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Boston Itinerary Oct 24-28

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Boston Itinerary Oct 24-28

Hi! My husband and I are going to Boston for 4.5 days next week for our anniversary. I've gotten the majority of our itinerary complete, but need some help with the finishing touches. Any help is appreciated for MUST-SEEs that I may have left out, and there are a few meals that I can't decide on where to eat. Help please! :)

Day One (Thursday Oct 24)

• US Airways 1980 departs Charlotte @ 7:55 AM & arrives @ 10:07 AM @ Terminal B

1. Buy a 7 day Link Pass @ the airport subway terminal or South Station

2. Take the Silver Line T to South Station & transfer to Red Line to Park Street

• Nine Zero Hotel – 90 Tremont Street Boston, MA 02108 (3 PM check in – drop luggage off)

• Sam LaGrassa’s for lunch – 44 Province St (right around the corner)

• Take the Green Line from Park Street to Science Park/West End

• Boston Duck Tour 3:00 PM - $34 each Museum of Science departure – 8 Charles River Ave (80 minutes long , leaves every hour – 4 PM last one)

• Take the Green Line from Science Park/West End to Arlington Street Station

• Walk to Shreve, Crump, & Low Jewelry Store – 39 Newbury Street

• Walk more of Newbury Street quickly(window shop in high end boutiques)

• Walk to Beacon Hill – Arlington St to Beacon St, left on Brimmer St, right on Mt. Vernon St, Louisburg Square is on left (John Kerry lives in Louisburg Square) Take Willow Street to Acorn street on right (most photographed street in America) Take left on W. Cedar St, right on Chesnut St, left on River St, right on Beacon St (Cheer’s on the right)

• Go to Cheer’s Bar for dinner in Beacon Hill – 84 Beacon Street

Day Two (Friday Oct 25)

• Take the Green Line from Park St to North Station and board 8:59 AM Train 1101 to Salem (Newbury/Rockport Line) $13.50 Round Trip each

• Take Bridge St to Washington St, Turn left on Church St, Turn right on Derby Square, Turn left on Essex St, Turn right on Central St

• Have brunch at Red’s Sandwich Shop – 15 Central Street

• Salem Open Market (Derby Square 11-6 & Essex Street 11-10)

• Haunted Happenings Carnival 2-10PM @ Derby Street

• House of Seven Gables ($12.50 each)– 115 Derby St – Open 10-7

• The Witch House / Corwin House ($8 each) – 310 ½ Essex Street

• Original Michael Myers @ 57 Wharf Street from 12-8 PM

• O’Neill’s Pub & Restaurant for dinner – 120 Washington St

• Captain Dusty’s Ice Cream- 143 Derby Street

• Spellbound Tour 8:00 PM (45 minutes) $13 each – Departs @ The Magic Parlor 213 Essex Street (buy online)

• Returning Trains from Salem : 9:32 PM (Train 1172), 10:38 PM (Train 1128)

• Take Green Line from North Station to Park St.

Day Three (Saturday Oct 26)

• Breakfast @ Thinking Cup – 165 Tremont Street

Freedom Trail (2.5 miles 2-3 hours)

o Boston Common – 147 Tremont Street

o State House – 24 Beacon Street

o Park Street Church – 1 Park Street

o Granary Burying Ground – 97 Tremont Street

o King’s Chapel – 58 Tremont Street

o King’s Chapel Burial Ground – 40 Tremont Street

o Benjamin Franklin Statue – 45 School Street

o Old Corner Book Store – 3 School Street

o Old South Meeting House $5 each (don’t have to go in) - 310 Washington Street

o Old State House $7 each (don’t have to go in) – 206 Washington Street

o Site of Boston Massacre – Devonshire & State St

o Faneuil Hall (Quincy Market)– Congress & North St

• Stop for lunch @ Pizzeria Regina – 2 Thacher St

o Paul Revere’s House – 19 North Square

• Mike’s Pastry (cannolis) - 300 Hanover Street

o Old North Church – 193 Salem Street

o Copp’s Hill Burying Ground – 21 Hull Street

o Bunker Hill Monument – 45 Monument Square

o USS Constitution – Charlestown Navy Yard (tour $5 each) Open T-S 10-4

• Walk back across the water and take the Green line from North Station to Park St back to hotel. Change for dinner.

• Dinner @ ____________________

Day Four (Sunday Oct 27)

• Breakfast @ _______________

• Take the Red line from Park St to Harvard Square

• Harvard Yard (right outside of subway station)

• Walk ½ mile up Brattle Street to Longfellow House (where George Washington lived during Revolutionary War)

• Walk back up Brattle St towards JFK St to Charles River, stop @ Curious George Store – 1 John F. Kennedy St (immediately next to Subway station)

• Eat lunch @ Mr. Bartley’s Burgers – 1246 Massachusetts Ave (straight up Massachusetts Ave from Harvard Square subway station)

• Take the Red line back to Park St.

• Go back to Hotel and get changed for dinner.

• Take the Green line from Park St to Fenway Station

• Walk past Fenway Park & down Boylston St to dinner.

• Anniversary Dinner @ Atlantic Fish Company – 761 Boylston St (MAKE RESERVATIONS)

• Take the Green line from Copley Square to Park St.

Day Five (Monday Oct 28)

• Breakfast @ __________

• Explore the Waterfront

• Boston Tea Party Museum $25 each 306 Congress St (75 minutes long – starts every 30 mins)

• Lunch @ _____________

• Go back to hotel & get luggage.

• Take the Red line from Park St to South Station & transfer to the Silver line to Terminal B @ Logan Airport.

• US Airways 1799 departs Boston @ 2:35 PM & arrives @ 4:56 PM.

Dallas, Texas
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1. Re: Boston Itinerary Oct 24-28

Wow!! That's A LOT of activities for 4.5 days.

I was there for 3 days this past weekend, and didn't even do half of that. You will see lots of autumn foliage at the Boston Common...will you be stopping by the Public Garden too?? I actually liked Public Garden more because its so pretty. Keep in mind that if the government is still shut down, that you wont be able to go to places such as USS Constitution, Bunker Hill Monument, Boston Tea Party, and Faneuil Hall.

I ate dinner at Atlantic Fish Company...service was great...food was good, We ordered the surf & turf meal...half lobster half steak...I love their clam chowder. We requested to sit out in the balcony...as the view of Boston at night was beautiful. I loved the experience.

I enjoyed walking around Back Bay as well as Beacon Hill.

Hope you enjoy your anniversary trip!! If this is your first time, you will fall in love with it as I have.

Dallas, Texas
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2. Re: Boston Itinerary Oct 24-28

Also, try Neptune Oyster(call for reservations) in North End and James Hook & Co by the waterfront.

We also ate at Mare at the North End.

Boston, MA
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3. Re: Boston Itinerary Oct 24-28

Sounds like a decent plan. My only concern is on your first day-- it gets dark early ( sunset is about 5:45 when you are here ) and Louisburg square and such is best viewed in daylight if possible. Maybe walk first and take the 4pm duck tour?

The Freedom Trail may take a bit longer than you think, but that's ok.

On your Harvard day .... in the morning ... walk through the Common to Charles street ... head down Charles and check out the Paramount diner or Cafe Vanille for breakfast. Then, continue down Charles and pick up the red line to Harvard Square at the. CHarles/MGH stop

Happy Planning!

Edited: 17 October 2013, 03:44
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4. Re: Boston Itinerary Oct 24-28

Good thinking on the sunset time. We live in South Carolina and it's closer to 7:30 right now for sunset so I didn't realize there would be such a difference. Thanks for the restaurant suggestions! I'll look those up.

North Shore, MA
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5. Re: Boston Itinerary Oct 24-28

Just a few thoughts on your Salem day: Buy your train tickets at North Station before boarding to avoid a surcharge for buying them on the train. Your return ticket will not specify a time, so you can be flexible (but good that you've noted the times for a couple of trains back to Boston as they are not so frequent). Construction of a parking garage is underway at the Salem train station so don't be alarmed by the mess when you arrive. Signs will direct you to the stairs up to Washington Street.

Not sure if you're planning to do things in the order you listed, but you will pass Captain Dusty's on your to and from the House of the Seven Gables and may not want to go back after dinner. You might go to Ye Olde Pepper Candy Companie across the street from 7 Gables for a treat that won't melt and can be saved for later. Is the Spellbound tour just 45 minutes long? Finally, be prepared for crowds, especially in the evening!

Happy Anniversary!

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6. Re: Boston Itinerary Oct 24-28

That's an amazingly packed itinerary. Are you planning all that, in exactly the same order?

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7. Re: Boston Itinerary Oct 24-28


I'd like to commend you on your planning! I'm a planner myself. People often say to me, don't be a slave to your plan or I would rather be more spontaneous. I just laugh, what they don't realize is that a great plan gives you options!!! If you are running late or early or don't feel like doing xyz or want to be spontaneous, then you know exactly where your are in your plan and what you can do.

Also, I can't believe how many threads we all see that start out "we're in Boston for 4.5 days, what should we do?" I'd sometime like to answer, "just what you've got planned - nothing". Thanks for the opportunity to get that off my chest - LOL.

SO, just a couple things....

re: Cheers bar, what you'll see on Beacon St is the façade that you see on the TV show. Inside is not a replication. THat's not to say go or not go, I don't know anything about the food or experience. Just setting expectations. There is also a Cheers Bar in Quincy Market (along the Freedom Trail), never been because it's always been packed, but I understand that's more of a replication of the interior.

re: Salem, you may consider a visit to the Peabody Essex Museum, it is IMHO, the real gem of any visit to Salem. It has exibits on the Orient, whaling and the maritime industries that build Salem. The best part is the East India Room because the walls are filled with ship figureheads. Unfortunately, just checked the website and that room is under renovation thru 11/1, so your mileage may vary.


The House of Seven Gables is good, some of the Witch type attractions are kitchy (sp?), IMO.

re: Back Bay and Public Gardens, make sure you walk at least a few blocks of Commonwealth Ave. East/West traffic is separated by a park which runs the distance. Lots of statues along the way and should be lots of color. Comm Ave starts at its east end at the Public Gardens, also all the way to the west end at Kenmore Square and Fenway, if you are in the mood for a walk. Public Gardens is very nice to just stop, relax and people watch, great foliage. Adjacent to the west of the Common and to the south of Cheers and Charles St, so you really can't miss it in your travel plans.

re: waterfront, is adjacent to the Freedom Trail at Quincy Market, so easy to combine some stops w/your waterfront morning, if time got short. Also, many will split their Freedom Trail walk in 1/2. 1/2 on day, 1/2 another. 1/2 way is appx Fanueil Hall/Quincy Market or the North End. So just a consideration in breaking thing up depending on time and weather.

Also worth saying, as I'm sure you know in your planning, Boston Common is the beginning of the trail, it's next to Beacon Hill and the Public Gardens, so a logical combination.

I know you are "planning" to have a great trip, LOL! Enjoy!


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8. Re: Boston Itinerary Oct 24-28

Quite the itinerary, I agree it is best to do beacon hill at a different time, it is a lot of walking plus you may be a bit tired from the morning flight. Also, on your day in Salem, I would highly recommend the Peabody Museum and you may want to visit the Corwin house first as it is more out of the way than the rest of sites (which are closer to the harbor). Straight down Washington, right on Essex... down a few blocks.. if my memory serves correctly. On the freedom trail, I recommend that people do it 'in reverse', in the morning start at the USS Constitution and go back the other way. It is much easier to visit the Constitution in the morning as it is the most likely to have a crowd and you have to talke the tour as it is wonderful. I would recommend going into the Old State House (the 'new' State House is also worth going into), the museum inside is very insteresting.

Another thing to keep in mind, Bartley's Burgers, Regina's may be crowded and they do not take names, you literally wait in line. (this is an issue if it is raining.) If Mike's Pastry is too crwded you can walk across the street to Modern Pastry.

Enjoy your visit...

Edited: 18 October 2013, 01:10
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9. Re: Boston Itinerary Oct 24-28

That is a lot packed into a few days, just be sure to go with the flow and don't be rigid about sticking to your schedule if things go slightly awry, as they always do. Secondly, don't eat dinner at Cheers. Have a drink or two there, but there are many really good places to eat so don't waste calories there!

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10. Re: Boston Itinerary Oct 24-28

Thanks for all of the help! Yes, I realize the itinerary is very packed. I'm a little OCD and very much a planner, but that's the only way I like to travel. I like to know what I'm going to do as soon as my feet touch the ground and waste no time wondering what to do first and how to get there. My sister and I did NYC in 3.5 days in May, and no one thought our itinerary was possible but you better believe we hit everything on the list! (Even in 3 days of rain) So hopefully, this trip goes just as smoothly (better weather hopefully). How cold is it currently in Boston? We've packed sweaters and light jackets. I see the temps in the 50s but I learned in NYC that 50-60 degrees is WAY cooler than a South Carolina 50-60 degrees due to wind chill between the buildings. Is it the same in Boston since it's on the water?