In my opinion, the best way to travel is with the assistance of a top-notch travel advisor. The good ones know the destinations, the hotels, and the most interesting experiences.
You may say you can find the same information online or in a guidebook. What you won’t find is the names of the best tour guides and insider knowledge on which suites have the best views – and which ones face the parking lot.
More than that, advisors have personal relationships with the managers at the top hotels and can organize VIP treatment. They also have the clout from the volume of bookings their agency and networks do.
It’s still a perfect time to take a late-season visit to Greece, so this week I’ve enlisted the experts at Virtuoso agency SmartFlyer to share the perfect first-timers trip.
New Jersey-based advisor Abby Kastin says, “The combination of Athens, Santorini, and Mykonos 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.”
As a major international hub, many Greece trips begin and end in Athens. But the capital is much more than a few jetlagged hours.
Los Angeles-based advisor Lauren Tulp Cichocki says, “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 were surprisingly bustling; it felt like walking through New York’s 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.
Reservations are set at Cherchez La Femme for cozy vibes and Greek mezedes, tapas-style eats. This light lunch is the perfect transition into a walking tour of the city. Your VIP guide will take you to Athens, old and new, 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 will give you a personal course on the five different varietals from across Greece. Naturally, there will be 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.
Hotel Grand Bretagne – Royal Suite
Located on the fifth floor, the Royal Suite is an unequaled one-bedroom, two-bathroom residence, spread across 4,500 sq. ft. Evocative of the historic legacy of the hotel and totally unique in the city, the interiors are appointed, with intricate cornice detailing, plush silk furnishings, and museum-quality antique furniture.
The master bedroom includes a private sitting room, walk-in closets, and dressing room. Ornate and luxurious, the large en-suite bathroom features a centerpiece bathtub with massage jets, separate steam shower, double basin, and flat-screen television. Leading from the bathroom and with views across Vassilissis Sofias Avenue and Parliament, you have your own private gym, complete with LifeFitness equipment and a sauna.
The master bedroom has been supremely designed with signature The Luxury Collection King Bed, walk-in closet, and original marble fireplace. Leading through to a separate sitting room, guests can relax on the silk chaise lounge, watch the 32” flat screen television or make full use of the modern technology where the entertainment center, drapes, and lights are controlled at the touch of a button.
The living room features a grand piano and original artwork. Double doors lead into the dining room with a table that seats up to 14 guests, while the media room with two sofas and modern-day technology provides an ideal location for television interviews.
After enjoying your included breakfast on The Grand Bretagne rooftop (pictured in the lede), depart from Marina Flisvou for a morning out at sea. Cruise the Athenian Riviera 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.
After docking, you’ll be greeted by your VIP tour guide and make your way to the Acropolis. Enjoy a private afternoon tour after the crowd has left to see this historical site before getting the prerequisite Instagram shot. 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. Enjoy 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. Even though it’s your first time, SmartFlyer will ensure you are known to the hosts.
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. Choose between frequent commercial flight, a private charter, or your own jet if you brought it along. SmartFlyer will work to your preferences.
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.”
Blue for days at Bill & Coo Mykonos
You’ll love the perfect welcome amenity, Grecian sarongs. Relax at the infinity pool with an 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 treatments use Swiss brand Valmont, sure to put you into an even deeper state of peace.
One-Bedroom Villas feature a king-size bed, a sofa bed, an open plan living room, indoor and outdoor dining, and lounging area and each villa comes with its own private pool. There is 860 sq. ft. of interior space and additionally 1,300 sq. ft outdoors to enjoy the Greek sunshine.
The three brand-new accommodations can be booked individually or combined into a private standalone three-bedroom Villa with pools. They are well-suited for couples or friends traveling together as well as families whose different generations prefer a little more independence or seclusion, as these are connected to each other via lockable wooden doors set in their fragrant gardens, offering easy access when open but complete privacy when closed.
Refresh for dinner at Le Maison de Katrin (above), 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 10 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.
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 (pictured below). 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 clams, sea bass carpaccio, shrimp, and more.
New York City-based advisor Melissa Gulotta says, “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.
It’s time to relax. Enjoy your pool and private terrace set-up at Bill & Coo (pictured below) 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 your next home, one of the Canaves boutique luxury hotels.
There is Canaves Epitome, Canaves Oia Suites (Cave Villa with Infinity Pool pictured below), Canaves Oia Hotel, and Sunday Suites. Each hotel has its own unique offering, so whether you are honeymooners, feel like honeymooners, or a family seeking a kid-friendly setup, SmartFlyer advisors will help you select the perfect option.
Wrap up your first night in Santorini with dinner at an off-the-beaten-track restaurant in Exo Gonia village. Metaxa Mas offers Cretan and local 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.
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 meals, salads, fruits, and Santorinian 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 (pictured above) 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. 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.”
Start thinking about your return trip to Greece!