Everyone knows that person who spends weeks sniffing around travel blogs, going deep into Tripadvisor rabbit holes, collecting Google docs from friends of friends, and creating A Beautiful Mind–style spreadsheets to come up with the best vacations and itineraries possible. In this recurring series, we find those people who’ve done all the work for you and have them walk us through a particularly wonderful, especially well-thought-out vacation they took that you can actually steal.
To celebrate my 40th birthday, ten friends joined me on a weeklong trip to Greece. I don’t normally go on big personal trips like this, as trying to corral such a large group can be a daunting task. But if there’s a time to make the effort, it’s now.
We decided on Athens and Crete for the end of May, when it was warm enough to have glorious Mediterranean vibes on an island but not so deep into the season that we were saddled with crowds and higher summer prices. Friends from both coasts of the U.S. (and one from Europe) made the journey to Greece, but we weren’t all arriving on the same dates or even staying in the same hotels. Some did both Athens and Crete, some did just Crete, some did a few days in Crete, and then there were the three of us who randomly decided to head to Santorini after, a totally last-minute addition to the itinerary, because, well, why not?
All the planning passed through me, and I had to be exceptionally organized. I had spreadsheets about everyone’s arrivals and departures, who was coming to which destinations, which Athens hotels they were booked into, who was renting a car, what were the room assignments in the villa on Crete, and who was paying for what. The one thing that helped simplify this process was that I was spearheading most of the decision-making. Yes, we had a big email chain in which dates, destinations, and activities were discussed, but it turned out my friends were agreeable to all my suggestions. That’s the benefit of not only being the celebrant but also a travel writer who was already familiar with the destination: My friends trusted me to take care of it, and I did.
I booked the villa, the boat, some of the tours, and our group meals. I researched flight times between Athens and Crete as well as which beaches we should go to and where we should pick up breakfast along the way. If my friends got themselves to Greece, I was happy to plan the whole thing. (Thank goodness for Venmo, Splitwise, and WhatsApp, which helped make everything else easier to manage.)
If I may pat myself on the back, I think I put together an epic trip. Most of them had never been to Greece before, and this itinerary gave them classic cultural sightseeing and island relaxation. And even when our days got a little too busy, there was always a fantastic meal coming and more wine flowing. And when you’re in our age range, that’s pretty much all you want out of a vacation anyway, right?
Days 1–3: Athens
The Athens portion was a mishmash of sightseeing, shopping, eating, and drinking as friends trickled in from all over. Because I booked my accommodations rather last-minute, I had to split my stay between two hotels. First, a night at A77 (Adrianou 77) in Plaka, the neighborhood directly underneath the Acropolis. The hotel stuffs 12 spacious and elegantly decorated suites into a three-floor townhouse. I had a simple but charming room with a soaring ceiling and marble bathroom. A77 was lovely: There were jars full of candy scattered everywhere, and they served a massive breakfast tray to your room.
Then I relocated to Monument Hotel (Kalamida 11) for two nights. The year-old Monument is in a heritage building from 1881 (built by architect Ernst Ziller, who was behind over 500 buildings in Greece). It took three years to transform the city-center property into a nine-key hotel in which every room is individually decorated. It’s all poured concrete, ceiling frescoes, antique rugs, and a picturesque medley of sculptural seats. It’s incredibly photogenic there, and everything is exclusively for hotel guests; I loved the quiet intimacy.
I was originally booked into a standard room, but a guest cancellation led to an unbelievable upgrade. (Always note that you’re celebrating something when booking hotels; you never know what surprises it will yield!) I ended up in the attic suite, which has a patio and a hot tub with unobstructed views of the Acropolis. I never used the tub, but my friends did join me for predinner sunset wine one night.
On day three, my friends (Joe, Joelle, Kathryn, and Luigi) took a private walking tour with Alternative Athens. Having been to the city before, I skipped that to instead check out the Sunday flea market, buy a pair of linen shorts at decades-old Greek brand Parthenis (Dimokritou 20), and peruse the Museum of Cycladic Art (Neofitou Douka 4) for its ancient marble figurines and bronze tools.
Dinner at Akra (Aminta 12) on night one produced one of the best dishes of the trip: goat terrine that’s charred with a super-crispy exterior but still juicy and tender. It was paired with grilled eggplant slices — unbelievably tasty! Right around the time we were finishing dessert, a musical troupe marched in, singing and playing their instruments. Our server told us it was a totally random moment.
There was a long lunch at Taverna ton Filon (Argous 66), a modest but bustling spot on the northwestern edge of the city center. Luigi fell in love with taramasalata, the fish-roe dip, so we basically had to order that plus peppers stuffed with rice and herbs, fresh tomato salad with a block of feta on top, and different preparations of fish.
We had a blowout dinner at Pharaoh (Solomou 54), one of the hottest dining rooms in Athens, known for wood-fire cooking, natural wines, and its DJs. We ordered yellow-split-pea purée topped with slivers of anchovies, grilled pork sausage, and a slice of galaktoboureko, a semolina-custard pie.
Day 4: Crete
8 a.m.: Visit ancient ruins and eat lunch at a winery
Our group of six (Marya arrived from Jersey the night before) took an early-morning, hourlong flight to Chania, one of Crete’s largest cities and located west of the island. We landed a little before 9 a.m. and immediately picked up our rental cars from Enterprise so we could get a breakfast of hazelnut pastries and slider-size ham-and-cheese brioche sandwiches at Red Jane Bakery (Kidonias 101).
We then drove 20 minutes east to Aptera, an ancient city-state that dates back to the Minoan period from 3500 to 1070 BC. There were cavernous cisterns, the remnants of a bath complex, and a small outdoor amphitheater, where I received a lecture for loudly singing “Circle of Life” as if I were headlining my own concert. Mortified, I begged my friends to leave.
Lunch was 45 minutes away at Manousakis Winery, one of Crete’s most famous producers, and one look at the outdoor tasting setup, with tables and chairs under the shade of olive trees, and you could understand why. My friend Lane (and her Pomeranian, Indiana Jones) met us here from Paris. The white and rosé wines are some of the winery’s most popular because they pair so well with whipped fava-bean dip, stewed gigantes beans, and fries.
We made our way back to Chania to check into our villa rental. But to make sure we had the necessary amenities, we stopped at the whimsically named booze shop the Lighthouse of Mr. Vertigo (Andrea Dikonimou) to pick up a dozen bottles of Greek wines.
4 p.m.: Check into the villa and relax for a few hours
When I was researching for a house that could accommodate at least ten people, this eight-bedroom villa 15 minutes from Chania’s airport was noticeably cheaper than the rest, so I booked it. It’s a massive complex with a pool, two separate buildings into which the eight rooms are split up, and lots of outdoor lounge spaces, including a separate dining area with a grill. When we arrived, Chrissie and Dani (friends from home) were already there taking full advantage of sunshine by the pool. So we popped open a bottle and raised a glass to our Greek odyssey.
8 p.m.: Order fried anchovies by the sea
For dinner, we headed to Thalassino Ageri (Vivilaki 35 Tabakaria), a seaside fish tavern 15 minutes away. The outdoor tables were right next to rocks on the water offering a very pretty sunset vignette. The menu was fairly simple: more taramasalata, tomato salads, grilled octopus, fried calamari, and fried anchovies. Overall, a wonderful welcome to my favorite Greek island.
Day 5: Crete
8 a.m.: Set sail
After collecting Bianca, who flew to Crete from Jersey through Rome, our three cars (packed with sunscreen, bottles of wine, and a bag of ketchup chips) set out for the 90-minute drive through the mountains to Sfakia Port to board a boat for a day of sailing. We booked Sailing South Crete, led by Annie and Christos, who — surprise! — got married the weekend before we met them. They operate a chic 50-foot yacht sailing Crete’s less touristy southern coast.
We hit three beaches, starting at Sweetwater beach, surrounded by cliffs and outfitted with a sweet little beach club under some trees. Some of us swam; some of us started drinking wine. The water was a gorgeous shade of blue but is impossibly cold for those of us who prefer bathwater beaches. Next was Marmara beach, four miles west, where we stayed for 90 minutes to give Joe as many opportunities to scramble up, then jump off, the cliff. There was wine-fueled merriment for those of us who opted to stay dry.
Our final stop was Loutro, a larger village giving classic seaside vibes with the white-washed buildings and seafood tavernas lording over the blue of the Aegean. For lunch, Annie recommended a restaurant with striped umbrellas called Ilios, where we ordered most of the classics: moussaka, grilled squid, Greek salad, and more white wine. It was a quick lunch because we still had to sail to Sfakia and drive the 90 minutes home.
9:30 p.m.: Share pulled pork and birthday cheesecake
Emily, another childhood friend, arrived in time (via London from Brooklyn) for the largest group gathering of the trip: dinner at Maiami (Akti Miaouli, Mesologgiou), a beautiful dining room–design studio in Chania’s historic Venetian port. At nearly 10 p.m., you couldn’t see much, but the restaurant features the artsy design genius of Alexandra Manousakis, who I learned, during the booking process, shares my birthday.
Foodwise, we took a break from traditional Greek cooking; Maiami’s menu was more globally influenced. There was a pulled-pork sandwich spiked with pickled watermelon rinds that the group really liked. I loved Mama Sharma’s Shrimp, a red stew sitting on some rice. The biggest surprise, however, was the beautiful cheesecake sparkling with birthday candles that arrived at the end of the meal.
It was the busiest day of the trip but also, maybe, the best day.
Day 6: Crete
10 a.m.: Tour through the mountains
We said good-bye to Kathryn and Joelle, who took an early-morning flight back to Jersey. The rest of us had a half-day tour of Crete’s interior with Anastasia, who runs the travel company Greek Like Me. She took us to visit an olive-oil facility before lunch at Ntounias (Keramion, Nerokouros), a family-owned agritourism project that has a restaurant with a cult following. At arrival, we found the team fussing over an outdoor kitchen by the entrance. But we’re seated under what looked like a dining gazebo with expansive views of the surrounding valley.
Anastasia brought a few bottles of wine for us to try with our lunch of sticks-to-your-bones mountain fare: fried potato wedges dusted with oregano, a stew of tender beef chunks and beans, and a super-juicy chocolate cake.
8 p.m.: Eat souvlaki at home
After the twists and turns of the drive back to Chania, the group was feeling the breakneck pace of the past few days, and we decided to hang at the villa for dinner. We stocked up on more wine, and Marya and Emily, who explored downtown Chania for a couple of hours, picked up pork souvlaki, chicken salads, fries, and some dolmas from Delish (Tsouderon 69).
Day 7: Crete
10:30 a.m. Visit a beach with goats
We started at Seitan Limania, a small rocky beach at the bottom of a cliff with goats. The hike down was not technically difficult, but it was steep and you needed to pay attention to where you were stepping. I don’t know how people did it in sandals while carrying children. It was worth it, though; the water was clear and frigid. The goats did eventually make it down, and, boy, were they frisky, trying to steal everyone’s stuff.
1 p.m.: Grab lunch and hit one more beach
Ninety minutes later, we decided to make the trek back and onto the next: Stavros, a calm, sandy beach 30 minutes away. There were lots of families, and the area had more restaurants and bars. We lunched at Almyriki (Stavros 731 00), which we chose for its windmill. Luigi said that the taramasalata, topped with a squid-ink sauce, was one of his favorites. But the crab pasta and marinated anchovies were also very delicious.
Beach time at Stavros was brief because we needed to be back at the villa to receive Afshin Molavi, the chef at Salis. He came over to make dinner for our final night on Crete. After a few days of bopping around the island and eating at various restaurants from the sea to the mountains, a cheffy last supper in the villa would be the perfect end to the trip.
7:30 p.m.: Have a farewell dinner followed by karaoke
Afshin’s coursed-out dinner was Greekish. The group’s winner might have been the glazed eggplant with fermented fava. It was spectacularly packed with umami flavors. I also liked the spinach pie that he served with preserved grapes, which added an unexpected tartness. Then, for dessert, baklava. Afshin also gifted us a few bottles of his super-exclusive pét-nat. Between that and the rest of the wine we ordered, it was no wonder the group ended the night with some makeshift karaoke courtesy of the wireless mic Chrissie brought from Jersey.
Days 8–10: Santorini
While in Crete, Bianca revealed that there was space in her two-bedroom Airbnb in Santorini. And that’s why, at 5 a.m., Bianca, Lane, Indiana Jones, and I were in a taxi for the port in Heraklion for an 8 a.m. ferry.
The adorable two-bedroom apartment was just outside Oia, the island’s most popular village. It was easy to walk into town whenever we wanted but thankfully far enough away that we were spared the noise and traffic. There were two bathrooms, too, and a small outdoor terrace with a plunge pool, where you could catch some nice sunsets.
Because everything was so last-minute, we booked what we could when we could, starting with a wine tasting at Vassaltis Vineyards (Vourvoulos) to sample its assyrtiko, Santorini’s trademark grape. The tasting came with a selection of savory tapas, like a spoonful of taramasalata and a piece of bread topped with butterflied sardines.
The rest of our meals on Santorini were some of the fanciest of the trip. One night, Lane and I splurged on Botrini’s (Main Street Oia), an offshoot of a Michelin-starred restaurant in Athens. Every moment was beautifully orchestrated. My favorites were the small chickpea tartlet topped with chopped green beans that were meant to mimic seashells and a gorgeous plate of phyllo pastry topped with a sculptural arrangement of zucchini slices. Both were refreshingly light, and the wines were fantastic, too.
The best restaurant views, though, were at Mia’s (Perivola Oia), a Greek hot spot overlooking the caldera. From the terrace, we watched the amber glow of the sun drop behind Santorini’s white-washed buildings. That’s what people come here for, but the food was equally stunning — dialed-up family cooking. I’m still dreaming about the oxtail pastitsio (plump agnolotti stuffed with meat) and the hearty bowl of orzo topped with lobster. A bottle of local assyrtiko from Kyanos Wines — only 3,000 bottles were produced — extended our party mood.
For another boat moment, we booked a public sail with Vista Yachting. I wasn’t sure how joining strangers on a catamaran would pan out, but mercifully we ended up with a chill group. The perspective you get of the island from the water is special. You’ll actually see beaches, from white sand to black rocks. Vista Yachting’s operation was awesome, too. Wine, beer, soft drinks, and lunch were all included. Obviously, we brought our own bottles from Vassaltis.
On our last day, our flight to Paris wasn’t scheduled until 7 p.m., so we splurged on Korres facials at the spa at Vedema (Megalochori), one of Santorini’s top hotels, then lunch at Nobu (Imerovigli). After all the Greek food, I was craving something different. Nobu Santorini was incredibly sexy and tranquil, which was the ideal vibe before we tackled the madness of an airport. I’ve never tried Nobu’s iconic spinach salad with the truffle-yuzu dressing; it was as yummy as advertised. As was the salmon sashimi. But I did try to hold on to my Greek fantasy a little bit longer by sipping as much Santorini rosé as I could with every bite.
Chadner’s Greece Packing List
You may already know that I love a linen shirt. But I didn’t have classic white in my inventory, and a birthday trip seemed like a great time to invest. I wore this to the beach, while walking around, to meals — a true closet workhorse.
Like the shirt above, these breezy navy pants were picked up specifically for the trip. And they blended very seamlessly with the rest of my travel wardrobe. I liked that these are designed to look more like trousers (rather than with a drawstring closure), making them a lot more versatile for that one fancy-night dinner on Santorini.
This might be my favorite clothing item at the moment. The linen is so soft and comfortable; it drapes beautifully, too. I own it in “bone,” but I already placed an order for “night.”
This was one of the items I gifted everyone who attended the trip. And it came in handy, because while it wasn’t blazing hot in Greece yet, we were outside a lot. Every now and again, we were all giving ourselves a refreshing spritz.
Lane and Bianca gifted me a Bao Bao tote for my birthday, which I received the morning we went sailing. I used it immediately. It’s a great beach bag because of the PVC. You wipe dry. You wipe it clean. It’s surprisingly sturdy. They got it for me in teal, which matched my Greece outfits perfectly, but you could never go wrong with black.
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