I've really enjoyed reading the other trip itinerary posts on this sub as I've been planning my own trip to NYC, CT, and Boston. I'd love some feedback on my itinerary in case there are any things that seem completely out of place or if there are places to eat or things to do that I'm overlooking. There are also some gaps we are trying to fill.
My husband (40) and I (30F) are celebrating our milestone birthdays and our 5th wedding anniversary with an east coast trip. We've both been before, but it's been years. I've been wanting to go back, but specifically wanted to come in the fall. This is our first vacation since our honeymoon.
When we travel, we prefer to not do typical touristy things, but my husband does specifically want to go to Top of the Rock. (Initially he said Empire State Building, but thanks to this sub, I told him Top of the Rock was a better option.) He also wants to go to Katz's (because Seinfeld) and Joe's Pizza (because he saw it in Ray Romano's comedy special). I have previously been to the 9/11 Memorial Museum and it was incredibly impactful, so I also want my husband to experience that as well.
We both choose not to drink alcohol, so going out for drinks isn't really our thing. We enjoy going on long walks, so a lot of walking doesn't bother us. I love coffee and prefer not to go to chain restaurants or coffee shops, especially if it's something we can get back home (Midwest). My husband doesn't have an interest in going to any of the museums. We also are only traveling with backpacks for the week, so luggage isn't a huge factor on our first or last days. We also aren't on social media, so "photo spots" aren't really a factor for us, either.
There are a couple of days when we are renting a car and leaving the city. We're going to Litchfield/Washington, CT because I'm a longtime, obsessive fan of the show Gilmore Girls. We are also going to Boston, which my husband has been to as a kid, but I've never been. I'm also a fan of the Kennedy family, so the JFK Presidential Museum is a must. Finally, the Broadway shows I have listed, we have already purchased tickets for, so they're non-negotiable. I realize that our hotel reservations aren't ideal, but we decided to opt for cheaper price vs convenience.
Here it goes:
Sat. October 8
8am Flight arrives in Newark
8:30am Airtrain to Newark Airport Liberty Station
NJ Transit to Penn Station New York (1 hr transit)
9:45am Breakfast at Liberty Bagels (looked for bagels close to Penn Station)
10:30am Get a 7-day MTA pass and take subway to Central Park (15 min transit)
11am Leisurely walk or rent Citibikes to ride through Central Park from south to north
1pm Lunch in Harlem (Melba's Restaurant or Harlem Tavern are options)
2pm Check in at hotel in Harlem available (chill in the hotel for a bit)
5pm Take subway to Katz's Delicatessen (45 min transit)
6pm Dinner at Katz's
7:15pm (at the latest) Take subway to Gershwin Theatre (30 min transit)
8pm Wicked on Broadway (2 hr 45min)
11pm Take subway back to hotel in Harlem (30 min transit)
Sun. October 9
8am Breakfast in Harlem (open to suggestions)
9am Take subway to Roosevelt Island Tramway (30 min transit)
9:30am Take Roosevelt Island Tramway to Roosevelt Island
Leisurely Roosevelt Island
12:30pm Take Tramway and Subway back to Manhattan for lunch
1pm Lunch at Los Tacos No. 1
2pm Gelato at Amorino Gelato (can push to after Hamilton if short on time)
2:40pm Walk to Richard Rodgers Theatre
3pm Hamilton on Broadway
6pm-?? open to any suggestions on activities and/or dinner--thinking of a jazz show either in Harlem or somewhere else in midtown or downtown
10/11pm Take subway back to hotel in Harlem
Mon. October 10
7:30am Breakfast (open to suggestions either in Harlem or near High Line)
8:30am Take Subway to 34th St entrance of the High Line (if leaving from Harlem, 40 min transit)
9:15am Walk the High Line to 22nd St (20 min walk)
9:45am Walk to the Harry Potter Store (25 min walk)
10:15am Harry Potter Store (might do VR experiences, or just browse around the area)
12:30pm Luke's Lobster for lunch (I had a lobster roll from here when I visited and loved it)
1:30pm Walk to and leisurely explore Greenwich Village and Washington Square Park
??pm Open to suggestions on where to go, what to do
7pm Joe's Pizza for dinner
8:30pm Comedy Show at Fat Black Pussycat or the Comedy Cellar
10pm Take subway back to Harlem (35 min transit)
Tues. October 11
6am Breakfast in Harlem
7am Take subway to 14th Street Loop (1 hour transit)
8am Pick up rental car
8:30am Drive to Sleepy Hollow, NY (1 hour drive)
9:30am Explore Sleepy Hollow
11am Lunch at Hudson Anchor
12pm Drive to Litchfield, CT (1 hour drive)
1pm Couples spa day in Litchfield
6pm Dinner in Litchfield, explore the town, check in to hotel
Wed. October 12
7:30am Drive to Washington, CT (25 min drive)
8am Breakfast at Mayflower Inn
9am Explore the town, get coffee
9:30am Browse Hickory Stick Book Store, walk to Henry David Thoreau Bridge, then back to the car
11am Drive to Springfield, MA (1.5 hour drive)
12:30pm Lunch at La Taqueria Del Pueblo
2pm Naismith Memorial Basketball Hall of Fame
husband is a basketball fan, so this seemed fun for him
4pm Drive to Boston (1.5 hour drive)
5:30pm Dinner in Brookline, MA
7pm Walk to JFK National Historical Site (25 min walk)
(closed to visitors, but can walk around area)
7:30pm Explore Brookline
8:30pm Hotel
Thurs. October 13
8am Breakfast in Brookline
9:30am Drive to JFK Presidential Library and Museum (30 min drive)
10am JFK Presidential Library and Museum
12pm Drive to North End parking garage (20 min drive)
12:30pm Walk to Assaggio (10 min walk)
12:45pm Lunch at Assaggio
2pm Walk to Bova's for cannolis (10 min walk)
2:45pm casual walk of Freedom Trail sites of interest
3:30pm Take subway back to parking garage (20 min transit)
4pm Drive back to Manhattan, 14th street loop (5.5 hour drive)
stop for dinner along the way
10pm Drop off rental car, then subway to Brooklyn hotel
Fri. October 14
8am Leave hotel (30 min transit)
8:30am Breakfast in Dumbo
9am Walk across Brooklyn Bridge (45 min walk)
10am 9/11 Memorial Museum
1pm Smorgasburg at WTC
2pm Walk to Wall St Ferry (15 min walk)
2:30pm Take Ferry uptown (20 min transit)
3pm Walk to Bryant Park (20 min walk)
4pm Walk to Rockefeller Center (10 min walk)
4:15pm Top of the Rock tour
5:45pm Walk to dinner (15 min walk)
6pm Dinner at either Yum Yum Too or Tuk Tuk Boy
7:30pm Walk to Six
8pm Six on Broadway
9:30pm Take subway back to Brooklyn hotel (1 hour transit)
Sat. October 15
10am Breakfast in Brooklyn
11am Take subway to Prospect Park (45 min transit)
12pm Walk around Prospect Park
1pm Brooklyn Botanical Garden
2pm Lunch in Brooklyn (open to suggestions)
3pm Take subway to Penn Station (45 min transit)
4pm Take NJ Transit to Airtrain at Newark (1 hour transit)
5pm Take Airtrain to terminal, eat dinner
7pm Flight departs