Vacation Inspiration

Road trips, long weekends, family travel, food tours and more

As far as I can tell, the perks of empty nesting are as follows: There are fewer pairs of shoes crowding the foyer, the car backseat no longer resembles an archaeological dig, and, when it comes to traveling, I’m not beholden to the school calendar. And that’s pretty much it. (I MISS THEMMMMM!) But I’ll say this: We’ve been good about taking advantage of that last perk. Part of the reason is, of course, because I work for myself, which means I can work from anywhere, making it easy to visit friends over long weekends (free room and board) or piggy-back on one of my husband’s business trips (free hotel room) or hop on a round-trip Amtrak to visit my daughter, on, say, Monday morning and be home by Tuesday night. There are also my now somewhat regular work trips to Italy hosting food tours, and you would be forgiven if you are shaking your head at the word “work” in that sentence.

The point is, my idea of travel has expanded over the years. There are the Big Trips and Family Vacations, yes, but now there are also road trips, long weekends, and spontaneous overnights. Over the years, I’ve written about all of them, so consider today’s newsletter a little Vacation Inspiration Table of Contents for your perusing pleasure. Where would you like to go next?

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We hit Midcoast Maine a few summers ago.

And a few years earlier, we explored further up the coast, in and around Acadia.

There was a last-minute family trip to Death Valley, only a few weeks before Covid shut everything down.

There were lots of trips to South Carolina, back when we had family down there.

When I want to think of happy things, I close my eyes and picture the view from this Airbnb window in Switzerland…

Not to mention all the public swim clubs there.

The Berkshires are just two hours from New York, making it easy to shoot up the Taconic Parkway for a long weekend.

There is nothing quite like Vermont in the summer. (Stay tuned for extremely exciting details on an upcoming Dinner: A Love Story Vermont retreat.)

I’ve only ever been to Chicago for long weekends: Once with college friends, and once with my daughter.

There was that whirlwind 72 hours in (and around) Seattle, which included cold plunges, oyster feasts, and some A-plus shopping.

I first went to Sicily in 2018 and loved it so much, I went back to host my first Via Rosa food tour there…

And the year after, I hosted my second Via Rosa food tour in Puglia. My third will be in Parma in a few weeks — you can be sure I’ll update you on that one.

After hosting the food tour in Puglia this past October, I met Andy in Rome for a few days. I’m writing that one up for you right now, so, again, please check back!

Lisbon was the first real trip we took as empty nesters back in 2023.

Then there was London…

…and beautiful Oxford.

Lastly, I moved to New York two and a half years ago, and yet I still wake up most mornings feeling like I’m on vacation. If you’re planning a trip to my city soon, here are five locals Yorkers (including me) sharing their ideal days. And here is where you should eat.

Happy travels, and thanks for reading.
Jenny

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