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Choose Your Greece

With Greece open to Americans, our team and clients have been making it their mission to become experts in all things Athens, Santorini, Mykonos and beyond.

With so many incredible places to visit in Greece, there was no question that our group would have a fast-paced itinerary optimized to see and do as much as possible during their trip. So, we’ve modified the below to be a bit more slow-paced, in line with the kind of vacation we’d recommend for clients traveling to Greece perhaps for the first time. But as with any trip booked through your travel advisor, all hotel choices and activity inclusions are moldable to your preferences! You truly can #ChooseYourGreece.

Trip Notes:

NJ-based advisor Abby Kastin shares, “The combination of Athens, Santorini and Myknonos is well-suited for any traveler that is looking to experience all that Greece has to offer. This itinerary gives the best of everything from Ancient Greek history, amazing food, romance, beautiful sunsets and scenery, shopping, being near the water, culture, boating and nightlife. Not everyone likes all the same things and some clients are traveling as couples versus families, so your travel advisor can tailor an itinerary to their specific interests.”

Where to Stay:

The Grand Bretagne Hotel

In Athens, The Grand Bretagne is a “grand dame,” but it doesn’t feel too stuffy or dated. It is old world luxe in the best possible way, and definitely the way to go for your stay in the city according to our advisors. We love it for its views of the Acropolis and Parthenon. Established in 1874, it is a historic landmark in and of itself, not to mention situated in the very heart of Athens. | Book Now

Bill & Coo Suites & Lounge

In Mykonos, Bill & Coo is a great choice because it feels small and intimate with great service and decor. Just a few minutes walk from the center of the vibrant Mykonos Town, it’s the perfect location to enjoy the romantic Mykonian sunsets over the Aegean Sea. A place to see and be seen, this is a great spot for those look for a contemporary and trendy stay. | Book Now

Canaves Epitome

In Santorini, we love all things Canaves particularly because the Owner/Managing Director, Markos Chaidemenos, pays incredible attention to detail in all they do. With four different properties, there’s something for everyone, and our advisors know the ins and outs of each hotel from first-hand experience. For this particular trip, our group stayed at the newest in the collection, Epitome. From the views to the food to the service, you won’t be disappointed here. | Book Now

Trip Highlights:

  1. A private After-Hours Acropolis visit.
  2. Greek Wine Tasting in Athens
  3. Private Yacht Trip from Mykonos with Fresh Seafood Lunch on Beach
  4. Oia Sunsets, followed by evenings at the best nightlife spots in town.
  5. Private Catamaran Sail around Santorini


Day One: Welcome to Athens

As a major international hub, many Greece trips begin and end in Athens. But, we love this city for so much more than a few jetlagged hours. When we checked in for her impressions of the city, LA-based advisor Lauren Tulp Cichocki shared, “Athens really surpassed my expectations. 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 I highly recommend staying for two nights! The food and nightlife scene was surprisingly bustling; it felt like walking through the West Village at night.”

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.

Day Two: Private Yacht Excursion + Parthenon

After enjoying your included Virtuoso 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. Enjoy lunch on board before heading back to the marina by late afternoon.

Our incredible advisor crew, from left to right: Abby Kastin (NJ), Kelly Smith (Chicago), Josie Schiavone (DC), Melissa Gulotta (NYC), Lauren Tulp Cichocki (LA) & Amy Selling (NJ)

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 night cap at old time classic “Bar 42” makes for the perfect final cocktail of the night if you want just one more.


Day Three: Quick Flight + R&R

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 it’s 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. To sweeten the deal, you’ll have a $100 USD spa credit available to apply towards your treatment as Virtuoso client. 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 night life to end the night.

The Bill & Coo pool? Yeah, we could stay (or float) here for awhile...
Poolside at Bill & Coo, Mykonos

Day Four: Yachting + Bohemian Lunch

Today you’ll embark on a very special excursion out to Rhenia 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, “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! 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.

Tasting the freshly (literally) caught seafood beachside

Day Five: Sunning + Shopping

It wouldn’t be a trip to the Greek islands without some time in the sun. Enjoy your the 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.


Day Six: Ferry + Exploring Oia

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, and with each hotel having its own unique offering, we love helping our clients find the perfect location for their Santorini stay. 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 form 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.

Lauren Tulp Cichocki, Kelly Smith, & Markos Chaidemenos (Owner / Managing Director, Canaves Oia, Luxury Resorts, Santorini)
Lauren, Kelly, and Ruthie with Markos Chaidemenos, Managing Director of Canaves Oia

Day Seven: Catamaran Sail

Enjoy your included breakfast at Canaves before heading down to Ammoudi Bay for a private sailing day tour. According to Ruthie Wysor, “Nothing makes you appreciate the stunning views of the Santorini caldera from your hotel suite like heading out on a luxury catamaran, jumping into the crystal-clear waters of the Aegean Sea, and 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 meal, 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.”

Day Eight: R&R + Sunset Savoring

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. The Eclectic Greece team facilitated the most delicious meals for us, but 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.”

Cotton candy skies taking in the iconic Oia sunset
Sunset in Oia

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

Day Nine: Homeward Bound

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.

To book a Greece vacation of your own, get in touch with a SmartFlyer advisor to craft the perfect itinerary for you.

Book Now

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