New islands, fresh itineraries, and how to start planning your Greek escape
There’s a reason Greece keeps appearing on travel wish lists year after year. It’s one of those rare places that manages to be both completely iconic and endlessly discoverable. You can stand beneath the Acropolis in the morning and be swimming in a quiet cove by sunset. And with more than 200 inhabited islands, there is always another corner waiting for you, no matter how many times you’ve been.
If you’ve been dreaming about Greece, 2027 is a wonderful year to make it happen. Here’s why, plus a few fresh ideas and how to get started.
Why Greece Is Worth a Spot at the Top of Your List
It’s a strong value for US travelers. Compared with many Western European favorites, Greece still offers a lot of beauty, flavor, and experience for your dollar, from long, lingering taverna dinners to boutique island hotels and private villas. The dollar has also gained ground against the euro this fall, which helps when you’re budgeting for next year.
The beaches are truly world-class. Greece’s coastline is one of the longest in Europe, and the variety is remarkable: the soft white sand of Kefalonia’s Myrtos Beach, the moon-like volcanic coves of Milos, the pink-tinged shores of western Crete, and countless small bays you can reach only by boat. Whatever your idea of the perfect beach day looks like, Greece has it.
It truly offers something for everyone.
- History lovers can walk through 3,000 years of it, from the Acropolis and Delphi to the Palace of Knossos on Crete and the ancient theater at Epidaurus.
- Food and wine lovers will find some of the most satisfying cooking in the Mediterranean, built on olive oil, fresh seafood, and local cheeses, along with a wine scene that has come into its own. Santorini’s Assyrtiko, Kefalonia’s Robola, and the vineyards of Nemea are all worth seeking out.
- Adventurers can hike Crete’s Samaria Gorge, kayak sea caves, sail between islands, or explore the dramatic landscapes of the Peloponnese and the mountain villages of the mainland.
- Romantics will find no shortage of sunset dinners, cliffside suites, and quiet islands perfect for a honeymoon or anniversary.
It’s wonderfully family-friendly. One of Greece’s best-kept secrets for families is its large selection of private villas. A villa gives everyone room to spread out, with a private pool, a kitchen for easy breakfasts and snacks, and the freedom to set your own pace (nap time included). Many villas can add a private chef, daily housekeeping, or a driver, so parents get a real vacation too. Add in calm, shallow beaches, endless gelato, and kid-friendly history (yes, the myths are a big hit), and Greece is ideal for multigenerational trips.
New Itineraries and Ideas for 2027
Santorini and Mykonos will always be beautiful, but they are also the busiest. Greece now charges cruise passengers a per-person fee at its most visited ports, highest at Mykonos and Santorini in summer, as part of an effort to manage crowds. It’s a good reminder that some of the most memorable Greek trips happen just a little off the most-traveled path. Here are a few routes I’m excited about for 2027:
1. Tinos, Syros, and Sifnos (fly into Mykonos). Here’s a smart way to use Mykonos: as your gateway rather than your whole trip. Fly in, then hop a short ferry to Tinos, a mountainous island dotted with dozens of traditional villages, hundreds of ornate dovecotes, and a celebrated tradition of marble carving. It has also quietly become one of the best food islands in the Cyclades. Next comes Syros, home to Ermoupoli, the elegant neoclassical capital of the Cyclades, with grand mansions, a marble town square, and a lively, lived-in feel that’s very different from the resort islands. Finish on Sifnos, beloved for its pottery workshops, whitewashed villages, and some of the best traditional cooking in Greece (it’s the birthplace of Greece’s first celebrity chef). Together, these three offer classic Cycladic beauty with a fraction of the crowds.
2. Naxos with Paros and/or Milos. Naxos is one of the best all-around islands in Greece, with long sandy beaches, fertile valleys, marble mountain villages, and wonderful local cheese and produce. It’s a fantastic base for families. Paros is just a short ferry ride away, adding charming fishing villages like Naoussa, great dining, and a stylish but relaxed vibe. For something truly unforgettable, add Milos, with its otherworldly volcanic coastline, colorful fishermen’s houses, and sea caves best explored on a boat day. Choose one or both depending on how much time you have.
3. The Dodecanese: Rhodes, Kos, and Patmos. Close to the coast of Turkey, the Dodecanese have a flavor all their own. Rhodes is home to one of the best-preserved medieval old towns in Europe, a UNESCO World Heritage Site where you can walk the walls built by the Knights of St. John. Kos pairs long sandy beaches and easy cycling with the Asklepion, the ancient healing center linked to Hippocrates, the father of medicine. And Patmos is pure magic: a peaceful, spiritual island crowned by the Monastery of St. John and the Cave of the Apocalypse, with lovely beaches and a sophisticated, low-key atmosphere. It’s an ideal route for travelers who love history, culture, and a slower pace.
4. The Peloponnese, a year-round option. If you only think of Greece as a summer destination, the Peloponnese will change your mind. This large peninsula southwest of Athens is packed with treasures: the romantic seaside town of Nafplio, the ancient sites of Mycenae, Epidaurus, and Olympia (birthplace of the Olympic Games), the medieval fortress town of Monemvasia, and the wild, tower-dotted landscapes of the Mani. Add the vineyards of Nemea, Kalamata olives straight from the source, and luxury resorts such as Costa Navarino and the new wave of properties around Porto Heli, where Six Senses chose to open its first Greek resort. Because so much of its appeal is culture, food, wine, and countryside, the Peloponnese is wonderful in spring, fall, and even winter, when the ancient sites are blissfully quiet. It’s also an easy add-on before or after the islands.
Getting there is getting easier, too. Nonstop service from the US keeps expanding. For summer 2027, Alaska Airlines will launch the first-ever nonstop from Seattle to Athens beginning May 12, giving the West Coast its only direct link to the Greek capital, and Delta will add a new Detroit–Athens route beginning June 8. These join an already strong lineup of nonstops from cities including New York, Newark, Atlanta, Boston, Chicago, Charlotte, and Philadelphia.
When and How to Get Started
A few things I always share with clients as we start planning a Greek getaway:
Villas are wonderful for families, but plan around the calendar. A private villa can be the best way for a family or group to experience Greece. Just know that in July and August, nearly all villas require a minimum stay, usually seven nights running Saturday to Saturday. That shapes the rest of your itinerary, including your flights and which islands you pair together, so it’s one of the first things we’ll want to lock in. It’s also worth knowing that most island hotels and villas are open only from May through mid-October. If you have flexibility, the shoulder months of May, June, September, and early October are a sweet spot: everything is open, the sea is warm, and you’ll often find better availability, more flexible stays, and fewer crowds.
Location is everything. Where you stay on an island matters just as much as which island you choose. Some travelers love being able to walk to the harbor, the beach, and dinner each night; others dream of a hilltop hideaway with sweeping sea views. If you’re leaning toward somewhere remote and beautiful, plan on having a rental car (or a driver) to get around. It’s very doable, but it’s important to know before you fall in love with a property.
Don’t forget about Athens. Too many travelers treat Athens as a one-night stopover on the way to the islands, and they miss out. Athens has become one of Europe’s most exciting dining cities and is home to some of the best cocktail bars in the world. It’s also incredible for kids, with hands-on experiences like archaeology workshops, stargazing, and creating pieces alongside local artists. Give it at least two or three nights; you’ll be glad you did.
Every island itinerary deserves a day on the water. A private or small-group boat day may sound like a splurge, but it’s one of the experiences my clients rave about most. You’ll reach hidden coves, sea caves, and beaches that simply can’t be reached on foot, swim in impossibly clear water, and often enjoy a fresh lunch on board. It’s a truly local way to see the islands, and it’s worth every penny.
Let’s plan it together. Greece rewards thoughtful planning: the right island combination, the right ferry or flight connections, and the right place to stay make all the difference. If Greece is calling your name for 2027, reach out and let’s start dreaming up your perfect itinerary.
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