My Chic Friend Is A Luxury Travel Specialist + I Got Her To Spill All Her Summer Travel Secrets.

Travel insights from a former fashion exec I completely trust? Say less.

When it comes to trusted travel advice, there are very, very, very few people I turn to for insight. In my experience, while travel advisors can be great about many things, the industry can be a little dated, to say the least. 

Plus, I have just enough knowledge to be dangerous; growing up, my dad was a commercial airline pilot, so I’m pretty good with that piece of it, and I’m enough of a research and travel nerd that I always have a running list of places I want to go, where I want to stay, and what I want to do in any given destination. 

That said, I know what I know, and I know what I don’t know, and I’d long dreamed of finding a travel collaborator that I could really trust. Someone who understood my taste. Someone who understood the vibes. Someone who fundamentally understood why The Bowery has long been the go-to hotel for fashion people traveling to New York, and who also knows that Nine Orchard might be the new Bowery. (Controversial, but what can I say? People are talking about it.)

Bearing all of this in mind, you can imagine my delight when I reconnected with a friend from high school (of all places!) who is truly the chicest, coolest, most connected human ever, and also happens to work in the wonderful world of luxury travel. 

Even better: After a little begging on my part, she’s agreed to share some of her best travel secrets with this wonderful community!. With no further ado, I’m so pleased to introduce my friend, Rebecca Bullen. (PS: If you have any questions for her, or travel suggestions for anyone who reads this, please drop them in the comments, below.)

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Who: Rebecca Bullen, independent luxury travel advisor

Background: A former luxury fashion executive, Rebecca spent two decades working in very fancy merchandising and retail positions for brands like Louis Vuitton, Gucci, and Burberry. (Also Barneys, RIP.) A lifelong traveler, she pivoted her career into the wild world of travel in 2019, and while her knowledge set is truly global, she specifically specializes in travel to Italy, France, Japan, Southeast Asia, and Australia.

Walk us through your career pivot a little bit, please? 

I knew that my career in fashion would inform my career in travel, but it wasn’t until I launched this business that I realized just how much overlap there is between the two worlds. 

I didn’t grow up knowing exactly what I wanted to do with my life, but with parents from San Francisco and Sydney, I spent a lot of time flying back and forth across the Pacific. Some of my earliest and fondest memories consist of staring out the window and just marveling on how big the world is. 

Fast forward to my career in merchandising and retail: Every time I was on a buying session in Paris or London or Florence I was surrounded by my counterparts from Tokyo, Shanghai, and other parts of Europe. It really opened my eyes to what the trends were in different markets. 

Fashion people love to travel and always seem to be one step ahead when it comes to where to go, next. On weekends I would check out other European cities; one time I flew to Morocco for three days. Thanks to a tip from a colleague, my husband and I honeymooned in Tulum 12 years ago, when it was still off the grid and showers were filtered seawater. 

Working exclusively for luxury fashion houses, I became so well versed about the client experience and specifically what the luxury consumer expects. This training has made the transition to the travel industry quite seamless in terms of growing my network of clients.

Where are some of your favorite places for travel this summer?

In my mind “summer” is synonymous with long lazy days on the water. Italy and France are forever favorites, but during peak summer months I try to avoid the most well-known spots. Places like Amalfi, Capri, St Tropez…unless you want to see and be seen, those destinations are best visited in May or September. 

I’m currently obsessed with the other Italian islands: Ischia, Sardinia, Sicily, and the Aeolian Islands, Pantelleria and Ponza. In France, I’m mad for Marseille, Cassis, and the Calanques or Biarritz on the west coast. They have a great surf school there and perfect beginner waves.

Closer to home, this is a great summer to discover the US. After being jam packed with tourist hoards the past few years, we’re still seeing some availability at the best resorts in and around the national parks. 

Further afield, northern Australia has extraordinarily warm weather year round and you’re better off visiting now than in January. Think: Queensland, The Whitsundays and the Great Barrier Reef, or Kakadu National Park in the Northern Territory.

Remember, Australia is a country but also a continent. It's not a "one and done" destination. For West Coast folks, the distance to Australia is barely farther than traveling to Italy. It's the most unique and naturally stunning country with biodiversity that will blow your mind. The city hotel scenes are hotter than hot right now. Capella Hotels just opened their first Australian property in Sydney and my oh my, she's a stunner and a total game changer for the city. 

What are the most popular requests from your clients, versus where you'd suggest they go instead? 

Perhaps this is a consequence of social media but it never fails to amaze me how people request the exact same places at the exact same time. In March 2021 I traveled to Egypt; I couldn’t sell a trip to Egypt that year to save my life. The general consensus was “it’s not safe,” never mind that I’d spent three weeks there alone. Now I’m selling the heck out of Egypt without even suggesting it.

The same holds true for Italy. I get the same request over and over, which doesn’t even make any sense in terms of geography: Venice. Tuscany. Cinque Terre. Rome. Amalfi. 

Where would I go instead, especially if we’re talking summer? Instead of Tuscany, try the neighboring region of Umbria. There’s the coolest new spot called Vocabolo Moscatelli. They only have 12 rooms and suites (Disclaimer: I have a thing for smaller, unique accommodations) and at night you’ll be hanging out at the fire pit with the owners, Fred and Cathi. 

Umbria has cooler evenings then Tuscany, making it a great summer choice. Instead of Amalfi head to unspoiled, casual, cruisy Puglia for a fraction of the price. I have a great yacht guy and a few genuine friends with renovated or restored masseria (HK note: Italian farmhouses!) down in Puglia, and when I have a request, I can reach them via WhatsApp. Personal connection is the new luxury.

In Europe, I’m noticing a big uptick in, for lack of a better term, “passion projects.” Hospitality people pivot too, and there are some exciting new projects popping up. The type of places where you arrive as a guest and leave a friend. What’s cooler than painstakingly and lovingly refurbishing a run-down estate and turning it into a 24-suite stunner with private access on Lake Como? Nothing, that’s what (here’s looking at you, Passalacqua).

Last summer everyone seemed to head to Portugal en masse; this year there’s still space for summer holidays. My recommendation? Check out the Azores and the cool and well priced Octant Hotels. The topography reminds me of Hawaii, and there are nonstop flights from Boston and New York. 

Speaking of Hawaii, the Big Island (my personal favorite) is about to have a moment with Rosewood Kona Village opening this summer. We used to holiday at Kona Village Resort when I was a kid, and now it’s finally reopening after having been destroyed by a tsunami in 2011. I was just shown a few photos from the site and oh my, it is going to be a gem. Rosewood did a superb job of maintaining the thatched-roof castaway aesthetic of the former resort, while updating it for today’s discerning luxury traveler. 

Another consistent request is Japan for cherry blossom season. With climate change this precious two-week window is getting more and more difficult to predict, and spoiler alert: we have cherry blossoms in DC and they're lovely, as is the DC cherry blossom festival. Save Japan for the autumn, when the festival calendar is chock-a-block, the days are warm, and the nights are cool. I spent Thanksgiving 2019 in Tokyo eating sushi and taking in teamLab Borderless and can report that I did not miss turkey in the least. I'm also planning a loosely inspired Lost in Translation birthday trip for a sizable group in February. Tokyo isn’t nearly as cold as the northeast in winter, and the trade off is lower rates and fewer crowds. 

Okay so say someone wants to work with you. Is there anything folks should do in terms of prep to get the most out of their experience? Or something they should know before booking travel with an advisor, in general? 

My dream client comes to me with a destination in mind but is open to suggestions. After all, my key value add is first-hand experience, and my network of personal relationships. I’m also affiliated with the most amazing agency, In The Know Experiences, and my colleagues’ collective knowledge is indispensable. After all, I’m just one person who is meticulous about matching each client to the best destination specifically for them, and it’s a big world filled with places I have never personally vetted (yet).

A key factor in working with an advisor is trust. If you don’t trust me to deliver a perfect holiday from start-to-finish you’re making my job difficult, if not impossible. I realize that it can be scary to relinquish control over something as important – and costly – as a holiday and I try to be sensitive to this but one non-starter is co-planning trips. Same with your cousin’s buddy’s favorite restaurant: Nine times out of 10 that spot is an overpriced tourist trap.  

Sure, you can DIY your travels online. You can also DIY your taxes online, but at some point you probably stopped and realized you needed the professional help that an accountant can provide. The same thing goes for travel; most of my clients actually never worked with an agent before. My goal is to build meaningful relationships with clients over time and help craft their travel strategy for the coming months and years. Think of me as a wealth portfolio manager, but for your travels. After all, what’s the saying? “Travel is the only thing you can buy that makes you richer.” I very much believe this.

Do you have any insider tips and tricks for travel this summer?

1. Arrive early. 

I used to roll up to the airport barely an hour before a flight. Now I am arriving two or three hours prior to departure. With flights completely sold out, there is often no space to accommodate you should you miss your scheduled departure.

2. If you can avoid connecting, do so. 

The money you may have saved making a stop won’t seem all that awesome when your bag didn’t make the connection. Individual airports set minimum connection times. I ignore these. Fifty five minutes to connect in Frankfurt? It’s just not going to happen. I recommend two hours at an absolute minimum. You’ll never regret the extra hour you spent at an airport bar, but you will very much regret missing your connection and sleeping on the floor of an airport terminal.

3. Carry on whenever possible. 

If you simply must check a bag(s), the following items should be in your carry-on bag: medications, a fresh change of clothes (or at least undergarments) for longer flights, your swimsuit, favorite toiletries or makeup, and anything you simply cannot live without for up to one week.

4. Customs and luggage concierge services are worth it.

I strongly recommend customs and luggage concierge services for my clients in peak travel months. I can have someone meet you directly off the plane and whisk you through that pesky customs line or pre-ship your luggage to your final destination. Shipping ski or golf equipment ahead of time is clutch, and less expensive than you might think.

What are some of your travel essentials?

I never travel without my airplane hydration kit (yes, it's labeled as such): Saline eye drops (single-use droppers, because airplane germs), hydrating nasal spray (ideally Fess Frequent Flier Nasal Spray, which I pick up in Australia), Paw Paw ointment for dry spots, a cuticle oil pen (I have one from LOFT in Shibuya, Tokyo, but this one looks sumptuous), Aesop hand cream, and Pacifica’s rose and peptide sheet masks. I've tried fancier options but these do the trick. I’m also pretty militant about wiping down my tray table and other high-touch areas.

Also in my LL Bean zip-top canvas tote (the large size, in yellow, FWIW): A silk sleep mask (mine is Frette, and no longer available) and Brooklinen’s silk pillowcase, double-face RoToTo socks from Japan (new colors come out every fall), a great paperback book and the most recent YOLO Journal, a swimsuit (no matter the destination or season), and both of my passports, even when I travel domestically. I like to be prepared.

Packing cubes have been a game changer for me, in terms of both space-saving and general organization. I’ve seen some fancier versions, but mine are from Target. My go-to checked suitcase is a Samsonite Cosmolite Spinner, but one of these days I'm going to upgrade to a Globetrotter Centenary. 

Perhaps my best packing tip is to go easy on the footwear. Wear your heaviest or clunkiest shoes on the plane and I swear you can get away with one, two additional pairs maximum. Cutting back on footwear options really helps keep your packing streamlined. 

If someone wants to work with you, what should they expect in terms of cost/turnaround time, etc?

With very rare exceptions, I work on a referral-only basis. I wish I could say “yes” to every project that crosses my desk or every person who reaches out, but in terms of my client base the old adage “good people know good people” has proven to be true. You know how Slim Aarons’s whole thing was photographing “attractive people doing attractive things in attractive places”? My passion is working with interesting people, who like to do interesting things in interesting places.

If you’re looking to work with a travel advisor in 2023, expect to pay a planning fee. Why? Well, planning any trip takes a lot of time and expertise. Each trip is customized by leveraging decades of collective expertise, connections, and industry relationships to create the BEST possible experience for you. We don’t get paid commission until/unless you travel. If your plans fall through and I didn’t charge a fee, I just did a ton of work for free. And who likes to work for free? 

Again, I'm affiliated with the most phenomenal agency, In The Know Experiences. We're a group of independent advisors each running our own business, but we're constantly sharing expertise, information, updates and even new client requests on the regular. So if I'm too busy to take on a project, or if a request is completely out of my wheelhouse or comfort zone, I'll pass it along to another advisor within my group. 

What’s your dream summer trip?

My dream summer is spent at home in upstate New York, watching fireflies and barbecuing or walking down to the lake for a lunchtime SUP session. (HK note: That’s stand-up paddle boarding, if you aren’t sporty.)

Blame it on the fact that I very much dislike crowds or blame it on the fact that in fashion we weren’t allowed to take PTO between Thanksgiving and New Year’s, but I don’t like to go anywhere during peak seasons, which happens to be when the bulk of my clients are traveling. 

I personally do not think I can do my job to the best of my ability unless I am available and reachable when my clients are on holiday. They may not realize it, but I always have my eye on their flights and itinerary so that I can address and correct any unexpected hiccups in real time. 

That said, I do love to travel. In September I’ll head to Marrakech for a really exciting experiential travel show called PURE. After that I’m visiting friends in Palermo, Rome, and Venice. On my wishlist at the moment are the beaches of Zanzibar and the desert and Skeleton Coast of Namibia. Closer to home I want to visit Jamaica. I have a feeling about Jamaica in particular; get ready for this to be the new “it” island of the Caribbean.

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Okay friends, that’s it for now. If you want to follow me on @hillarykerr, I’d love it. And if you have anything to say or ask (preferably nothing terribly mean), please drop me a note either via DM or in the comments below.

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