Let's Get Personal
A new series with non-professional travelers who mean the world to me.
A while back, I had this crazy idea about extending my scope of interviews from industry trendsetters to include the people closest to me—family, friends, loved ones—who I often travel with.
The idea lingered but there was always this pesky thought in my head questioning, “will people really care about personal connections?” But then I realized that outside of work, none of my immediate social or familial circle have a professional connection to travel. Yes, they take trips but they aren’t traveling as frequently as myself or my colleagues and they certainly aren’t traveling to scout the best bars or bites to eat—they’re traveling for enjoyment. They are real travelers!
So, I revisited the idea as I thought their lens of leisure could lend a fresh perspective to an often insular industry. Given I’m out this week celebrating my wedding in Tuscany, I thought of no better way to start this series than with my now husband (though he was still my fiancé when I interviewed him for this piece).
Neil and I have been traveling together pretty much since we met. Our first trip together was to St. Thomas about three months into dating, where the days of poolside painkillers, ceviche snacks on the beach and nights of coconut rice and spiny lobster really solidified our mutual interest in traveling to appreciate the world at full stimulus. We heeded the advice in Neil’s response to question five about seeking out a local bar—deviating from our cushy surrounds at The Ritz-Carlton, St. Thomas to the Red Hook haunt, Duffy’s Love Shack, per the recommendation of our favorite bartender.
We’ve since traveled to many other places together from Sonoma to Scotland, Maine to Mexico, signing up for countless adventures along the way like fly fishing in Vermont, rappelling down a 150-foot cliff in Montana, clay shooting in Tennessee, truffle hunting in Tuscany and waddling through fresh snow with the penguins in Antarctica. All along, it’s been truly exciting to expose him to my world so I thought it was time to dive into it from his point-of-view.
My goal is to sprinkle in more of these personal interviews, so I hope you find these questions as entertaining and useful, as some of the “professionals” that I interview on this platform. And as always, I look forward to your feedback.
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When we first met, I was definitely impressed by your interest in travel. What was one of the first trips you remember taking that sparked this interest?
I went to England one summer with my dad and family when I was younger but I didn’t realize how cool travel was until we went to Paris the next summer. I was with my dad and brothers, grandparents, my uncle, my stepsister and even though we did all the generic things, like the Eiffel Tower, the Louvre and Normandy, it was just really fun to be able to experience something different together.
Was there a specific moment or experience on the trip that encouraged your desire to travel more?
Hearing the French accents and the way the waiters would talk to my dad — he could speak French but none of us could. Also, the different architecture; there’s nothing in Boston that looks like Paris.
What’s one of your favorite tours, hotels or events that you’ve experienced in travel (with or without me) that stands out?
When we stayed at Rosewood Mayakoba. It was a true world-class resort but the setting was so beautiful with how it was built into the waterways that wind through Mayakoba. Yes, the service was excellent, especially the butler amenity, but the design and the way they had each bungalow all tied together into something that was really unique. Also, I loved having dinner underneath the Ceiba tree with other guests. It was just an exceptional location.
You’ve done some planning for our trips in the past—how do you go about organizing that? What sites are you looking at?
Anything that I’ve planned I’ve known about through hearsay. I’ll browse Instagram for inspiration but usually it’s word of mouth or something I saw in a movie. But I do like to do research before each trip to make sure we’re spending our time efficiently. It’s always good to ask friends who’ve been to the destination before, too—like when we went to Piazzale Michelangelo in Florence and we gathered provisions on the way to picnic at the top—that tip came from a friend.
Yeah, I would have been so sad if we climbed all the way up there and I didn’t have cheese and wine to enjoy the view. On that note, how do you judge a destination?
Definitely by going off-the-beaten path, straying away from the tourist spots. Whether that’s a walk for coffee or grabbing lunch at a hole-in-the-wall restaurant, I think it is the best way to get a true vibe for a place. And mix in a few pints at a local bar. Gotta find the real everyday experiences of the place, not just what the tour operators would have you see.
What’s been your favorite hole-in-the-wall bar you’ve found?
There’s two — do you know them?
JD: I think I know one, which is in Rome because we spent about four hours there last year!
Yeah, Ma Che Siete Venuti A Fà in Trastevere, Rome because it’s a really good selection of beer and there are always locals there who you have no idea what they do in life besides talk for hours, drink beers and smoke cigarettes. The other is the Dunvegan in St. Andrews — it’s an epic spot but it feels like home and your neighborhood pub even though it’s so well known.
What’s a memorable bite from your travels that you still think about?
The beef tongue we ate in Rome (laughing hysterically) because it was so viscerally just a tongue. (JD note: this multi-course meal at a wine bar—I’ll save the name—was actually incredible but one of the courses was a beef tongue presented exactly as is. We both could not get over the image of it).
OK. Let me be more specific. What about a good memorable bite?
I was blown away by the meal at Poggio Rosso at Borgo San Felice but I can’t remember the exact dishes. (JD note: I remember the Chianti risotto with wild boar and cypress nut shavings as one of our favorites that night but there was also Tuscan Guinea fowl with pumpkin and guava nutmeg roasted-pigeon with hibiscus that stood out among the eight courses).
We also had some really good duck in Scotland. Oh actually, and the fermented barley dish at The Macallan Distillery was exceptional; it was so warming and unexpected. It could have been a throwaway first course but it was a stand out with flavor and texture. (JD note: fermented barley with caramelized yeast puree and malt foam—it was a delight!)
As emphasis on different categories with travel have evolved over the years, have you noticed a difference in the consumer you’re interacting with on vacations?
I think the consumer I interact with now has definitely changed but that’s because I’ve changed and grown up as a traveler. In my early 20s, I wanted to do everything and hit all the spots I could. Or like when I went to Thailand for example, I was fresh out of college so it was all about drinking and experiencing the things you see on TV. Now, it’s more about really enjoying the destinations I’m in thoroughly and the service and hospitality of the places we visit.
As you’ve taken some trips with me over the last five-plus years, is there something about the travel-for-a-living lifestyle you now realize that maybe others might not understand from the constant picturesque photos I post on the ‘Gram?
Yeah, there’s certainly more work that goes into it than people realize because you have to remember and document everything. You’re constantly taking notes on the details, experiences, menus, and you are working so you can’t relax quite as well as if you were on vacation.
Is there a trip (besides our honeymoon) you’re dreaming of taking?
I would love to go somewhere in Scandinavia like Finland or Norway—in the summer. I just think they are very different cultures than the rest of continental Europe and we’ve done a lot of travel to England and Italy, so I want to experience what life is like in that region.
As a Boston native, what’s your hot tip for a first time visitor? What can’t they miss?
It sounds cliché—and they stink right now—but a Red Sox baseball game is kind of a must if you visit when they are playing. Just because you get a feel for Bostonians but also the sports culture and if you catch a good weather day, it’s a beautiful experience.
What about for a return visitor to Boston? What’s an inside spot they need to seek out?
I think the South End has a lot to offer and many people on their first visit skip over it. But it’s definitely worth making a trip to the neighborhood for its food, wine, drinks and hospitality. It’s great to just bop around and see what calls to you but for a couple anchors, be sure to check out SRV and Delux.
Essential of the week: Parallelle cosmetic bag
Before you roll your eyes, it’s all over Instagram for a reason—this is truly the best cosmetic bag I’ve ever owned. I love the verticality of it so my products are always upright and ready to use. I also appreciate that I never have to unpack my toiletries now which saves me time when I’m hotel hopping on a work trip.
A place for everything and everything in its place, is a phrase I grew up with—and everything certainly has it’s own place in this bag from the adjustable velcro slots that can fit a rounder bottle to long makeup brushes to bulkier items in the main center compartment. I have it in a medium which I think is the perfect size if combining toiletries with makeup.
Recent work:
Never know when to use frozen versus fresh produce? Top chefs weigh-in.
Hate checking luggage but can’t avoid it? How to have a worry-free experience.
Mental Health Awareness month is coming to an end but these wineries are year-round advocates.
XO,
Love how you correct the culinary deets. ;)
Tanti Auguri, Jillian! Hope you’re having a truly wonderful time in Tuscany.