Greece has a way of making you feel like you have stepped into a painting. The light is different here — warmer, softer, almost golden — and it turns everything it touches into something worth photographing. White buildings against impossible blue water. Fishing boats bobbing in tiny harbors. Bougainvillea spilling over stone walls. It is a country that has been inspiring travelers for thousands of years, and it has not lost a single bit of its magic.
With over 6,000 islands scattered across the Aegean and Ionian Seas (roughly 200 of which are inhabited), Greece offers one of the world’s great travel experiences: island-hopping. Each island has its own personality, its own rhythm, its own reason to visit. The trick is knowing which ones to string together, and how to move between them without spending your entire vacation on a ferry.
Greece does not rush you. It feeds you, pours you another glass of wine, and reminds you that the best things in life are simple — good food, warm water, and people you love.
When to Go
The best time to visit the Greek Islands is May through June or September through October. These shoulder months offer warm weather, comfortable swimming temperatures, and significantly fewer tourists than the peak summer months. July and August are hot and crowded, with higher prices and fully booked hotels. If you do visit in peak summer, book well ahead and consider staying on quieter islands to avoid the worst of the crowds.
The Islands You Need to Know
Start in Athens
Most Greek island itineraries begin in Athens, and it is worth spending at least a full day here before heading to the islands. The Acropolis, the ancient hilltop citadel crowned by the Parthenon, is one of the most important archaeological sites in the Western world. Standing at its base and looking up at columns that were built nearly 2,500 years ago puts everything in perspective. The surrounding neighborhood of Plaka, with its narrow pedestrian streets, outdoor tavernas, and tiny shops, is one of the most charming corners of the city.
Santorini
Santorini is the island everyone pictures when they think of Greece. Perched on the rim of a volcanic caldera, the towns of Oia and Fira look out over a flooded crater that drops hundreds of feet into deep blue water. The sunsets here are legendary — hundreds of people gather along the clifftops every evening to watch the sky turn pink and gold. Beyond the views, Santorini offers remarkable wine (the volcanic soil produces grapes found nowhere else), black and red sand beaches, and some of the finest boutique hotels in the Mediterranean.
The Greek Islands offer a different shade of blue at every turn
Mykonos
If Santorini is about sunsets and romance, Mykonos is about energy. This island has long been one of the most popular destinations in Europe, with beach clubs, rooftop bars, and a vibrant social scene. But Mykonos is more than its reputation. The old town, known as Chora, is a maze of whitewashed streets lined with boutiques, galleries, and excellent restaurants. The beaches — Paradise, Super Paradise, Elia — are some of the best in the Cyclades. And a short boat ride takes you to Delos, a tiny uninhabited island that was once one of the most sacred sites in ancient Greece.
Paros and Milos
For travelers who want the beauty of the Cyclades without the crowds of Santorini and Mykonos, Paros and Milos are the answer. Paros has a laid-back village feel, excellent windsurfing, and the charming fishing village of Naoussa, where octopus dries on lines outside waterfront tavernas. Milos, famous as the island where the Venus de Milo statue was discovered, is known for its surreal coastline — sea caves, volcanic rock formations, and over 70 beaches, many reachable only by boat.
Where to Stay
The Greek Islands are home to some of the most beautiful boutique hotels in the world. These three properties each capture a different side of the island experience.
Canaves Oia Suites — Santorini
Canaves Oia Suites — cliffside luxury with private plunge pools above the caldera
Carved into the cliffs of Oia overlooking the caldera, Canaves Oia Suites is the kind of hotel that ruins you for every other hotel. The whitewashed suites open directly onto the volcanic caldera, with private plunge pools that seem to spill into the Aegean far below. The sunsets from your terrace are the same ones that crowds gather to watch from the village — except you see them from a private infinity pool with a glass of Assyrtiko wine in your hand. Service is warm and personal, and the in-house restaurant serves refined Greek cuisine with views that make every meal feel like a celebration.
Book through us for complimentary upgrades, resort credits, and VIP amenities.
Cavo Tagoo — Mykonos
Cavo Tagoo — the iconic infinity pool with Mykonos town in the distance
Cavo Tagoo is one of the most recognizable hotels in Greece, and for good reason. Its signature infinity pool, jutting out over the Aegean with the town of Mykonos in the background, has become one of the most photographed spots in the Cyclades. But beyond the iconic pool, this is a seriously polished property — sleek rooms with private pools, a spa carved into the rock, and a restaurant that draws both guests and locals. It is close enough to the action of Mykonos town to walk in for dinner, but far enough away to feel like a private retreat.
Book through us for complimentary upgrades, resort credits, and VIP amenities.
Parilio — Paros
Parilio — minimalist Cycladic design and a cross-shaped pool on the island of Paros
For travelers who prefer understated design and a quieter pace, Parilio on the island of Paros is a revelation. This minimalist luxury hotel takes its cues from the Cycladic landscape — clean white lines, natural stone, and open spaces that let the light do the decorating. The cross-shaped pool is a work of art, the suites are calm and airy, and the location near Naoussa puts you close to one of the most charming villages in the Greek Islands. Parilio is the kind of place where you settle in and feel no need to leave.
Book through us for complimentary upgrades, resort credits, and VIP amenities.
Ready to plan the perfect island-hopping itinerary tailored to your travel style and pace?
Request Your ConsultationWhat to Do
Experiences Worth Building Your Trip Around
- Santorini caldera sailing cruise — board a catamaran and sail across the flooded volcanic crater, stopping to swim in hot springs, snorkel at Red Beach, and watch the sunset from the water with dinner and wine on board
- Mykonos beach hopping — spend a day exploring the island’s best stretches of sand, from the upscale sun loungers of Psarou to the long, relaxed shoreline of Elia
- Athens Acropolis guided tour — walk the ancient hilltop with a knowledgeable guide who brings 2,500 years of history to life, then explore the world-class Acropolis Museum
- Wine tasting in Santorini — visit the island’s unique vineyards, where grapes grow in basket-shaped vines close to the volcanic soil, and sample crisp Assyrtiko wines
- Cooking class on Paros — learn to prepare traditional Greek dishes using fresh local ingredients, from hand-rolled phyllo pastry to slow-simmered stews with family recipes
- Sunset at Oia — join the nightly ritual in Santorini’s most famous village, where hundreds line the clifftops to watch the sky turn pink, orange, and gold
Three Restaurants You Cannot Miss
Selene — Santorini
Selene has been a pioneer of contemporary Greek cuisine for decades, and it remains one of the finest restaurants in the Cyclades. Located in the village of Fira, the kitchen works closely with local farmers and foragers to showcase the unique flavors of Santorini — fava from the island’s volcanic soil, cherry tomatoes that are impossibly sweet, and capers picked from the cliffs. The tasting menu is a journey through the island’s terroir, and every dish is as beautiful as it is delicious.
Scorpios — Mykonos
Scorpios is not just a restaurant — it is a vibe. Set on the beach at Paraga, this bohemian seaside spot blends Mediterranean and Middle Eastern flavors with a laid-back, communal atmosphere. Think grilled whole fish, wood-fired flatbreads, and shared plates meant to be passed around the table. During the day, it is a beach club with sun loungers and music. As the sun sets, the DJ sets get deeper, the lanterns come out, and dinner feels like a celebration. It perfectly captures the spirit of Mykonos at its best.
Funky Gourmet — Athens
If you are passing through Athens on your way to the islands, Funky Gourmet deserves a spot on your itinerary. This two-Michelin-star restaurant in the Keramikos neighborhood takes Greek ingredients and reimagines them through avant-garde techniques and playful presentation. The multi-course tasting menu is full of surprises — dishes that challenge your expectations while still honoring the flavors of Greece. It is creative, bold, and a lot of fun, making it the perfect way to start or end an island-hopping adventure.
The Food
Dishes You Cannot Leave Without Trying
- Grilled octopus — charred and tender, drizzled with olive oil and lemon, served at nearly every waterfront taverna
- Fresh Greek salad — thick slabs of tomato, cucumber, onion, and a block of feta, dressed simply with olive oil and oregano
- Moussaka — layers of eggplant, seasoned ground meat, and creamy bechamel, baked until golden and bubbling
- Souvlaki — grilled meat skewers wrapped in warm pita with tzatziki, tomatoes, and onions, the ultimate street food
- Baklava — flaky phyllo pastry layered with nuts and soaked in honey syrup, the perfect ending to any meal
Getting Around: The Ferry System
Island-hopping in Greece revolves around the ferry system, which connects dozens of islands with regular service. High-speed ferries can get you from Athens (Piraeus port) to Mykonos in about two and a half hours, or from Mykonos to Santorini in roughly two hours. Slower ferries are cheaper and offer open-deck seating with great views. During peak summer months, ferries book up fast, so advance reservations are strongly recommended. For smaller or more remote islands, domestic flights and private boat charters are also options.
Why Work With a Travel Advisor
Island-hopping sounds simple, but the logistics can get complicated quickly — ferry schedules change, hotel availability varies wildly between islands, and the difference between a good itinerary and a great one often comes down to knowing which islands pair well together and how many nights to spend on each. A travel advisor takes the guesswork out of the planning and ensures your trip flows smoothly from island to island.
What You Get With Parrish Signature Voyages
- Preferred rates and complimentary upgrades at top island properties
- Private boat charters and seamless ferry logistics
- VIP restaurant reservations and chef’s table access
- Custom island-hopping routes matched to your pace
- Private guided tours of Athens, Delos, and historic sites
- 24/7 on-trip support and concierge service
Our relationships with the finest Cycladic properties mean you experience Greece at a level most travelers never reach.