Summer Travel Plans from the Coolest Travelers I Know
I tapped my favorite travel insiders to find out where they're headed this summer...
Everyone has that friend they turn to for travel advice. I like to think I’ve become that friend for you—even if we’ve never met, I’ve loved getting to connect with so many of you in our Substack chat. As for me, I feel lucky to be surrounded by friends with deep, firsthand knowledge from years working in the travel industry—plus impeccable taste, original points-of-view, and a real gift for storytelling—so many of my best travel insights come directly from conversations with them.
The six friends I’ve asked to share their summer travel plans are my version of that friend. From far-flung adventures like horseback riding through Mongolia and trekking through Transylvania, to new discoveries in some of our favorite destinations—think secret Italian islands, a still under-the-radar coastline that’s about to blow up, a ‘floating boutique hotel’ (what!?), and a Greek island B&B that came up twice—here’s where the coolest travelers I know are headed this summer…
Yolanda Edwards, Founder of Yolo Journal
Does Yolanda even need an introduction? With a career spanning over 25 years—including roles as Executive Editor at Martha Stewart Living and Creative Director at Condé Nast Traveler—she launched her own editorial empire in 2019 with Yolo Journal, a masterfully curated, encyclopedic print magazine (and website and Substack!) that has become something of a travel oracle for discerning travelers around the world. Across her various platforms, Yolanda shares personal stories, aesthetic inspiration, and authentic travel experiences—think of it like a dreamy travel scrapbook for well-traveled globetrotters. Her content offers a beautifully curated, visually rich, and deeply personal take on travel, showing how cool people travel, not just where they go.
Follow Yolanda’s lead: “During the summer, I usually travel a little less than I normally do—it’s more complicated with everything being booked up and crowded—so we end up staying in the sleepy region of the Médoc (the Bordeaux wine region), where we’ve had a house for many years. When I do travel, it’s usually because I’ve been invited to something, or it’s my husband’s birthday, and he always wants to be in a hotel for it. This means I have to get very strategic—everything is too expensive or has no room, and I don’t want to spend precious summer days being annoyed with crowded airports and beaches and all the things that come with summer holiday season. This particular summer our daughter graduates from college in Edinburgh, so we’ll head there for several days, staying in Leith—the port neighborhood which is the least touristed part of the city, and attracts a lot of young creatives who have opened up well curated shops and cafes. For my husband’s birthday, we’ll head to Ischia for several days and stay at Mezzatorre, flanked with a couple of days in Naples, and at the end of summer, we’ll go back to Patmos to see my dear friends who own Pagostas, a tiny dreamy hotel. Because it’s such a challenge to get there (Patmos has no airport) we’ll probably start in Leros or Rhodes, or maybe we’ll try Bodrum, which has a ferry to Patmos daily that only takes an hour and a half. This I learned from my friend who lives in Turkey—you won’t find this on the ferry schedules online!”
David Prior, Founder of PRIOR Travel
There’s sooo much to learn from David, whose journey began with a scholarship to the University of Gastronomic Sciences in Italy, where he had the chance to work alongside icons like Alice Waters. From there, he carved out a career in journalism, contributing to publications like Condé Nast Traveler and Vogue Living. Over the years, David’s built a vast global network and became known for his fresh, thoughtful approach to luxury travel enriched by his infectious curiosity and natural gift for storytelling. In 2018, that vision led to the creation of PRIOR, a luxury travel company that blends the rich storytelling of a travel magazine with the intimacy of curated and deeply immersive journeys—from bespoke personalized trip planning to immersive group trips led by local experts. He’s truly one of the few people I’d blindly let plan any trip for me!
Follow David’s lead: “I’m mostly based in Milan this summer, which makes Europe a dartboard for me. It means I’m perfectly positioned to escape when I like. It gets hot, like an oven hot, so I’ll be heading to Greece for a week—I just haven’t decided which island yet. Ironically I’m personally very last minute. I’m leaning toward the Ionian Islands or maybe the Sporades because I like my Greek islands with a bit of green. That said, I will finally make it to Patmos this year. Pagostas, because of you, and all the other chicest people love it. My best friend, the chef Skye Gyngell went in October last year and she’s my favorite person to travel with and we have basically the same taste. Then in August, I’m going to Australia. I’m hoping to get to Garma festival, the annual indigenous gathering in Arnhem Land. It’s political, it’s cultural and it’s important. I’m really interested in how travel can build communities and by shifting the narrative internationally it might change some things domestically. The world is chaotic, nothing is guaranteed, and I just want to go because life is short. This year has been a lot about doing things I’ve been putting off. Mongolia’s been on the cards for years. At last, I’ll be going there at the end of August—hosting a PRIOR trip—and then to Japan in September. I want to get out of the cities [in Japan] and into the countryside to meet makers and farmers, but also, frankly, want to go see the architecture at the World Expo in Osaka. And finally, I’m going to Dar Ahlam, which I’ve shamefully never been to. Thierry Teyssier, who created it, is someone who I admire, and he’s been telling me I have to come for ages and so I’m going. Finally.”
Ari Heckman, Co-founder & CEO of Ash Hotels
If you’ve had the privilege to stay at an Ash hotel, you’ve already had a glimpse into Ari’s mind—where his attention to detail and deep love of romantic, historic spaces come together to create one of the coolest boutique hospitality brands around. Ari co-founded Ash, a hotel company defined by its commitment to storytelling through design, and in my opinion, it has set a completely new standard for modern hospitality. Ash is known for their distinctive, cinematic hotels (which I’ve written about many times) that celebrate local culture and architecture by repurposing landmarked or old buildings and designing evocative spaces that reflect the unique history and spirit of their location, making them feel both nostalgic and contemporary. Plenty of hoteliers will try to sell you this dream—but few pull it off as seamlessly as Ash. That’s because the brand feels like a natural extension of Ari and his co-founders’ deep passion for travel, design, and storytelling. So when Ari travels somewhere and comes back raving about a hotel, I’m listening.
Follow Ari’s lead: "Summer travel is very much on my mind and I've been weighing the pros and cons of various destinations–I wish I could go everywhere on my list but alas, we have an Ash Hotel to open in Richmond, Virginia. I've settled on starting my summer travel in Istanbul, a city I've shockingly never visited. I'm obviously excited to visit the Grand Bazaar and scour for antiques and souvenirs, but I am also dying to check in on some of the city's stock of grand old hotels, some elegantly faded from their glory days and others newly revitalized. As a lover of classic hotel bars, I'm excited to check out Orient Bar in the Pera Palace Hotel. I hope they haven't ruined it! I imagine I'll be mostly exploring Galata and Bebek [neighborhoods on the European side of Istanbul] but I'm also excited to crossover to the Asian side. Following Istanbul, I'm heading down to Salento, the tip of Puglia. I've been once before and I love southern Italy where the African winds blow in. I always quest to find hidden rocky swimming holes and elegant restaurants tucked away in sleepy towns. I'm also excited to visit Palazzo Daniele again and finally check out Il Convento. From there, I'll head up to Rome to check in with my friends for a quick reset before heading back to NYC."
Pia Riverola, Travel Photographer
I love seeing the world through Pia Riverola’s lens—literally. She’s one of my favorite travel photographers and the first I really started following when I transitioned from fashion to travel (she also straddles both worlds so I instantly felt like we understood each other). Pia’s passion for photography began at the age of 12 when her grandfather gifted her a point-and-shoot camera, which she swiftly began using to capture moments from her everyday life. This early exposure to the art sparked a lifelong passion. She went on to study film in Barcelona and documentary filmmaking in NYC, but it was her move to Mexico City that led her back to photography. Immersed in the city’s local culture, she refined her distinctive style, capturing subtle, spontaneous moments in photos infused with a cinematic quality and bathed in warm tones and natural light that somehow transform the mundane into the magical. Her debut book Flechazo, her visual love letter to Mexico City, is a clear reflection of the tenderness she feels towards the city. (Btw, you can buy her new book Día’s here.) Today, Pia's work can be found across hospitality brands like Belmond and The Luxury Collection, as well as in top publications, such as The New York Times, Architectural Digest and Vogue.
Follow Pia’s lead: “In the summer I’m heading to Costa Brava — it’s an area that’s tied to so many memories from growing up. I’ve spent every summer there with my family since I was a baby, so going back always feels easy and familiar. The pace is slow, the days are long….It’s not just about the beaches or coves — it’s the feeling of being there, the late lunches, the light, the quiet. No matter how busy my summer gets, I always try to make time to go back for at least a few days. Costa Brava is the Catalan coast, dotted with small coastal towns — each with its own charm. Most of them started as fishing villages, so the seafood is obviously great (gambas de palamos!), but what I really love is how much local life still runs through it. You’ve got farmers selling seasonal produce, little old-school patisseries, and a pace that hasn’t really changed. It hasn’t been overrun by mass tourism, and it still feels very much true to itself — which is rare. New businesses pop up, but the overall feel doesn’t really shift. It’s familiar in the best way — updated just enough to stay interesting, but still holding onto its character. I’m looking forward to spending time at properties by Viu Empordà, a project that offers stays at some of the most beautiful houses and villas across Empordà and Costa Brava. The places they curate are effortlessly stylish — rooted in the landscape and the land, but with a clean, contemporary feel. Every house has its own rhythm. It’s the kind of setup where you can slow down, be present, and really enjoy off-time — whether it’s a quiet morning with a view or a long dinner that rolls into the night.”
Tommaso Mardegan, Co-Founder of N2S Italia
Tommaso is one of those impossibly cool friends whose epic trips around Italy (and beyond) I’m constantly trying to emulate. I even featured his road trip from the north to the south of Tuscany for New York Magazine’s Strategist, wrapped up in a neat little guide you can steal here. He is my ultimate resource when it comes to the lesser-known, hidden corners of Italy. He seriously knows all of the country’s best kept secrets. His deep love for his country and passion for spotlighting authentic, under-the-radar places led him to launch N2S, a luxury travel company that creates bespoke experiences (the coolest kind) and events across Italy. (Side note: I convinced my best friend to hire N2S for her wedding in Tuscany, and they absolutely crushed it.) Tommaso always has a pulse on what’s new and cool in Italy, tipping me off to places brewing with fresh energy—long before the crowds catch on.
Follow Tommaso’s lead: “This summer, I’ll do mostly an estate Italiana [an Italian summer]. I always love to include some islands—I am an island lover. But this summer, to avoid crowds I won’t go to Capri, which I love to visit in low season instead. I will visit Elba island—very green. Here you can enjoy the good Italian life in a natural, slow-paced setting. You can find yourself alone in a wild beach in the middle of August—hard to believe, right? My Florentine friends Ginevra and Max, founders of Daisy’s and House of Nine, have launched what can be called a ‘floating boutique hotel’, after the refurbishment of their yacht Curiosity you can book 2-3-night private cruises along the Tuscan Archipelago and even book rooms individually, so that you don’t have to embark on a weekly charter of such a big boat. Pretty cool new concept of hospitality and I’m excited to test it out! In the smaller sister island Giglio, there is a b&b that not many know, Pardini’s Hermitage. Apparently even Audrey Hepburn was coming here for some privacy. If you find availability, book the room right away! As I do every summer, I will also spend a few days in the Dolomites. It’s been a while now that I’ve been wanting to experience the Berghoferin. It’s only 13 suites and so chic! A buy-out with family and friends for a private celebrations would be a dream. It’s a short ride from wonderful spots like Alpe di Siusi where you have the best hiking and biking routes, as well as the Bozen wine route. Last but not leas, after Egnazia Hospitality’s opening of Santavenere, there is a new interest on the Cilento Coast and Maratea. I am so excited to stay with friends at the villa rental Casa di Maratea, also part of our N2S collection.”
Júlia Juste, Founder of Outliers
I’ve been a fan of Júlia’s for about as long as I’ve been a travel editor, following her dreamy adventures on Instagram as she documented the kinds of places that linger in your imagination. What sets her apart is her instinct for discovering the kinds of small, authentic rural stays that rarely appear on curated lists, often favored over more conventional luxury properties we see featured time and again. Her passion for travel and connection was shaped early on by a childhood spent traveling frequently with her family. Her parents eventually wrote a book on the best rural homes in Catalunya and later founded Behomm, a home exchange platform for creatives. That upbringing deeply informed her point of view and ultimately led her to launch Outliers in 2020, which is an incredible resource for soulful stays around the world.
Follow Júlia’s lead: “I’m just back from four months of intense traveling, so I don’t have anything planned yet and I need to be home for a while, but I’ll share some places that are definitely on my wishlist for summer and beyond. In my own country, I love Galicia in the northwest of Spain. I go every summer because I have many friends from there. I love it because it feels truly authentic—its beaches and natural landscapes are spectacular, the food is incredible, and the weather is never too hot. Although it's getting more popular, it still retains a strong and unique character. I’m really looking forward to experiencing Casa do Castelo de Andrade and Casa de Aldán. Also in the north of Spain is Asturias. I’ve heard wonderful things about this region, and it’s also a great place to escape the heat that’s so common in the rest of Spain. There are a couple of hotels I’m dying to visit, like Solo Palacio and El Faro Unkempt. I also want to visit Transylvania, a region in Central Romania, which is a destination that only recently started to catch my attention. I spent a lot of time researching and came across some truly special places—especially in terms of accommodations—which are now featured on my website. There are many people there working on projects focused on preserving their traditions, culture, and architecture. São Tomé and Príncipe, [an island country in Central Africa], is without a doubt one of the destinations that’s been on my mind the most lately. It’s one of the least visited countries in the world, and I know a few people who have been; they all talk about how pristine and untouched it is. Despite the low number of visitors, there’s a high-end hospitality company there that looks really promising, called Príncipe Collection. Then finally, Popoyo, a small beach town in Nicaragua. This isn’t as much of a wishlist destination as it is a recommendation, as I just visited and absolutely loved it! It’s a surf spot that’s still very much in development. There are already a few hotel projects and more on the way, but it still feels like a place that’s just getting started. I loved the sunsets, the laid-back vibe, the perfect weather, the unpaved roads... it’s the kind of place where you can truly switch off and be on holiday.”