Whether it’s the scenic whitewashed buildings of Santorini and the rugged sheer rock face of its volcanic caldera you crave, or the medieval architecture in Rhodes, bridging Europe and the former Ottoman Empire, the Greek islands deliver. Sunny days, rich culture, romance, history, high-end shopping, and al fresco dining are all but guaranteed. There are thousands of islands and islets scattered throughout the Aegean, Ionian, and Mediterranean Seas, but less than 200 are inhabited. Each has a distinct history and personality, so once you’re there, you might as well see a few. Dance the night away in Mykonos before recovering with a laid-back stay in Santorini, where the sunsets are impossibly beautiful. Venture beyond the main tourist hotspots to lesser-known islands like Ios and Kythira, if you’d prefer to be far from the madding crowds. Consider visiting in the shoulder season of May or after Labor Day, for fewer visitors and more favorable room rates. Weather is unpredictable, but it’s often still pleasantly warm into October.

Cruising is the most comfortable, convenient, and relaxing way to see multiple islands on one trip. Silversea is the premier small ship luxury cruise line in the Greek islands. Both of its newest ships, Silver Moon and Silver Dawn, will be sailing the Mediterranean this summer. Silver Dawn will debut Silversea’s new Otium wellness experience inspired by the ancient Roman culture of lavish leisure, with the ethos that being well and living well are not mutually exclusive. Both ships feature new immersive culinary programming through S.A.L.T., too. Book shore excursions and spa appointments before boarding to ensure availability.

Fully vaccinated American travelers are welcome in Greece, but to board a Silversea cruise you’ll also be subject to a rapid antigen COVID test right before boarding, and daily temperature checks by your butler in the comfort of your suite. Hand sanitizer stations are conveniently located throughout the ship and guests are asked to wear masks indoors when not eating or drinking (but there’s no reason not to have a drink in hand at all times on board).


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Fira is Santorini’s capital, and from the small port you can choose how to get to town: walk up 587 stone steps on a zig zagging mountainside path, ride a donkey, or take the cable car. The cable car is the most comfortable and efficient transport, and from the station you can get lost in the city’s alleyways and enjoy panoramic ocean and caldera views. Shoppers will find a few boutique gems amidst the tourist traps, including Ilias Lalaounis for gold jewelry and Milo Boutique for globally curated fashion.

One of the most important archaeological sites in all of Greece, this majestic ancient castle stands tall above a Doric village lined with souvenir shops and whitewashed homes. Weave through the cobblestone streets and summit the steep, narrow path to the fortress for spectacular views of Lindos and St. Paul’s Bay. Peruse the remnants of past civilizations, including the Doric Temple of Athena Lindia and the Byzantine church of St. John. Lindos 851 07, Rhodes


Unpack once for a journey of pure indulgence and instant gratification. With spacious balconies, Jacuzzi soaking tubs, exquisite restaurants, and attentive butlers that anticipate your heart’s desires, Silversea’s all-inclusive experience sets the standard in luxury cruising. The new Otium wellness programming extends beyond the spa, where treatments are naturally accompanied by champagne and chocolate fountains, to your suite, with new bath rituals, a pillow menu, a plethora of comforting snacks (truffle popcorn and boozy ice cream, anyone?), and a plush new mattress that makes it hard to get out of bed, especially on the morning of disembarkation.

Lounge on the black sand beach of Santorini’s southeast coastline at Istoria, a member of Design Hotels. Half of the 12 suites are converted from horse stables and many feature private plunge pools or Jacuzzis. Treatments at the intimate spa are inspired by different Cycladean islands, using Greek ingredients like white clay and Cretan crocus. The 32-meter pool is one of the longest on the island, with enough sunbeds for every guest. Mr. E restaurant keeps things fresh and light with salads, freshly grilled local seafood, and Greek cheeses. Perivolos, 847 03, Santorini,

This flora-filled retreat augments Aegean hospitality with an emphasis on slow paced, soulful island living. Sustainability is a top priority and botanical gardens lead to the sparkling Aegean Sea, while a fresh renovation seamlessly blends indoor and outdoor spaces with colorfully patterned tiles and local art. Menus emphasize traditional vegan and vegetarian Cretan dishes like tomatoes and peppers stuffed with rice and fresh herbs, charred in the wood fired oven, so guests can get a taste for why Cretans have one of the longest life expectancies in the world. Malia, 700 07, Crete,


Take an off-road adventure in the Cretan countryside for a memorable wine tasting at one of the most famous vineyards on Greece’s largest island. Race through the rugged hills of northern Crete to Vatolakos Hill before arriving at Manousakis Winery, which only recently opened to the public for tastings and tours. Visit the family’s stone home and stroll the gardens before tasting several of their organic wines including Syrah, Grenache, Mourvèdre, Roussane, and Assyrtiko, all paired with locally made Cretan cheeses and wheat rusks. Vatolakkos 73005, Chania, Crete,;

Learn from third generation cheese maker and farmer George Syrianos and taste a half dozen different cheeses, along with hearty portions of homemade dishes like tzatziki, tiropita cheese pastries and pastitsio, or Greek lasagna. Syrianos is passionate about his craft and his flock of sheep. He’s a wizard with cheese and phyllo dough, churning out endless variations of sweet and savory dishes. “If you work with Mother Nature, you are rich,” he said. “Simplicity is sometimes the most pure and tasty.” Don’t miss the kopanisti, a soft spreadable and slightly spicy cheese that Mykonos is famous for. It’s best enjoyed on crunchy barley rusks with fresh tomatoes and olive oil which Syrianos also makes himself from 700 olive trees. Agios Lazaros, 84600, Mykonos,


Silversea’s newest destination-focused restaurant has quickly become its most popular, bringing authentic menus aboard the ship that correspond to each port of call, paired with more than 60 Greek wines. The menu changes daily to highlight local specialties, like fava croquettes and karaboloi snails in Mykonos and fanouropita walnut cake with honey ice cream in Rhodes. Next door, the impressively well-appointed S.A.L.T. Lab test kitchen hosts cooking classes on mezze, moussaka, and the versatility of phyllo dough. Available on Silver Moon and Silver Dawn,

Watch the caldera sun set poolside at this lively bistro by Greek-American chef Ari Vezené, known for his open fame preparations of dry-aged meat and local, line-caught seafood. There are red prawns and lots of tomatoes on the menu, along with whole fish crudo dressed in lemony olive oil. Opt for wine pairings including Greek favorites like crisp Assyrtiko and Mavrotragano, a dry red that pairs well with grilled meats. Order a playful interpretation of Greek coffee reminiscent of île ottante for dessert. It perks you right up and mitigates food comas. Hotel Cavo Tagoo, Imerovigli 847 00, Santorini,

This organic Greek bistro is a lovely choice for a leisurely lunch with an ingredient-driven menu full of fresh linecaught seafood, olive oil, local cheese, and Greek classics like slow-cooked lamb shank with creamy hummus. Plus, Nice n Easy has the best views of Mykonos’ famous windmills and the spacious patio is great for people watching. There are plenty of stellar vegan options too, including quinoa lentil veggie power bowls and a luscious hazelnut olive oil ice cream. Alefkandra Square, Little Venice, 84600 Mykonos,