Itinerary & Restaurant help
We (myself, husband, & parents) are driving in from Portland ME on Sunday 11/3. We have an Airbnb booked in the Charlestown area. Plan to do the freedom trail walking tour that first afternoon. Would like a dinner and if there is an evening activity recommendation.
For day 2 in Boston, what else should we see & do? We don’t want to just exclusively focus on history. Considered a tour of Fenway or TD since we enjoy sports. Are there other tours to recommend?
Arriving in Charlestown on Sunday, November 3, is a great starting point. The Freedom Trail is a must-do on your first afternoon. Since you’re staying nearby, you can start at the Bunker Hill Monument and work your way through Charlestown and then head into downtown Boston for a few key sites along the trail. The walking distance is manageable, and the historic scenery is rich without being overwhelming.
Dinner on your first evening: Consider something close to Charlestown or downtown. For seafood and classic Boston fare:
- Legal Harborside – near the Seaport, great seafood and views of the harbor.
- Union Oyster House – historic spot downtown, casual and iconic.
- North End Italian – for a cozy Italian dinner; try Giacomo’s or Carmelina’s for authentic flavors.
Evening activity: Since it’s November, early evening sunsets mean you can enjoy:
- A stroll along the Harborwalk near the North End or Seaport area.
- Catch a performance at the Boston Opera House or Wang Theatre if shows are running.
- Visit the Skywalk Observatory at Prudential Center for panoramic city views.
Day 2 in Boston: Since you want to mix history with other activities, here are suggestions for a full day:
- Sports tours: Fenway Park Tour – iconic for baseball fans, even if the season is over, the stadium tour is year-round. TD Garden tours are available, especially for Celtics or Bruins enthusiasts.
- Science & Nature: New England Aquarium – fun for all ages, plus you can see the harbor nearby.
- Art & Culture: Museum of Fine Arts or the Isabella Stewart Gardner Museum – both offer unique experiences beyond history.
- Shopping & Walking: Newbury Street – historic street with boutique shops, cafés, and galleries.
- Optional Tours: Boston Duck Tours (amphibious vehicle) – fun, lighthearted city overview combining history and humor.
Lunch ideas:
- Boston Public Market – local foods, casual, and easy to sample different things.
- Sam LaGrassa’s – famous for sandwiches downtown.
For dinner on Day 2, consider the North End for Italian again or head to Seaport for seafood and harbor views, depending on your group’s preference and walking distance from your activities. Overall, the mix of walking tours, sports, cultural museums, and relaxed dining gives a balanced experience without feeling like a full history marathon.
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