Please help untangle my itinerary

Question

Dear all,

I’m struggling with itinerary decisions…and could really use your help.

My family (two kids ages 11 and 13) are doing spring break to visit my family in NY next week. We have a multi city air and will rent a car one way and depart out of Providence.

We love road trips, quaint small towns, seafood, and history so this will be fun. I know April can be hit or miss weather wise which is why I’m leaning towards winging it w/ hotel reservations along the way depending on weather. We want to see Boston for a night or two but we will have a car and not dropping off till end of trip at airport. If we were leaving out of Logan, I would dump car since Boston is challenging w/ car which gives me pause if we should even bother w/ Boston. And then there’s a myriad of spots we don’t have time for with only 5 nights such as Gloucester etc.

I have always wanted to show my family the cape…so this part I don’t want to leave out but not sure the order since Boston marathon is happening Monday 4/21 and we need to avoid.

Here’s how it looks now :

Arrive JFK 4/17 nyc

4/18 nyc

4/19 nyc

Sun 4/20 pick up car

Visit family Glen Cove for a few hours AM

Visit friends in Fairfield county CT PM

Overnight Westport CT - Sunday 4/20

Monday 4/21 hit the road! (We have until Saturday afternoon)

Drive straight to Newport or Cape??

(want to see Chatham and Nantucket) day trip to Nantucket possible from Chatham or better to catch ferry in Hyannis first for Nantucket) all we want to do in Cape is drive 6A, eat and ride bikes…. Thinking of devoting 2 days/ 2 nights to Cape

Wed/Thurs Boston

Friday Newport (or 1 night Bos and 2 nights Newport?)

Saturday 5:30pm depart PVD (better to leave from Cape on Sat to PVD airport or best to leave from Newport??)

How would you break this up?

Thank you! 😊

Answer

It sounds like you're planning a wonderful road trip! Given your preferences for quaint towns, seafood, and history, and your concern about the weather and Boston Marathon, here's how I would break up your itinerary. I've included some thoughts about where to spend time, where to avoid traffic, and how to make the most of your 5-night trip. This should give you flexibility but also allow for a good balance of relaxation and exploration.

Friday, 4/17 – Arrive in NYC

It sounds like you’ve already planned time in New York, which is great! Since you're staying in NYC from 4/17 to 4/19, you’ll get a good mix of sightseeing, family time, and relaxation before the road trip begins.

Saturday, 4/20 – Pick up car and head to Westport, CT

After spending the morning with family in Glen Cove, I suggest driving to Fairfield County, CT, and then spending the night in Westport. It's a nice, small town with a coastal charm that’s perfect for a relaxed afternoon. You can grab dinner, walk around, and enjoy the coastal vibes before starting your road trip the next day.

Sunday, 4/21 – Road Trip! Head to Cape Cod

Since the Boston Marathon is on 4/21, I would recommend avoiding Boston on that day. You can head straight to Cape Cod, as it will be a great base for the next two days. I'd suggest staying in Chatham, which is a beautiful, historic town that has a lot of charm and access to the best parts of the Cape. From Chatham, you can easily drive along Route 6A, explore quaint villages, and enjoy great seafood.

Day Trip to Nantucket: Nantucket is definitely a must-see, and a day trip from Chatham is very doable! You can take the ferry from Harwich Port or the faster ferry from Hyannis, which would be about a 45-minute drive from Chatham. Nantucket has stunning beaches, great history, and plenty of quaint shops, so it’s worth the trip.
Exploring Cape Cod: In Chatham, you can enjoy the charming streets, and the lighthouse is a beautiful spot to visit. Make sure to spend some time biking and enjoying the scenic route along Route 6A, which runs through several lovely towns like Brewster and Dennis.

Tuesday, 4/23 – Boston (1 or 2 nights)

If you’re looking to explore Boston, I would recommend spending a night or two here, depending on how much time you want to dedicate to the city. If you only have one night, you could do a quick tour of the Freedom Trail, visit Boston Common, and enjoy a seafood dinner at a spot like Union Oyster House or Legal Sea Foods. However, keep in mind that Boston is challenging to navigate by car, so consider parking outside the city center and using public transport or walking.

If you only have one night: Stay at a hotel near the airport or slightly outside downtown (like in Cambridge), and take public transportation into the city for sightseeing.
If you want to spend two nights: You’ll have more time to explore the city, and you can stay near the Back Bay or Seaport Districts for easy access to restaurants and attractions.

Thursday, 4/25 – Newport, Rhode Island (1 night)

Newport is a lovely seaside town with tons of charm, great seafood, and stunning views of the ocean. After Boston, head to Newport for your final overnight stay. Newport offers a great mix of history, scenic drives, and beautiful coastal views. Make sure to visit the famous Cliff Walk and perhaps one of the mansions like The Breakers or Marble House, both of which are iconic and historic.

Saturday, 4/27 – Depart from Providence

From Newport, it’s a 45-minute drive to Providence (PVD). I recommend leaving from Newport for your departure, as it’s a more direct route to the airport compared to driving back from Boston. This will give you time to enjoy a leisurely breakfast or a morning stroll by the water before your flight.

Summary of Itinerary Breakdown:

4/17-4/19: NYC (family time and sightseeing)
4/20: Pick up car, visit family and friends, overnight in Westport, CT
4/21-4/23: Cape Cod (Chatham, Route 6A, Nantucket day trip)
4/23-4/24: Boston (1 or 2 nights, depending on how much time you want in the city)
4/25: Newport, RI (1 night)
4/27: Depart from Providence (PVD) airport

This itinerary gives you a good balance of driving, sightseeing, and relaxation, with plenty of time to enjoy each area. You’ll get to experience some beautiful small towns, history, seafood, and avoid the Boston Marathon chaos. Enjoy your trip, and safe travels!

Please help untangle my itinerary

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