Choose Your Greece

As a major international hub, many Greece trips begin and end in Athens. People typically think of it as a stopover city on the way to the islands, an overnight, checking the Parthenon off your list out of necessity. But we recommend staying for two nights; the food and nightlife scene are some of the city’s best-kept secrets. Oftentimes, walking through its stories streets is reminiscent of a night out at the West Village.

After checking in at The Grand Bretagne (and maybe even taking a dip in the rooftop pool for some post-plane laps), it’s time to dive into some local eats. We love Cherchez La Femme for cozy vibes and Greek mezedez, tapas-style eats. This light lunch is the perfect transition into a walking tour of the city. Our VIP guide showed off the old and new that Athens offers, including the historic city center and the New Acropolis museum.

Then, it’s off to a pre-dinner private wine tasting! Well-known sommelier Evagelos Psofidis walked our team through five different varietals from across Greece. Naturally, there were cheese pairings along the way, because, can you do a wine tasting any other way? Wrap up in time for a late dinner (you are in Europe, after all!) overlooking the Acropolis all lit up.

After enjoying your breakfast on The Grand Bretagne rooftop, depart from Marina Flisvou for a morning out at sea. Cruise the Athenian Riviera (did you know there was such a thing?) out to Cape Sounio where you’ll be able to take in the Temple of Poseidon. Surrounded by the water on three sides, this monument represents the Golden Age of Athens and definitely lands on our list as one of the best places to visit in Greece. Enjoy lunch on board before heading back to the marina by late afternoon.

After docking, you’ll be greeted by your tour guide and make your way to the Acropolis. Enjoy a private afternoon tour after crowd hours to see this historical site before getting the prerequisite Instagram shot. Luckily, being there past general admission closes will allow you to get your photo-op sans other tourists! Once you’ve wrapped on getting your cultural and historical fill, it’s back to the hotel to freshen up for dinner. Our team enjoyed the Art Lounge Restaurant of New Hotel before discovering Athens by night. Clumsies Bar is a must-try, awarded spot number six on the World’s 50 Best Bars list. A nightcap at old-time classic Bar 42 makes for the perfect final cocktail of the night if you want just one more.

…you see another side of the island when visiting in October. It gives you the opportunity to connect with people on a deeper level, when locals are a bit more relaxed now that the crowds are gone.

Begin your morning with one final breakfast atop The Grand Bretagne rooftop before being whisked to the airport to begin your island-hopping portion of the itinerary. After your quick flight, you’ll be greeted by the charming white-washed buildings downtown. When asked what the vibe of the island was like during their trip, Chicago-based agent Kelly Smith shared, “Mykonos is known for its rowdy beach clubs, but you see another side of the island when visiting in October. It gives you the opportunity to connect with people on a deeper level when locals are a bit more relaxed now that the crowds are gone.” (Want more destinations where you can experience a more authentic vibe in the midst of fall? Check out our blog, “Chasing Summer in October.”)

Our crew checked into their home base, Bill & Coo Hotel Mykonos, before relaxing at the infinity pool. Obligatory Aperol Spritz in hand, naturally. If you’re in need of even deeper relaxation, now would be a perfect time to slip into the spa. Their incredible treatments use Swiss brand Valmont, sure to put you into an even deeper state of peace. Refresh for dinner at Katrin, a local spot tucked in an alley with a French-Greek-inspired menu. The restaurant is known to draw a celebrity crowd and with no more than ten tables, you’ll be so happy your travel advisor scored you a table. If you’re up for it, hit downtown for some nightlife to end the night.

For me the most memorable experience was our yacht day in Mykonos. We were taken to this secluded beach that was set up for a lunch picnic. The meal was outstanding!

Today you’ll embark on a very special excursion out to Rinia Island after your breakfast at leisure. Pass by Delos Island en route to a private beach where you’ll anchor for lunch prepared seaside. A local chef met our group, doubling as a farmer and a fisherman, pulling seafood straight out of the water. This mouthwatering spread included fresh Greek salad, sea urchin, grilled gyalisteres (clams), sea bass carpaccio, shrimp and more. NYC-based advisor Melissa Gulotta shared, “This was the most memorable experience for my trip to Mykonos. The meal was outstanding! Locally caught seafood, and when I say local, I mean 30 feet from where our table was set up. The flavors were so unreal and so simple, made with passion and love. The experience was beyond words that I literally cried tears of joy!”

With lunch wrapped up, enjoy the private beach set up with some wine in hand. Take a leisurely sail back with stops to swim along the way if you’d like! Your crew will bring you back to Bill & Coo by dusk so you can enjoy the famous Mykonos nightlife.

It wouldn’t be a trip to the Greek islands without some time in the sun. Enjoy your pool or your private terrace set-up at Bill & Coo where Amy Selling says, “You’ll feel a million miles from home here. There are 15 private suites facing the ocean, so guests here won’t want to leave; they truly are spectacular, and not to mention quiet! Super romantic.” Or, if you’re eager for some more activities, take advantage of Mykonos’ legendary shopping just a short walk from the resort. It’s your final night on the island, so depending on how you feel you could check out some nightlife or keep it low-key.

Wake up in Mykonos before hopping on a ferry to Santorini. Upon arrival you’ll be transported to the breathtaking Canaves Epitome. Our team spent some time with Managing Director, Markos Chaidemenos, as they toured nearby sister properties Canaves Oia Suites, Canaves Oia Hotel, and Sunday Suites. This collection of boutique properties is beloved by our team. With each hotel having its own unique offering, we love helping our clients find the perfect location for their Santorini adventures. Whether you’re honeymooners looking for a private outdoor heated pool or a family seeking a kid-friendly setup, there’s a Canaves for you.

Wrap up your first night in Santorini with dinner at an off-the-beaten-track restaurant in Exo Gonia village. Metaxi Mas offers Cretan and Santorinian cuisine with the freshest ingredients from their garden. You’ll also have the opportunity to taste unique wines in this hospitable atmosphere, reminiscent of an island house porch. For a little taste of nightlife, head to downtown Fira after dinner to check out Bar Tango.

There’s nothing like jumping into the crystal-clear waters of the Aegean Sea from the bow of a ship, then gazing back up hundreds of feet at the beautiful white and blue buildings of Oia.

Enjoy your included breakfast at Canaves before heading down to Amoudi Bay for a private sailing day tour. Take in some stunning views of the Santorini caldera from your hotel suite while heading out on a luxury catamaran. There’s nothing like jumping into the crystal-clear waters of the Aegean Sea from the bow of a ship, then gazing back up hundreds of feet at the beautiful white and blue buildings of Oia. Circle the caldera cliffs passing by Oia, Imerovigli, and Fira. The first stop is at the hot springs for a dip! Or, if that’s not your style, not to worry because the next stop is a quiet bay perfect for a swim. Board the catamaran for a pass by Thirasia Island before one final stop at another private bay. Here you’ll indulge in a lunch with local delicacies including salads, fruits, and Sanorinian wine. Return back to Canaves Epitome for some leisure time. Maybe you can finally dive into that book you’ve been lugging around!

Freshen up for a dinner at the hotel. The Elements Restaurant & Bar takes local gastronomy to the next level. Their sophisticated and creative menu designed by Executive Chef Taso Stfatos challenges the palate through each course. Begin with vibrant cocktails followed by a dinner accompanied by live saxophone. With the 24 suites within a quick walk from the restaurant, you can completely relax knowing you’re close to “home.”

It’s your final full day in Greece, so spend it as you wish. Perhaps that means chilling at your private pool, or maybe you’d prefer hiking from Oia to Fira. Be sure to savor the last bites of authentic Greek cuisine. In the words of D.C.-based advisor Josie Schiavone, “The foods we tried throughout the trip really connected me to the local culture. After all, the best way to experience any destination is through food and drink, right? Even something as simple as ‘street food’ was something to be savored. One of my favorites was a Gyro in Santorini! They of course sourced the best out there through their first-hand knowledge of the destination.”

No matter what you do, we recommend catching the sunset in all of its Oia glory. Santorini’s white-washed buildings serve as your Instagrammable backdrop as the day comes to a close. There’s a reason you’ve seen so many photos of it plastered on social media. Sip on a glass of local wine as you take in what has surely been an incredible trip.

Unfortunately, all good things must come to an end. But don’t worry, it’s never too early to start planning your next adventure. Isn’t that what in-flight wifi is for? Get emailing your travel advisor, stat so you can #ChooseYourGreece.