Cape Cod, Nantucket and Boston with a Baby and a Dog (Plus Newport and Cape Ann)
Two weeks around New England in our van with a six-month-old and a German Shepherd: Newport, a Cape Cod base camp, Plymouth, a Nantucket day trip, Provincetown, Boston, sailing in Marblehead, Rockport and Gloucester.
New England in July is hydrangeas, shingled houses, lobster rolls and very old towns, and we tried to fit as much of it as we could into two weeks. Andi turned six months old on this stretch. She saw her first ferry, her first sailboat and roughly ten thousand hydrangeas.
The trick that made it work was not moving the van every day. We set up a home base on the South Coast of Massachusetts for almost a week and did Cape Cod, Plymouth and Nantucket as day trips. Then we moved up to Boston and Cape Ann.
- Route
- Newport → Cape Cod base (Rochester, MA) → Plymouth → Nantucket → Provincetown → Boston → Marblehead → Rockport → Gloucester
- How long
- 2 weeks, part of our 5-week East Coast van trip
- Who came
- Colin, me, Andi (6 months) and Jack, our German Shepherd (he sat out Nantucket and the sailboat)
- Where we slept
- Our van at a campground in Rochester, MA, plus a couple of nights at the Hyatt Regency Boston
- Best for
- Families who love beach towns, history and walkable cities
Our route, day by day
- Newport, Rhode Island (Jul 14–15)
- Cape Cod base camp in Rochester, MA (Jul 15–21), with day trips to Plymouth (Jul 17), Nantucket (Jul 19) and Provincetown and Truro (Jul 21)
- Boston (Jul 22–23)
- Marblehead and Salem (Jul 24)
- Rockport (Jul 25)
- Gloucester (Jul 26–27)
Newport
Newport was our first taste of New England summer. We walked along the cliffs by the mansions, went by The Breakers, and wandered Bowen’s Wharf. Hydrangeas were everywhere, and the American flag over the bay made for my favorite photo of Colin and Andi from the whole trip.
Our Cape Cod base camp
Instead of hopping between Cape Cod campgrounds, we stayed put at one campground in Rochester, MA, for about a week. It was a short drive to the Cape, Plymouth and the Nantucket ferry, and it had a pool, which mattered more than we expected in July.
A week in one place also gave Andi a real routine. Her travel crib set up in the van and stayed put, and we did our day trips around her morning nap.
Plymouth
We spent an easy day in Plymouth seeing the Mayflower II in the harbor and walking along the water. Andi rode on Colin’s shoulders along the seawall and thought it was the funniest thing that had ever happened.
Nantucket with a baby
Nantucket was our biggest photo day of the entire summer, and you’ll understand why the minute you step off the ferry. Every lane is gray shingles, white trim and hydrangeas. We took the ferry over from Hyannis for the day and spent it walking: the harbor, the cottage lanes and the hydrangeas.
Andi got her Nantucket pop-up in front of the prettiest hydrangea cottage we could find.
Tips for Nantucket with a baby:
- Bring the carrier, not just the stroller. Downtown has real cobblestones, and the stroller rattles. We used both.
- Go in early to mid-July for peak hydrangeas.
- Book the ferry ahead on summer weekends.
Jack had a rest day for this one, so I can’t speak to Nantucket with a dog yet.
Provincetown and Truro
At the far end of the Cape, Provincetown is colorful and fun, with rainbow flags on half the houses and great people watching. We had a proper lobster roll, then drove back through Truro to see Highland Light. Andi and Jack spent the drive home cuddled up together in the back.
Boston with a baby and a dog
For Boston we traded the van for a hotel. We stayed at the Hyatt Regency Boston, right downtown, and it was an easy, dog-friendly base. Andi and Jack took over the bed immediately.
We spent our days picnicking on Boston Common, walking through the Public Garden and down Newbury Street, and finding patios where Jack could lie under the table. Boston was much more dog friendly than I expected. Plenty of patios welcomed him, and the Common is great for a midday break.
Sailing out of Marblehead
On the 24th we drove up to Marblehead and went out on a sailboat. Colin took the wheel, and I kept Andi bundled up, because it gets windy on the water even in July. She was completely unbothered, and honestly it might have been her favorite day. Jack sat this one out too.
If you’re taking a baby sailing: bring a warm layer, a hat with a strap, and a baby life jacket that fits her weight. Ask the charter ahead of time whether they have one or whether you should bring your own.
Rockport and Gloucester
Cape Ann was the slow end of this leg. In Rockport we went for ice cream at The Ice Cream Store at dusk and had an Aperol spritz watching the sunset over the water. Andi and Jack rolled around on the grass together like old friends.
In Gloucester we climbed around on the rocks at Stage Fort Park, walked the harbor, and gave ourselves two easy days before heading into Maine.
New England with a baby: what worked
- Pick a base and do day trips. Our week in Rochester, MA, was the reason the Cape didn’t feel exhausting.
- Pool access is worth it in July. Afternoons got hot, and a dip saved our sanity.
- A carrier plus a light stroller covers everything, from cobblestones to city sidewalks.
- Layers for the water. Ferries and sailboats are much colder than land.
New England with a dog: what worked
- Boston was easy. Lots of patios welcomed dogs, and a dog-friendly downtown hotel meant we didn’t worry about the van.
- Plan dog-free days honestly. Ferries, sailboats and mansion tours are better without a 90-pound shepherd. Having a plan for him on those days made everything smoother.
- Cape Ann is relaxed. Parks like Stage Fort in Gloucester gave him room to stretch out.
Would we do it again?
Yes, and next time I’d give Nantucket an overnight instead of a day trip. If you only have a week, base yourself near the Cape, do Nantucket and Provincetown, then spend two nights in Boston. Next on our route was Maine, which you can read about in our Maine coast and Acadia guide.
