10 Days in Greece
Like a Local
There’s nothing quite like summer in Greece. If it’s your first time exploring the islands, this itinerary is designed to give you a taste of everything—bustling city life, stunning beaches, iconic sunsets, and, of course, the magic of my home island, Samos.
Days 1-3: Athens
Start your journey in the heart of Greece. Athens often gets a bad rap, but it’s genuinely one of my favorite cities on earth. It’s a place where ancient history and modern energy collide—where you can wander through ruins in the morning and sip cocktails at a rooftop bar by night. The city oozes culture, character, and life. And if you have time? Make the effort to visit the Riviera—an unexpected slice of coastal luxury just outside the city. Here’s how I’d do Athens as a first-time traveler to one of the world’s richest cultural hubs.
Must-Do: Visit the Acropolis & Acropolis Museum.
Where to Eat: Enjoy modern Greek cuisine at Nolan or a chic dinner at Hytra.
Rooftop Drink: Dolli, Art Lounge rooftop, Zillers, Stork rooftop
Shopping: Stroll through Kolonaki for high-end boutiques or head to Plaka or Ermou for a mix of local and international brands.
Where to Stay: Hotel Grande Bretagne for luxury, or Perianth Hotel for a more boutique experience. Other heavy hitters include: The Dolli, Ergon, Mona & Shila, and Monsier Didot, NEW Hotel.
For luxury on the Riviera, The 4 Seasons and One & Only Aesthesis
Days 3-5: Milos
Milos is a dream. Think lunar-like landscapes, crystal-clear waters, and hidden beaches only accessible by boat. When I think about luxury, I think about these islands in Greece. Luxury is in the crystal waters, the food so fresh it doesn’t have time to be leftover, undeniable kindness from locals. This is Greece. I feel this when I am in Samos, where my family is from, and I had that exact familiarity when visiting Milos.
Must-Do: Take a boat day around the island. We booked through Milos Adventures and spent an entire day cruising around the perimeter of the island. This, to me, is an absolute must and the best way to explore the island. You will take multiple stops throughout the day to swim, explore, and enjoy a delicious Greek meal at sea. 10/10
Moon Beach: or, as the locals refer to it, Sarakinko. This is the pièce de resistance. This is what, in my opinion, makes Milos so unique from the other islands. This beach is truly otherworldly and a must-see.
Sunset Spot: Head to Plaka for a drink at Utopia a feast for the eyes.
Where to Stay: Adamas is the main town on the island and the most accessible. Plaka resembles the charm of Mykonos with its winding, narrow streets filled with shops and beautiful restaurants with views. We stayed at Milos Cove—though not the most centrally located, it was the definition of tranquil. You’ll need a car to explore, but if you’re comfortable driving, the resort’s serene atmosphere and incredible amenities make it worth the distance.
*note: you may want to consider renting a car when visiting Milos*
Days 5-7: Santorini
Where to Stay: We opted for an Airbnb option in Oia. Oia is bustling with life. There were endless tavernas, caffeneos, restaurants, and shops. There are endless options of resorts and hotels in Oia to choose from as well.
Must-Do: We booked a cab to take us to Roka at the Cavo Tagoo Hotel for sunset drinks and dinner. If you are able to make this happen, I cannot recommend it enough. I sometimes scroll back in my photos just to look at the sunset from that night again. Magic. And the food was elite.
Food & Nightlife: Kyprida was one of our favorite dinner spots in Oia. Very traditional and authentic cuisine that was just oozing with charm. Oia is packed with amazing food & nightlife, this city is alive.
Days 7-8: Mykonos (or Ios for a budget-friendly alternative)
Daytime: Spend the day at Nammos, Scorpios, Eterne, or Paradise Beach.
Evening: Head to town for dinner, drinks, and boutique shopping.
Ios Alternative: If you want a more affordable party vibe, swap Mykonos for Ios—it’s just as lively, with a younger, more laid-back crowd. I highly recommend making a reservation at Ios Club, one of the most gorgeous sunset dinners of the trip! Chora, the main town in Ios transforms into a young lively vibe after hours! During the day, head to Mylopotas beach. Grab a delicious bite at one of the many restaurants surrounding the beach- reserve a beach bed in advance!
Days 8-10: Samos
Where to Stay: Pythagorio—charming, close to the airport, and filled with great tavernas. I highly recommend Casa Cook - an elevated, modern, luxury stay. Doryssa hotels (there are a few options) are all great stays as well.
Must-Do: Rent a car and explore the island at your own pace. Top places to visit: Kokkari, a fisherman village with charming restaurants, shops, and beaches. You will under no circumstances want to pass up the Gryo at το περασμα του kοkkαριου.
Best Beaches: Navagos, Kaladakia (cliff jumping), Asteria Beach Club, Seitani Beach (for adventure), Tsamadou Beach (for crystal waters), and Livadaki
Food: Take the ride up to the authentic village of Platanos to enjoy one of the best sunset dinners from Orizontas. This is a true staple on the island; the owners are the kindest, most passionate people you’ll ever meet. It’s an absolute joy to be in their restaurant. When you’re done, take a stroll into the village center and enjoy a drink at the square. Enjoy fresh seafood and breathtaking views at Bella Vista or a traditional taverna meal at Triantafillos. Other favorites include Beach House at Casa Cook, Pergamonto, and Rematiki.
*note: you will want to consider renting a car when visiting Samos*
Kyprida is such a great spot!