Greece · Island Guide
Where to go, where to stay and how to island-hop in style
For a luxury Greek islands trip, I recommend two or three islands over 10 to 14 days, starting or ending in Athens, and traveling between them by private boat or helicopter rather than crowded ferries. Go in late May, early June or September for beautiful weather and fewer crowds, and pair a social island like Mykonos with a quieter one like Milos or Sifnos.
Greece is one of my favorite places to send travelers celebrating something special, from anniversaries and milestone birthdays to multigenerational trips. It offers the perfect blend of adventure, history, natural beauty and relaxation, and there's so much more to discover beyond Santorini. This guide covers what I tell every client before they go. See my Greek islands picks.
01
When is the best time to visit the Greek islands?
The best time to visit the Greek islands is late May to early June, or September: the weather is beautiful, every hotel and beach club is open, and the crowds are lighter than in July and August. The season runs from about May through October, and most island hotels close for the winter.
02
Which Greek islands should you choose?
Choose islands with different personalities, and give each at least three to four nights so you're not spending your trip in transit. Most of my clients start with two or three nights in Athens, then visit two or three islands.
My favorite pairings: Mykonos and Milos (glamour, then calm), Santorini and Paros (icons, then ease), or Athens, Mykonos and Santorini for a first trip that hits the classics.
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Island hopping in style: skip the ferries
The public ferries are how most visitors get around, but in peak season they're crowded, and schedules can shift with the wind. For a seamless trip, I arrange private transfers by boat or helicopter between islands, timed around you.
Private boat
- The experience
- A scenic sail with swim stops along the way, turning a travel day into a day on the water
- Best for
- Nearby islands, such as Mykonos to Paros or Paros to Milos
- Good to know
- Crossings depend on the weather, especially when the meltemi winds blow in July and August
Private helicopter
- The experience
- Spectacular views over the Aegean and the fastest way between islands and Athens
- Best for
- Longer hops, tight schedules, and getting from Athens straight to your island
- Good to know
- Luggage limits apply, so pack light or send bags ahead
I also coordinate private transfers on arrival, so a driver is waiting at every port and helipad. It's one of the simplest ways to make a Greek islands trip feel truly effortless.
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Athens: start or end your trip here
Two or three nights in Athens is the perfect bookend to the islands, whether to recover from the flight or to unwind before heading home.
Where to stay
Hotel Grande Bretagne, Syntagma Square
The grande dame of Athens, with a rooftop restaurant and bar facing the Acropolis. Ideal for exploring the city on foot.
Virtuoso benefits when you book through usAn upgrade on arrival when available, daily breakfast for two, a complimentary lunch or dinner for two once during your stay, and early check-in and late check-out when available.
Four Seasons Astir Palace, Athens Riviera
On a private pine-covered peninsula on the Athens Riviera, with beaches, a spa and sea-view rooms. City and seaside in one stay, and a beautiful last stop before your flight home.
Four Seasons Preferred PartnerAsk us about Four Seasons Preferred Partner benefits.
The Dolli at Acropolis, Plaka
A chic boutique hotel in a neoclassical building, with a rooftop restaurant and infinity pool facing the Acropolis, and Acropolis views from many rooms. A Forbes Four-Star hotel, steps from the city's sights.
Virtuoso benefitsA Virtuoso hotel: ask us about the benefits for your dates.
What to do in Athens
- Visit the Acropolis with a private guide first thing in the morning, before the heat and the crowds.
- Explore the Acropolis Museum, with its glass floors over ancient ruins and a terrace looking straight up at the Parthenon.
- Wander Plaka and Anafiotika, the old neighborhoods below the Acropolis, for tavernas, boutiques and whitewashed lanes that feel like an island village.
- Spend a day on the Athens Riviera, with beach clubs, seafood lunches and the Temple of Poseidon at Cape Sounion at sunset.
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Mykonos
Mykonos is Greece at its most glamorous: windmills and whitewashed lanes, sunset cocktails in Little Venice, and the Aegean's most famous beach clubs. Stay three to four nights to balance the social scene with a boat day and some quiet time by the pool.
Where to stay
Four Seasons Mykonos, Kalo Livadi
New for 2026, the island's first Four Seasons, with sea-view suites and villas, plunge pools, infinity pools and a spa on one of Mykonos's most beautiful beaches.
Four Seasons Preferred PartnerAsk us about Four Seasons Preferred Partner benefits.
Kalesma, Ornos
Hillside suites and villas, most with private pools, overlooking Ornos Bay, with a calm, minimalist design.
Virtuoso benefits when you book through usAn upgrade on arrival when available, daily breakfast for two, a $100 food and beverage credit, a welcome bottle of wine and fruit, complimentary parking, a complimentary four-course dinner for two on stays of five nights or more, and early check-in and late check-out when available.
Santa Marina, a Luxury Collection Resort, Ornos
Sea-view rooms and villas with a private beach and a spa, a classic for families.
Marriott STARSAsk us about Marriott STARS benefits.
Cali Mykonos, Kalafatis
A stylish resort on the quieter east coast, with marble interiors, Greek art and private beach access.
Virtuoso benefits when you book through usAn upgrade on arrival when available, daily breakfast for two, a $100 hotel credit, and early check-in and late check-out when available.
Bill & Coo Coast, Agios Ioannis
Beachfront suites with sunset views, a beach restaurant and a spa.
Virtuoso benefitsA Virtuoso hotel: ask us about the benefits for your dates.
Beach clubs
- Scorpios, Paraga Beach: bohemian and beautiful, famous for its sunset ritual, when the music builds as the sun goes down. Reserve daybeds weeks ahead in July and August, and arrive by late afternoon.
- Nammos, Psarou Beach: the island's most glamorous long lunch, with a yacht crowd, celebrity sightings and fresh seafood by the water. Book tables several weeks ahead for summer weekends.
A boat day to Delos
Just off Mykonos, Delos is one of the most important archaeological sites in Greece and a UNESCO World Heritage Site: according to myth, the birthplace of Apollo and Artemis. I arrange a private boat day that combines a guided visit to the ruins in the morning with lunch and a swim off neighboring Rhenia, whose clear coves are among the most beautiful in the Cyclades. There are no overnight stays on Delos, and the site keeps limited hours, so a private boat lets you time it perfectly.
Don't miss
- Sunset in Little Venice, with cocktails over the water and views of the windmills.
- Dinner in Mykonos Town, then wandering the lanes of Chora late into the evening.
06
Santorini
Santorini is the Greece of postcards: whitewashed villages on the edge of a volcanic caldera and some of the world's most famous sunsets. Stay in Oia for the classic views, and plan time away from the busiest viewpoints.
Where to stay
Canaves properties, Oia
A collection of cliffside hotels on the caldera, with suites carved into the cliffs, private plunge pools and some of Santorini's most famous sunset views. Each Canaves property has its own feel, from intimate and romantic to sleek and contemporary, so I match the one that best fits your style.
Virtuoso benefitsAvailable at several Canaves properties; ask us about the benefits for your dates.
Andronis properties, Oia and Imerovigli
A family of boutique clifftop hotels, each with its own personality, from tranquil hideaways to cave-style suites with caldera views and private pools. I'll recommend the Andronis property that suits your style and the experience you're after.
BenefitsAsk us about the benefits when you book through us.
What to do in Santorini
- Sail the caldera at sunset on a private catamaran, with swimming, snorkeling and dinner on board, passing the Red and White Beaches and the volcanic hot springs.
- Taste Santorini's volcanic wines on a private winery tour.
- Hike from Fira to Oia along the caldera rim.
Where to eat: Ambrosia, Elements and Lycabettus.
07
Milos
Milos is my favorite answer for travelers who want natural beauty without the crowds: a volcanic island of sea caves, colorful fishing villages and some of the most striking coastline in Greece.
Where to stay
Domes White Coast Milos
An adults-only, Small Luxury Hotels of the World beachfront resort with minimalist suites and private infinity pools.
Virtuoso benefits when you book through usA $50 to $100 hotel credit, daily breakfast, an upgrade when available, and early check-in and late check-out when available.
Eréma, a Member of Design Hotels
An all-suite retreat on Milos's quiet southeastern coast near Provatas Beach, where every suite has its own private pool and Aegean views. Its stone, marble and earth-toned design echoes the island's volcanic landscape.
What to do in Milos
Explore Papafragkas Cave, the moonlike white rocks of Sarakiniko Beach, the ancient catacombs and the fishing villages, then spend a day on a private boat to Kleftiko Bay and the island of Polyegos.
Where to eat: Mikros Apoplous, Nostos Seafood Experience and Yialos.
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Paros and Antiparos
Paros is relaxed, stylish and easy, with pretty villages, beautiful beaches and a laid-back beach club scene.
Where to stay
Cosme, a Luxury Collection Resort
Upscale, with Aegean views and a blend of local culture and polished service.
Benefits when you book through usA $100 food and beverage credit, a welcome amenity, daily breakfast, an upgrade when available, and early check-in and late check-out when available.
Andronis Minois, Parasporos Beach
A five-star hotel steps from Parasporos Beach, with a beautiful seawater pool and an ESPA spa.
Virtuoso benefits when you book through usA €90 hotel credit, a welcome amenity and an upgrade when available.
Avant Mar, Naoussa
A Leading Hotels of the World beachfront hotel on Piperi Beach, a short walk from Naoussa's harbor, with whitewashed buildings around a curving saltwater pool, a spa and a Matsuhisa restaurant in summer.
What to do in Paros
Take a private boat to Antiparos for a swim in its turquoise lagoons and lunch at Rooster, then wander the island's bougainvillea-draped village, enjoy the beach clubs, or join a Greek cooking class.
Where to eat: Blue Oyster, Siparos and Barbarossa.
09
Crete
Greece's largest island rewards a longer stay, with history, mountains, wineries and some of the country's most beautiful beaches.
Where to stay
Daios Cove
A luxury resort and villa property on its own secluded bay.
Virtuoso benefits when you book through usAn upgrade on arrival when available, daily breakfast for two, a $100 hotel credit (a total of $250 on stays of seven nights or more), and early check-in and late check-out when available.
Minos Beach Art Hotel, Agios Nikolaos
Bungalows and villas right on the water of Mirabello Bay, with two private beaches, three restaurants and dozens of contemporary art installations throughout the grounds.
Virtuoso benefitsA Virtuoso hotel: ask us about the benefits for your dates.
Rosewood Blue Palace, Elounda (coming soon)
Rosewood's first hotel in Greece, a reimagining of the iconic Blue Palace on the Elounda coast, with private pools and two spas. Ask us about opening dates and early bookings.
What to do in Crete
- Pair a private guided visit to the Minoan Palace of Knossos with an afternoon of wine tasting at a local winery.
- Spend a day on a private boat to Spinalonga, the Venetian fortress island in the Mirabello Gulf, with swim stops in the bay.
- Take a 4x4 Jeep safari to Zeus's Cave.
- Spend a beach day at Elafonisi or Balos.
Where to eat: Maistrali Taverna, Gioma and Karnagio by the Lake.
10
A lesser-known island: Sifnos
For travelers who want the Cyclades the way they used to be, I love Sifnos. This quiet, unspoiled island is known across Greece for its food and its centuries-old pottery tradition, with whitewashed hilltop villages, walking trails between chapels and monasteries, and calm, sandy bays. It pairs beautifully with Milos, a short private boat ride away.
Where to stay
NOS Hotel & Villas, Faros
An intimate boutique hotel of just 18 suites in four stone buildings above the fishing village of Faros, with views of the Aegean and the 17th-century Monastery of Panagia Chrysopigi. Its rustic-chic design uses stone, marble and pieces by local craftspeople, and there's a pool, an open-air spa and a terrace restaurant cooking with ingredients from local producers. Faros, Fassolou and Chrysopigi beaches are all within walking distance.
What to do in Sifnos
Wander the hilltop villages of Apollonia and medieval Kastro, visit the Chrysopigi monastery on its rocky point above the sea, browse the island's pottery workshops, and settle in for a long lunch of revithada, the slow-cooked chickpea stew Sifnos is famous for.
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Planning your Greek islands trip
- How long10 to 14 days is ideal for Athens plus two or three islands. With a week, choose Athens and one island, or two islands close together.
- Getting thereFly into Athens, which has nonstop flights from several US cities in summer. Mykonos and Santorini also have international airports with seasonal flights from Europe.
- When to bookFor June through September, book hotels 9 to 12 months ahead. The best suites, especially those with private pools and caldera views, go first. I also reserve beach club daybeds, dinner tables and private boats well in advance.
What to pack
- Light linen and resort wear, plus a chic cover-up for beach club lunches
- Flat sandals or sneakers: cobblestone lanes and steep steps are everywhere
- Sun protection: a hat, sunglasses and reef-safe sunscreen
- A light layer for windy evenings and boat days
- A soft-sided bag if you're taking a helicopter, which has luggage limits
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Greek islands FAQs
How many Greek islands should I visit in one trip?
Two or three islands in 10 to 14 days, with three to four nights on each. Any more, and you spend too much of your trip in transit.
Which is better, Mykonos or Santorini?
They're very different. Mykonos is social, with beach clubs, nightlife and a boat day to Delos. Santorini is about dramatic caldera views, sunsets and romance. Many first-time visitors do both.
What is the best way to get between Greek islands?
Private boat or helicopter transfers are the most comfortable and flexible. They skip the crowded ferries and are timed around your plans, with a driver waiting on arrival.
Which Greek islands are best for families?
Paros, Crete and Milos are relaxed and easygoing, with calm beaches and plenty to do. On Mykonos, I recommend hotels on quieter beaches with space for families.
Is September a good time to visit the Greek islands?
Absolutely. The sea is at its warmest, the summer crowds have thinned and the light is golden. It's one of my favorite times to go.
Why book Greece through a travel advisor?
The best suites, beach club tables and private boats book up months ahead. An advisor plans the island route, arranges private transfers between islands, and adds Virtuoso and Four Seasons Preferred Partner benefits such as hotel credits, daily breakfast and upgrades at many of Greece's top hotels.
Begin your escape
Plan your Greek islands escape with Bespoke Escapes
The best of the Greek islands, from caldera-view suites to beach club daybeds and private boats, is booked months in advance. I'll design your island route, arrange private boat and helicopter transfers between islands, and secure your hotels and reservations, with Virtuoso and Four Seasons Preferred Partner benefits at many of Greece's top hotels.
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