nantucket_harbor1I have a friend in her sixties who has never been to the Atlantic Ocean. She’s a die-hard Montanan, chops all her wood for winter, feeds 40 head of horses twice a day, says “It’s busier than Grand Central Station,” not knowing just where Grand Central Station is. The other day, on the trail, a string of words came out of her mouth that I hadn’t expected. In fact it was like that Sesame Street game: One of these things doesn’t belong here. She said, “I want to go to Cape Cod. And Nantucket.”

Well, as much as I’ve become a Montanan, I admit to having hailed from preppy-land central. I spent summers on the Cape and Nantucket as a child. I know them both well and from the inside out. I know the exclusive, cranky Yankee, world of pink and green and salt-kissed, tanned, cancer-be-damned, skin. I know yacht club life and Lily Pulitzer and mildewy grandmother cottages. I had an inner cringe.

She wanted a list of things to do. I imagine it would be like me telling her that I wanted to enter a horse in the Four H County Fair competition. But I love this woman and I love that part of the world…so I did it. A bit disoriented…but all heart. It’s a rare thing that a tourist can become an insider. And an interesting and mind-bending exercise thinking from the outside in. Here’s what I came up with for a cowgirl wishing to visit Nantucket and the Cape.

On the way to the Cape:

Take a trip to Cap Cod

Photo credit: Pixabay


  • The Mayflower II replica is right on the waterfront which you can take a tour of. It might also be interesting to check out the Plymouth Plantation which is a town set up like Colonial America and you learn all about how things were done back then.
  • There is a great lobster shack called Lobster Hut. Yum! Fried clams and the best lobsters around.
  • Whale watching: The Captain John— guaranteed to see whales (3-4 hour commitment)—right at pier by Lobster Hut

Head over the Sagamore bridge to the Cape.

Get off of rte. 6, and on to rte. 28 (it’s the road that goes right along the water—through the little towns, authentic Cape views vs. highway.)

Not-too-touristy up-your-alley towns:

Chatham (45 min. from the Sagamore bridge) – This is a nice shopping  area and it offers local-style places to eat. Check out Lighthouse Beach, it is a wonderful destination where you can find seals (beautiful!) and sharks (beautiful in their own way) at far right at point! There are riptides too…so be careful swimming!!! But it is so beautiful to walk on this beach and take it all in.

Hyannis (15 min. from bridge): more touristy but lots going on in this town! This is where you get the ferry to Nantucket: Steamship Authority (9$ vs. 35 $ for the fast ferry).

If you are traveling by car it might be hard to take it over to Nantucket depending on the time of year, (have to have a reservation) but if you have a car, go to little village of Madaket at far west end where you can find Siasconcet Beach, Brant Point beach and a lighthouse. Always be really, really careful of the swimming. I would quite possibly NOT get in past your knees, unless you are a strong ocean swimmer. The surf can be killer… But sitting in the sand watching the waves and walking along the shore: positively healing.

Check out the lighthouse when you vsit

Photo credit: Pixabay

I’d probably opt for walking and biking. You can check out the town, great shopping/window-shopping, cobblestone streets—soooo charming! You can rent bikes right next to the ferry dock and ride all over. Check out little lanes, wonderful old crooked houses and gardens and beaches.  Go into the old churches and imagine what it was like in the 1600s and 1700s. Not much has changed in that sense…

Be sure you also go to the Whaling museum right in town to see some really interesting artifacts.

Food in Nantucket

There is GREAT food on the island. I love the Strait Warf restaurant right in town on the water. Remember everything is pricey, but you can always eat at the bar for less and share appetizers, which is the way I usually go. I like to see the nice spots, but not necessarily pay top dollar for a big meal.


If it were me visiting Nantucket, I’d do the trip in two days (or more if I had the $$$). Word to the wise: Cape traffic is a bear (see: grizzly). Don’t make this trip on a Friday when there is a mass exodus from Boston and its burbs to the Cape. Mid-week is smart all the way around.

Day one:

I’d go to Plymouth, then Chatham, and then finish in Hyannis. I’d pend the night in Hyannis ( but remember you need reservations).

Day two:

Take ferry to Nantucket and spend all day there before you ferry back to Hyannis where you can spend night or drive home. Or you could spend the night on Nantucket. It’s pricey. The White Elephant is a really nice place to stay right in town if splurging is in the cards… Or if you decide to stay in Chatham, the Chatham Bars Inn, also really pricey, but it has a great pool and view and it is wonderful old building that has been recently restored. You could also look into Vacation Rentals by Owner but they generally want a week’s stay. I’m sure there are little motels or B&Bs along the way, but still I’d DEFINITELY make reservations as this is their high season.

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