As far as the Cape and Martha’s Vineyard go, after 25+ years of vacationing there, my favorite spots are Wellfleet, Provincetown and Vineyard Haven (on MV). If you plan on going to the beach, those in Wellfleet (beyond White Crest and the parking lot at the Beachcomber) require parking stickers which are only available to those who have evidence that they are residents or renters with leases. Race Point in Provincetown is spectacular, as is South Beach on the Vineyard. It probably won’t work for your trip, but there is a passenger ferry between Boston and Provincetown which I like when I’m staying in P’town. Parking there can be a challenge. Have a great trip!

Thanks for the info. As far as beaches, we’ll want to do some walking and just enjoying the views but won’t be going for typical beach activities. We’ll have parking available at our lodging in P’town. Is the town walkable? With parking being difficult we’d like to just leave our car parked and walk as much as possible… at least in town. (I realize we will need to drive to other towns.)

Leave the car parked and walk - or rent bicycles. There are some great trails through the dunes for riding. There’s also a (long) walk out a jetty on the far end of town that is quite nice. It is a little challenging without grippy soles, but memorable. Pay attention to tidal chart!

Awesome! Was hoping to leave the car parked and walk as much as possible. Love the idea of bikes too. 🙂 Thanks!

parking available at our lodging in P’town. Is the town walkable?

Yes as long as your rental is truly IN town, not a distance on the outskirts. It's a fantastic town to walk around. Interesting shops, bars, restaurants, etc.

Yes, it’s in town… not outskirts. Really looking forward to our time there!

Thanks for the tips! We have been overwhelmed with all of the thoughtful tips and suggestions from everyone who has replied in this thread. We truly do appreciate it.

June is probably the best month of the year to visit Martha's Vineyard. Perfect weather for walking and hiking and the crowds haven't quite descended at that point. There are miles and miles of trails - I find the TrailsMV app great for showing distances, terrain info and useful notes. If you're just there for 2 days, I'd recommend an island tour - they range from 3-6 hours but you can see so much in that time, especially if you're travelling there without a car. Edgartown and Oak Bluffs are really walkable so choose accommodation in one of those towns to cut down on taxi fares. The MVTravelTips website has a great Edgartown guide. The Martha's Vineyard food and wine festival is on in June this year if you can time your visit with that. So much good food on that island! Enjoy your trip :-)

Great and chock full itinerary and it’s not for everyone and I can see why some are suggesting other alternatives. I, for one, see nothing wrong with your agenda whatsoever. If you like driving from place to place and seeing just a bit of everything. To each their own. In 2007 my wife and I, then living in NYC, took a little vacation. Initially it was just going to be a trip to the Cape for a few days and then off to NH and VT to see a few sites and just see the beauty. Somehow, in the middle it changed into a covered bridges tour and we ended up changing it all and going out of our way to see all of the covered bridges possible in New England. There’s a lot of them. I ended up driving more than 1500 miles on that trip and we learned a lot about cheap hotels too. The moral is just do how you feel best. Regarding the traffic on the Cape, yes the bad traffic usually starts in mid May and goes all the way till September and it’s as bad as July and August. As a resident of one of the islands I speak from experience. Good luck!