How to Spend Two Weeks Island-Hopping in Greece

November 1, 2022 1:35 pm

A Greece vacation has been at the top of my list for a decade, so I was thrilled when I found the perfect reason to travel to the Cyclades this past summer: my daughter’s high-school graduation. I roped in my daughter, my teenage son, and two of my best friends – one with a college-bound daughter and the other with a teenage son – and we called it a “Moms and Daughters Graduation Trip to Greece.” The mother-daughter bonding comes easy when it’s over amazing scenery, shopping, and sunbathing.

Here’s where a Virtuoso travel advisor is necessary: With a group this big, two weeks for travel time, and a desire to see as much as possible and still have room for impromptu decisions, I knew it was best to utilize Virtuoso connections. Our two weeks included stops in Athens, Mykonos, Santorini, and Crete. Here, a few favorite highlights, photos, and travel tips from our getaway.

Days 1-3: Athens

Hellenic Tours picked us up from the airport and took us straight to the centrally located Hotel Grande Bretagne. While the kids napped, the moms toasted to our trip by the gorgeous rooftop pool. You’ll find the city’s best souvlakis (shish kebabs) in the Monastiraki neighborhood – don’t miss rooftop dining at Kuzina, with breathtaking views of the Acropolis after dark. Your travel advisor can book you a table.

Of course, you can’t leave Athens without seeing the Acropolis and the Parthenon. We had a knowledgeable, English-speaking guide who schooled us all on ancient Greek history. We learned about the duel between Poseidon, the god of the sea, and Athena, the goddess of wisdom: Athena won by dropping an olive seed to the ground as an offering to the citizens, which is why you see an abundance of olive trees on the hike up to the Acropolis. (Pro tip: Wear sturdy shoes; the monument’s sleek marble steps are slippery.)

Virtuoso travelers staying at Hotel Grande Bretagne, a Luxury Collection Hotel, receive breakfast daily and a complimentary lunch for two.

Days 4-7: Mykonos

Hands down, this hip, lively island was our daughters’ favorite stop. Boutiques, restaurants, all-night parties, spectacular views, and, yes, cruise-ship crowds all await. While the ships are in port, head out on a private or semi-private yacht cruise to the surrounding smaller islands of Rhenia and Delos. Leaping into the chilly Aegean Sea made for great photo ops.

I met Anastasios Naoum, the commercial director of the Myconian Villa Collection, who showed me around the gorgeous 59-villa retreat on a hillside overlooking the Aegean. It’s one of the best places to stay if you want to be away from the crowds; the beach and town are accessible via bus transfers, so no rental car is needed. During dinner at Cabbanes at the Myconian Villa Collection, we sampled Greek wines and feasted on locally sourced dishes prepared with style – beef tartare with Greek yogurt, squid ink quinoa crackers, and tomato and sweet pepper sorbet. (Have I mentioned that Greece has the sweetest tomatoes in the world?) On our last night in town, we took the late-night bus transfer to town and chaperoned the girls at a disco club – or maybe they were chaperoning us?

Virtuoso travelers staying at the Myconian Villa Collection receive breakfast daily and a $100 dining credit.

Days 8-11: Santorini

Everything they say about sunsets on Santorini is true. And they’re especially gorgeous from Canaves Oia Epitome, a quiet and minimalist 24-villa escape on the northern edge of the bustling town of Oia. Groups will love the two-bedroom villas, which have their own pools overlooking the sea. Two essential Canaves Oia experiences: An olive-oil tasting and a goat’s milk hair treatment at the spa, perfect after long days spent in the sun.

For the best sunset views on Santorini, head to the tiny fishing village of Ammoudi. Have your travel advisor make a reservation at the Sunset Taverna for a memorable and amazing seafood meal. (Order the grilled octopus, trust me.) And if it’s a day lounging on the beach you’re looking for, plan for a morning at the chic Seaside Santorini beach club in Fira.

Virtuoso travelers staying at Canaves Oia Epitome receive a welcome amenity, breakfast daily, and a $100 dining credit.

Day 12-14: Crete

Crete was bigger and more beautiful than I expected, and I wish we had more time to explore. We stayed at Blue Palace, a Luxury Collection Resort & Spa, and loved the funicular that transported us down to the hotel’s private pebble beach. Plaka town is a 15-minute walk away, and we spent our one full day eating, shopping, and relaxing. If you can only bring home one souvenir, make it a bottle of Cretan white wine from the Maragakis Winery.

We raised our glasses to Greece every night on our trip – they were full of wine, ouzo, raki, or mastika (an after-dinner liqueur made of anise and other spices) – thankful for an epic graduation celebration, beautiful friendships, and for finally making dream trips come true.

Virtuoso travelers staying at Blue Palace receive breakfast daily and a $100 resort credit.

More people are turning to experts for help designing their ideal trip, given the complexities of navigating the travel world today. Coastline Travel has kept on top of the changes and nuances of getting around the world and can make the booking experience seamless so you can enjoy quality time with your loved ones while on the trip of a lifetime! Call us today at 714.621.1040, or find us on our Facebook page here.

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