5 day itinerary for family with teens!

Question

Hi All

Thanks so much for all the information on these forums. Invaluable information. I’m trying to plan our trip and I kind of know things we want to do but struggling to put into itinerary/ locations etc

Don’t want to be hopping all over the place!

So we are staying in Seaport area (Hampton inn)

Want to do: freedom trail, Harvard, Fenway tour, going to Celtics on NYE, shopping, etc.

happy enough to chill close to hotel in the evening

Teens are 17/15/13.

Would love evening restaurant recommendations along the way.

Like walking but don’t mind Uber/ public transport

We arrive Friday evening 27th dec

Day 1: arrive late. Just explore seaport Christmas markets etc. local restaurant maybe? Legal?

Day 2: first full day. Freedom trail….assume we try spend the day going along full route. Eat along the way? Maybe north end of close. We love Italian

Day 3: 29th December. Harvard. Fit more in this day?

Day 4: 30th dec: Assembly row for shopping? Again maybe leave this until evening and do some in the morning

Day 5: 31st dec. morning activity… maybe beacon hill. Game at 3pm

Day 5. Have 6-7 hours here. Any suggestions. Leave sbout4pm for airport

Thanks in advance

Answer

Here’s a suggested 5-day itinerary for your Boston trip with teens, balancing sightseeing, walking, and some downtime near your Seaport hotel.

Day 1 – Friday, Dec 27: Arrival Evening

Arrive late, settle into the Hampton Inn in Seaport. Explore the Seaport Christmas markets if still open and take in the holiday lights. For a casual dinner nearby, you could consider:

Legal Sea Foods – classic Boston seafood, family-friendly
Yankee Lobster – casual, quick seafood
Indoor Seaport restaurants with views – check for open patios or festive decor

Relax early to recover from travel.

Day 2 – Saturday, Dec 28: Freedom Trail

Spend the day walking the Freedom Trail from Boston Common to Charlestown. For convenience with teens, consider breaking the walk into segments or using the T for longer stretches.

Lunch options along the route: Quincy Market/Faneuil Hall for casual eats, or try an Italian spot in the North End
Dinner in the North End: Giacomo’s or Pizzeria Regina – casual Italian, great for families

Evening: Return to Seaport and enjoy a relaxed stroll along the waterfront if energy allows.

Day 3 – Sunday, Dec 29: Harvard & Cambridge

Take the T to Harvard Square. Explore Harvard Yard, Harvard Museum of Natural History, and the surrounding shops and cafes.

Lunch: Felipe’s Taqueria or Clover for casual options in Harvard Square
Afternoon: Optionally visit MIT nearby, or walk along the Charles River for views
Dinner: Return to Boston proper and try something near Back Bay – e.g., Stephanie’s on Newbury for classic American fare

Day 4 – Monday, Dec 30: Morning/Evening Shopping

Morning: Explore nearby attractions or take a short museum visit – the Boston Tea Party Ships & Museum is fun and interactive for teens.

Afternoon/Evening: Assembly Row for shopping. Lots of brand stores, food court options, and occasional evening entertainment.

Dinner near Assembly Row: Legal Harborside (upscale seafood with a view) or casual chain restaurants in the area

Day 5 – Tuesday, Dec 31: Morning & Game

Morning: Walk through Beacon Hill – admire the architecture, historic streets, and grab a coffee or snack at a local bakery. Optional stop at Boston Common for last-minute photos.

Early afternoon: Head to TD Garden for the Celtics game (3 PM tip-off). Allow plenty of time for public transport or Uber from Seaport.

After the game: Limited time before heading to the airport (~4 PM). If your schedule allows, a quick snack or coffee near Seaport before departure.

Additional Tips:

Consider using the T for Freedom Trail segments and Harvard day – teens usually enjoy the experience and it reduces walking fatigue.
For restaurants in the evening, reservations are highly recommended, especially around holidays.
Keep casual snacks and water handy – walking all day in winter can be tiring.

This itinerary clusters activities geographically each day, balances walking and sightseeing, and keeps evenings more relaxed, ideal for teens and adults alike.

5 day itinerary for family with teens!

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