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There are thousands of Greek islands to choose from but only a few hundred are inhabited. Pick one (or more) that suits your vibe and appreciate how they all have very different personalities. Pro tip: Avoid peak crowds and still enjoy warm seas and open restaurants by booking your trip in September.

Crete: The diverse landscape island

The largest island in the Mediterranean, Crete exists at the intersection of three continents (Europe, Asia, Africa) and demands at least a week to fully begin to understand the diversity of microclimates. Because the snow in the mountains lasts between five and six months and feeds the island with springs, the land is very green. Limestone eroded over time and created 15 giant plateaus and many caves. What I saw of Crete in two days reminded me of Malibu, if we could go back a century in time to a coastal paradise with no highways or clusters of multimillion-dollar homes. I have never seen so many olive trees in my life and recognized numerous flora often seen in California. However, many plants and herbs are endemic to the island – like dittany, an herb in the oregano family grown in the high mountain grounds and used as tea and medicine.

Dittany in Crete

The locals say it’s impossible to get bored in Crete, as there are unlimited adventures. Our tour guide driver told us: “It is a geological paradise, a hiking paradise, and a food paradise, and we ask, what does the garden have to offer us today? It is impossible to starve here as we have wild mushrooms, greens, snails, rabbits, birds, fish, and many goats. Every dish is 3-4 ingredients – nothing spicy because our ingredients are so fresh. There are different varieties of dishes depending on where you are on the island.”

Crete olive trees

Although Cretans are friendly people and we are told no criminal activity exists, you might be startled by guns being shot in the air in celebration, as such possession is permitted in tradition. In Greek mythology, Hercules, who is worshipped in Crete, was sent to the island to wipe out all the dangers. Crete was also home to the Minoans, the earliest advanced European civilization, peaking around 1950 B.C. before “the ancient Greeks” of Athens.

Which Greek island is right for you?Stay:  Grecotel Amirandes is a glamorous property on the ocean in the city of Heraklion, styled after the water palaces of Minoan Kings and Venetian nobles that once ruled Crete. Hotel life is staged around a lagoon (that you can dine in) and caters to all ages. Book a modern beachfront villa with a plunge pool and go to bed to the sounds of crashing surf. Each morning, sample numerous Greek specialties at breakfast with an endless array of local ingredients. Disclosure: Thank you to EZGReece DMC and Hotel Grecotel Amirandes for hosting us on a Greek travel advisor FAM trip.

Spinalonga Island, Crete

Experience: Food lovers rejoice! Discover traditional life in rural Crete at Peskesi, a gorgeous organic farm where visitors master their cooking skills. Scale up to the rugged Cretan mountain to the Lasithi Plateau to learn what the locals eat and help prepare a lunch feast while exploring the abundant land. Farm to table, table to farm, Chef Agelos Mpougias indulges guests with local wine and raki (an alcoholic aperitif) along with cooking techniques like preparing food “under the bell”, making cheese from sheep’s milk, and concocting dishes like vegetable fritters, snails, and lamb.

Snails in Crete

Don’t miss a 10-minute boat trip to beautiful Spinalonga Island, a leper colony until 1953, and return to the lovely Greek Plaka town for lunch at Giovanni’s, where the local fisherman provides the daily catch and the restaurant offers sardines, mussels, Greek Salad, taramasalata, grilled and fried octopus, and salt-casked fish the length of an arm – all with jewel-like ocean views. Learn how skincare and beauty products are being made from herbs and olive oil at Bioaroma Crete and visit the Vassilakis Estate farm that produces Charisma Cretan olive oil.

Giovanni's in Plaka, Crete

Santorini: The fantasy caldera island

The captivating Caldera island is celebrated worldwide for its distinctive volcanic landscape and perfectly placed whitewashed villages, accented with azure domes and situated on the rim of a collapsed volcanic crater. According to the National Park Service, “calderas are collapse features that form during large-volume volcanic eruptions when the underlying magma chamber is partially emptied and the ground above it subsides into it.” Before tourism, the pumice stone soil proved perfect for digging cave houses as shelters for fishermen and animals. The remnants of these caves still dot the landscape today and the concept has inspired modern architectural design for decades.

Which Greek island is right for you?There is a lot to see in Santorini – like over 600 churches that every old family had for private places of worship. The most picturesque and geologically interesting island offers colorful beaches in red and black, boutiques and restaurants with dizzying views, and a mix of old and modern wineries in the countryside. Once filled with tomato factories, “tomato balls” (fritters) are on every menu and were considered at one time the “meat” of the island. For wine lovers, adventure seekers, or those who just want to fall in love all over again with the scenery or each other, become spellbound with the landscape and don’t miss the sunsets.

Amaze Suites in Imerovigli, Santorini

Stay:  Newly opened Amaze Suites sits on the caldera’s edge, in view of popular Oia (“eee-ahh”) town. This charming boutique hotel, perched on the cliffs of Imerovigli, features classic simple rooms and offers everything needed to enjoy the enchanting setting. The adorable pool terrace – with netted sun umbrellas atop the caldera – offers dreamy sunset views both in the common areas and right from each room’s jacuzzi terrace. There’s no need to leave the mesmerizing sprawling views of the Aegean Sea. Take your complimentary breakfast outside next to the pool to sample numerous Greek delights. This location may be the best spot between Fia and Oia, and is a more affordable option that feels like a private compound. Disclosure: A big thank you to Amaze Suites for hosting me so I could write this review.

Amaze Suites in Santorini, Greece

For those looking for a modern, full-service, accessible resort with amenities like an on-site spa, childcare, 24-hour gym, and a fantastic restaurant led by a star chef, brand new Domes Novos Santorini is your answer. A complimentary 2-minute shuttle delivers guests up the hill to and from buzzing Oia town. Choose from 2 villas and 50 spacious modern chic suites – all with private terraces, plunge pools, and some with views of the dramatic sunsets. Try a sunset painting class, float in the spa’s underground grotto, or dine at the rooftop restaurant where the chef rolls out elevated Michelin-level Greek cuisine with an emphasis on seasonal ingredients. Breakfast poolside is perhaps the best way to explore the island’s dishes. Disclosure: Thank you to EZGReece DMC and Domes Novos Santorini Hotel for hosting us on a Greek travel advisor FAM trip.

Domes Novos Santorini

Experience: A wine and lunch pairing is a must at one of the many old or modern wineries, as Santorini’s dry fresh crisp white wine, with minerality, is the best of the Greek islands. Known as assyrtiko, try this varietal at any restaurant or Anhydrous Winery. You will see these low-growing vines manipulated into circular baskets all over the island to protect the grapes from the wind and sun. Dry farmed, it’s amazing how the pumice stone holds the moisture for the plants to grow.

Melissa in Greece.For adventurous travelers, a breathtaking and rewarding 4-mile hike each way atop the Caldera from Imerovigli to Oia town isn’t complete without a stop for exquisite strawberry and pistachio gelato at Lolita’s in Oia. With transportation, explore the island’s black rock beach, Cycladic alleys of Megalochori village, and Akrotiri, an ancient settlement dating back to 4,000 BC that was later buried under ash.

Santorini Catamaran launch

Perhaps the most extraordinary way to experience Santorini’s dramatic scenery is on a sunset catamaran cruise. Rent a private boat charter from Santorini Sailing Center on the Daiquiri, which leaves Ammoudi Bay at 2:00 and includes swimming at several stops like Thirassia Island and Sulfer Springs volcanic waters. Stand in awe of grandiose volcanic rock bays, white towering rock faces, and red sand beaches. The mesmerizing sail includes unlimited wine and drinks served right to you and an incredible Greek meal cooked by the captain on the grills off the back of the boat.

Santorini Caldera Sunset from Amaze Suites

Milos: The beautiful colorful rock adventure island

If Block Island off Connecticut had a baby with old-school NY Hamptons, Milos might resemble their offspring, with the ocean smells, relaxed attitude, active options, and adventurous spirit. Milos was the island of Aphrodite, the goddess of beauty and love, whose history includes marble extraction, concrete factories, and ancient obsidian mines. The famous Venus di Milo statue, now in the Louvre, was discovered on this island. It is the most laid-back of all the islands we visited – its 14-mile length dotted with fishing villages, rocks in colorful hues, and some of the best authentic Greek food. Rent a car to get a real feel for this unpretentious land.

Fishing Village in Milos, Greece

Stay: White Pebble Suites is a dreamy boutique hotel and spa for couples or solo travelers, with several suites anchored around a classy pool setting at the sea’s edge, where room views blend into the cascading rock formations. Expect incredible service throughout and guests mingling poolside over cocktails, whispering about their good fortune to find this exquisite place. Sleep in a deluxe coastal view room with an outdoor terrace and jacuzzi plunge pool to relax your sore muscles after a day of adventure. A generous breakfast spread made-to-order and delivered in-room or poolside, is an exciting way to start each day.

White Pebble Suites in Milos, Greece

Experience:  From White Pebble Suites, it is an easy walk to the fishing village of Polonia, where each day a new restaurant can entice you with the freshest produce and some of the best meals on any island. Devour Greek salad, shrimp saganaki, seafood pasta, lamb, eggplant, mussels, octopus, and more from some of our favorite spots – Akrotiri, Enalion, and Rifaki.

Moon rocks in Milos, Greece

Cruise the island to visit the “moon rocks” at Sarakiniko Beach with caves and cliff jumping. Stop in the colorful fishing village of Klima, where many of the bright-hued boathouses have been renovated as AirBnbs. And don’t miss an authentic lunch at Medusa Restaurant in the charming fishing village of Mandrakia. To get a real feel for one of the most beautiful islands in the Cyclades – with its volcanic ground, pink and red tinted cliffsides, and beaches adorned with white and colorful rocks in astonishing formations – book a full-day catamaran cruise around the island with Captain George (Milos Adventures), featuring swim stops in Kleftiko and breathtaking Blue Bay on Poligos, an island off Milos. Add in surprise snacks, lunch, unlimited wine and beer, and new friends, and it’s the perfect day in the Cyclades.

Milos catamaran sail around the island in Greece

Paros: The relaxed flower-scented island

Like a relaxed Greek dream with intoxicating flower scents conjuring up distant childhood memories of beach roses from New England, this island is perfect for many personalities. Insects larger than I have known before were everywhere (massive wasps, bees, and spiders) and these grandiose island creatures bring pollination, making Paros one of the most fertile islands in the Cyclades, where you must taste the local produce and wine.

GreeceThe island’s charm includes rustic fishing villages, a variety of beach styles and landscapes, and the buzzing, stylish, developed town of Naoussa, located in a huge bay and stuffed with high-end boutiques, Greek souvenirs, and idyllic Greek outdoor restaurants – situated in whitewashed alleys that you imagine from photos of Greece. Paros still feels authentic but with all the development we noticed, we hope the island preserves its charm. A car is the best way to explore the beauty of the wild land but only with someone who can handle rough, narrow, and steep roads.

Melissa Curtin in Greece.Stay: Paros Agnanti Resort and Spa impresses with laid-back “White Lotus” vibes. Just a 5-minute drive from the port town, the property’s 55 Cycladic architectural-style rooms harmonize with the natural landscape. Mature flowers bring an intoxicating scent with gentle ocean breezes. Take your breakfast or sunset dinner on the sprawling terrace with inspiring ocean views and sample a dizzying array of local Greek products. Dinner here is a noteworthy surprise, with delightful Mediterranean options like the outstanding short rib truffle gnocchi.

Paros Agnanti Resort and Spa, Greece

For those who tire of the pool, play a round of mini golf on their wildly fun course, beat your partner in pickleball, or play a round of tennis on their turf court. A new spa is opening for summer and current construction on a neighboring property will be complete by 2025. Retreat to one of the new luxurious suites with private terraces and grand plunge pools hanging off the cliff. Or mosey along the private pathway to the tranquil beach just down the hill, with crystal clear waters and several café bars that are abuzz in summer. While Agnanti is family-friendly, we never saw more than a couple of well-behaved children. We realized after exploring the island by car, checking out 3 different beaches (Monastiri, Kolymbithres, and Golden), and exploring fabulous Naoussa town about 15 minutes away, that there are few reasons to leave Agnanti’s Shangri-La. Disclosure: A big thank you to Paros Agnanti for hosting me so I could write this review.

Paros, Greece

Experience:  Rent a car to get a sense of the island’s beauty. Shop and dine in popular trendy Nouassa with an international vibe and relax your legs over gelato or Freddoccino on the water, as several alleyways lead to ocean cafes or restaurants. Consider a sunset dinner in the slow coastal village of Aliki, where traditional Greek food at local tavernas like TO MYPATIO have you feeling like you are one with the sea. Hiking the Byzantine Trail in the center of the island is a must – from the small charming mountain village of Lefkes to Prodromos, connected with a double arch bridge built in the Byzantine era, in the 14th century. Be sure to bring water and go early before the heat as there is no protection from the sun. Many of the ancient statues now in museums were birthed from the marble quarry nearby.

Drying octopus in Paros, Greece

Mykonos: The cosmopolitan party island

Did you know Mykonos tops the list – together with Ibiza and St. Tropez – as one of the most expensive places in the world to visit? Think Miami Rockstar vibes with private yachts pulling up and hefty budgets ready to spend on top-shelf drinks and grilled whole fish or fresh sushi, in places where celebrities and artists mingle. One of the most popular and sophisticated islands for partying late night, many don’t start dining until after 10 PM. Enjoy numerous stunning beaches, striking white Cycladic architecture, and lively restaurants and bars. Get lost in the town’s winding streets to shop, dine, and admire the homes built right by the sea, many with hanging laundry and cats milling about. For those who like to be in the limelight surrounded by beautiful people, this is your island. Just don’t go in July or August unless you can handle mega crowds at tip-top prices.

Bill & Coo Mykonos, Greece

Stay: Bill & Coo Suites and Lounge is the best place to stay for the ultimate luxe experience with stellar service, bougie restaurant options, and a 2-for-1 vacation that offers “hidden” value.  A complimentary shuttle whisks guests from this centrally-located oasis to a private beach club location in a scintillating wind-protected cove 5 minutes away (Agios Ioannis), where plush beach chairs await that would cost the public $100 or more, but are free for guests. The sexy beach is situated at legendary hotspot Beefbar (that dishes up street food like Kobe Gyros and comfort food like Filet-Frites) and adjacent to sister property Bill & Coo Coast Suites/Villas and restaurant CooZest, where dishes like Moussaka, Greek Meatballs, Slow Cooked Lamb and Potatoes, and Wood Fired Pizza are accompanied by poolside Aegean Sea views. When you don’t feel like lounging beachside, the primary hotel closer to town offers modern rooms and sits atop a sprawling cliffside pool that almost dips into the sea – perfect for sunset cocktails and just a 5-minute walk to Mykonos town. The pool sits snugly next to a tiny blue-domed Greek church with the town’s windmills in the distance, adding to the ambiance.

Bill & Coo in Mykonos, Greece

Breakfast here is reason enough to get out of bed in the morning, with mouthwatering options like Greek Eggs Kayanas, fresh Greek yogurt, and oversized croissants with pistachios, chocolate, or strawberries and cream. Chef Aggelos Bakopoulos showcases modern Greek cuisine rooted in Greek tradition with 5 and 7-course set dinner menus. Book one of the 30 modern rooms at either location with ocean view terraces (some with jacuzzies) and embrace the “Bill & Coo Way of Life”. The name “Bill & Coo” is an idiom for relaxed and happy, flirting with one another, courting like doves, and perhaps talking quietly about it. The experience lives up to the name! Disclosure: A big thank you to Bill & Coo for hosting me so I could write this review.

Little Venice in Mykonos, Greece

Experience: Dubbed “Little Venice,” this seaside corner of old Mykonos town comes alive an hour before sunset, where revelers score a seat at one of the many oceanfront bars and tavernas to watch the glowing orb sink into the ocean with hundreds of other visitors. Order an Ouzo-tini or glass of local wine, with views of the traditional windmills. For the energetic, hit up one of the day or night parties at a swanky beach club but be prepared to spend a lot of money. Visit the island of Delos just a short boat ride away to admire the archeological site that played a major role in ancient Greek history.

Mykonos, Little Venice, Greece

Athens: The ancient history city

While Athens isn’t an island, you’ll most likely want to stay in this 4,000-year-old sprawling congested city on the way to or from the other islands. The cacophony of noise, smells and vibrant young energy is somewhat intoxicating, if only for a couple of nights. Walk a few miles through the oldest city in Europe and expect to come across ancient ruins and churches, outdoor markets, street performers, authentic bites, and new food concepts. Experience a sea of stores in the Plaka neighborhood selling unique items and every Greek souvenir imaginable. Motorcycles whizz through traffic, so exercise caution in the streets. The city’s energy is exhilarating.

The Dolli Athens, Greece view

Stay: For affordable rates, choose The Moxy, a modern Marriott brand, or Grecotel Pallas Athena, an eclectic artistic boutique on the older side but right in the action – both with stellar breakfast spreads. The Perianth is situated in a super happening neighborhood where upper-floor mid-century-modern rooms can offer Acropolis views even from the bathroom, but weekend late-night partying outside may prevent the best sleep. Breakfast options will make up lack of Zzzz’s as soon guests will be able to savor in the newly revamped restaurant, opening later this year. For luxury travelers enamored by design and art, stay at The Dolli, steps from the historical Plaka, with stunning high-ceilinged rooms and a rooftop restaurant with a pool, all gazing at the Acropolis.

Experience: The best way to get to know a city is often through a walking food tour. Of course, the Acropolis is a must-visit. Book tickets way in advance on the GetYourGuide app to get preferred appointment times. If you can only book one dinner, make it a table at the rooftop restaurant at The Dolli, perched in front of the Acropolis, where fine dining courses include lobster pasta, octopus, Greek Salad, fish, and lamb. Find stellar deals on fashion and clothes in the Monistiriki neighborhood. Meander around the fish, meat, and spice markets. Get lost on a Sunday at the area’s flea market, where vintage finds and lost junk might amaze.

Explore and be in awe of Greece!


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