Multi-City Trip Logistics

Question

Hi.

Our family, 2 adults/2 kids are planning of summer vacation and I’d like some help. We are going to NYC and then would like to go to Cape Cod and then to Boston for a couple days (we’ve been before). We are try to figure out the best options to get to each place.

I see there are pretty affordable flights from New York to Hyannis. We obviously would need to rent a car once we get there and looks like we could get at the airport in Hyannis. Ideally we’d like to avoid driving back to Boston just to drop off the car.

We thought of returning to the airport and taking the ferry to Boston but it seems like a long distance from Hyannis to Provincetown and not sure how we we do that.

We are likely flying out of Logan but open to other airports too, Providence maybe.

We do not have exact dates but probably would be early July, also don’t know exactly where we are staying. Last time we stayed in Dennis, which we loved, but maybe a bit further up this time.

Thanks, everyone here has been so helpful.

Answer

It sounds like you're planning a great multi-city trip, and I'd be happy to help you sort out the logistics! Given that you want to avoid backtracking and make the most of your time in the region, here are some options for traveling between New York, Cape Cod, and Boston.

1. Travel from New York to Hyannis (Cape Cod): Since you’ve already found affordable flights from New York to Hyannis, this seems like a great option to skip the long drive up from NYC. Hyannis is a central hub on the Cape, and having a car rental there will give you the flexibility to explore the region. Renting a car at the airport in Hyannis is straightforward, and you’ll have easy access to all the Cape Cod attractions.

Hyannis Rental Car Option: Renting a car at Hyannis Airport is definitely the best option once you’re on the Cape, as it’s more convenient than using public transport. Hyannis is centrally located, so you’ll be able to access different parts of Cape Cod easily. Once you’re done with your time on the Cape, you can drop the car off in Hyannis rather than driving all the way to Boston.
Alternative - Providence Airport: If you are considering flying into Providence (about 1.5 hours from Cape Cod), this can sometimes offer cheaper flight options. However, you’ll need to rent a car from Providence and drive to the Cape, but the drive is scenic, and it’s a great way to start the trip. This could be a good option if flights into Hyannis are too pricey or inconvenient.

2. Getting From Cape Cod to Boston: It sounds like you want to avoid driving back to Boston just to drop off the car, and there are some good alternatives for getting from Cape Cod to Boston without the hassle of driving all the way back. While the ferry option from Hyannis to Provincetown is beautiful, it’s not quite ideal for your situation, since Provincetown is farther from Hyannis and doesn't connect directly to Boston. Here's what you can consider instead:

Drive to Hyannis or Barnstable, Then Take the Ferry to Boston: If you’d like to avoid driving all the way into Boston, you can take a ferry from Hyannis or Barnstable to Boston’s Long Wharf. This ferry ride is about 1.5 hours long and can be a pleasant, scenic option. You’d just need to plan the drive from Cape Cod to Hyannis, where you'll park and board the ferry. However, it’s worth noting that taking the ferry to Boston does not eliminate the need for driving at least part of the way.
Take a Bus or Train to Boston: Another option is to take a bus or train from Hyannis to Boston. The CapeFlyer train service runs seasonally from Hyannis to Boston’s South Station, and it’s a comfortable and efficient way to get to the city. The bus option (Peter Pan Bus) also runs regularly between Hyannis and Boston, taking about 2 hours and 15 minutes. Both options are good for avoiding driving into the city.
Drive Directly to Boston: If you find a rental car drop-off point in Boston that works well for you, driving directly from Cape Cod to Boston might still be your easiest option, especially if you don’t mind a 1.5-hour drive. There are several car rental agencies in Boston, including at Logan Airport and in downtown, making it simple to return your car before heading to your next adventure.

3. Where to Stay on Cape Cod: If you’re considering staying further up the Cape this time around, there are plenty of charming towns to choose from, each offering its own vibe. Some great options are:

Chatham: A quaint, picturesque town with beautiful beaches and a lovely downtown area. It’s great if you're looking for a classic Cape Cod experience.
Orleans: A bit more centrally located, offering easy access to the Outer Cape and a great base for exploring.
Wellfleet or Truro: If you prefer something quieter and off the beaten path, these towns provide peaceful beaches and easy access to nature. They’re further out on the Cape, but perfect if you want to escape the crowds.

4. Flying Out of Boston or Providence: Both Boston Logan International Airport and Providence T.F. Green Airport are great options for flying out, with Logan being the larger hub and offering more flight options. Providence is smaller and can sometimes offer cheaper flights, especially for regional travel. Both airports are easily accessible by car or public transit, so you can choose the one that best fits your schedule and pricing. Boston is about 1.5 hours from Hyannis, and Providence is about 1.5 hours from Cape Cod as well.

In summary, I recommend flying into NYC, then taking a flight from NYC to Hyannis, renting a car in Hyannis, and exploring Cape Cod. For getting to Boston, taking a bus, train, or ferry from Hyannis to Boston would be convenient, but if you're comfortable with it, driving straight to Boston and returning the car there might be your simplest option. There are plenty of beautiful places to stay on Cape Cod, and you can easily plan for your trip based on what you’d like to see and do!

Hope this helps, and enjoy your summer vacation!