I get asked about Europe every single summer. And every summer I see the same itineraries — Greece, Italy, Spain. But as Euro Summer has been ramping up over the years, so are the crowds, the queues, and the feeling that you’ve flown 8 hours to stand in line with 10,000 other people who had the exact same Pinterest board.
So here is my honest, no-fluff guide to what cities / towns I would go back to — and which I would skip. I have done these all!
Skip: Santorini
Go: Milos or Hydra
Let me be clear — Santorini is beautiful. We spent an incredible family trip there celebrating my dad’s 60th trip around the sun and I have core memories there. BUT the crowds. Oh my god, the crowds. Santorini is a major ferry and cruise ship drop-off point which means during sunset — the very thing everyone goes there for — you are literally queuing up to watch it. You queue. For a sunset. That’s where I draw the line.
If you want the Greek islands magic without the madness, Milos is your answer. We loved it for the unique boutique hotels (Skinopi Lodge is a must), the rustic charm, and the fact that you’re surrounded by half the Americans you’d find in Santorini. The sunsets and aperitivo spots are just as stunning. We rented a vespa and spent days exploring secret beaches, tiny cobblestone towns, and petting a hundred stray cats.
Food highlight: Medusa restaurant — fresh octopus, tables right by the water, lunch for two with wine for under $100. Order the Tsiros Kapnistos. Go to Polonia for dinner and watch the sunset from Utopia. For beaches, head to the south side where it’s less windy — Tsigrado beach (only accessible by ladder, very dramatic), Fyriplaka for beach chairs and a great restaurant, and Sarakiniko, which genuinely makes you feel like you’ve landed on Mars.
Hydra I haven’t personally been to yet — it’s firmly on my bucket list — but it’s about 30 minutes by ferry from Athens and it has a very specific kind of devotee: the chic fashion people I follow on Instagram who go back every single summer without fail. No cars on the island. Which means fewer people. Which means more of the Greece you actually came for.
Skip: Positano
Go: Praiano
I’m going to be blunt: Positano in the summer is a special hell. I’m sorry. I said what I said.
When Chase and I went in 2018 it was already crowded. When we went back in 2023 for his parents’ anniversary, getting off the boat and walking up into town meant forming a single-file line going up while another single-file line came down. You literally could not move in either direction. The Amalfi Coast no longer has a shoulder season — May, September, October used to be the escape hatch. Not anymore.
The saddest part? Franco’s Bar at Le Sirenuse — one of the most iconic aperitivo spots in the world, perched on the side of the hill with those views — now has a queue before it even opens. In 2018 we walked right in. Now there’s a line. OOF. Skip.
Praiano is 25-30 minutes away. Literally the next town. It’s still touristy, still has Americans, but nothing like Positano during peak season. Cute little shops, the freshest fish at the restaurant below our hotel, their own little beach club on the rocks, and water taxi access to other towns whenever you want to explore. We stayed at a gorgeous little boutique gem with insane views and I would go back tomorrow.
If you truly cannot resist Positano (I understand, I’ve seen the photos too), then stay at Il San Pietro instead of Le Sirenuse. It sits about 15 minutes outside of town on the outskirts toward Praiano — away from the foot traffic frenzy — and it is a dream. You can still go into Positano for dinner or drinks once the cruise ships have left, then retreat back to your quiet, beautiful hotel. Best of both worlds.
Other luxury boutique options in Praiano worth knowing: Casa Angelina and Casa Privata are both insane. But know that during peak summer months you will still pay peak summer rates — because that’s just the Amalfi Coast now. Wherever you stay on this coastline, be prepared to spend good money. Budget accordingly and don’t be surprised.
Other alternatives worth knowing: Ravello is still touristy but significantly calmer than Positano, and the properties up there are stunning, like the pink hotel, Palazzo Avino.
Everyone seems to be on the same itinerary: Hike of the Gods, boat to Capri for a day, lunch at Da Adolfo or Conca del Sogno. But the key to escaping the tourists is to have a beautiful home base. Just be prepared — this is peak tourist territory and you will pay peak tourist prices. That’s just the Amalfi Coast now.
Skip: Capri
Go: Ischia (or Procida)
Capri is chic. I won’t pretend it isn’t. The biggest yachts I have ever seen in my life are in Capri. We chartered a boat from Praiano and did a full day there — skipped the town entirely and went straight to La Fontelina beach club for lunch. Getting a reservation there is an art form: book months in advance through your hotel, ideally one where someone speaks Italian. If that fails, have your boat captain call in a favor. That’s how we got in. IYKYK.
We did one night in Capri in 2019 and I will say — when the day tourists leave, there is real magic there. But it is stupidly, almost offensively expensive. Starting with those convertible taxi cabs from the port to the top of the island. I cannot even remember what they cost but I remember thinking it was genuinely absurd. The whole island operates on that energy.
Ischia is Capri’s lesser-known sister island — or at least she used to be lesser known before she blew up. We went in 2023 and I loved it. Same views. Same ocean. Same dramatic topography. But with actual Italians on vacation, which in my opinion is the entire point of going to Italy. Families, kids, people who live there and love it. Real.
Ischia is also where The Talented Mr. Ripley was filmed, and we found the exact location of the famous photo of Gwyneth Paltrow and Jude Law in the water and recreated it. Truly felt like the scenes depicted in that movie with Matt Damon running around the little piazzas down to the beach.
We stayed at Mezzatorre and it was wonderful — a genuinely international crowd, a good amount of Aussies, not the wall-to-wall Americans you find elsewhere. I did a whole Mezzatorre vs Hotel Il Pellicano (another favorite hotel of ours) you can read about in depth here.
While you’re there, consider a day trip to tiny Procida — a short ferry away, more of a quaint fishermen’s village vibe, fewer luxury hotels but incredibly charming. It’s still on my list.
Anyways, I know a lot of people prefer a scene and want to be seen so you can always do both. And if you really want your Capri fix, you can always charter a boat and do a day trip from Ischia. Get your La Fontellina lunch in, see the big yachts, and come home to somewhere that doesn’t cost you your firstborn to exist in.
Skip: Cinque Terre
Go: Santa Margherita (with day trips to Portofino)
Cinque Terre is a postcard. A beautiful one! But that’s kind of all it is. Getting from town to town requires actual hiking — like physically hiking — and the foot traffic has turned it into another Positano situation. Like everyone just came to take the exact same picture they have seen on Pinterest or a postcard, snap and leave. I got bored. I would skip.
For Northern Italy coastal vibes, Santa Margherita is your answer and she is a GEM. Think of it like the Ischia of Northern Italy — same gorgeous coastline, but with actual Italians. Specifically, the Milanese. This is where people from Milan summer vacation and own houses. It’s elegant and real in a way that Cinque Terre just isn’t.
We stayed at a beautiful hotel with its own little beach club down by the rocks — La Fontellina energy but without the scene. I knew I was in the right place when I ordered an iced coffee and they laughed at me, then brought me a hot espresso with a side cup of ice. Perfetto.
Portofino is nearby and worth a day trip — the allure is real: fancy Dior beach clubs, glitzy Milan restaurant outposts, and of course the Belmond Splendido, one of the most gorgeous hotels I have ever seen in my life. Dinner there is a must, and also dinner at Da V Mare down at the port — I still think about their Paccheri alla Vittorio red sauce pasta. I still think about it. But Portofino as a home base? Very touristy, very American, and very tiny. It's a place you visit for the scene and the Splendido, not a place you settle into. Think of it as the Capri to Santa Margherita's Ischia — go for the day, come home to somewhere that actually feels like Italy.
Skip: Barcelona
Go: Madrid
If you have to choose one Spanish city — either for a few nights to break up a trip or to get a quick city fix — choose Madrid.
Barcelona has its charm. There’s a great Soho House, decent shopping, beautiful architecture. But it gives me study abroad energy. Lots of English, lots of party tourists, and ironically for Spain, very little Spanish — they speak Catalonian in Barcelona, so you won’t get the immersive Spain experience you’re probably looking for.
Madrid is just SO chic. The people are dressed to the absolute nines. Spanish is everywhere. The restaurant scene is extraordinary, the parks are gorgeous and immaculate, and the shopping is equal to if not better than Barcelona. I think of it as the London of Spain — equally chic, equally clean, equally city-that-takes-itself-seriously.
And the children’s clothing boutiques. Do not even get me started. I could spend an entire day just going from shop to shop buying things for Millie. It is a problem I am not trying to solve.
We stayed at a stunning 1895 French-style neoclassical mansion that we just loved and was on Marriott points - who knew?! I have my Madrid guide linked here where you can find more on where we ate, shopped, and stayed in that post.
I know Euro summer this year in 2026 is complicated — the ongoing conflict, fuel shortage warnings, and flight costs OOF it’s bad. May the odds be ever in your favor, truly.
But if you’re going, go somewhere worth it. Go somewhere the locals still love. Go somewhere you can actually move through the streets without forming a single-file line.
These are just my two cents from someone who has done it. I’d love to hear yours — comment below if you agree or if you disagree. Especially about Cinque Terre. I know some of you love it and I respect that. Kind of.
OH and deciding what to pack?! Here is my summer capsule collection. Literally was designed to be in your suitcase to Europe this summer. Shop it all here!
Kalimera, ciao, and hasta luego my friends.
xx
Steph
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