Hot Travel Tips For Summer 2026 + Beyond From The Coolest Luxury Travel Advisor, Ever!
Rebecca Bullen is back with insanely good info, and I'm so excited.
Hi everyone! I am so thrilled for today’s newsletter, because it features one of my favorite experts in the world: Rebecca Bullen, my go-to resource for all things luxury travel. Longtime readers know that Rebecca has a wildly insightful understanding of all things travel, she makes the best recommendations, and she gives incredible insight on everything from the key airports to avoid to the best time to book travel. If you don’t believe me, just go back and check out her stories from 2025, 2024, and 2023; she really knows her stuff.
Also, for those of you who are getting this in newsletter form, you need to click through at the end! This one is too long to go out in entirety as an email, so click to read on my landing page. Oh, and stay tuned all the way to the end for a special surprise that Rebecca is sharing for the first time ever.
I’m so curious about your recommendations for summer travel this year? Are there any newer hotels or destinations that you’re already booking?
I’m just back from my first visit to Scotland and the Scottish Highlands with WildLand, a project I’d been tracking long enough that I’d already booked a family there last December, before I’d ever set foot on the property myself. WildLand owns 225,000 acres across three Highland regions, with options ranging from one-bedroom self-catering bothies to fully-staffed 12-bedroom Aldourie Castle on the banks of Loch Ness. I don’t consider myself a crunchy granola nature gal, but the rugged beauty of the Highlands really stirred something in me, and I think it has something for everyone.
Their newest property, Hope Lodge, will flex between a hotel-style guesthouse and exclusive-use property depending on the time of year. It opens in just a few weeks. I scored a hard-hat tour and it is going to be extraordinary. Hope was designed by Cécile & Boyd, the South African studio behind Singita’s lodges for three decades. The thread connecting those two worlds - conservation-led hospitality in landscapes of almost impossible beauty - is one I find increasingly compelling. Both WildLand and Singita genuinely feel like forces for good in the world, and that matters more and more to me in terms of where I’m sending clients.
Italy is a perennial favorite, and the Dolomites are hitting their stride. Forestis continues to earn rave reviews, and now in addition to their adults-only hotel they have Forestis Villa, a high-end private rental suitable for guests of all ages. One of the reasons I love booking Italy is the high concentration of family-owned and independent properties. One of the finest examples is Le Sirenuse on the Amalfi Coast. Their stunning, ultra-exclusive beach club, Le Sirenuse Mare, opens in late April, and I’m certain it will be one of the hottest tickets of the summer.
I’ve been planning a lot of holidays in France this year. It feels like Paris is having a moment, the vibes are really great right now and the hotel scene has never been more exciting. I’m very much into Provence; it’s vast and varied and endlessly rewarding. Aix-en-Provence, the Luberon, the Alpilles, the Camargue—the region is wonderfully varied and chock full of fab places to stay. Mid-September through October is my personal favorite time on the Côte d’Azur. The crowds have thinned and the sea is still plenty warm. Oft-overlooked Nice is brilliant as a base, with a hotel scene that has transformed completely with the opening of Hôtel du Couvent.
What are the hardest bookings to make and how early should folks think about them?
Japan is the most challenging request to navigate right now, without question. Demand shows absolutely no signs of slowing, and the shortage of English-speaking guides and drivers means the best ones are booked up to a year in advance. If you want a properly curated, end-to-end luxury experience with the right guides, the right ryokans, and the right private access you need to be talking to me twelve months out. That said, Japan has a lot of hotel inventory, and if excellent hotels with a more flexible on-the-ground experience is what you’re after, I can work with a shorter window.
African safaris are in the same category. Properties like Singita, Jack’s Camp and Duke’s Camp operate with intentionally limited capacity to keep their environmental footprint low. Twelve to eighteen months is the rule here, not the exception. Singita Elela is opening their first Botswana property in the Okavango Delta this December, so now is a good time to think about 2027 or 2028. Just eight individual stilted camps, each with a private guide, host and vehicle. It is one of the most sought-after bookings in Africa, and the time to secure it is now.
For end-of-year travel the stakes are higher than any other time of year, because unlike summer there is only one festive season and the window to course-correct is essentially zero. The most finite resource in travel is space. I can pull many a proverbial rabbit out of the hat, but I cannot conjure a room that doesn’t exist. Anything remotely bucket list-y will book up a year or more in advance. Exploring Raja Ampat aboard Rascal Voyages was hands down the best travel experience of my life thus far, and is one such example.
If you have any 2026 travel plans on the horizon, book your flights now. Premium cabin inventory has never been tighter and fares are going to go up thanks to the recent spike in fuel costs, unfortunately. That said, I’ve yet to personally see some of the more hysterical fare increase predictions come to pass. So don’t panic, but do plan ahead. Fares are not going to go down.
And while we’re talking logistics: Pull out your passport right now and check the expiration date. You’d be surprised how many people don’t think about this until the week before their trip. You need a minimum of six months validity beyond your return date. If you’re traveling with under-18s, remember their passports are only valid for five years. One of my own passports expires in May 2027 and I’m about to renew it, to give you an idea.
Are there any locations that you’re avoiding right now? Obviously there are safety concerns in the Middle East right now, but is that impacting Egypt and Morocco bookings? Or are there any spots that will be overly crowded due to major events?
Honestly? I’m personally trying to avoid travel within the United States that requires flights. I hate crowds and I hate long lines of any kind, and between TSA chaos and the general state of domestic air travel right now, traveling within the US feels more stressful to me than almost anywhere else I could go. I’m also personally avoiding anything World Cup-related and keeping an eye on dates and cities hosting key matches. I just can’t see a scenario where travel to and from these matches goes smoothly with just over two months until kickoff, but that’s just me. I’d love to be proven wrong!
On the Middle East question: I like to cross-reference US State Department guidance with advisories from other countries. Australia takes a very cautious approach and is a good one to check, as is the EU or UK. Looking at multiple sources gives me a more holistic, less politically charged read on any given situation. That said, I have had zero cancellations for Egypt and Morocco in 2026 and am actively booking both. It helps enormously that these are two countries I know deeply and personally. My clients can see that I was in Egypt with my dad in February—the trip of his lifetime, he said—and in Morocco last fall. That firsthand presence matters. It signals that I wouldn’t send someone somewhere I wouldn’t go myself.
Ultimately, every traveler has to make their own assessment of what feels right for them, and I deeply respect that. My job is to give you the most accurate, well-rounded picture I can and then support whatever decision you make.
Are there any airlines that are doing a really great job?
I can’t believe I’m about to say this but: United is trying, and it’s working. I’ve seen a lot of improvements here, from upgraded cabins to Starlink wifi, which by contract has to be offered for free. Food has suddenly become edible. United has been on a tear with some fab new nonstop routes: Newark to Bari (for Puglia) and Palermo (for Sicily), Split (Croatia), Glasgow (Scotland) and Bilbao (Spain) to name a few, as well as Washington Dulles to Reykjavik, Iceland. From SFO they now offer nonstop service to Adelaide, Australia.
That said, I don’t think any of the US carriers are doing a truly great job. The moment you fly the likes of a Singapore Airlines, you realize quite starkly how low the bar has been set domestically. Last year I took what is currently the longest commercial flight in the world—Singapore to New York, 18.5 hours—and I’ll be honest, it was strange, but not awful. The business class seats were cavernous, service impeccable and food incredibly tasty. It’s just in another league when you compare with what we’re used to domestically.
The Middle Eastern carriers—Emirates, Etihad, Qatar—deserve real credit for how gracefully they’ve navigated the current crisis affecting their hubs. They’ve been genuinely wonderful at looking after passengers who found themselves stranded, including covering hotel costs. That kind of care under pressure says a lot about an airline.
Air New Zealand is another one I rate highly. And when I’m booking for myself, I actively seek out the A380 or A350. Both are quieter, more comfortable, and easier on your body over long distances. It’s worth checking the aircraft type before you book. It can make an enormous difference.
What about airports or connections to avoid? A couple of years ago there were lots of snafus with the airport in Amsterdam, and more recently Newark has been a problem. Do you have any predictions for this summer?
It’s no secret that the US aviation system is under real strain. ATC staffing shortages haven’t improved since we spoke last year, when I called out Newark. So what to do? If you’re connecting through a major US hub this summer, build in as much buffer time as you possibly can—three hours at an absolute bare minimum. All three New York area airports are problematic at the moment, and I’d avoid them where possible. We’re in a “lesser of three evils” situation when it comes to JFK vs Newark vs LaGuardia.
The fewer US connections in your itinerary this summer, the better. If you’re flying from the US to Europe, for example, get across the Atlantic as directly as possible. Once you’re in Europe, most major hubs are running smoothly, with Zurich and Munich being the easiest to navigate. Even London has improved vastly, helped in no small part by the rollout of new security scanners. No more removing liquids from your hand luggage, no more silly ziploc bag limits.
Two airports I’d actively try to avoid for European connections are Paris CDG and Madrid, both of which have layouts that are confusing and simply not conducive to transfers. If you must connect at either, a customs concierge service is less of a luxury and more of a necessity.
For anyone based on the west coast, this might be a good year to consider visiting Australia, New Zealand, Fiji or Tahiti or anywhere in Asia really. There are heaps of nonstops from the west coast to Japan, Singapore, Hong Kong…between the three you easily connect to so many wonderful destinations. Vietnam Airlines even has a nonstop between SFO and Ho Chi Minh City. I absolutely love Vietnam and I wish I had more time to elaborate!
For anyone who hasn’t read our other interviews, I want to point out that you and I have similar hotel preferences, in that we like smaller, boutique hotels, generally speaking. What are some of your favorite, extremely special hotels on your list right now? Big or small!
Let’s start with Italy and the absolutely brilliant Collegio alla Querce, Auberge Resorts’ first European property, set just barely outside of Florence city center. I just spoke about it at length on Travel Weekly’s podcast The Last Resort. My personal city favorites—the ones I book for myself—are Rhinoceros Roma and Singer Palace in Rome, Londra Palace Venezia or Ca di Dio in Venice, The Place in Florence and Vico Milano. On the full service 5-star luxury side of things, post-renovation Four Seasons Milan is the best hotel in a city that is absolutely chock-a-block with brilliant options.
On Lake Como, Passalacqua gets all the attention, and rightfully so, but don’t overlook Mandarin Oriental Lago di Como. Please ignore the rumor that one side of the lake is sunnier than the other. One side gets sunrise, the other gets sunset. They are equally glorious. Oh, and the darling and super-stylish couple who own Vico Milano will be opening their second property on Lake Como in 2028. I just found that out last week so you heard it here first! Villa Igiea, a Rocco Forte Hotel in Palermo, is one of my favorite hotels in the world, full stop. I could wax poetic about boutique properties that I love on Sicily: Casa Lawa, Principe di Salina, Monaci delle Terre Nere, Le Calette Hotel…just to rattle off a few favorites off the top of my head.
I know that we both adore Chateau Voltaire in Paris. I stayed there in the fall and it’s still great—in fact I think the service has improved. I also stayed at newcomer La Fondation in the 17th and it is a find, let me tell you! It’s giving TriBeca vibes with interiors by Roman & Williams, a rooftop bar with Eiffel Tower views, a semi-Olympic pool in the basement and a rock climbing wall. It functions simultaneously as a hotel, a wellness club and a co-working space, and is particularly great for a longer stay. I loved being in that neighborhood. It’s very much the Paris that locals actually live in.
Beyond Italy, I want to talk about Capella, which I think I’ve mentioned before. It’s not a widely known brand among casual travelers, particularly here in the States because it’s a relatively small collection with fewer than ten properties globally, most of which are in Asia. Capella Ubud is in my personal top five hotel stays ever. You can find this luxe tented camp all over my Instagram. Other standouts are Singapore and Hanoi, and I’m busting to visit their new hotel in Taipei. And while we’re talking Asia, the Shinmonzen in Kyoto might just be my favorite hotel in Japan right now. That or the resplendent Bulgari Tokyo.
You know what you would love? Sterrekopje Farm. It’s in South Africa, about an hour outside of Cape Town. All meals, drinks, a daily spa treatment and a whole philosophy of life included in the rate. Ingredients are harvested from the garden before they reach your plate, and the days are structured around the rhythms of the farm rather than a hotel schedule. Pottery, yoga, sound healing, bakery classes, horses. The owners Fleur and Nicole are just the absolute nicest and are very much part of the magic.
There are more than a few openings I’m really excited about, and they’re probably not the usual suspects you see on every “best of” list. I believe lists make travel more boring and I personally wish they would go away. Number one for me is Casa Bonavita on Malta opens this summer, perfect to pair with Delta’s new nonstop from JFK. I’m really hoping to visit before word gets out. NIHI is expanding from Sumba with a second Indonesian resort, NIHI Rote, as well as NIHI Santo Tomás in Costa Rica. And Orient Express is expanding on the success of La Minerva in Rome with Orient Express Venezia. I’ve been privy to some pre-opening images and videos and it is going to be a hotel of epic, extraordinary beauty.
Are there any new hotels or flight routes that have caught your eye?
The nonstop route expansion in 2026 is genuinely exciting, and as a bit of an Avgeek I could talk about this all day. Here are a few that have caught my eye in addition to that nonstop between JFK and Valetta, the capital of Malta.
Alaska Airlines is making its transatlantic debut with Seattle to Rome, a huge deal for travelers based in the Pacific Northwest who’ve always had to connect before reaching Italy. Delta has also expanded significantly out of Seattle with nonstops to Rome and Barcelona, and Royal Air Maroc is launching the first-ever nonstop between the US West Coast and Africa: Los Angeles to Casablanca.
American is launching Dallas to Athens and Dallas to Zurich, plus Philadelphia to Prague. And JetBlue has new service from Boston to both Milan and Barcelona, though a word of caution here: JetBlue and increasingly American Airlines are relying on the long range narrow body A321neo. In layman’s terms this means long haul flights on a relatively small 3-aisle-3 plane. I wouldn’t recommend this in economy class.
More nonstops between secondary cities means more interesting itineraries, fewer connections, and less time in airports. All good things.
Let’s talk local: Are there any destinations in the United States or North America that are looking great for summer holidays?
In North America, Auberge Resorts continues to deliver and The Lodge at Blue Sky, Stanly Ranch, Mattei’s Tavern, and Mayflower Inn are still favorites. Ted Turner’s Vermejo Reserve in New Mexico. San Ysidro Ranch, and Hotel Bel-Air remain Southern California icons, One & Only Moonlight Basin is exceptional in Montana, and I’m watching the new Oketer Collection Vinetta in Palm Beach.
For something truly extraordinary: Sheldon Chalet in Alaska. Five bedrooms, accessible by helicopter only, 6,000 feet up inside Denali National Park, private chef and guides included. Nothing else like it on earth.
Summer is my favorite time to visit Hawaii and the Caribbean. Rates drop, crowds thin—no waking up at 5 a.m. to snag a beach chair, because what’s relaxing about that? A few Hawaii favorites: Kona Village, a Rosewood Resort; Four Seasons Resort Lanai; Sensei Lanai; and the adults-only Hotel Wailea on Maui. One update worth knowing: the Montage Kapalua Bay that you booked for spring break last year is reportedly becoming a St. Regis. For the Caribbean, I love St. Barths, and Turks and Caicos in May, June, and July. A few favorites: Eden Roc and Fouquet’s Saint-Barth, COMO Parrot Cay, and Pine Cay on Turks and Caicos.
Nimmo Bay in British Columbia’s Great Bear Rainforest is a family-owned wilderness retreat reachable only by floatplane. Glacier hikes, grizzly bears, floating sauna and another bucket-list worthy nature forward property that I’m currently crushing on.
Can we talk more about family-friendly spots that don’t feel like a Disney cruise?
For families who want something more active and nature-forward, Switzerland, Austria, and Germany are great options, and easy to combine with one another. Switzerland in particular is extraordinary. The train network alone is a lesson in how infrastructure can be genuinely joyful, and the lakes and mountains give kids something real to do. The Alpina Gstaad and Badrutt’s Palace in St. Moritz both do family hospitality beautifully, with seriously great programming tailored to children. In Austria, Rosewood Schloss Fuschl—a restored 15th century castle on the banks of Lake Fuschl—is magical for families, with hiking, biking, kayaking and swimming on the doorstep. Bavaria is underrated as a family destination: Munich is endlessly entertaining for kids, and the surrounding countryside, castles and lakes make for one of the great European road trip circuits. This part of the world rewards slow travel and curious families in equal measure.
Greece is another wonderful destination for families. The Four Seasons Astir Palace on the Athens Riviera is a brilliant base with three private beaches just 30 minutes from the Acropolis. Older kids who are into ancient history will have their minds blown by Athens, and the hotel gives everyone the downtime and beach access to balance it out. I also love pairing Athens with the Peloponnese on the Greek mainland. Ancient ruins, incredible beaches, and no need to hassle with Athens airport to reach your destination.
Let’s talk “fly & flop”, those easy breezy beach resort destinations perfect for splish splashing around. Four Seasons Punta Mita for family friendly pools, calm beach and a quick flight from California. Jumby Bay, Antigua—a private island that’s genuinely magical for little ones. Sandy Lane, Barbados is a classic that’s impeccable for families. Four Seasons Hualalai, Big Island is arguably the best for tiny kids in Hawaii. Round Hill in Jamaica. None of these are a bargain, but in summer rates will be much less than they are during festive or spring break.
Once you’re traveling with two or more kids plus grandparents or extended family, a fully staffed exclusive-use property often makes a more financial sense than a hotel and delivers a far better experience. Your own pool, your own schedule, someone cooking breakfast while the kids are still in their pajamas. When you split the cost across multiple bedrooms, the per-person price often compares very favorably to several hotel rooms at a luxury resort.
What about a girls’ trip? Whether it’s for a bachelorette party or a milestone birthday, where are some great places to celebrate with friends?
My current obsession for a group or celebration trip? Aldourie Castle, part of the Wildland portfolio I mentioned earlier. A 400-year-old castle on the banks of Loch Ness, pink-turreted, fully staffed, sleeping up to 24 across 12 suites with space for more in adjacent cottages, set within 500 acres of gardens, woodland and wildflower meadows. Private chef, daily housekeeping, a wine cellar or whisky snug, a sauna yurt hidden in the trees by the loch, a boathouse, a glasshouse. You arrive as guests and within about four hours you feel like you’ve always lived there. For a milestone birthday or a bachelorette with taste, I genuinely cannot think of anything better.
I’m so glad that you asked about milestone birthdays. I’ve been planning a lot of these lately. Part of my job is staying ahead of what’s opening, and one of the ways I do that is by attending carefully curated trade events that most travelers will never hear about. Earlier this year I attended Do Not Disturb, an extraordinarily exclusive gathering dedicated to private and seclusion-focused travel, and came away with a list of discoveries that I’m really excited about.
A few standouts: Dun Aluinn in the Scottish Highlands, a design-led nine-bedroom estate just 90 minutes from Edinburgh, fully staffed and utterly beautiful. Villa La Guettière on Cap d’Antibes, affiliated with and billed as a mini Hôtel du Cap-Eden-Roc. Nine bedrooms, private chef, infinity pool overlooking the Mediterranean, and full access to Hotel du Cap’s amenities including the Dior spa. Oka, the brand new nine-bedroom private villa from the Barracuda Group in Bahia, one of Brazil’s most special stretches of coastline, has an extraordinary Scandi-meets-Bahian aesthetic. Islas Secas in Panama, a private island archipelago with some of the best diving in the world. Lopud 1483, a restored 15th century Franciscan monastery on a tiny island off Dubrovnik where the Beckham family have been known to holiday. Opening this summer in Portugal’s countryside: Quinta Filippa, a 16-room estate that’s not exclusive use but could technically be bought out entirely. Farm-to-table dining, wellness, extraordinary sense of place. With the exception of Villa La Guettière, the rates across all of these are shockingly fair for what you get.
This is a selfish question, but can you give me some highlights for Cabo? It feels like there have been a ton of new hotels that have opened in the last few years, but I don’t know what’s great and what’s mid.
Cabo has exploded with new openings and the quality varies wildly, so it’s worth having someone help you navigate. For families, two tried-and-true properties stand out. Las Ventanas al Paraíso is genuinely exceptional. The programming for children and families is among the best I’ve seen anywhere, with activities that actually keep kids engaged rather than just babysat. And the Montage Los Cabos works beautifully for younger children in particular, with a shallow wading pool that tiny ones love. Both deliver that effortless, everything-handled feeling that you need when you’re traveling with kids.
I have a friend who is getting married this summer; do you have any non-cliche honeymoon destinations in mind?
How much time have you got?! I have a robust honeymoon business and as such, this question is nearly impossible to answer without knowing the couple. I’ve planned honeymoons to Italy, Japan, Costa Rica, Southeast Asia, Australia…
If I were taking a honeymoon today, I’d be looking seriously at Morocco and specifically the three Royal Mansour hotels. Marrakech is the original and still one of the finest hotels on the planet. Casablanca opened in 2024 in a restored 1950s Art Deco palace. It has completely different energy, is more cosmopolitan, but maintains the same extraordinary standard. Tamuda Bay, on the Mediterranean between Tetouan and Tangier, is the beachfront option. Three wildly different expressions of Morocco under one collection.
For a money-is-no-object option to bookmark for late 2026 or 2027: Fregate Island in the Seychelles is reopening after a complete rebuild. Fourteen private pool villas and three estates on a privately owned island. It’s one of the most anticipated reopenings in luxury travel, perhaps ever, and it is going to be extraordinary.
Also, I know this is so last-minute, but do you have any suggestions for spring break travel next month? Is it even possible to do it at this point if you haven’t planned ahead?
The three places where you simply must plan ahead for spring break are Hawaii, Mexico beach destinations, and the most popular parts of the Caribbean. If you have your heart set on one of these you should book that trip as soon as you know your kids’ school schedule. And don’t forget about flights! Everyone wants those coveted Saturday departures and they fill up fast.
One of the biggest trends I’m seeing is families choosing to spend spring or ski week holidays in European cities rather than beach destinations. This winter and spring I had clients in London, Edinburgh, Milan, Florence, Tuscany, Madrid, Seville and Lisbon, to rattle off just a few. My favorite Venice is a foggy Venice — a bit chilly, but moody and magical, and in my opinion far preferable to the steam heat and mosquitoes of summer. In February you can experience Carnivale, and I’m really enjoying planning trips around local festivities like this. The availability is there, the cities are at their most livable, and your kids will come home having experienced something totally new. Skiing in Europe is another amazing experience that will cost you heck of a lot less than a comparable US ski week.
Could we do a round of places you’d suggest as an alternative to more known destinations? Like if you like _____, instead try _____?
Instead of Ireland, try Scotland. Genuinely underexplored, dramatically beautiful, and Edinburgh is one of Europe’s great city breaks. Right now WildLand is doing something in the Highlands that simply doesn’t exist anywhere else in the world.
Instead of Mexico, consider Belize or Guatemala. The cenotes, the jungle and the ruins are all there — without the overtourism or the high nightly rates that have crept across much of the Yucatán.
Instead of Tokyo — or in addition to it — try Seoul or Hong Kong. Seoul is having its biggest cultural moment ever and is still genuinely underestimated by Western travelers. Hong Kong, meanwhile, has quietly become one of the world’s great luxury hotel cities again and is absolutely worth another look.
Instead of Capri, try Sardinia. The island is enormous — something for everyone, from wild coastline and prehistoric ruins to glitzy Porto Cervo and excellent family resorts. A wave of exciting new hotels is arriving in 2026, and Delta is launching a new nonstop from JFK to Olbia. It’s one of the most versatile islands in the Mediterranean and still wildly overlooked by American travelers.
I always ask about your go-to travel uniform, as I know mine evolves over time. What does yours look like these days?
I’m still married to wearing a pant and/or jacket with zip pockets on flights. You’re less likely to lose a boarding pass or lip balm when it’s zipped safely away. Adidas Beckenbauers are still my go-to, as is the Adidas Firebird track jacket, though not together, ever. One or the other, usually the pant, unless it’s too hot outside. Then it’s the Vuori women’s performance jogger or Uniqlo cotton relaxed ankle pants.
My travel shoe must slip on or off easily, so I swear by Birkenstocks of some sort. The Boston works well here, and I prefer a completely tonal option where the upper, buckle and sole are all one color, like this. Thick, comfy socks are still a must and Rototo are still my favorite. One of my packing hacks is to wear things that are almost worn out and leave them behind. Nothing that could be donated or reused, but socks and pajamas fit the bill here.
When in Rome I always hit Schostal, and I now have a lovely little collection of comfy cotton button-downs. They’re known for pajamas, but you can ask about the shirts, and they offer embroidered monograms which I think are so cute and chic. My last few purchases at Schostal have actually been knits, again they’re not always obviously on display, so just ask. I recently picked up the most gorgeous navy double-breasted heavy cotton cardigan that’s become a travel staple. It’s giving Audrey Hepburn vibes when paired with a slim cigarette pant and a ballet flat. Thanks in no small part to your leopard print newsletter suggestions, I was inspired to splurge on these flats, also purchased in Rome, because not only do Italian-made shoes cost less in Italy and Europe more generally, but you get a tax refund on top of that! I find myself shopping less and less in the States and waiting until I’m overseas for exactly this reason.
Also thanks to you, I finally relented and sprung for the Negative Underwear whipped tops. They’re not inexpensive, so I started with just one: your crewneck recommendation. I now also have the henley version, which I personally prefer. They are so versatile that I am now, for better or for worse, ruined for all other long-sleeve travel and layering tops. Fortunately I save a bit of money pairing them with a Uniqlo wireless ultra stretch bralette. (Looks like they’re on sale right now, but this is a carry-over style.)
I made the mistake of not packing a sleep mask on my last trip. I had daytime flights, I thought I didn’t need one. I was wrong. Never not bringing one again. In far north Scotland the days are already getting long, and I could have used it there as well as for napping on those daytime flights. Sadly, my new favorite is not at all cool. I read about it in The Strategist and purchased a rather garish blue color, because anything black I tend to lose or leave behind on the plane. (Click here, feel free to judge.) If you or any of your readers can help me find a version that’s slightly less hideous, ideally from a small vendor, I would be forever grateful.
For outerwear, I genuinely needed a new all-weather jacket and found one in Edinburgh. I saved a not insignificant amount purchasing this Paul Smith x Barbour Bedale waxed jacket in the UK.
Lastly, I don’t know what took me so long, but I finally ordered Bose noise-cancelling headphones in a smoky white color (never black, as mentioned). They’re a bit bulky and therefore mildly annoying to travel with, but so worth it.
If folks who read this want to work with you, what should they know before shooting you an email or giving you a call?
A few things worth knowing before you reach out. First of all, thank you—I don’t take it lightly that you’re considering trusting me with your money and your time.
Like any professional relationship, the fit has to be right on both sides. I work with a deliberately small client base and prefer long-term relationships. Quality over quantity is not a slogan, it’s how my business actually runs.
I work with clients all over the world, so if you’re based outside the US—let’s chat. I’d love to hear from you.
Please be patient if you don’t hear back right away. I promise I will get to you. I don’t always catch messages on Instagram, so using the contact form on my website is the surest way to reach me.
I charge fees for my time and expertise, as do most advisors worth their salt in 2026. I’m affiliated with SmartFlyer, one of the most respected luxury travel agencies in the world, which means my clients benefit not just from my experience but from the collective knowledge and relationships of an extraordinary network of advisors.
The best trips I’ve ever planned are for clients who trust me. Whenever I’ve had someone jump in and make their own tweaks or add a stop that a friend told them they simply must make, something always seems to go wrong. Ask me everything, tell me your non-negotiables and then let me do my job. That’s when the magic happens.
If you’ve read this far and have your eye on any of the hotels I’ve mentioned—here’s a little gift, just for Hillary’s readers. I’ve created a temporary special booking form on my website where you can request a hotel booking directly. I’ll personally VIP your reservation and throw in all of the perks and amenities I can find. Consider it a taste of what it feels like to have a professional in your corner.
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.
As always, thank you for taking the time to read this post. I’m truly so glad you’re here. If you like what you’re reading, please consider sharing this newsletter. (And if you have the time to like it, that would mean a lot to me!) All products mentioned are independently chosen, and some may be affiliate links. Your support is appreciated.
Amazing! Thank you! I just returned from Copenhagen and am dreaming of my next destination. Also, is Rebecca hiring? Asking for a friend…
Best interview yet? Thank you both!