it in.

  • 14. Times
    Times, Boston, Massachusetts

    Times is a great little bar with indoor and outdoor seating just down from the Hilton F.D. on Broad Street. Everybody was super friendly from the door guys to the bartenders to the waitresses. Good beers on tap and a nice place to catch a beer...or two.

  • 15. Black Rose
    Black Rose, Boston, Massachusetts

    We'd heard about the Black Rose from a co-worker in the local area. She said her husband made fun of her for wanting to go there the first time because it was touristy...but that he no longer cares because the food is so good. We got right in on a Saturday night and it seemed to just get busier as the night went on. The food was excellent (two different steak dishes and Shepherd's pie), wine was good and the desserts (black & white bread pudding and Boston Cream Pie) were to die for! One of the best meals we had all weekend. At some point an Irish band started playing, which just cranked up the atmosphere just that much more. We also quickly checked out the scene upstairs which had another live band and a younger crowd. Yes it's touristy (they sell t-shirts with their logo, for Pete's sake!), but who cares?!? Go for the food...and the music ain't at all bad either.

  • 16. Cask 'n Flagon
    Cask'n Flagon, Boston, Massachusetts

    Cask 'n Flagon is the huge bar located just outside Gate A of Fenway Park and has been rated the #2 baseball bar in America by ESPN. The place is so big, we were able to get a table after the game, but there were plenty of folks just standing around the bar as well. CnF is a great place to catch a drink and some food before braving the crowds heading back on the T.

  • 17. Giacomo's Restaurant
    Giacomo's Restaurant, Boston, Massachusetts

    Giacomo's came highly recommended by a friend and we were not disappointed. Located in the North End (Boston's Italian neighborhood), Giacomo's is tiny and probably has only 15 tables so if there's a wait, you'll be doing it out on the sidewalk. If a table for four opens up and there's only two of you, plan to keep waiting....they'll seat you when a two-top opens.

    Now for the food....mmmm.... The menus are on chalkboards on the walls, but they bring paper copies too. Everything is homemade and many of the dishes feature seafood. There are also daily specials that change. From our appetizers (fried calamari and caprese salad) to our entrees (two classics and two specials), everything was simply AMAZING.

    Literally this was one of the best meals of my life. And, it was soooo affordable! Every bottle of wine on the menu is just $16, which is a steal. We got out of there for four people for $120 -- what a great deal!

    The kitchen is right there where you can watch them preparing stuff as it is ordered. A waitress called for a caprese salad and one of the cooks started slicing the tomatoes and mozzarella right then. It's that fresh.

    You must try this place...but please don't be there when I am....I'm hoping for a short line. :)

  • 18. Bell In Hand Tavern
    Bell In Hand Tavern, Boston, Massachusetts

    Bell in Hand is right across from the Union Oyster House and is known as the longest continually running bar in the U.S. What did I tell you about all the "oldest ____ in the U.S." in this city?!?!

    Bell in Hand is shaped like a triangle and there are tables all along the top point with big open windows, so you can sit, have a drink and watch the people go by. The staff was super friendly and drinks were good.

    The only drawback is the foul smell that blows in from time to time that is left over from the Farmer's Market, which is held on Saturday just around the corner.

    Great folks, great place.

  • 19. Bean & Leaf Co
    Bean & Leaf Co, Boston, Massachusetts

    Bean & Leaf is just down the street from the Hilton Boston F.D. It's closed on the weekends (boo!), but we stopped in here on Monday morning before we headed out sightseeing again. They have baked goods, breakfast sandwiches and burritos. We tried two variations of the burritos and they were very yummy and filling -- more than we could eat. Their lunch menu looked delicous as well, with all kinds of salads and sandwiches, including hummus and falafel. Great little corner location.

  • 20. Farmer's Market

    The Farmer's Market is just around the corner from the Bell in Hand and Union Oyster House on Saturdays. There are tons of booths with fresh seafood, gorgeous veggies and colorful fruit. It gets super crowded, but the prices are great and it's fun to just look, even if you don't have a kitchen to take stuff home to.