10 Days in the Greek Islands: Santorini & Milos
Here's the thing about Greece; it’s amazing and if you haven’t been at least once, you need to fix that ASAP. I am going to share one of my favorite itineraries because it’s perfect for a summer vacation with friends, a girls trip, family vacay, or couple’s getaway. You can customize it to your travel-style because Greece is made for everyone and every island offers something different.
The Itinerary: 5 Nights Santorini, 5 nights Milos
Santorini: 5 nights
Santorini's entire identity are the views. If a gorgeous view is not the first thing you see in the morning and last thing at night, you're paying Santorini prices for a hotel room that could be anywhere. The private pool? Non-negotiable, especially in peak season. Imagine fighting for a lounge chair at a crowded infinity pool instead of sitting in your private pool, drinking a glass of Dom Perignon, while you watch the most gorgeous sunset.
Day 1
Arrive in Santorini. There are taxis but not enough of them so if you want flexibility, hire a driver. You can hire one for your entire stay or I have a company you can call when you need them. Today, all you have to worry about is settling in and relaxing. This could mean a walk around, taking a nap, a dip in the pool, another nap in the sun. Whatever feels best for you (remember, you’re on vacation). My best piece of advice? Go find an Aperol Spritz. It tastes like the start of vacation and no one makes it better than Greece (…and Italy). Order in for dinner or eat at a restaurant onsite if one exists. Tonight is all about relaxing so enjoy the sunset and make sure you’re rested for tomorrow.
Day 2
Easy morning, even if you’re up early due to the jetlag. Around 11, head down to Ammoudi Bay. While it may be 300 steps down (and 300 steps back up), this is where you’ll find fisherman boats, amazing seafood restaurants, and you get to be right on the bay, feeling the sun kiss your skin and hear the sound of the waves. This is what vacation feels like. After lunch, you can talk to the local fisherman, head back to your villa, or walk around. For dinner, go to a rooftop restaurant to enjoy amazing Mediterranean food and another gorgeous sunset.
Day 3
You’re on an island, time to get out on the water for a half-day catamaran cruise. See Santorini from the water and visit the natural hot springs at Nea Kameni. Lunch onboard. Mid-afternoon you’re back on land with time to get ready for a fine-dining experience and another gorgeous sunset (I promise, they never get old).
Day 4
Time to use your private driver and spend the morning at Akrotiri, the excavated Minoan settlement (Greece's Pompeii, minus the crowds), then to Emporio to see the Venetian Castle while walking through the local village. Minimal tourists, more locals. Afterwards, head to Pyrgos, another local village,for the view from the Kasteli ruins. Lunch and wine tasting at Venetsanos Winery or Santo Wines, both on the caldera edge with none of Oia's crowds. The wine on Santorini is special as its made with assyrtiko, the grape that only grows in the volcanic soil. Have dinner here too, it’s better than in Oia.
Day 5
Enjoy your villa, or head out for one more winery visit at Domaine Sigalas, visit Fira (the lively less-luxurious area of Santorini), if you’re feeling really adventurous, book a flying dress photoshoot (I regret not doing this). If you decide to stay in, order champagne, snacks, and pick up (or order delivery) a gyro from Pitogyros Traditional Grill House for lunch or dinner (you’ll thank me later). Enjoy your last Santorini sunset in the privacy and quiet of your villa. This night will be the one you remember because the moment was yours and whoever you’re traveling with.
Santorini Accommodations
Oia (high-end luxury, beautiful pedestrian walkway, tons of shops, gorgeous views, what you see when there is a photo of Santorini)
For Couples & Groups:
Canaves Oia Epitome —Private-pool suites, direct caldera view, discreet service, on-site fine dining. The only property on the island that offers both sea and sunset views from every room.
For Couples
Katikies Oia — the original cave-suite hotel and still the most iconic; perfect if you want the classic Santorini photograph, this should be your pick.
Perivolas — 300-year-old restored caves, three private-pool suite types, the island's best wellness facility. Quieter than Katikies, equally luxe.
For Groups
Charisma Villa - An ultra-luxury villa with amazing sea views situated at the entrance of Oia. Private everything (pool, hot tub, working stations, gym, sauna, bbq, terrace, views).
Aenaon Villas - This truly idyllic and unique retreat consists of seven luxurious villas built with respect for the traditional Cycladic architecture, in perfect harmony with the natural setting.
Ascani Villa - The largest of them all and and space for 16 people, there are 8 bedrooms and 7.5 baths, making this the perfect location for a girls trip, family vacation, or small group trip. Also has two pools, does it get any more dreamy than that?
Imerovigli (quiet, less crowds, more privacy)
For Couples
Grace Hotel by Auberge Resorts - Serious restaurant on-site (Varoulko, Michelin-recognized chef Lefteris Lazarou). The pick for repeat visitors or anyone who's done Oia before.
For Groups
Francisca Villa - With the most perfect and panoramic views of the Aegean Sea and infamous sunsets, an ideal sanctuary for those who are looking for comfort, class, tranquility and privacy, highly recommended for honeymooners or family and friends seeking a quiet comfortable setting.
What To Skip?
The Fira–Oia cable car and donkey path at midday. Cruise-ship hours turn this into a nightmare, not an experience. If you really want it, go before 9am.
The "blue dome" photo spot in Oia. Yes, of course it’s worth seeing, but it’s not worth fighting a crowd for at sunset. Go at 7am instead; same domes, nobody there.
Booking every dinner in Oia. The island's better cooking is inland (Pyrgos, Exo Gonia, Megalochori). One caldera night is plenty; the rest should chase the food, not the view.
Milos: 5 Nights
Milos, while gaining popularity, is a totally different island vibe when compared to Santorini. It’s less built up, a bit more authentic, and charming in a way that I fell in love with. The island also has the most beautiful beaches and are a must-visit. If you don’t like the beach, this island is not for you (there are only 225 more to chose from).
Day 6
Say Αντίο (goodbye) to Santorini and take an early morning high-speed ferry to Milos. Get an ATV if you’re comfortable but a rental car is also an option, no driver needed here. Once your bags are safe and sound at your accommodations, head into Plaka, the downtown of Milos. Here, you can shop, find a nice bar, have lunch, and just enjoy. In the evening, drive down to Klima, the fishing village where houses are painted in bold colors right at the waterline (they are known as syrmata). Have dinner at Astakas, a waterside restaurant with the freshest seafood. Even though you just witnessed some of the most beautiful sunsets in Santorini, make sure you stay for the one here; the sun turns into a bold orange and reflects off the water and illuminates the fisherman's houses. Talk about a true golden hour. This is a night you will talk about for years (and it is not because the sunset is anymore special than in Santorini but you are finally relaxed and really just soaking it all in).
Day 7
This is personally my favorite day and what I built this trip around. A private boat day sailing around the island. Visit Kleftiko Sea Caves, where white rock formations rise straight out of the clear turquoise water. Perfect for swimming and snorkeling, including through the caves themselves. Other stops may include Sikia Cave, Polyaigos, and Glaronisia. Lunch onboard the ship. This day is the "invest where it matters" moment of the whole itinerary. Everything else on this trip could flex, but not this. In the evening, dinner in Plaka or Pollonia. Plaka for the sunset, Pollonia to be near the beach.
Day 8
Early morning (out by 8am) to go to Sarakiniko Beach. The lunar white rock beach that looks fake until you're there. They call it the Moon Beach for a reason. It's not a lounge-chair beach, it's a quick walk-around-and-stare-at-it beach, maybe some cliff jumping if you’re up for it. You only need an hour, max two. Once you’ve had your fill of the moon, drive to Mandrakia and have lunch at Medusa, another waterfront restaurant with raving reviews and what you see in the dictionary when you type in “perfect greek restaurant on the water”. In the evening, head to O! Hamos!in Adamantas for a family-style dinner. They don’t take reservations and they are well-known (for a good reason), so make sure you arrive before you’re hangry. This place will forever hold a special place in my heart for their kindness as they gave us a table beyond the time they should have and never made us feel like we were a burden. Worth any wait you may have.
Day 9
Start at Firiplaka, the most beautiful beach I have ever seen. You should arrive by 8am, before the beach bar opens and the crowd settled in. This beach is small and can get crowded, hence arriving early. Swim while it's still just you and the water, feel the sand between your toes, and know this is truly the best morning you will have on this entire trip. Mid-morning, head to the Catacombs and ancient theater near Trypiti (Milos's Christian-era history and the discovery site of the Venus de Milo). Afternoon, is up to you. You can stay at Firiplaka, go back to your accommodations, or something else. You’re on vacation, every moment should not be planned. Dinner in Trypiti.
Day 10
At your leisure as this is your last day and you should enjoy it however you want to. Wake up, have some coffee, go for a swim, go to a beach bar…Milos is your oyster today. Don’t forget to pack your bags depending on what time your flight leaves. I recommend dinner in Plaka, Klima, or Mandrakia.
Day 11
Time to go home. You will need to fly to Athens to catch your flight home. If your flight time allows it, a final swim before you leave as these beaches will live rent free in your memories, and they should. The water temperature is perfect, the water is wildly clear, and you just had the best Greek vacation of your life.
Accommodations
In Milos, accommodations are more limited as the island is still developing to accommdated tourism, which is part of it’s charm.
Pollonia (easy beach access, low-key luxury part of the island)
For couples:Milos Breeze Boutique Hotel— cliffside, panoramic sea views, some units with private pool or spa bath. The most romantic room in the village.
For groups:Delmar Beach House - 1- & 2-bedroom units for 3–5 guests plus a 2-bedroom villa sleeping up to 7, fully equipped kitchenettes, private terraces, steps from the beach and Pollonia's restaurants. Consistently the best-reviewed group-scale option in the village — praised for design, cleanliness, and breakfast, not just capacity.
Plaka (great for a central and lively location, better for sunsets)
For couples:Eight Infinity Suites — new cliffside residence, caldera-like view, full concierge for yacht charters and private picnics. Adults-only.
For groups:Plaka Suites — design-boutique, village-center, walkable to restaurants and the Catacombs. Better suited to a group that wants to split into a few rooms and reconvene on foot than to book one giant villa.
Agia Kyriaki (extremely-private beach, very quiet)
For couples:Milos Cove Hotel— private beach access, the most secluded and romantic base on the island.
Mandrakia (included because the villa is gorgeous and group accommodations in Milos are hard to come by)
For groups:Villa Mandrakia — modular hillside villa with 4 independent units and multiple verandas, heated pool, 10 minutes from Plaka and the airport, Medusa taverna next door. Built for groups or extended family who still want privacy from each other.
What to Skip in Milos
Renting a standard car (only if the group is comfortable on an ATV/quad) — most of Milos's best coves have no real parking and dirt roads. An ATV handles it better (and it’s less expensive!)
An "island tour" boat with 40 people on it — Milos's is about experiencing peace and quiet. You want an empty cove. Pay for private or small-group; a packed catamaran defeats the purpose. You want to experience this, not just see it.
Skipping Pollonia for "just Adamas" — Adamas is the port town, functional but forgettable. Don't judge Milos's charm by it (even though Adamas is cute too).
Why This Combination Works
Santorini gives you the version of Greece you already had in your head while Milos gives you the version you didn't know to ask for. Put them back to back and the trip becomes unforgettable and diverse with luxury vs authenticity. I have traveled quite a bit but this trip is one I keep coming back to as one I would love to do over and over again.
Other Tips
If you’re visiting in the summer, skip Athens unless you absolutely feel you need to visit it. It was incredibly hot and humid and honestly, ending the trip there was not a good idea. It is my one regret I have about the trip I planned for my family.
Get to know the locals. They are so friendly, you just need to show them respect. Learning a little Greek goes a long way (we are not talking sentences, just ‘hello’, ‘thank you’ and ‘goodbye’. Smile back when they smile at you.
Know the weather before booking. Greek summers are HOT but the shoulder season for swimming is short.
I hope your next trip is to Greece after reading this…I can see it in my future very soon.