Take the coast of the Cyclades from guidebook covers straight to your own social media feed with this laid-back 10-day Greek getaway. These famous islands have captured travelers' imaginations for centuries, and now it's your turn to explore via boat, bike, and more. Along the way, you'll cruise around Santorini by catamaran, cycle between idyllic beaches in Naxos, and sit down to an evening of dinner and stories on a Mykonos farm.


  • Tour and taste your way through the fragrant food markets of Athens
  • Cruise along the volcanic Santorini coastline by catamaran
  • Bike between Naxos' charming villages and picture-perfect beaches
  • Taste local wines and savor home-cooked farm-to-table fare in Mykonos

Brief Itinerary

Day Highlights Overnight
Day 1 Arrive in Athens, Welcome Dinner or Wine Tasting Athens
Day 2 Varvakios Market Visit & Athens Street Food Tour Athens
Day 3 Transfer to Santorini, Explore the Island at Leisure Santorini
Day 4 Self-Guided Tour of Fira, Catamaran Cruise Around the Island Santorini
Day 5 Ferry to Naxos, Afternoon at Leisure Naxos
Day 6 Guided Bike Tour of Naxos' Beaches & Villages Naxos
Day 7 Authentic Greek Cooking Class Naxos
Day 8 Ferry to Mykonos, Explore the Island at Leisure Mykonos
Day 9 Mykonos Farm Visit, Hosted Traditional Dinner with a Local Family Mykonos
Day 10 Transfer to Athens, Depart  

Detailed Itinerary

Day 1: Arrive in Athens, Welcome Dinner or Wine Tasting

Athens Old Town
Visit the Anafiotika neighborhood, Athens' Old Town

Welcome to Greece! Upon arrival at the airport, meet your driver and transfer to your hotel in downtown Athens. Greece's buzzy capital city is an eclectic mix of ancient and modern, with towering temples to ancient deities rubbing shoulders with lively nightlife, crowded flea markets, and contemporary cuisine. Settle in and relax after your flight, then head out to discover the city's sights.

It's possible to walk up the hill to the Acropolis, a vast fifth-century complex on a rocky hilltop overlooking the city, and together with the Parthenon (the temple dedicated to Athena), this should be top of your list of places to visit. Wander back down to stroll the colorful stalls of the Monastiraki flea market before settling in for a cold drink at one of the neighborhood cafés. In the evening, you'll sit down to enjoy either a welcome dinner with dazzling views of Athens' ancient ruins or discover the region's wine with a tasting at a local bar. 

Day 2: Varvakios Market Visit & Athens Street Food Tour

Vendors in the market
Discover Greece's delicious fresh produce with a tour of the Varvakios Market

Today is dedicated to the sights, tastes, and smells of Greece's delicious fresh produce, and there's no better way to start than with a tour of Athen's bustling food markets and street food stalls. Meet your guide in Syntagma Square for a Greek coffee at one of the city's landmark kafenio (cafés), and pick up some street snacks to sample on the go. Discover the city's neighborhoods and foodie hotspots as you weave through alleyways to explore the city's main spice street, filled with the scent of mint, cinnamon, and mountain oregano.

The nearby Varvakios Market, Athens' most prominent and most popular fish, meat, and vegetable market, is your next stop. Sample a variety of cheeses, honey, and olive oils from local producers and across Greece alongside delicious cured meats, olives, honey-soaked baklava, and mouthwatering souvlaki for lunch. Spend the afternoon exploring under your own steam, and as night falls, head to the Koukaki neighborhood. Here, you'll find off-the-beaten-path wine bars and plenty of great local restaurants. 

Day 3: Transfer to Santorini, Explore the Island at Leisure

Welcome to Santorini
Savor the sights of Santorini's blue-domed churches and clifftop architecture

It's an early start this morning as you catch a ferry to Santorini, the southernmost island in the Cyclades famous for its volcanic beaches. It's a sight to behold as you watch the sunrise over the island's iconic cliffside architecture and see the central caldera, the site of one of the largest volcanic eruptions in history, rising above you. Settle into your hotel, then the rest of the day is yours to spend as you choose. Relax on one of the black or red-sand beaches formed from lava pebbles and take a dip in the inviting waters, or wander the whitewashed streets of the island's capital, Fira.

If you're feeling energetic, head out on one of Santorini's many scenic walking routes, ranging from 2 to 8 miles (3-12 km). Opt for a light seaside hike that takes in the island's main beaches, Perissa, Perivolos, and Agios Georgios, or tackle the walk along the cusp of the caldera from Fira to the spectacular village of Oia. Here, you'll be rewarded with sweeping views of the Aegean, olive groves, and the village's colorful houses that tumble across the cliffs. In the evening, dine on freshly caught seafood alongside the island's signature cherry tomatoes and white eggplant.

Day 4: Self-Guided Tour of Fira, Catamaran Cruise Around the Island

Fira at sunset
Take to the water this evening for a cruise around the island

Spend the morning exploring Fira at your own pace. Scope out the small shops and boutiques that line the alleyways, then learn a little more about the island's history with a visit to the capital's excellent museums. The Archaeological Museum of Santorini and the Church of Hypapante should be top of the list for history buffs while the Museum of Prehistoric Thera houses many extraordinary finds from the excavated Bronze Age settlement of Akrotiri. You'll also find fossilized olive tree leaves from within the caldera that date back 60,000 years.

 As the afternoon unfolds, you'll head to Vlychada Port to board your catamaran cruise around the island. Your captain will drop anchor at Santorini's Red Beach and White Beach, where you can swim in the crystalline sea and admire the distinctive volcanic sands. Then, sail past landmarks at Aspronisi, the Ancient Lighthouse, and Indian Rock while the crew serves a delicious barbecue and drinks. Look out for the archaeological site at Akrotiri, then head to the uninhabited island of Nea Kameni, where you can immerse yourself in the therapeutic waters of the island's hot springs. 

Plan your trip to Greece
Chat with a local specialist who can help organize your trip.

Day 5: Ferry to Naxos, Afternoon at Leisure

Looking back from the Portara
Don't miss the short walk from Naxos Town to the ancient Portara, one of the island's hallmarks

Today, you'll catch a ferry and make the 1.5-hour crossing over to Naxos, the largest and most fertile of the Cyclades, known for its expansive white-sand beaches, archaeological treasures, Venetian architecture, and laid-back charm. Check into your hotel, and the rest of the day is yours to unwind or explore as you wish. Spend the day in Chora (also known as Naxos Town), and amble up the hillside lined by quaint shops and restaurants. Then, head along the causeway to the islet of Palatia, where you'll find the Portara, the ancient entrance to the Temple of Apollo and one of the island's hallmarks.

If you're feeling energetic, hike to the summit of Mount Zas, the mythological childhood home of Zeus and the highest point in the Cyclades, where you'll be rewarded with wonderful views over the island. Alternatively, head inland to Chalki, home to the island's oldest market and a petite, shady square perfect for whiling away the afternoon with a cool drink. As evening falls, wander up the hill in Chora to the Kastro neighborhood, where you'll find plenty of tempting family-run tavernas. 

Day 6: Guided Bike Tour of Naxos' Beaches & Villages

Discover Naxos' hidden gems on today's bike tour
Discover Naxos' hidden gems on today's bike tour

This morning, you'll discover Naxos' hidden spots and best beaches on a relaxing two-wheeled tour of the island. You'll bike with a local guide through a string of nearby beach-orientated villages and gorgeous coastal stretches on the island's west side, extending from Agios Prokopios to Mikri Vigla. On your way back, pass through the villages of Vivlos, Agios Arsenios, and Glinado before returning to Chora in time for lunch. 

Spend the rest of the day relaxing in town. Wander up the narrow streets to the Venetian Castle in the center, stopping at the neighboring Catholic Cathedral and Archaeological Museum of Naxos along the way. After a short walk around the site, pause for a bite to eat and refreshments at the café housed in the castle's Ursuline school building. It's a particularly scenic spot with splendid panoramic views over whitewashed Chora.

Day 7: Authentic Greek Cooking Class

authentic Greek cooking class
Get hands-on today with a locally-led cooking class

Today, you'll be welcomed into the home of a local family to learn how to prepare a traditional Greek meal. Meet your host in the tiny village of Kaloxylos, a picturesque setting where alleyways adorned with centuries-old olive trees and flower-filled courtyards are home to just 30 residents. After a warm welcome, you'll cook together and prepare a locally sourced three-course meal using traditional recipes passed down through generations while the family shares stories about life on Naxos and the secrets of Naxian cuisine, renowned throughout Greece. 

Day 8: Ferry to Mykonos, Explore the Island at Leisure

Mykonos traditional whitewashed narrow street
Stroll the artsy, whitewashed alleyways in Mykonos' Little Venice

Today you're off to Mykonos, the most famous of the Cyclades archipelago, known for its whitewashed houses, art scene, and jet-set crowds. After a 2.5-hour ferry to the island, check into your hotel, and the rest of the day is yours to spend at leisure. If the beach is calling, head to remote Agios Sostis, an unspoiled, gorgeous sandy stretch away from the crowds. Windsurfers should opt for Ftelia Beach, where the strong winds from the north transform the bay into a surfer's paradise. 

As the sun dips, enjoy a stroll through Little Venice, an 18th-century neighborhood and an excellent spot for dinner at one of the seafront restaurants overlooking the sea.

Day 9: Mykonos Farm Visit, Hosted Traditional Dinner with a Local Family

Traditional Greek Dishes
Enjoy delicacies such as dolmades (stuffed vine leaves) at tonight's hosted dinner

The morning is yours to explore, so head to a beach to lounge or stroll through the cosmopolitan streets, scoping out the boutiques that draw the island's stylish crowd season after season. In the afternoon, you'll pay a visit to an organic farm and winery in a former monastic vineyard. Talk to the farm's caretakers to learn how vegetables are grown on the island and new-age viticulture techniques, including playing classical music over the vineyards to cultivate full-flavored Cycladic wines. You'll also get to meet the farm's resident animals, including Konstantis, the good-natured donkey.

In the evening, as the sun sets, you'll be welcomed into a local island household to experience traditional Greek hospitality. Spend your last evening on the island sipping on free-flowing local wine and feasting on hearty Hellenic dishes such as dolmades (stuffed vine leaves) and kleftiko (baked lamb) while your hosts share stories of Mykonian culture and their family history. 

Day 10: Transfer to Athens, Depart

Farewell Greece
Until the next time, Greece!

Sadly, it's time to say goodbye to the Aegean. After one last stroll around the harbor, you'll transfer to the airport in time for your flight home or onward journey. Safe travels!

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Map of Relaxed Athens, Santorini, Naxos & Mykonos - 10 Days
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