Hot Summer 2025 Travel Tips (& Beyond!) From The Coolest Luxury Travel Advisor Ever!
It's a long and juicy read, and well worth your time. Also: Book your travel with Rebecca. It's truly an 11/10 experience.
Before we get into today’s story, I just wanted to thank everyone who left me a comment, sent me an email, or texted after last week’s newsletter. Being vulnerable on main—about the difficulty I feel traveling for work, especially with a little girl who hates it when I leave—about mom stuff is not my favorite thing, and I always get nervous about the judgement.
I shouldn’t have been worried; not only did so many of you come through with great ideas for how to make my work trips easier for my kids, you also just were incredibly understanding about this part of parenting. That it is both a privilege to be able to have a career I love and get to travel to cool cities for work, and also that it breaks me into a thousand pieces every time I have to leave my family. One friend suggested talking my kids through it one day in advance—but not before a separation like leaving for school or going to bed—so I’m going to try that this coming week, ahead of yet another work trip. Yep, I’m off to New York on Tuesday for client meetings, Marie Claire’s first Power Moms event, and I’m hosting a shopping event with the iconic stylist, consultant, and fashion exec Tiffany Reid on Thursday, so there’s a what-I-packed story and kid-coping update to come.
Also: I am aware that next weekend is Mother’s Day, which longtime readers know is not a holiday that resonates with me. (I’m lightly unpacking why it’s not a thing for me, but haven’t really done the work. I wonder if it would mean more to me if I didn’t have a really great co-parent in my husband? That’s not meant to be triggering! Just a question! I also wonder if it doesn’t resonate because I don’t do a lot of the trad mom things and feel quite distant from the way culture portrays motherhood? So therefore maybe I don’t deserve it and am rejecting the holiday because I don’t feel worthy? Woof, this is getting messy; I’m going to stop abruptly!)
That said, my own mother really likes the holiday, so aside from time together, which we are doing later in the month, does anyone have any great ideas for a 70-something mom? Oh wait, I think I just got it: Mom, if you’re reading this, how about we get a closet organizer for you? And I can come down and supervise/handle it?
Okay! And now the main event!
At this point, I feel like she barely needs an introduction, but in case you don’t remember, my dear friend—the kind and cool Rebecca Bullen—is an incredible fashion exec-turned-luxury travel advisor. In addition to being my guide for all things travel, she’s also a Conde Nast Traveler Top Travel Specialist, and has been kind enough to share some incredible insights with this lovely community over the last few years. When I interviewed Rebecca for this newsletter two years ago, I learned so much, an education that continued last year with her summer travel tips and tricks. This year, we’re doing our annual check-in chat a bit earlier, in the hopes of helping you all travel better this season, and frankly all year long. And now, with no further ado: Hot summer 2025 travel tips from the coolest luxury travel specialist ever!
Where are some of your favorite recommendations for summer travel this year?
First, Say hello to the summer of Sicily! Finally, nonstop flights from the states are here, which makes it easier to visit not only Sicily, but also the adjacent Aeolian Islands and Pantelleria.
Paris is back after last summer's collective zeitgeist kept people away from the city (and France more generally) due to concerns about overcrowding surrounding the Olympics. Pair Paris with something more unexpected, like the Loire Valley or the southwest of France and beaches on the Atlantic coast.
Instead of just focusing on a trip to one country, think in terms of geography. Spain pairs well with Morocco. Bavaria and Munich with the Dolomites and Venice. Cote d’Azur with Genoa and Liguria. These make for really interesting itineraries.
On that note: What’s the ideal time to book for the big vacation times? When should folks ideally book for spring break, summer travel, and end-of-year holidays? (And yes, I know there are always going to be last-minute travelers like me!)
The less flexibility you have in terms of the ‘where’ and ‘when’ the earlier you need to book. Same goes for larger families or groups who have very specific requirements when it comes to sleeping configurations.
End-of-year is the stickiest because unlike spring breaks or summer there is only one end-of-year. So think about what we call ‘festive travel’ now. Want to experience New Year’s in Sydney? Visit Santa in Finland? Ring in the New Year on a Nile Cruise? Let’s talk now.
The sweet spot for spring break? January to early February. The toughest part about spring break travel is flights, because everyone wants those coveted Saturday or Sunday flights.
Summer travel has the most flexibility of the three. If you’re open to new ideas or destinations and do not have to be somewhere on a specific day (I am thinking weddings, honeymoons or celebration trips) then the world really can be your oyster.
In terms of domestic vs international and continent-to-continent here are my CliffsNotes for the remainder of this year and early 2026 at some of the most requested destinations.
USA: Inbound arrivals continue to trend down to last year. If this holds up, you’re going to see more last-minute deals on places like New York, Florida, and California as the summer approaches because we’re missing those international visitors.
Europe: Book now for summer, if you haven’t already. That said, you know I love a last-minute request and after last summer’s interview, I pulled off some truly insane feats of travel planning for a few of your readers, like last minute Capri in July.
Africa: Safari you’re after? 12-18 months.
Asia: Travel to Japan is booming and shows no signs of slowing down. If you want the full nuts-to-bolts luxury travel experience and English-speaking guides you need to book 10-12 months out.
Last year, you mentioned La Dolce Vita Orient Express was opening. I saw that you got a sneak peek of it! Is it what you expected? Who is it ideal for and who should book something else?
Yes I sure did! The Dolce Vita Orient Express train exceeded expectations in ways I didn't anticipate. The elegant, private pre-departure terminal in Rome set the tone, it was just so pretty and just the right amount of lively for a morning departure. The level of detail here and on board is just staggering. It’s definitely a more grown-up experience that I’d recommend to couples, friends, and for celebrations or milestones. Journeys are one-to-two nights and the trains travel on stretches of track that take you to corners of Italy that really make you feel like you stepped back in time.
Last month, the first hotel from the Orient Express group opened in Rome. Located a stone’s throw from the Pantheon is the Orient Express La Minerva. French-Mexican wunderkind Hugo Toro has designed interiors that exist in perfect synergy with Rome's warm, distinctive light—soft terracottas, aged ochres, and mellow amber tones flow through spaces that feel simultaneously fresh and timeless. Later this year, their second hotel will open in Venice. I’ve been privy to some recent pictures and videos as it’s coming along, nearing the end of a seven-year renovation. It’s really going to be something, a real work of art from top to bottom, and located in my favorite neighborhood of Venice, just far enough from the crowds of San Marco.
And what are we skipping this year? Is Rome a no-no because of all the construction and the Jubilee 2025?
On the contrary, I might argue that 2025 is one of the best years in recent memory to visit Rome. You might opt to avoid key dates on the Jubilee calendar, but otherwise Rome has never looked better. In 2024 the entire city got a glow up. The past few years have seen a swath of new hotel openings. Six Senses Rome, Bulgari Roma, and Palazzo Talia are a few that deserve mentions. One of my favorite times to visit Rome is over New Year’s; I love the relatively temperate winter in Rome
I always ask you this because it always changes, but here we go again! Are there any airports or routes you try to avoid booking for your clients? For example, Amsterdam was a no-no a couple of years ago, right? And I feel like you’re less bullish on LHR in this post-Brexit world, right?
Correct. Connecting in London isn’t what it used to be since the UK is no longer part of the EU. New for 2025 is the UK visitor visa and the UK transit visa. Both are quick and easy to apply for but still, just one more level of complication.
The number-one airport to avoid transiting this summer? Newark. Number two: JFK. They’re really struggling with FAA staffing issues, particularly Newark. I would avoid connecting here at all costs, and avoid departing Newark if you are trying to connect elsewhere. I rolled the dice en route to Singapore, because I found a points redemption, and sure enough we were delayed enough to make me miss my connection in Heathrow. Yes, the same Heathrow I said to avoid. Do as I say, not as I do. The issues with JFK have more to do with slot control, so if JFK is the only available connecting option you need to allow three hours between flights.
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!
Rascal Voyages all day long, which is essentially a five-cabin floating villa. I could wax poetic about my recent experience for hours. The custom-built phinisi yacht, the food, the water and wildlife and biodiversity, and the people. Most of all, the people. I miss the friends I made on board and I miss the crew dearly.
Capella Ubud. Designer Bill Bensley said this tented camp built into the Balinese jungle is “not for everyone” because if he tried to design to appeal to everyone it would result in creating something that resonates with no one, and I really fell in love with this idea! With so much choice out there, why on earth wouldn’t you want to stay at a hotel that’s not for everyone, yet perfect for you? Capella is a name you might not be familiar with—yet. Other standouts are the Capella hotels in Sydney, Singapore, Hanoi, and Bangkok.
When I’m in Cairo—and I’m finding myself spending more time here, especially during the arctic northeast winters—my home is the Immobilia apartments. They’re part of a collection of properties run by Egypt Beyond, each of which is extremely special. Rick Owens described sister property Al Moudira in Luxor as “the closest thing I could find to the Chateau Marmont of the late eighties...unassuming and grand at the same time.”
In Portugal I love the Christian Louboutin-designed unique and quirky Hotel Vermelho, the brand new The Largo in Porto, and Sao Lourenço do Barrocal. In Paris I love the Plaza Athenee or Le Meurice for fancy, as well as Chateau Voltaire (still) and Hotel Balzac, which are slightly more low key by comparison.
There’s something homegrown and special happening on the east coast of Australia from Byron Bay south. Old hotels or motels are being given a new lease on life and reopened as boutique boltholes. The Atlantic and The Sunseeker in Byron are faves, as is Il Delfino in Yamba, about 90 minutes south of Byron.
In Italy I continue to pine over Palazzo Durazzo Suites in Genoa (and Genoa more generally) and the 12-room, adults only (14 and up, technically) Vocabolo Moscatelli in Umbria. File both under “stay here NOW.” Two other favorites, coincidentally independently owned by young couples, as is VocMos, are Lupaia in Tuscany and Castello di Vicarello in Grosetto, which is still Tuscany, but closer to the sea. Also Villa Igiea in Palermo, Sicily. I could die happy at Villa Igiea. It’s a Rocco Forte hotel, all of which are unique and just the best, as are the people who work for the company.
Are there any new hotels or flight routes that have caught your eye? Seems like Barbados is becoming more accessible, in terms of flights, for example.
Yes, heaps! I don’t think I’ve seen this broad of an expansion in nonstop international routes in recent years. The biggest news here is Sicily, now accessible via nonstop flights from Newark to Palermo on United or via JFK on Delta. Nonstop flights to Puglia are here, too. Neos Air offers JFK to Bari and JFK to Palermo.
I’m also excited about the expansion of nonstop options to Marrakech. Last fall United launched service from Newark and Delta service launches from JFK in October.
Looking ahead, American is going all in on nonstop service to Hawaii. Later this year they will launch Chicago to Honolulu, Dallas to Maui, and Dallas to Kona. In terms of late 2025 and winter 2026, these seasonal route announcements are rolling in now, but look for more nonstops to warm weather destinations in the Caribbean and Central America.
Let’s talk family trips: Where are some of the best, most worth-it destinations for traveling with young kids and/or extended family?
In the states I find that dude ranch or dude ranch adjacent destinations and resorts are family crowd pleasers. On the fancier end of things I still love The Lodge at Blue Sky, as well as Brush Creek Ranch, and Vermejo, a Ted Turner Reserve. Under Canvas offers well-priced glamping near national parks. Tropics more your vibe? Hawaii and the Caribbean are better priced during the less popular summer months.
Staycation in SoCal? The Beverly Hills Hotel offers VIP Kids check-in with their very own Pink VIP credit card they can redeem for free soda/milkshake or juices at the Fountain Coffee shop.
For older kids learning about ancient history and civilizations, family trips to Egypt, Greece, and Italy are timely and memorable. I can guarantee that your family will be talking about the time they saw the pyramids for years to come. Paris is amazing for kids! There are heaps of cool kid-tailored activities here. Think treasure hunts at the Louvre, mini sculptor for a day at the Rodin Museum, and sidecar tours of Montmartre.
Most people think of an African safari as an adult trip, but I beg to differ. Picture this: Your children's (or grandchildren’s) eyes lighting up at their first glimpse of a wild elephant, or the infectious excitement when spotting a lion pride lounging under the African sun. An experience like this is absolutely transformative for kids. I’m especially partial to Singita properties, not just because of what they are (intimate, luxurious, special) but also because of what they stand for. It’s a brand that prioritizes low impact, high-value tourism along with conservation and community development.
Anything specific that you like to do when booking a family or extended family? Are there specific places that do a really good job at catering to larger groups without feeling like a Disney resort? (Don’t come for me on Disney!) For example, I know the Montage hotels have multi-room residences for groups or families, and the Rosewood hotels often have suites with connecting bedrooms.
The key is understanding that family travel is about creating connections while respecting individual needs for space and preference. I always book at least one "wow" experience that becomes the family story for years to come. Over-scheduling can lead to cranky and tired kids and grown ups alike, the enemy of family harmony, so downtime and staggered morning starts can be key. I work with guides who are not only experts in their fields but able to read the room and adapt accordingly. This is one of the big differences between a run of the mill tour guide you may find online and the professionals I trust with my clients.
The Four Seasons Walt Disney World Resort is one of the best family-friendly resorts I can think of. I took my sister and nephew last summer, that’s how highly I think of it. Four Seasons generally does a fantastic job with family-friendly options, particularly for families with younger children. They deliver a superb consistency of experience.
Rosewood is another group with wonderful family-friendly resorts. The best Little Explorers Clubs are at Rosewood Phuket and Rosewood Mayakoba. Rosewood Castiglion del Bosco is magical for families and grown ups alike, and really shines at the holidays when local artisans converge on the main square to set up a traditional Christmas market. For outdoorsy Alpine pursuits such as hiking, biking, kayaking, and swimming, I love the new Rosewood Schloss Fuschl, housed in a restored 15th century fairytale castle that graces the banks of Lake Fuschl, Austria.
Villas and home rentals can also be a great option for families traveling together. I work with a handful of carefully vetted rental companies that provide both fully staffed and self-catered options. When booking for a family or extended family (or friends who are like family) I really take the time to get to know each and every traveler profile so that I can customize absolutely every detail.
Let’s talk solo travel: Do you have any go-to recommendations for women who love to travel and want to do so alone and safely? And any places you’d avoid right now? A reader specifically said: “I want to feel safe, have fun, enjoy a high-end experience, but not be lumped in with the honeymooners or families, nor in a crazy nightlife spot like Ibiza.”
I get questions related to solo female travel a lot, and I never quite know where to start because I have so much to say on the topic. I actually prefer to travel alone. The summer I turned 20, I did the Eurail Pass thing on my own and never looked back. This was the late 90s, so no cell phones (let alone Google maps), no influencers, and no Instagram, of course. I did however have a yellow Walkman and a few cassettes on repeat, boundless curiosity and awe, and a healthy sense of intimidation. It was my first time in Europe, and I was hooked.
That summer I figured out how to get from A to B with a paper map, and by talking to people I met. The thing about solo travel is that you’re never really alone, are you? You can do what you want, when you want. You are 100% guaranteed to make new friends if you choose to. If this sounds intimidating, start small. Try having dinner at a restaurant alone. Perhaps take a trip somewhere familiar in your own state or country first.
In terms of international solo travel, again, don’t go from zero to full third-world language-barrier territory if you’ve never even tried the UK, to give an easy example. Start small and go from there. One thing that makes me more comfortable is doing a ton of research in the lead up to visiting somewhere new. I do this anyway, but on steroids when I am alone. I usually pick up a Lonely Planet guide and read it cover to cover (you can skim). Then I watch any and all relevant Anthony Bourdain episodes on the topic, as well as Rick Steves. I binge documentaries and occasionally YouTube videos. I do my homework.
In terms of safety, this might be obvious to some but I always dress low key. Always. I never drink too much alcohol, again seems obvious, but maybe not? I also tend to keep to myself at night if I am feeling a place out. The first time I went to Egypt I stuck with American chain hotels and I hung out at the hotel at night, for example. Now I’m more comfortable, but that’s just one example of how I ease into things.
I went on Rascal Voyages’s Raja Ampat cruise alone and that would be the perfect way to get your feet wet! Something self contained. Safaris also make for great, safe solo travel. Adventure, but self contained.
There aren’t many places I would avoid as a solo female traveler that I wouldn’t avoid more generally. Did I miss out on some international nightlife when I was younger? Probably. Do I care? Not a bit. Travel is the biggest gift. My world and my worldview and my life have all been enhanced by the places I’ve seen and experienced and the people I’ve met, many of whom I wouldn’t have engaged with if I had a friend or family member in tow.
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 (or in addition to) Bali, try Sumba. Or Flores. Or Komodo or Raja Ampat with Rascal Voyages.
Instead of Kyoto try Kanazawa. it's honestly criminal how little attention it gets.
Swap Bora Bora for the Cook Islands. Same French Polynesian paradise, actual overwater bungalows, but at half the price.
Love Whistler? Consider Queenstown. All of the adventure, open spaces and jaw-dropping natural beauty plus world class wine tasting in the Central Otago.
Everyone's obsessed with Costa Rica for wildlife and beaches, but Panama gives you the same cloud forests, the same surfing, and honestly better coffee at a lower price point.
Every time I book one of these alternatives, my travelers come back saying, "Why doesn't everyone know about this place?" And honestly, that's exactly why they're still magical. I am personally passionate about steering people away from places that run the risk of being “loved to death” or at least encouraging them to visit off season.
I always ask about your go-to travel uniform, as I know mine evolves over time. What does your look like these days?
Like you, I try to carry on whenever possible, so depending on the season you’ll find me wearing a coat. Last year I splurged on Toteme’s signature wool cashmere coat which is incredibly versatile and doubles as an on-board blanket. In terms of versatility and price per wear, this has been a real winner. I’m still devoted to my Adidas Beckenbauer track pants and their handy zip pockets. I’ve also been traveling in ultra soft and comfy slim-fit Vuori performance joggers. They run really short so I go for the long version, and I’m barely 5’6”.
I swear by Uniqlo ultralight packable down for bouncing from freezing to tropical destinations, and my new Uniqlo hero piece is their AIRism UV protection zip hoodie, also very packable. Slim-fit cotton t-shirts are still my go to. My trusty James Perse tees are a few years old now and holding up well, but I also love MUJI men’s seamless t-shirts. The XS is a bit long, but still slim enough to look tidy, and they cost about $9.
I’m a creature of habit when it comes to footwear. In summer months I’ll often wear my canvas Superga 2750 Cotu classic sneakers. These run a bit big, FWIW. I rely on two other pairs of footwear for summer travel: a Birkenstock Arizona or Madrid Big Buckle or a pair of my most beloved Piedaterre Venezia slippers. They pack practically flat and are so chic and versatile.
Accessorizing is key in avoiding overpacking. I always travel with a crossbody bag. Clare V Grande Fanny is a good option. I pack one bag and a few fun bag straps for different looks. Mansur Gavriel’s Moon Sling bag is a bit more elevated and sleek. I have a plum leather version that is surprisingly versatile, and am coveting the cute rafia version for summer.
It feels like there are more elevated airport travel options these days, between companies like PS and the Windsor Suite at LHR via VIP Assist. How do you feel about these services? Any that are worth it? Are there some that feel expensive for what they offer or great value for the service?
PS (Private Suite) at LAX is genuinely revolutionary. You essentially get your own private terminal with TSA screening. PS is also available at Delta’s hub in Atlanta and coming soon to Dallas and Miami. Windsor Suite at LHR is more traditional luxury – think expedited immigration, private lounges, and dedicated hosts. These options are pretty pricey, and sometimes a customs greeter is the way to go.
I recently had a connection in Jakarta that involved changing terminals. I wouldn't ordinarily have relied on a greeter for myself, traveling solo with a long connection time, but following a friendly face who was fluent in English through an unfamiliar maze of terminals in my jet-lagged fugue state was a sanity saver.
Generally speaking, these services shine for tight or complex connections, traveling with family, or when privacy matters most. But here's the savvy traveler's approach: Assess your actual needs versus the bundled luxury of a PS or Windsor. Early morning flight? You might not have time to enjoy all that they have to offer. Why pay for what you don't need when à la carte greeter options can give you exactly what matters most?
What about luggage concierge services? Any you like or recommend?
Luggage concierge services are phenomenal for pre-shipping things like ski gear or golf clubs. Not only are these annoying to check and wait for on the receiving end, but if they don’t show up you’ve kind of blown a day or two on the slopes or green while you wait for them to show up. I rely on Luggage Free and their services are not nearly as pricey as you might think.
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.
I’ve loved these Rebecca interview issues - pragmatic tips and a helpful pulse on the travel space mixed in with aspirational (for me) hotels. The dreaminess is part of the appeal!
Always look forward to the reoccurring series! Thank you Rebecca!!