Monday, October 18, 2021

Travel: 6 day itinerary for an action packed, family trip to Boston, Massachusetts.

 At the end of the Summer, my husband and I took the kiddies on a trip to Boston and the surrounding areas.  While still very conscious of the pandemic, we knew that this trip could scratch our travel itch with very little risk.  We'd travel by car and do almost all outdoor activities.

To say that we had a good time is a serious understatement.  Both of my children said on multiple occasions "This is the best day EVER!".  

When planning our family vacation to Boston, I made sure that there was plenty of action because we don't like down time, plenty of stuff for the kids, great eats and drinks for the hubby, and a sprinkle of education and history for me everyone.

top things to do in boston for a family vacation

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6 Day Itinerary for a family vacation to Boston, MA

Where should we stay?

We chose to stay at the Hilton Boston Downtown Faneuil Hall (link) hotel.  This hotel won out because of it's key location with most local sites in walking distance, reasonable prices, valet parking because city parking is the worst, and family friendly atmosphere.

top things to do in boston for a family vacation

Day One

2.  Dinner at the famous Giacomo's Ristorante (link) North End of Boston
Is this really the best Italian food in Boston?  I'll let you know what I think in a future post.

top things to do in boston for a family vacation

Day Two

Tip:  We chose the Duck Tour because of the kids.  The Boston Duck Tour is FUN, especially when the amphibious bus drives right into the Charles River.  If you're traveling with an older, more serious crowd, then I would recommend the Boston Old Town Trolley Tour (link).

2.  First half of the Freedom Trail (link). - We have kids and the Freedom Trail can be a little boring, so we chose to break it up into two days and walk it ourselves.  For those who are looking for a more serious experience, book a Freedom Trail tour (link).  You'll learn a lot and can experience it in one shot.

3.  Boston Tea Party Experience (link) - This really was an experience!  It is an actual reenactment and everyone is a part of it.  You get role playing cards and the option to speak.  You can throw fake boxes of tea into the harbor and are encouraged to speak like they did back in the day.  The coolest part of the experience for me was seeing an actual box from the Boston Tea Party and learning everywhere it went before it made it into this historic museum.

4.  Dinner at a local restaurant.

5.  Boston Lights:  A Lantern Experience (link)  This unique experience was unexpectedly both of my children's favorite activity on the trip.  It took almost two hours to walk through and really was spectacular.

top things to do in boston for a family vacation

Day Three

2.  Dinner at the Ye Old Union Oyster House (link)  - This is way more than a dinner and one of my favorite stops.  A full post to follow.

top things to do in boston for a family vacation

Day Four

1.  Drive out to Salem, MA.

3.  Witch Dungeon Museum (link)  You're going to see a lot of museums regarding the Salem Witch Trials.  We did two of them this time around and I've done several others in the past.  Of all of them, this was my favorite, especially with kids.  It was relatively short and is a live reenactment of a real trial.  Afterwards, you're brought into a replica dungeon with an engaging host walking you through what an imprisoned life was like.  In other words, it's the most kid friendly of all the museums.

4.  Stop by The Coven's Cottage (link).  This is the only shop that made it's way into my itinerary because it really was an experience in itself.  First off, it's absolutely beautiful inside but, unfortunately, no photography is allowed.  Second, the staff is knowledgeable and super-friendly.  Third, I bought way too many things but at reasonable prices.  My favorite purchases were stones specially picked out by me for each of us, dried herbs, and a plaque of The Green Man with all different colorful birds hanging from him.  It really is a MUST STOP in Salem.

4.  Dinner at a restaurant of choice along Pickering Wharf (link).

5.  Walk down the historic Derby Wharf and visit the Derby Wharf Light Station (link).

Day Five

3.  Boston Public Garden (link) - This magnificently beautiful, historic park dates back to 1837 and is very conveniently located near the start of the Freedom Trail.  In other words, if following my itinerary, walk it backwards.  It is also the home of the famous Swan Boat Rides and Duckling Statues.  You'll want to carve a significant amount of time for this park because it's that gorgeous and with that many things to see.

4.  Dinner near or just outside of Quincy Market (link).  Make sure to follow this up with some light shopping and watching street performances.

Note:  My daughter and son found a street performer that they adored.  They felt like stars as the two of them slow danced for several songs in the middle of the cobblestone road and surrounded by an audience.  It's been a few weeks and baby girl is STILL talking about this with sparkles in her eyes!

top things to do in boston for a family vacation

Day Six

1.  Breakfast at The Friendly Toast (link) aka the BEST breakfast spot in Boston!

3.  Tour the Mayflower II and participate in their interactive experiences.

4.  Spend lots of time at the Plimoth Patuxet Experience (link).  Here you'll feel like you stepped back into the 1600s.  You'll walk through recreated villages where you'll meet real life Native Americans and actors pretending to be pilgrims.  They're engaging, friendly, and really dedicated to making the experience as realistic as possible.  Shout out to the woman who entertained my son with "mowing the lawn" (ripping up the grass) for an hour!

If I had to do it all over again, I'd add another day in Boston and spend a night in Plymouth.  I was pleasantly surprised with how incredibly beautiful Plymouth was.  We didn't have time to eat here nor did we get to fully enjoy the parks surrounding Plymouth rock or shop in the quaint village.  A full day here would have been perfect to get it all done.  We also missed quite a few things in Boston that an extra day would have helped with.  It's all good, though, because now we just have to make sure we go back again!

Do you prefer a full itinerary or a relaxing one?


  1. When I was a witch in a previous life, I didn't like dungeons very much but that museum sounds like great fun, especially since I'm still a kid in this life. Dez will concur. But seriously, you sure had a great trip. I'm jealous. Yes, I am. You know how not to get bored, all right.


    1. LOL, if I dislike anything, it's being bored!! I'll scrub the floors with a toothbrush first.. haha Miss ya, Blue!

  2. Wait, what, you did not have a Boston tea party?
    I bet it is even more lovely visiting now in Autumn with all the leaves and trees changing colour.

    Blue sure is a kid, for many years I thought he was a teenage girl, actually, thus I often call him missy still.

    1. LOL @ Missy!! I'm sure he giggles like a teenage girl every time he sees it. :)

      It must be gorgeous in the Autumn. Wait until you see the pictures from Callicoon! It was literally raining Fall leaves over our heads. Absolutely gorgeous.

  3. I hope to visit Boston one day

    Going to Miami soon

    1. You should go! It's so pretty. Have fun in Miami.

  4. Well, I’d love to know more about Plymouth Rock, but your link took me to an insurance company! Lol! Is it inside a cage? It looks different than the picture I’ve seen in the past, but may have been quite a long time ago.

    I’d love to visit Boston, but my husband went once for work and thought the traffic sucked and he still brings up how bad the cab smelled that he was in! We do like a busy itinerary on vacation because we really don’t want to miss anything. We can relax at home!

    1. LOL, at least I had the name right. I just fixed it. It's not in a cage, it's in like a memorial? But the water comes up in high tide so there are grates to let the water come in and out of the area where plymouth rock is. It really was quite beautiful. I wish we spent more time there!

      The traffic didn't bother me b/c I'm used to that, but the roads are all over the place! New York is a grid so the crazy directions drove us nuts.

  5. We had a great time in Boston, but I'd really like to go back with just Jason. We only had 2 days planned there, and the second day I was really sick and ended up sleeping in the hotel all day while the family explored. I did get to do the Freedom Trail and walk the city for a bit. We did manage to spend a little time in Salem too, but sadly didn't hit up any witch museums because the kids (mainly my niece) were cranky from a 10 day trip that was coming to an end and I didn't want to waste admission money on an experience they wouldn't have appreciated at the time. It sounds like you all had a lovely getaway!

    1. There is so much to do there that even 6 days wasn’t enough! What I was afraid of was there not being enough for things to do to entertain the kiddies, but they loved everything. The only thing they didn’t get super excited about was the ghost tour. It was lame as far as ghost tours go.

    2. That's too bad about the ghost tour. I've never done one myself (thought about it in NOLA but really didn't want to be out after dark with the teens) but I always thought I'd probably find them a little lame. IDK maybe I'll try one on our next Boston or NOLA vacation just to say I did one once in my life.


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