Expert: Christos Stergiou, founder, TrueGreece
Length of trip: 10 days
Highlights: Historical Athens, beaches of Patmos, and sunsets on Santorini
DAY 1: ARRIVE IN ATHENS Check into the design-forward Periscope Hotel in the Kolonaki area of Athens—if you can swing it, book the penthouse suite with its private outdoor jacuzzi—so nice after a long flight... Spend the afternoon exploring the neighborhood's stores, restaurants, and quaint cafes.... Check out the traditional Plaka and Monastiraki market areas, or visit the new Acropolis Museum.... Then dinner at Kuzina restaurant, which has a stunning view of the Acropolis at night.
DAY 2: OFF TO PATMOS Catch a flight to Kos then connect by catamaran to Patmos, my home island; its beaches, quaint villages, and excellent culinary scene make it the perfect place for honeymooners.... Check into the Petra Hotel, a small (just 12 rooms), romantic spot close to the beach that remains undiscovered by the herds of international tourists.... Spend the afternoon wandering around Chora (the capital city) and check out the circa 1088 Monastery of St. John.... Have dinner at Benetos restaurant; you must try the cheese and spinach phyllo.... Take an afterdinner walk around Chora, followed by cocktails and dancing at Café 1673.
DAY 3: PATMOS Board a caïque (traditional Greek boat) for a private cruise to a series of nearby islands.... Try lunch at Pantelis, one of two restaurants on a beach with nothing else on it—they make incredible fish, among the best in Greece.... Enjoy some unstructured downtime.... Have dinner at Vegghera restaurant overlooking the marina in Skala.
DAY 4: PATMOS Visit Psili Ammos, arguably the island's most beautiful beach, or check out Grikos, a picturesque fishing village with a long beach.... Spend your last night dining and taking in the colors of the sunset at Diakofti Taverna.
DAY 5: ON TO SANTORINI Head back to Athens and connect by plane to Santorini.... Stay at the Carpe Diem Hotel, in the up-and-coming village of Pyrgos—the rooms are modern and spacious, and each has a private pool.
DAY 6: SANTORINI Head to the capital city of Fira for some shopping, or spend the day relaxing on one of the black sand beaches.... Walk around the town of Oia in the evening and take in a world-renowned Santorini sunset.... Finish the day with dinner on the terrace at Ambrosia restaurant.
DAY 7: SANTORINI Start with a day trip to Thirasia, a tiny island that has a really authentic, Old World vibe, or explore one of the Santorini wineries, like my favorite, Domaine Sigalas.... Eat dinner at the super-romantic 1800 Restaurant, housed in a restored mansion in Oia.
DAY 8: SANTORINI Enjoy your private pool and relax!
DAY 9: BACK TO ATHENS Return to Athens and check back into the Periscope Hotel.... Sign up for a guided city tour to see the Acropolis and other major sites.... Have dinner at Varoulko restaurant, known for its creative seafood dishes fresh from the Aegean.
DAY 10: FLY HOME