168. A Five Star Nantucket Weekend Inspired by the Hit Show | Set Jetting Luxury Travel

Have you binge watched Five Star Weekend yet? I cannot express how much I loved it! In this episode, I’m unpacking how the series turns Nantucket into more than a beautiful backdrop—and why it's inspiring me to imagine a five-star girls’ getaway of my own. From choosing one meaningful friend from every chapter of your life to curating thoughtful welcome gifts and visiting during Nantucket’s quieter September season, tune in to discover how set jetting can transform a favorite show into an unforgettable luxury trip.

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This episode was produced by The Podcast Teacher: www.ThePodcastTeacher.com. 

Transcript

OPENING

Welcome back to another episode of Jet Setting with Me. It's me, Michele, your friendly wanderlust instigator.

I owe you a small confession before we get into today's episode. Last week I promised you Little House on the Prairie. I told you the Netflix reboot had just dropped and I had set-jetting thoughts. That part is true — Little House is on Netflix. Prairie skies. Laura Ingalls. The whole thing.

Here is what actually happened. I watched the reboot. I watched it with genuine enthusiasm and an open notebook and the very best of intentions. And it gave me absolutely nothing. Not a single moment where I thought: I need to stand there. The nostalgia was real — I grew up on that original series and it lives in my bones — but the reboot did not give me a destination. It gave me a feeling for a show I already loved, which is not the same thing.

Then I sat down with Five Star Weekend.

Eight minutes and twenty-six seconds. That is how long it took. By the time I closed my laptop that night, I had a new show, a new destination, and honestly a new entry on my 2028 group trip slate. Peacock giveth, and Peacock giveth some more.

We are talking about Five Star Weekend today. We are talking about Nantucket. And we are talking about why sometimes the best episodes are the ones you didn't plan.

SECTION ONE: I WASN'T EXPECTING TO FEEL SEEN

Five Star Weekend is based on the novel by Elin Hilderbrand, who is — and I say this with full reverence — the undisputed queen of Nantucket fiction. The Peacock adaptation centers on Hollis Shaw, a woman who has built her life around cooking, curating, and caring for other people. She has lost her husband. She was raised by her father on the Cape after losing her mother young. And in the wake of her grief, she does what any reasonable woman with exceptional taste would do: she plans a girls weekend. A five-star one.

I am not a widow. I did not grow up on an island. I genuinely cannot cook — and I mean that in the most complete way possible. My relationship with a kitchen is one of mutual respect from a safe distance.

And yet. Within the first episode, I had seen myself twice.

The first moment was the guest list. Hollis doesn't invite her closest friends. She invites one woman from every chapter of her life — someone from childhood, someone from college, someone from her career, someone from her present. One person who knows each version of who she has been. When I was an event planner, I used to say that what makes or breaks an event is not the budget, not the food, not the decor. It is who is in the room. The same is true of a girls weekend. The same is true of every group trip I design. Hollis understood this instinctively, and watching her build that guest list felt like watching someone articulate something I have believed for twenty years.

I tried to build my own five-star weekend guest list after that episode. One woman from every chapter. It is harder than it sounds — and more revealing than I expected. But I have some extraordinary women in my life right now, and I know exactly who would be on that list.

The second moment was the welcome gifts. Hollis lays them out — each one chosen specifically, each activity with its own notecard, its own theme, its own intention. That is not hosting. That is curation. That is the difference between a trip that is assembled and one that is designed. It is also, not coincidentally, exactly why set-jetting works as a travel niche. Every set-jetting trip comes with a theme already built in. The show gives you the world. The travel gives you the chance to live inside it.

I give welcome gifts on every group trip I curate. Always have. Because the moment someone opens a gift that was chosen with them specifically in mind, they understand: this trip was designed for me. That feeling is worth more than any excursion on the itinerary.

SECTION TWO: THEN NANTUCKET SHOWED UP

Here is the thing about Five Star Weekend as a set-jetting property: the destination is not a backdrop. Nantucket is a character. The show makes that clear from the first frame — the grey-shingled cottages, the harbor, the cobblestone streets downtown, the particular quality of light that comes off the Atlantic on a clear New England morning.

The show takes you through everything the island offers and does it without ever feeling like a tourism reel. The whale museum. The bookstore. The ice cream that appears in the kind of casual, inevitable way that tells you this is simply what you do there. The downtown shopping along streets that were clearly designed for wandering rather than efficiency. The lectures. The harbor at dusk. A cottage with a water view and a private chef and the particular stillness that comes from being somewhere that has decided, collectively, that it is worth slowing down for.

I have not been to Nantucket — at least not in any memory I can access. I have been to Cape Cod. My father took me when I was young, and what I remember is the wind off the water in my hair, the absurdity of the lobster bib everyone wears at the outdoor tables, and my father's hands showing me how to crack the shell, get the meat out, and soak it properly in butter before eating. It was the first lobster I ever had. I developed a shellfish allergy years later, so it was also, as it turns out, some of the best lobster I will ever have. There are things you don't know you're doing for the last time until you can't do them anymore.

Nantucket sits thirty miles off the coast of Cape Cod, accessible only by ferry or small plane, which gives it the quality that the best travel destinations share: the journey in tells you that you have arrived somewhere that required intention. You do not end up on Nantucket by accident. You choose it. And Five Star Weekend makes a very convincing case for why that choice is worth making.

SECTION THREE: WHY SEPTEMBER IS THE ANSWER

If Five Star Weekend has made you want to book a flight to Nantucket immediately — and if it hasn't, I encourage you to go watch the first episode and then come back to this conversation — here is what you need to know about timing.

September is the answer. Not July, not August, not the peak of summer when the island is at capacity and the ferry lines stretch past reason. September is when the crowds thin, the light turns golden in that particular way that only happens when summer starts its long exhale, and the weather remains genuinely beautiful. September is Nantucket at its most itself.

September in Nantucket is also when Elin Hilderbrand — the woman whose novel gave us this entire world — is in residence on the island. She signs autographs in the basement of the bookstore. That is not a detail I invented. That is a real thing that happens, and it is exactly the kind of insider, specific, only-if-you-know-to-look-for-it detail that makes a trip feel designed rather than assembled.

I will tell you that Nantucket in September is already living in my imagination in a very specific way. A boutique property with water views. A private chef — because some of us cannot cook and have made our peace with that. The whale museum. The cobblestone downtown. The bookstore. And if the timing ever aligned the way I hope it might, a moment in a basement with the woman who created Hollis Shaw and made me want to build my own guest list.

This is set-jetting at its most complete: a show that made me feel something, a destination that earned the feeling, and a trip designed to let you live inside both.

CLOSING

Have you watched Five Star Weekend yet? If the answer is no, I want you to consider this episode your permission slip. Clear your evening. Pour something good. And pay attention to the guest list scene in the first episode. Then tell me who would be on yours.

DM me at @jetsettingwithmichele. And if Nantucket in September with a group of women who get it sounds like the trip you didn't know you needed — file that thought away. More on that when the time is right.

COMING UP NEXT WEEK

Next week's episode is a different kind of travel story — and I want to prepare you for it gently. Episode 169 is about Nagasaki, Japan. It is timed intentionally to the dates in August that mark one of the most significant moments in modern history. It is not a light episode. It is a meaningful one. Travel has always been one of the ways we bear witness — to beauty, to joy, and sometimes to the weight of what the world has carried. Next week, we bear witness together. I hope you'll be there for it.

SIGN-OFF

Until next time, make every journey a memory worth savoring.