Hot Summer 2024 Travel Tips From The Coolest Luxury Travel Specialist, Ever!
She's a) my friend b) a former LVMH exec who has the best taste and knows her stuff and c) I trust her with my travel $$$ completely, and so should you.
On paper, I might seem like someone who has her summer travel sorted well in advance, but I’m actually shockingly slow to plan. Maybe it’s because I’m the daughter of a pilot, which meant we only did last-minute travel, as we flew standby and would decide where we were going based on same-day availability. Or maybe it’s because I live in a state of functional freeze? (Thanks Amy Poehler and Keke Palmer, for naming without shaming!)
Needless to say, I figured I couldn’t possibly be the only person out there who just woke up and realized that it’s already the middle of June (!!!), and apparently vacation plans aren’t going to make themselves? So I did what anyone in my shoes would do: I turned to my favorite expert for some help.
If you were around last year, you might remember when I interviewed luxury travel specialist Rebecca Bullen for this newsletter. (Here’s a link in case you missed that installment.) Quick reminder: She’s a former luxury fashion executive who worked for the likes of Vuitton, Gucci, and Burberry before pivoting her career to travel in 2019. Rebecca’s incredibly knowledgeable—she’s the one who turned me on to the Rosewood Kona Village, which is where my family went for spring break/a belated 50th anniversary trip for my parents—and has phenomenal taste in all things, especially travel.
I begged her for a little last-minute insight and some overall travel tips, and unsurprisingly, Rebecca delivered on both fronts. So if you’re looking for the new Puglia, wondering if Paris is impossible this summer, need some travel suggestions in the United States, or are simply curious which luxury hotel groups are actually worth it, today’s newsletter is for you!
As always, if you have any questions for me regarding this story, or anything, really, please don’t hesitate to drop me a comment below, and I will answer you! (And why am I prompting you to comment? Because while I love DMs and always try to answer you there, my inbox is messy, and comments here are much easier for me to find and use as source material as I’m working on new things. Also, I love comments; they make me feel seen.)
HK: It’s probably very late to ask this, but what are some of your favorite places for travel this summer?
RB: In Europe I’m very bullish on Portugal and Spain; both represent excellent value for the money. I also love cooler climate Europe; Scandinavia, particularly Norway, as well as Switzerland and Austria. Further afield, I like Indonesian alternatives to Bali, like Sumba and Lombok, paired with a few nights in Singapore.
And Italy, always. This year it’s Liguria for me; this region of Italy has over 200 miles of sparkling coastline, stretching from the French border to Cinque Terre.
I’m also a big proponent of off-season travel. I recently returned from the absolutely exquisite Belmond Maroma, which is located just half an hour south of the Cancun airport. The best rates here are right now and throughout summer. Mexico City is another great destination, with easy nonstop flights from most major US cities.
On that note: Is it too late to book summer travel?
Not at all, unless you have your heart set on a specific hotel or destination, and even then there can be pockets of availability. In terms of quintessential “summer on the Med” European hot spots—the south of France, the Amalfi Coast, certain Greek islands—June is now the month that fills up first. That said, I recently received a last minute request for a family of seven, and was able to find space at arguably the best resort on mainland Spain, Finca Cortesin.
Are there any airports or routes you try to avoid booking for your clients? I feel like the Amsterdam airport was a situation last summer, for example.
Great question and yes, the air travel landscape has indeed changed since last year. Things are going quite smoothly at the major European hubs, you just really need to be aware of airport-specific rules, as well as how much time you need in between connecting flights.
Fun fact: MCTs (minimum connection times) are decided upon by the airlines serving each airport. Their goal is to maximize revenue, so to be blunt, not a lot of actual thought goes into if a 50-minute connection is viable. Spoiler alert: It’s not. They just want to sell seats.
The biggest air travel pain point I’m seeing at the moment is connecting flights within the US. If you’re trying to get to an international destination and can avoid connecting in the US, do so. For example, if you’re going from San Francisco to Venice, Italy, and you can choose between connecting in the States or Milan? Connect in Milan. That way if something goes wrong with your connection, you have options, think: plane, train, or automobile.
When is it the optimal time to book summer travel?
It really depends on the destination and specificity of your request. If you have your heart staying in a sea-view room or suite at Le Sirenuse in June, let’s talk now for summer 2025. Same goes for European river cruises and some of my favorite yacht charters, like Blue Deer, as an example. Swoon.
Northern hemisphere summer is peak migration season in Africa, so safaris should also be considered a whole year in advance. Generally speaking, February is a good time to make your summer travel plans but again, if you’re willing to be more flexible, you can call me today and I can have you on a plane next week.
Last year, we talked about the lesser known Italian islands, a handful of places on the French coast, and one of my favorite places in the world, Australia. What’s at the top of your must-go travel list for 2024?
I’m really glad that you brought up Australia, and while I may be biased could not agree more. It’s also one of the most misunderstood places from a travel and tourism perspective, most likely because relatively few people have actually been. Did you know that the flight from Sydney to LA is just 2 hours longer than LA to Rome? Two hours; that’s it! (Shameless plug for having someone actually from Australia plan your Australian adventure.)
My must-go travel list for 2024 and beyond? I mentioned the Liguria region of Italy. Genoa blew me away. For the first time in a long time, I felt like I was back in the Italy I fell in love with over 25 years ago. It’s not slick, it’s not Americanized, and not everyone speaks English. (For me, part of the joy of travel lies in those sweet moments when you’re trying to communicate with a shopkeeper, despite the language barrier.)
The recently opened Palazzo Durazzo is reason enough to visit. It took seven years—seven!—for architect and co-owner Emanuela Brignone Cattaneo and interior designer Cesare Barro to lead the renovation of this 17th century palazzo. The Ligurian coastline is charming village after charming village. I especially loved the town Laigueglia and the vibe of Hotel Windsor. The latter’s restaurant and bar are phenomenal.
Also in the “run, don’t walk” category? Namibia for its otherworldly landscapes and remoteness of it all. Zannier Hotels have two luxury tented camps in Nambia that pair nicely. Also noteworthy: Jack’s Camp in Botswana, and the historic Rovos Rail, which you need to book one to two years in advance. Since we’re talking Africa, you can add my favorite Nile cruise, Nour el Nil, to the list. I am very much hoping that I’ll get back to Egypt in the coming year. It’s the most magical, memorable place I’ve ever been. The more you travel, the more you realize that a lot of the stereotypes we’ve been fed just don’t track, and that’s a great thing.
Are you still getting some of the standard summer travel requests—Italy, Portugal, Paris—or are there some newly popular places everyone’s asking about?
I’m getting more far flung international requests. Lots of Asia: Cambodia and Vietnam, and Singapore and Indonesia. African safaris and Morocco. Lots of Morocco. The hotel scene beyond just Marrakech is really booming. Villa Mabrouka in Tangier, La Fiermontina Ocean outside of Tangier, and Royal Mansour Casablanca are all newcomers. In Marrakech, I’m really excited to check out Riad Yasmine when I’m there in September.
It seems that everyone overestimated demand for travel to France this summer in advance of the Paris Olympics, which kick off on July 26th. Consequently I’m seeing some amazing last-minute airfares and sane hotel rates for the weeks prior and remainder of the year.
You suggested Umbria as an alternative to Tuscany last year, which I loved. What are some other less-obvious options that you really like?
South of Liguria you have a beautiful stretch of Tuscan coast. In Porto Ercole, Hotel Il Pellicano and, because Pelli is always booked, the brand new La Roqqa as an alternative. The island of Ischia is still a wonderful alternative to Capri. Along the Côte d’Azur I’ve always been fond of Nice. With the Hôtel du Couvent opening this week you now have another reason to make Nice a stop on your south of France itinerary. Mark my words: this hotel is going to be a game-changer for Nice.
The Balearic Islands, which are off the coast of Spain, are awesome. Not just Mallorca, but also Menorca, Ibiza, and Formentera. Yes, that Ibiza. The northern half of the island is everything the party side is not: Yoga and hiking, wellness and agriturismos, and for luxury you have Six Senses Ibiza.
We are similar in that we prefer smaller, boutique hotels, but there are also incredible gems within larger portfolios and corporations, like the Rosewood Kona Village. (You mentioned it last year, then booked me and my family there for spring break, and we loved it.) What are some of your favorite, extremely special hotels on your list right now? Big or small!
I’m so glad that you asked. Clearly I have a soft spot for boutique hotels as well as family-owned businesses and passion projects that people pour their hearts, souls and savings into, but there are a lot of standouts in the larger hotel groups. In fact, I think it’s more difficult to excel when you’re dealing with hundreds of rooms and the complexities of a large hotel or parent company, not to mention shareholder accountability.
The St. Regis Venice is phenomenal, and worth every penny. They have the most WOW suites in town, amazing staff and service, divine bars and restaurants. Everything is thoughtful and considered, for example, each of their 10 or so signature cocktails is served in a separate, custom-designed Venetian glass.
On Lake Como, the Mandarin Oriental took my breath away. Again, it ticks all the boxes. It is absolutely neck and neck with Passalacqua for me. Coincidentally (or not) both of these hotels have ties to Bellini, the Italian opera composer. Speaking of Mandarin Oriental, their all-villa Marrakech resort is probably my personal favorite in a city full of phenomenal accommodations.
How do you feel about home rentals for bigger groups, families, or multi-generational travelers? Or just in general?
I book a lot of extended family group travel and am a big advocate for home or villa rentals, with one caveat: It’s not a vacation if the same people who do the cooking and cleaning at home are doing it on holiday. You need a staffed rental, and daily housekeeping. I work with a great portfolio of fully vetted, staffed homes and villas around the world.
Once you get into needing four or more bedrooms it just makes financial sense to book a home or villa. Heck, off of Dubrovnik, you and up to 11 of your friends can rent an absolutely breathtaking restored 15th century Franciscan monastery called Lopud 1483, fully staffed, for the same cost as five fancy hotel rooms.
I know we covered some of your favorite travel essentials last year—your airplane hydration kit, go-to packing cubes, and a great carry-on, for example. Has anything new made your list? And what are your feelings on AirTags?
I literally just had clients in Spain who’s luggage didn’t make their connection. They knew this the moment they landed and the AirTags were instrumental in helping them track down their luggage. So big yes to AirTags.
I’ve always included a swimsuit in my carry-on bag, but the next time I have to check I’m going to include a fresh set of undergarments, too. I think a good rule is to make sure your carry-on bag has everything you’d need to get through 24-48 hours, if your checked bag goes missing. Important things should be in that bag, like daily medications, for example.
Within the States, do you have any suggestions about great places to visit or hotels that are truly special and worth it?
I love that you bring up the idea of “is it worth it?” I always ask myself that question when I’m planning a trip: if this was my money to spend, would I spend it on this resort/experience/flight?
Within the US, I love The Lodge at Blue Sky in Utah, the Mayflower Inn in Connecticut, and relative newcomers Stanly Ranch and the Inn at Mattei’s Tavern, all of which are Auberge Resorts. The group is really on to something with the breadth of destination-specific activities, experiences, and dining on offer.
Last summer I popped down to Florida to experience the Four Season’s four hotels and resorts in the state, and I really, really liked Ft. Lauderdale; it reminded me of Miami 20 years ago. The Four Seasons here is a new build that opened in 2022, and I flipped for the design and dècor, which is nautically inspired, but not in a literal way. It’s more about textures and shapes and finishes and furniture. I plan a lot of honeymoons and a common request is that folks dream of staying in a Four Seasons property. Well, here’s one on our home turf at a very reasonable price point (for now).
Do you have a go-to travel uniform?
You know I do! Since I try to carry on as often as possible I’m always in a layered look, especially in the winter months. Underneath it all I’m wearing an Adidas track pant or Uniqlo Cotton Relaxed Ankle Pants ($29), a comfy tank or t-shirt (James Perse preferred), under the softest oversized Acne Studios chambray button-down shirt that I’ve had forever.
Shoes are Converse All Star High Tops ($65), Superga 2750 Cotu Sneakers ($70), or Birkenstock Milano Sandals ($180) with socks of course, depending on the season, destination, and occasion. My new travel hero piece is a long, packable down vest from Uniqlo. It’s a vest, it’s a jacket liner, it’s a pillow or blanket!
I always bring a scarf, heavier cashmere (Louis Vuitton or Burberry) in winter and lightweight cotton (Gucci or Uniqlo) in summer. I’m lucky to have collected some really nice substantial scarves during my former career. Big, dark sunglasses are clutch for rolling off a red-eye flight and managing to look chic. I stumbled upon Jimmy Fairly shops in France a few years ago and their affordable frames are now my go-to. [HK NOTE: Jimmy Fairly x Reformation is a pretty great collab, if you want to check out the brand Stateside.]
Any suggestions on what to pack so that you don’t stand out as an American tourist?
Less is more is a great rule of thumb. Think minimal, well-cut basics. Baggy or ill-fitting clothes shout: “I’m an American tourist,” as do cargo pants or cargo shorts (sorry, Dad). American professional sports jerseys as daywear are also pretty naff. Shoes can also scream “I’m not from here!”, so keep your sneakers simple, and think about whether the footwear you’re packing makes sense for your destination. High heels on the cobblestone streets of Rome? You can leave them at home.
One of the great things about travel is you often can spot trends ahead of time, based on new hotel openings and flight routes. As you look ahead to later this year and into 2025, what are you most excited about?
When this industry effectively shut down for several years—especially international travel—hospitality folks had a chance to daydream. What we’re seeing now is the consequence of that, and also a reflection of what travelers want now: Space. Fresh air. Genuine connection with people or nature. Having experiences and making memories that will last a lifetime. Travel feels special again because the trend is very much away from cookie-cutter experiences.
Slow travel—be it fewer stops on an itinerary or journeys by barge, boat, rail—is definitely trending. I am very excited about La Dolce Vita Orient Express, which launches early next year, as well as the expansion of Ponant’s small ship program, which will allow for a limited number of guests at one time to visit places you can only reach by boat, such as the Society Islands in French Polynesia.
All-inclusive options continue to be popular, and I expect this space to grow. Forget the cheesy versions that might come to mind; the new versions of these resorts are 5-stars all the way. The Brando and Nihi Sumba are two of the best.
I had a very high percentage of travelers spend the winter holidays in European cities visiting the holiday markets in Germany and Austria, Paris, Venice, Florence and Rome, and Athens. In other words: Places that are either too crowded, too expensive, or too hot in summer months.
Can you walk us through a trip you planned that you’re particularly excited about?
I’m always excited to plan someone’s first time in Italy/greatest hits trip: Venice, Florence, Rome. It never gets old because I have literally never planned the same exact itinerary twice. I love playing matchmaker in setting each set of clients up with the perfect accommodations and combination of experiences and activities for them. It’s also not lost on me that many folks may get to Italy once or twice in their lifetime.
I’m excited about an upcoming honeymoon that I designed in two acts. Act one: The Italian countryside, starring the Rosewood Castiglion del Bosco and Lupaia. Act two: The sea, starring Hotel Il Pellicano and her sister property, La Posta Vecchia.
As for myself? I’m excited about an October trip to Greece. I’m attending a niche trade show called Emotions in Athens and have bookmarked some very unique and exciting spots to visit on the oft-overlooked Grecian mainland. On the island front, I’m planning to hit some of the lesser known Cycladic Islands, as well as Rhodes.
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.
Thank you Hillary! This was inspiring and you ask the best questions a la Second Life. Endless respect for your interview skills and curated guest list. Brava!
Just want to share that I’m currently packing for my summer holiday, and what did I do to prepare?? I went through your articles for tips on travel and what you’ve packed. Your articles are my bible. Thank you!! ❤️