Where to Go and What to Pack If You're Planning a Chic Trip in 2023

It seems only right that we provide you with an ultimate guide to the chicest and most exciting holiday destinations of 2023 in our Summer Issue. Travel is, after all, well and truly back on our radar, and we couldn't be happier that exploring the world—both far-flung and close to home—has become an exciting, rather than stressful, prospect again. As Editor in Chief Hannah Almassi rightly said in her introduction to this issue, team Who What Wear is saying yes this summer—to travelling, trying new things, exploring new parts of the globe and wearing whatever the heck we want while we're at it. Won't you join us?

Travel may be back, but it's also seemingly more expensive than ever, so making the most of every trip is paramount, whether that means saving and booking a once-in-a-lifetime excursion or capitalising on the adventures on your doorstep. You'll also want to know exactly where the coolest hotels are, where those in the know are dining and watching sunsets and what to wear for those all-important holiday pics to make sure you're feeling your best and not heading home with any regrets weighing down your hand luggage. 

And that's what I'm here to help with. I may be a fashion editor but travel is my passion, and I'm nothing if not a thorough researcher when it comes to meticulously planning the chicest trips (much to my husband's dismay). I've also corralled a team of the most stylish travel lovers and experts I know to let us in on all their best-kept travel secrets, from unmissable local spots to the essentials they never leave behind. 

Below, we dig deep into the buzziest travel destinations of 2023—whether you're considering finally booking that safari you've always dreamed of or you're looking for a new, affordable city break to experience. Perhaps you're after a Provençal-style vineyard that you can reach in under an hour from London on a long weekend or a place to learn to surf from scratch on a solo trip. We got you. 

And while we would never encourage you to impulse-buy items with short-term goals in mind (say, looking great on a week-long holiday), I can also sympathise that there's nothing quite as exciting as shopping for a trip you're looking forward to. That's why I've included handy packing tips for each destination, making suggestions for how to shop your existing summer wardrobe. (A linen shirt looks chic anywhere—trust me.) But I've also added links to this season's most versatile summer-ready pieces that capture the spirit of each trending destination and will be ready to be rolled (always rolled) and packed into your case year after year, no matter where you're heading. 

Are you ready for some wanderlust? Keep on scrolling…

Where: California's Central Coast

Los Angeles is great and all but, if you're after a slice of California sunshine with an altogether laid-back approach, I can personally recommend renting a car and driving north out of the city and exploring some of the state's more low-key towns along the central coast. There are plenty of film-like white, sandy beaches with wooden staircases winding up to dreamy cliff-top houses along the way. (Look up Lechuza Beach and Hendry's Beach.) But if you head into the redwood-laced hills off the 101, you'll find it's also the kind of place the coolest Angelenos escape to for a ranch break or a spot of wine tasting in what they call California's "secret" wine country. The farm-to-table food scene is something to send a postcard home about, too. 

What: Wine Tasting and Horseback Riding

It's worth exploring Ojai—a small but in-the-know town less than two hours outside of L.A.—and Santa Barbara's Funk Zone. It's much cooler than it sounds. You can eat at The Lark, kit out your imaginary beach house with antiques from The Blue Door and drink at one of the many local tasting rooms or craft breweries. Fans of small-town Americana (and excellent wine) will love the Santa Ynez Valley—be sure to stop in Los Olivos, a tiny, old enclave focused around tasting rooms that manage to be both adorable and chic. The recently opened Inn at Mattei's Tavern is the place to stay to avoid driving after a few flights of wine. A more reasonably priced option is Skyview down the road in must-see Los Alamos or Hotel Ynez. Both are owned by the Nomada Group, who specialise in anything-but-your-average roadside motels.

If you're in search of an authentic "out West" experience, stop for a ride at Circle Bar B Ranch (I visited last year and could have listened to our genuine cowboy guide for days) or Alisal Ranch for a family-friendly experience. With more time, drive up through Big Sur (if you're blowing the budget, stay a night at Alila Ventana or Post Ranch Inn, but lesser-known Glen Oaks is a more affordable option that still feels special with fireside smores to boot) before hitting Carmel-by-the-Sea, then make stops at insider-loved Paso Robles and San Luis Obispo on your way back to LAX. 

Wear: Coastal Cowgirl

If you haven't already heard, the coastal-cowgirl aesthetic is one of 2023's biggest summer trends—at least, according to TikTok it is. Road-tripping around California's central coast may well be the perfect time to dip your toe (or fully dunk your head) into the look. From the beach to the ranch, layer up your creamy tones and dainty florals. Just don't forget the cowboy boots. Think denim shorts or jeans with pretty white blouses, suede jackets for the cooler evenings and pretty minidresses to pair with your boots. If all else fails, shade yourself from the sun with a cowboy hat while you're sipping on a pinot, and you're already halfway there. 

Where: South East England

When choosing a holiday spot close to home, you might not think to stay quite as close as Kent. Cornwall, Devon, Norfolk and the Isles of Scotland have all proven more popular in the past. But the South East, from Hampshire all the way across Sussex and through to the Garden of England, has had a flurry of extremely chic hotel openings in recent years—from the über-luxurious Heckfield Place to more low-key sites like the Port Hotel in Eastbourne. Along with the appeal of easy-to-reach vineyards that challenge the best France has to offer, it has become a bucolic escape, especially for those living in the capital. A car isn't essential since you can access most of it by train from London. However, if you want to explore it all at once, I recommend hopping behind the wheel—or even in a camper van—to get the full experience. 

What: Quaint Towns, Bucolic Views and Beach Walks

If you're in need of some R&R, make your first stop at Heckfield to experience the newly opened and absolutely stunning spa—The Bothy by Wildsmith. Just be prepared to leave with a whole new set of interior goals. Literary lovers will want to pop into Charleston house on their way to the coast. The old residence of the Bloomsbury group is a truly unique sight.

Take in the great British seaside with a night at the Scandi-inspired and influencer-loved Port or cosy up at the beachfront and very dog-friendly Gallivant, which is just outside of Rye. Who What Wear UK's managing editor, Poppy Nash, recommends whiling away the hours in this quaint seaside town with stops at Whitehouse bakery for breakfast, The Confit Pot for antiques, Cordelia James for clothing, Rae for unique pieces and Hunter Jones for gifts. When it comes to dinner or lunch, Nash says, "It's worth travelling a little outside of town to experience Tillingham—a picturesque vineyard which does tastings and locally sourced food, all in a setting that came straight out of a design magazine."

When you've had your fill of fish and chips, meander back to London through Kent, stopping to eat at the idyllic Boys Hall, a recently restored restaurant with newly opened rooms you can expect to see on your Instagram feed a lot this year.

If all you've got time for is a Bank Holiday afternoon jaunt, though, you can still experience the joys of the South East by hopping on a direct train from London Blackfriars to Shoreham to visit the unpretentious Mount Vineyard, a cute little spot to spend a summer's day with a tasting, pizza lunch or picnic at the outdoor bar among the vines. 

Wear: Cottagecore 2.0

Cottagecore may have peaked during lockdown, but that's because we were learning to embrace the joys of our own back gardens (literally and figuratively). Unlike most things from that time, this attitude is a relic that we're all keen to continue—especially if it means getting more wear out of our frilly throw-on dresses and cute accessories. "I always pack plenty of pretty midi dresses when I head to the south coast and a basket bag, of course, as well as cardigans, jumpers and a raincoat since you never know what weather you're going to be hit with, even in summer!" Nash says. "Birkenstocks, a comfy striped sweatshirt and jeans are also in my suitcase as well as some nice PJs and a swimsuit, just in case." 

Where: Southern Italy

You can't really go wrong with a trip to the land of fresh pasta and Aperol, but there are a few notable areas at the top of the style set's to-go list in 2023. Sicily is undoubtedly having a moment after The White Lotus's second season put the glamorous Taormina on the map. For the ultimate five-star experience, stay at one of the two (yes, two) Belmond hotels in town—Villa Sant'Andrea on the beach and Grand Hotel Timeo with spectacular views from the hillside—or the San Domenico Palace, where the show was actually filmed. The fashion crowd, however, still aren't over the Pellicano hotels, and it's Mezzatorre on the island of Ischia that's top of my list for the ultimate Italian escape. You'll likely recognise the iconic striped blue umbrellas (Slim Aarons would approve) and rich terra-cotta backdrop of the castle-like hotel from Instagram. Head back to the mainland for a stop in Sorrento, and pass up Positano for the lesser-known Atrani and Vietri sul Mare further along the well-trodden Amalfi Coast. Maximalists may want to head north to Lake Como for a stop at the Passalacqua Hotel, where the pool and bar areas have been designed by La DoubleJ. For a more low-key but no less elegant affair, take in Puglia's breezy streets and stay in one of the traditional whitewashed Trulli houses. 

What: La Dolce Vita 

In Taormina, stop at Bam Bar for a traditional Sicilian breakfast of granita and fluffy brioche buns as big as your head. Yes, you'll be going home a stone heavier—just accept it. Then, be sure to take a sunbathing break at low tide and tour the abandoned house on Isola Bella, a tiny island just off the beach.

Ischia is all about old-school la dolce vita—good times and even better food surrounded by the glittering, clear blue Tyrrhenian Sea. Take a boat trip around the island to get the full experience, stopping off at Procida (the neighbouring island) for a plate of vongole at Da Mariano. 

If you've chosen to explore Puglia, you'll probably want to see Polignano a Mare for the experience and to get a shot of its iconic cove. Whether you'll find a spot on the crowded beach remains to be seen. Instead, stay in Alberobello or Ostuni with a dinner stop at L'Osteria del Tempo Perso. (Make a reservation in advance, though.) Influencer and travel tastemaker India Sehmi—you might know her as @theindiaedit—suggests booking a room at the magical Masseria Moroseta. "If you can't get one of their in-demand rooms, though, few people know that you can actually eat there as a non-staying guest, and the food is just beyond!" Sehmi says. 

Wear: More Is More

Lily Russo-Bah, a fashion editor, resortwear expert and Who What Wear contributor, has Italian heritage and has spent most summers there from a young age. According to her, dressing up is key to looking the part: "No outfit is accidental for an Italian. Everything is carefully thought out, and accessorising is essential. And we love colour—my mother would always have a different bikini with matching kaftan, earrings, hair clip, sandals… You name it. Italians very much get dressed up to go to the beach." So more is more, and since I'm in my summer of saying yes, I've never been more ready to embrace this attitude. Think printed swimwear, statement jewellery and larger-than-life hats and sunglasses. Don't shy away from bringing your best, most ostentatious dresses (feathers encouraged) for the evenings or even for breakfast. "La dolce vita is all about enjoying life," Russo-Bah says. See you on the next flight out.

Where: Athens, Greece

If you want a city break but feel like you've exhausted the usual rotation of Barcelona, Lisbon, Paris, Amsterdam, etc., put Athens on your radar for 2023 and beyond. Who What Wear's branded content editor, Rebecca Rhys-Evans, is our team's arbiter of cool, and she won't mind me saying she hasn't shut up about it recently. "Yes, Athens is a little further afield with an almost four-hour flight time from London, but you do get more for going the extra mile. Not only has the city got a rich history, beach and a warmer climate (and let's not forget the feta), but it's also just that little bit cheaper than cities in Central and Western Europe," says Rhys-Evans. She's not wrong—I've suddenly seen so many stylish jet-setters heading there for a mini-break (Lucy Williams was there last month, in fact), and with a wave of new, affordable boutique hotels with exquisite interiors just waiting for their TikTok debuts, it's no surprise. 

While there are plenty of chic little apartments to rent if you prefer your own space, travel content creator Robyn Davis recommends booking a bedroom at Shila (where Williams just stayed too). "It's in a leafy neighbourhood within walking distance of the Acropolis and the buzzy Plaka area with a gorgeous terrace—make use of the honesty bar on the rooftop for drinks before the sun sets," Davis tells me. "The owner, Eftihia Stefanidi, is a creative director with an amazing vision, and Shila is essentially her mood board that you'll want to copy and paste. The rooms are seriously beautiful, with balconies and a delicious breakfast that heroes locally produce." If that's all booked up, try its sister property Mona, which is just as romantic but more industrial, and it's in a livelier neighbourhood closer to the city's nightlife. For a touch of luxe, book a room with a seriously impressive view at the newly opened Dolli. 

What: The New City Break

No trip to the Greek capital would be complete without a stop at the Acropolis. Davis recommends pre-booking online and going early to beat the heat. "Save your afternoons for drifting and drinking around Plaka, a sweet (and very pretty) historical neighbourhood. Earmark an afternoon for shopping, people-watching and taverna-hopping," Davis says. It's here that London-based concept store Mouki Mou has just opened its Athens outpost—stop by for under-the-radar clothes, jewellery and objects sourced by founder and Athens local Maria Lemos.

There's no shortage of hydration options either. Be sure to make a reservation for a drink at The Clumsies, which was voted one of the world's best bars last year, and for coffee, try Philos, which also has a hidden bar at the back if things take a turn. For those seeking the sea, grab a taxi to Krabo, a beach club to rival Mykonos's finest—just without the crowds.

Wear: Loose Linens and Flat Shoes

According to Davis, "It's easy to clock up a high step count in a city as interesting as Athens, so chic flat sandals are a must. You can even pick up a new pair at the Ancient Greek Sandals flagship. Linen shirts will take you from the Acropolis to the beach club, and since it gets really hot during the summer months, breezy outfits are a must." Personally, I'd pack a couple of shorts co-ords, light cotton dresses and a pair of comfy leather sandals—all of which fit nicely into a carry-on case. 

Where: Palm Heights, Grand Cayman

Of all the palm tree–lined Caribbean islands, Grand Cayman is the one that fashion people can't seem to get enough of at the moment. In fact, there's one hotel, in particular, that's drawing the coolest names in the industry: Palm Heights. Even if you've never heard of it, you probably have seen snapshots of its '70s-inspired interiors and beachfront sunshine-yellow umbrellas on your Instagram feed. It's far from your average Caribbean resort experience, as founder, creative director and all-around design guru Gabriella Khalil has created an impeccably stylish oasis on Seven Mile Beach, one of the Caribbean's most idyllic stretches. It captures the laid-back vibe of island life and merges it with cool antique interiors sourced from Paris. It shouldn't work, but it does. If you're looking to completely switch off and recharge while sipping Instagrammable daiquiris, you'll find yourself in the right place here. Influencer Emma Hoareau recently visited and says, "The attention to detail is truly what sets Palm Heights apart—they had hand-picked the books that would be in my room specifically for my friend and me. Everything is so tailored and carefully thought out. It may look incredibly cool in pictures, but the vibe is so welcoming and, most importantly, really fun." 

What: Resort Life (But Not as You Know It)

Palm Heights is the kind of destination where you don't even need to leave the resort, and there's certainly no risk of getting bored. Aside from working through your tailored reading list by the pool, there's the newly opened Garden Club Spa—60,000 square feet of wellness that features restorative bathing rituals, healing ceremonies, treatments and various hot and cold therapies. All are crafted with minimal intervention to the natural environment. If you're more the active type, Palm Heights Athletics has a running track, boxing ring, dance space and Olympians and professional athletes in residence to help you work off those rum punches. Sustainability is central to the workings of Palm Heights, so you'll find all-natural spa products and staff uniforms sustainably designed in collaboration with Matteau. Chic. 

Foodies won't be disappointed either. Jacqueline Falcon, a New York–based brand director and stylish industry insider, says, "All of the restaurants on property at Palm Heights are fantastic, truly. It's not your typical 'resort food' and ranges from sushi to curry bowls and wood-fired pizza. My favourite was Tillies, which serves classic Caribbean dishes inspired by local produce. I'm not a huge burger person, but it was by far one of the best I've ever had."

Wear: Funky Island Chic

So you've booked your flights and your hotel room. Now, what should you pack? Palm Heights guests tend to sport low-key resortwear brands only those in the know will recognise (think St. Agni and Calle Del Mar), but the key to looking the part, whatever your budget, is mixing natural tones with fun brights and prints that reflect the tropical destination—with a smattering of the hotel's own retro, sustainably made Tropical Fitness Apparel Collection for good measure. 

Falcon says the crowd at Palm Heights is funky but still chic: "There are no stuffy pastels. I packed Cherry LA sunglasses, St. Agni sandals, a Louisa Ballou bikini, and a see-through knit dress from & Other Stories. Don't skip the hotel merch. either I'm a big fan of the hats." Khalil told Vogue.com recently that she "often [wears] two-piece silk sets from Toteme at Palm Heights—casual but elevated." Whereas Hoareau was spotted sporting Faithfull the Brand's printed bikinis and relaxed linen pieces. "I recommend packing a bikini, a sarong and a minidress for dinner in the evenings. You barely need shoes, but they'll provide you with their own amazing slides if you're desperate," she tells me. 

Where: Coastal Portugal

The small fishing village of Comporta on Portugal's Alentejo coast has been the It destination for barefoot, laid-back luxury for a number of years now. Siting under an hour and a half from Lisbon, it has somehow still managed to maintain that under-the-radar charm, and those in the know often return year after year for a dose of its "back to nature" magic. Stay at Sublime or Quinta da Comporta, the town's two most blissful hotels, or live like a local and rent one of the area's private villas. Visitors are also exploring neighbouring Melides, which Condé Nast Traveler named one of its best places to go in 2023. There, you'll find a similar, albeit less well-trodden, landscape of pine trees, wild shoreline and rice fields. It's a place loved by fashion royalty like Christian Louboutin himself. The famous shoe designer has just opened one of the most exciting and one of the only boutique hotels in Melides, Vermelho, along with a restaurant to boot.

I've done my fair share of Insta stalking Comporta and its visitors' itineraries, but for an expert take, I called on Emma Campus, a former luxury fashion PR professional who left London behind to become the founder and director of @designescapesportugal—a concierge-like resource that's invaluable if you're looking to experience the real, slower-paced Portugal. When I ask her where she would stay, she says, "For a slice of luxury, the most spectacular new space just opened tucked away on a high hill overlooking the sea in Melides: four private houses designed by Portuguese architect Aires Mateus called Pa.te.os. It feels far from the madding crowd while being just a stone's throw from the nearby village. They even have a bespoke Perfumer H scent since the whole experience is about elevating the senses."

If it's a slightly more exhilarating but no less restorative trip you're looking for, continue the digital detox at Soul & Surf. It's down on the country's Algarve coastline (less than two hours from Melides by car but equally accessible directly via flights to Faro). This unpretentious surf and yoga retreat is a favourite for creatives and fashion people (Lindsey Holland is a regular) looking for a stylish, back-to-basics retreat aimed at counteracting burnout and reconnecting with nature. It's perfect for solo travel, too, and anyone from beginners to experienced surfers and yogis will get something out of it. 

What: Surf, Sand and Slow Shopping

Campus recommends renting a car or bicycles if you're making a base in Comporta, as most things are spread out across hectares of farmland. "Then you can explore the village, which, albeit tiny, is one of the best places to shop in Portugal. Lavanda has an amazing bazaar-like feel but is filled with beautiful independent resortwear brands," she says. "Côté Sud next door is great for swimwear, kaftans and basket bags by Muuñ." And when you start to get hungry? "Don't leave without eating at Cavalariça at least twice," Campus says. "It's the best restaurant in the country for me at the moment—casual, relaxed holiday dining at its best, housed in an old stable. Restaurante Sal on the beach is great for a feet-in-the-sand lunch to soak up the sun too." If there's one thing you shouldn't miss, according to Campus, it's a private horse ride with Cavalos na Areia, which will take you through the pines and orange groves, across the rice paddies and over the dunes onto the beach at sunset. "It's the most magical experience—even in the summer, there are stretches of sand that are totally empty. For a taste of old, real Comporta, though, take in the sunset on the 100-year-old fishing dock at Carrasqueira," she says.

In Melides, stop at Vida Dura—a little emporium hidden behind a village door and filled with interior objects in collaboration with local craftspeople. Condé Nast Traveler also recommends perusing the newly opened Melides Art and stopping for lunch at "beachfront restaurants like À Toa on Praia de Melides [which are adding] to the excitement around this buzzy destination."

Mr Porter's social content strategist, Sophie Hay, visited Soul & Surf recently and raves to me about the amazing food included in the retreat. "But be sure to also head into nearby Lagos while you're there and visit Orta at Casa Mãe for local farm-to-table fare, or grab a 'proper' Portuguese coffee at Black and White alongside the digital nomads who have set up shop there for the day," Hay tells me. To feel more like a local in the otherwise bustling Algarve, Hay recommends visiting the small Moorish fishing town of Olhão during your trip: "It's full of tiled buildings, cobbled streets, and it's off the tourist trail. Don't leave without hopping on a boat around the Ria Formosa national park to see birds, oyster farms and even a dolphin if you are lucky."

Wear: Effortless Basics With a Hint of Bohemia

Effortless is certainly the keyword to keep in mind when packing for Portugal. "Swap the stilettos for sandals and the foundation for a fresh face," Campus says. "Summer in Portugal is all about beautiful basics in cotton and linen and natural-fibre accessories. Wide-leg trousers will take you from beach to bar, and I always pack oversized linen shirts, a well-made one-piece that you can wear as a top too, a pair of slip-on shoes that can be worn day and night and, of course, a wide-brimmed woven hat for sun protection."

Soul & Surf calls for a similar aesthetic, with a few more practical additions, according to Hay: "When you are on a surf trip, you need comfy clothes that you can throw on for early trips to the beach and a giant tote bag for water, snacks and your reef-safe zinc sunscreen. I'd usually throw on a graphic T-shirt from Sporty & Rich and my favourite denim shorts. For the evening's communal dinners, you'll want to get a little dressed up after being in a wetsuit all day, so pack your favourite holiday dress and sandals too."

Where: Eco-Safari, Africa

Heading off on a safari is probably on most of our ultimate bucket lists, whether you're imagining the Masai Mara in Kenya, Tanzania's Serengeti or Sabi Sands in South Africa. With a few years of not travelling as much under our belts, now is as good a time as any to make it happen. It certainly feels that way, as a number of the best dressed people on my social feeds chose Africa's plains as their latest holiday destination. Perhaps you're thinking of following in Lucy Williams's footsteps and choosing it for your once-in-a-lifetime honeymoon. Whichever way you cut it, the nature of safari means it's likely to be a big-budget trip, especially if you want a less rustic, more refined affair. There are, however, so many different ways to do it, from luxe to low-key experiences. The all-important factor these days is to make sure you're picking an eco-conscious company that's focused on the conservation of community and the land. 

What: Off-Grid Adventures

If in doubt, Responsible Travel is a wise company to turn to since it offers an array of curated safari trips, plus many other experiences, that are sure to support the places and people that you visit as well as the planet. Its six-day Kenyan Masai Mara tour is hosted by members of the local Maasai community at one of only three gold eco-rated camps in the whole of Kenya. Its Trip for a Trip program also allows you to send a disadvantaged child or young person on an inspiring day trip somewhere in the world every time you book a holiday with Responsible Travel at no extra cost. 

Williams travelled from Arusha to the Ngorongoro Crater, eventually settling for her safari at the Singita Grumeti Reserves—an ecotourism brand with luxurious lodges all across Africa dedicated to environmentally conscious hospitality, sustainable conservation and the empowerment of local communities. 

Journalist, editor and influencer Katherine Ormerod is somewhat of a safari expert, having been on a number of excursions herself as well as picking up tips from her family's boutique South African travel company. "Ask for Bev," Ormerod says. "My mum just gets the kind of chic but still adventurous trips we're all looking for. I always recommend Chitwa Chitwa in the Sabi Sands as a relatively affordable luxury private game lodge, and if you can possibly stretch to the private four-seater plane in, do it. We've seen some amazing game from above and running beside us on the dirt runway."

Wear: Earthy Tones and Natural Fibres

Ormerod tells me, "Dressing for a safari is all about layers, as you're dressing for two climates—sunup and sundown. A khaki shirt-jacket is great and some comfy, casual full-length trousers that you can be confident jumping on and off the safari vehicle in. Then I'll usually pack comfy flats (I am a high-heels devotee, but I ditch even espadrilles for safari), a broad-brimmed hat (the sun really creeps up on you), great swimwear for the lodge and some kind of animal-print dress or blouse for the evening. Clichéd, yes. That doesn't mean it's not a must. Right now, I'd choose a sheer zebra-print Rat & Boa shirt ideal for a boma dinner—usually a candle-lit gathering under the stars."