European summer begins with a set of imagined scenes: days on the water, long lunches that flow into aperitivo, swims before sunset and the occasional cultural detour that calls for sensible shoes. Long before the suitcase comes out, the wardrobe for it all begins to take shape.
Then you arrive, and the picture becomes more specific. Some places fulfil an expectation; others are so memorable that you find yourself planning a return before you have even left. After a month travelling through Greece, Italy, France and Monaco, I came home with eight addresses that did exactly that. Some had been on my list for years, others were new discoveries, and one old favourite seems to get better every season.
I began in New York, flying Delta direct from JFK to Athens. My mother made the journey from New Zealand to join us, travelling via Hong Kong and Zurich. The contrast was not lost on me: after growing up with Europe as a multi-flight undertaking, I can now leave New York in the evening and be in Europe by morning.
What follows is my European summer edit: the hotels worth crossing the world for, what I wore along the way and what I’d recommend if you’re planning your own trip.
Kalesma, Mykonos
Mykonos can tip into overstimulation quickly, but Kalesma is a hotel you can happily build an entire day around. Set on the hillside above Ornos Bay, its whitewashed suites are designed with privacy in mind, many with their own pools and terraces looking out towards the Aegean.
Mornings might start with yoga before breakfast, followed by a swim or a visit to the spa for a Dr. Barbara Sturm facial. By evening, Pere Ubu becomes the centre of things, with sunset over the Aegean and, on Saturday nights, synchronised swimmers turning dinner into something of a show.
There are more unexpected reasons to stay at the hotel. My daughter and I spent an afternoon with Mykonos-based textile artist Faye Chatzi, learning traditional Greek weaving on a loom. It was hands-on enough to absorb a seven-year-old and interesting enough that I wanted to do it too, which is not always a given with hotel activities designed to appeal across generations.
What I wore
Mykonos calls for clothes that can move from the pool to lunch without requiring an entire change. A printed Hill House cover-up that could easily be mistaken for Missoni became one of the most useful pieces in my suitcase. I also wore a sheer white Dolce & Gabbana crochet cover-up over a black strapless bikini with high-waisted bottoms, a Jenni Kayne straw hat and white Chanel sandals I found on The RealReal. Evenings mainly involved one-and-done slip dresses with shoes that could handle rocky terrain.
What to know
Resist the urge to arrive with an overambitious itinerary. We returned to a beach club we had loved back in 2015 and spent almost two hours waiting in what felt like an airport customs hall, only to discover that the price of our sun loungers had climbed into four figures. The Mykonos I remembered had clearly moved on. Next time, I would spend the day at Kalesma instead, down by the newer pool at Kuveda, where the atmosphere is considerably more relaxed and, frankly, far more appealing.
Grand-Hôtel du Cap-Ferrat, A Four Seasons Hotel
I have been returning to Grand-Hôtel du Cap-Ferrat for years, and each summer seems to make a stronger case for coming back. Set at the tip of the peninsula between Nice and Monaco, it has the kind of Riviera glamour that is difficult to reproduce: grand without feeling stiff, immaculate without losing the sense that everyone is actually there to enjoy themselves.
It is set on one of the most beautiful stretches of the Riviera, surrounded by gardens that have been maturing for well over a century. Much of the day unfolds down at Club Dauphin, between the Olympic-sized infinity pool, the sea and long lunches, while the recently expanded kids’ club makes it especially brilliant with children. Back at the hotel, dinner feels like an occasion, served under the stars, often with live music drifting across the terrace. This is a hotel that understands the full arc of a summer day and caters to every part of it without any of it feeling overly orchestrated.
What I wore
Cap-Ferrat calls for the more romantic end of the summer wardrobe. A floral Zimmermann dress felt entirely at home here, which is probably why the label returns to my suitcase year after year. I also wore a printed turquoise sarong found on Revolve for under $50, twisted into a strapless dress that was repeatedly mistaken for Pucci.
What to know
Book the Jean Cocteau cabana at Club Dauphin for at least one day. If it is your first time in the area, you may want to make the roughly 20-minute drive inland to the medieval hilltop village of Èze. Otherwise, I would resist the temptation to over-schedule. The hotel creates its own complete Riviera world behind its grand gates, and my recommendation is simply to stay put and enjoy the atmosphere.
Grace Hotel, Imerovigli, Santorini
If I were choosing where to stay in Santorini again, I would choose Imerovigli. Oia may have the name recognition, but Imerovigli gives you the same caldera views with far fewer crowds. Grace Hotel occupies one of its most spectacular positions, looking across to Skaros Rock, with a long infinity pool that appears to disappear into the Aegean. We stayed in the newly reconfigured villa, which worked particularly well with three generations travelling together. There was enough space to disappear from one another when necessary, but we could still come together around the pool and terrace.
Oia is better treated as an excursion. We celebrated my husband’s birthday at Lycabettus, where the tables perch above the edge of the caldera and dinner unfolds with the sea far below. Petra at Canaves is another address to save for an occasion: a degustation menu through Greek regional cooking, with caldera views to match.
What I wore
Santorini is a place where wearing all white feels completely justified. I wore a white Dolce & Gabbana dress with white Schutz thong kitten heels, black Prada sunglasses and a Dolce & Gabbana top-handle clutch. By day, a crisp white shirt over a bikini, printed mini skirt and straw hat did most of the work.
What to know
Do not underestimate the ferries. They were a low point for all of us (and the other passengers around us, evidently). The water between the islands can be extremely rough, so Dramamine earned a permanent place in my bag, along with motion-sickness wristbands for my son. And again, I would opt to stay in Imerovigli and treat Oia as an evening out rather than a base.
Daios Cove, Crete
Daios Cove was the biggest surprise of the entire itinerary, and somewhere we will absolutely be returning to. Built around a private bay on Crete’s northeast coast, the resort has pools, restaurants, an excellent kids’ club and almost every conceivable way of getting onto the water, all arranged around a cove with some of the clearest water we encountered all summer.
Then there is the Residents’ Club, where guests with access move through much of the resort without signing a bill. This remains the case even if you order several bottles of Veuve Clicquot and multiple gelatos each day, which we absolutely did. KĒPOS, the wellness centre, goes well beyond the usual resort spa: cryotherapy, a hyperbaric oxygen chamber and even colon hydrotherapy alongside the expected treatments and gym. Our favourite afternoon was considerably simpler: a boat out into the bay at sunset, stopping to snorkel along the way.
What I wore
Crete is less about dressing for the scene and more about dressing for what you are actually going to do. I wore a white triangle Vitamin A bikini for snorkelling, then a coordinating bandeau and flowing maxi skirt with an elasticated waist for breakfast, a welcome feature after a multi-course dinner the night before. The clothes here can afford to be uncomplicated.
What to know
Book accommodation from The Collection. The newer rooms and suites have been updated with contemporary interiors, many with private pools looking directly across the cove. And be sure to reserve the sunset snorkelling boat trip before you arrive. It was one of our absolute favourite activities of the month.
Bulgari Hotel Paris
Paris has no shortage of hotels devoted to old-world grandeur, but Bulgari goes in the opposite direction. On Avenue George V, it is sleek, sexy and distinctly Italian, with the same confidence as Bulgari Milan rather than another interpretation of Parisian gilt and chandeliers. It has also recently been awarded France’s official Palace distinction, an impressive achievement for a hotel that feels so deliberately unlike the traditional Paris grande dame.
The spa is exceptional and worth setting aside a proper afternoon for, but part of the appeal is also where you are. The hotel sits in the heart of the Golden Triangle, with the fashion houses of Avenue Montaigne around the corner, Palais Galliera and Palais de Tokyo nearby, and the Eiffel Tower close enough to wander over after dark and watch it sparkle on the hour.
What I wore
Paris is where I come back to black. Trends change, but a classic black dress, great stilettos and a good bag have survived every version of Paris I have packed for. At Bulgari, mine was a silky black halter. For another night at The Ritz, I wore a black sequinned off-the-shoulder mini with sheer tights and black patent pumps. By day, wandering the Musée de l’Orangerie and Tuileries with the children, I opted for a breezy, Victorian-inspired Zimmermann dress with white block-heeled sandals that could take the gravel paths.
What to know
Bulgari’s position in the Golden Triangle means you can cover a surprising amount of Paris within a relatively small radius. Leave time to wander, shop and make proper use of the spa before getting dressed for the evening. And if you are in the mood for a bigger night out, the legendary Crazy Horse is nearby on Avenue George V. Bar Hemingway and Hôtel Costes are also favourites for a martini, music and people-watching.
San Domenico Palace, Taormina, A Four Seasons Hotel
San Domenico Palace was a fifteenth-century monastery long before it became the backdrop to season two of The White Lotus, and traces of that history remain everywhere. Cloisters and old stone courtyards open onto gardens, the Ionian Sea and the now-iconic infinity pool, while Dolce & Gabbana brings its prints to the pool area each summer, adding another layer of colour to a hotel where almost every corner offers a beautiful backdrop.
The pool became the centre of our days, with lunch a few steps away at Anciovi, where the seafood is excellent. San Domenico has all the polish you would expect at this level, but its greatest asset may be its people. The staff are charismatic and genuinely warm, many having been there for years. For a hotel that attracts this much attention, there is something reassuringly real underneath the fanfare.
What I wore
Sicily calls for a darker, more theatrical kind of glamour. By the pool, I wore a coordinating floral shirt-and-short set over a Monday bikini with my Jenni Kayne hat. A Dolce & Gabbana majolica-print shift dress took me from breakfast to sightseeing, while evenings called for a black floral Zimmermann dress. On more casual days, I wore a simple spaghetti-strap bubble-hem dress with my black Zara thong wedges that ended up doing far more walking than I had anticipated.
What to know
Secure a good pool lounger early and book Anciovi for lunch before you arrive. If you want to venture out, Grand Hotel Timeo is lovely for aperitivo and dinner with a view over the Greek Theatre, while La Botte is a Taormina classic when you want something more local and low-key.
One&Only Aesthesis, Athenian Riviera
If you want Athens with a side of beach, the Athenian Riviera makes a very good case for it. One&Only Aesthesis sits on the coast at Glyfada, close enough to head into the city for the morning and be back beside the water by lunch (it kind of felt like living on Auckland’s North Shore and heading into town). The fresh, modern bungalows are set through pine forest that runs down to the sea, while the main building has a glamorous mid-century feel. The Guerlain Spa is exceptional, the kids’ club is one of the better ones we came across, and restaurants including Sumosan for Japanese and Manko for Peruvian mean there is very little reason to leave.
We booked a private transfer to the Acropolis with a guide who had spent years working across Athens and ancient Egypt. The children listened to every word, which is not something I would take for granted on a cultural outing with three of them. By early afternoon, we were back at the beach, with the rest of the day still ahead of us.
What I wore
Athens calls for clothes that can manage both the city and the coast. At the resort, I wore a Monday Swimwear bikini with a white PQ Swim cover-up and Prada sunglasses. For the Acropolis, I wore a Bottega Veneta halter top with tailored Aritzia shorts, black Zara thong wedge sandals (which survived Disney World and now this) and a Chanel bag.
What to know
Arrange the Acropolis transfer and guide before you arrive, and ask for someone who really knows the site rather than a general tour guide. A private car means you can see one of the world’s great historic sites in the morning and still be back for an afternoon by the sea. Book dinner at Manko early in the stay if you want something livelier in the evenings.
Hôtel de Paris Monte-Carlo, Monaco
Few hotels are as closely tied to their surroundings as Hôtel de Paris is to Monte Carlo. It has stood on Casino Square since the nineteenth century, and its marble, chandeliers and old-world grandeur create a sense of occasion from the moment you arrive. It still feels like the centre of things, with the casino opposite and a steady procession of people arriving dressed for wherever the evening is taking them.
By day, head for the water. Monte-Carlo Beach has its famous diving boards and, this summer, Jacquemus by the sea. Come evening, return to Hôtel de Paris for Le Grill on the eighth floor, with sweeping views across Monaco, then cross Casino Square for roulette. Bar Américain downstairs is the right place to end the night if you are not ready for it to be over.
What I wore
Monte Carlo is one of the few places where conspicuous labels look completely normal. By the water, I wore an Agua Bendita bikini with Gucci raffia slides, a Dior headscarf and a Louis Vuitton Neverfull. After dark, the dress code shifts upwards, with evening dressing that is polished and entirely comfortable being noticed. This is the place for a proper dress, heels and the jewellery you might leave at home elsewhere.
What to know
Give Monaco both halves of the day. Spend the afternoon at Monte-Carlo Beach, come back to dress for dinner, then leave time for the casino afterwards.
Words: Amy Louise Bailey.
Imagery: Supplied.
