Head to Greece for 14 days of relaxation. Start with a culinary tour and winery day trip on the mainland before chilling island-style in the Cycladic Islands. Cruise through the caldera of Santorini, prepare a typical Greek meal on Naxos, and recline on sandy beaches throughout.

Highlights

  • Cruise through the caldera of Santorini
  • Learn to prepare a typical Greek meal on Naxos
  • Sample the vintages of the wineries of Nemea
  • Recline on Cycladic island beaches

Brief Itinerary

Day Highlights Overnight
Day 1 Arrive in Athens, Welcome Dinner Athens
Day 2 Athens Food Tour Athens
Day 3 Nemea Winery Day Trip Athens
Day 4 Athens to Santorini Santorini
Day 5 Santorini Catamaran Cruise Santorini
Day 6 Ferry to Naxos Naxos
Day 7 Naxos Bike Tour Naxos
Day 8 Cooking Class on Naxos Naxos
Day 9 Beach Day on Naxos Naxos
Day 10 Ferry to Mykonos Mykonos
Day 11 Farm Visit and Mykonian Dinner Mykonos
Day 12 Mykonos Beach Day Mykonos
Day 13 Return to Athens, Sunset at Cape Sounion Athens
Day 14 Depart Athens  

Detailed Itinerary

Day 1: Arrive in Athens, Welcome Dinner

Monastiraki Square and the Acropolis
Monastiraki Square and the Acropolis

Welcome to Greece! You'll begin your trip in Athens, home to both the iconic Acropolis and so much more. The mythology of this spectacular city precedes it, with towering temples to Classical deities and the ruins of ancient marketplaces rubbing shoulders with lively nightlife, crowded flea markets, and contemporary cuisine. Make the most of your time in the city at some of these spots:

  • Check out the views of the can't-miss Parthenon. (Pro tip: The Parthenon is the temple, the Acropolis is the hill.) This temple to Athena has enchanted visitors since its construction was completed in 438 BC. It's probably the first thing that comes to your mind when you think of ancient Greece and is visible from many of the city's high points.
  • Stop at the sprawling National Museum for a crash course in ancient iconography. Be sure to seek out the room housing the Antikythera mechanism, essentially an ancient astronomical computer.
  • Visit a smaller archaeological site at the Tower of the Winds, then stroll down neighboring pedestrian Aiolou Street to stop at shops and cafes. 
  • Find your perfect souvenir or sun hat in the busy stalls of the Monastiraki flea market. 

In the evening, you'll sit down to enjoy either a welcome dinner with views of the Acropolis or wine tasting in a bar in downtown Athens.

Day 2: Athens Food Tour

Vendors in the market
Market wares

Meet your guide in Syntagma Square to start sampling the best of what the city's street food stalls have to offer. You'll learn about the Mediterranean diet and its potential benefits while strolling the city streets in neighborhoods you may not have discovered yet and exploring bustling open-air markets.

Say good morning with Greek coffee at one of the city's landmark coffee houses, then pick up some street snacks to sample on the go. Venture into the aromatic Varvakios Market, the largest and most popular fish, meat, and vegetable market in the city, and explore the city's main spice street. Sample olive oils, honey, cheeses from around the country, cured meats, olives, and more. Everything from baklava to souvlaki is available to appeal to even the pickiest eaters.

If you haven't had your fill of adventuring during the afternoon, spend your evening in the Koukaki neighborhood. This area's off-the-beaten-path wine bars will introduce you to a wide selection of Greek wines amid friendly crowds, or if you're with the whole family a selection of great local restaurants await.

Day 3: Nemea Winery Day Trip

Fruit of the vines
Fruit of the vines

Spend your day among the wineries of Nemea, one of the country's most important wine-producing areas. They're especially known for their Agiorgitiko wine, believed to have been first grown from a vine brought by the god Dionysus. These grapes, which are similar to Merlot, are considered to be one of the finest Greek red varietals and have grown in the region for thousands of years—possibly since the 4th century BC. The ancient red wine called Fliasion was also believed to be produced in this area.

You'll visit three wineries to observe the wine-making process and stroll through the vineyards. And, of course, sample the varietals along the way, along with a lunch of local cuisine with wine pairings at one of the stops.

If you find yourself fondly remembering any particular bottles later that you wish you'd purchased, the local cooperative also operates an outlet where many of the wines are available.

Day 4: Athens to Santorini

Santorini's caldera
Santorini's caldera

After breakfast at your hotel, you'll get an early flight or ferry to Santorini. Nothing says "good morning" like watching the sun coming up over the island's iconic cubic architecture. Upon arrival, you'll take in the island's central caldera—the site of one of the largest volcanic eruptions in history—rising above you. 

The island's volcanic history has led to the formation of some of the more unique beaches in the Greek islands, along with the dramatic cliff views on the island's caldera side. Spend your day relaxing at the beach or catching some exercise—and even more views—from one of Santorini’s more than 12 scenic walking routes, ranging from between two to eight miles each.  At dinner, sample the island's signature cherry tomatoes and white eggplants as guest stars in seafood dishes or the main event.

Day 5: Santorini Catamaran Cruise

View from Fira
View from Fira

Enjoy a leisurely morning breakfast before taking some time to stroll and scope out small shops and boutiques. Explore Fira, the capital of the island, which offers plenty to check out. History buffs will be delighted by proximity to the Archaeological Museum of Santorini, the Museum of Prehistoric Thera, the Folklore Museum of Emmanuel Lignos, and the church of Hypapante.

As the late afternoon unfolds, you'll head toward Vlychada Port to board your semi-private catamaran cruise around the island. Your first stop will be at the Red Beach to swim and sun, followed by a second stop at the White Beach to take in all the distinctive-colored sands of Santorini.

Barbecue will be served onboard while you sail past landmarks at Aspronisi, the Ancient LighthouseIndian Rock, and the prehistoric city at Akrotiri, hidden away at the southern tip of Santorini. These ruins are the site of some of the Bronze Age’s most advanced settlements, which prospered for centuries before being destroyed by a great volcanic eruption in the mid-second millennium BC. Top it off with a jump into the hot springs at Nea Kameni, where the mineral-rich volcanic waters are believed to have therapeutic properties.

Day 6: Ferry to Naxos

Looking back from the Portara
Looking back from the Portara

Time to ferry over to bustling Naxos after breakfast. With an active main town where you can shop and admire the Venetian architecture, a historic Kastro (castle) area, and expansive beaches, the island offers opportunities for both laidback relaxation, as well as water or land activities. The rest of the day is yours to unwind as you choose. Try out some of these options:

  • Hike up to the summit of Mount Zas, the mythological childhood home of Zeus, the ruler of the gods, and the highest point in the Cyclades.
  • Head inland to the town of Chalki, home to the island's oldest market and a petite, shady square perfect for whiling away the afternoon. Stop at the kitron distillery to sample the local liqueur and learn about its distillation process over the years.
  • Visit the Temple of Demeter at Sangrion your way. Multiple deities of fertility were worshipped here, particularly the goddess Demeter. The temple was constructed in 530 BC, during the tyranny of Lygdamis, and represents a precursor of classical Athenian architecture. 
  • Stroll to the Portara, the entrance to the Temple of Apollo. Construction on the temple began in the sixth century BCE but was never finished, but the still-standing entranceway has become one of the hallmarks of the island. You can find it on the islet of Palatia, just over a causeway from the heart of Naxos Town (Chora).

For dinner, wander up the hill through the streets of the Kastro neighborhood to pick out your favorite of the area's tavernas, where you can sample the island's fresh produce in its best forms.

Day 7: Naxos Bike Tour

Cycle by the sea
Cycle by the sea

Discover Naxos's hidden spots on today's two-wheeled tour. You'll bike with an expert guide through the villages and attractions on the west side of the island. The western coast is also home to some of the island's best-known beaches, including Agios Prokopios, Agia Anna, Plaka, Orkos, and Mikri Vigla. 

On your way back, you'll see the villages of Vivlos, Agios Arsenios, and Glinado. The beginner-friendly route covers roughly 12 miles (20 km) and will take you about 2.5 hours. 

Spend the rest of your day exploring the main Naxos Chora, especially the Kastro district. Wind up the narrow streets to the Venetian Castle in the center of town, stopping at the neighboring Catholic church, Ursuline school, and Archaeological Museum along the way. Even the houses are part of the experience, once home to the descendants of Duke Venetians.

Day 8: Cooking Class on Naxos

Pass the kitron please
Pass the kitron please

Take a leisurely morning after breakfast, adding more shopping or time in the sun to your itinerary. At your choice of time in the afternoon, you'll head to Kaloxylos village to learn how to prepare a typical Greek meal in a local home. Join in the village life, with a menu that you can help determine based on your personal preferences, season, and what's growing in the village garden. 

At sunset, head to the Portara if you haven't yet. The unfinished entrance to the Temple of Apollo on an islet outside of town is one of the island's best views as the sun goes down.

Day 9: Beach Day on Naxos

Aliko Beach on Naxos
Aliko Beach on Naxos

What's a trip to the islands without a day on the beach? With smaller crowds than its Cycladic neighbors, Naxos makes it easy to find your own slice of paradise, whether you want privacy or a more lively scene. Terminology tip: If a beach is described as "organized," that generally means it has sunbeds and umbrellas available to rent and plentiful restaurants.

Agios Georgios is the closest to the main town and generally filled with families enjoying the shallow waters. Neighbors Agia Anna and Agios Prokopios also have plenty of amenities on their sweeping sands, with enough shoreline that you'll be able to stake out a spot but sufficient tavernas to keep you fed.

The more isolated beaches of the southwest coast—including Plaka, Mikri Vigla, and cedar-lined Aliko—are some of the best on the island. They're farther out from the main town, and your travel will be rewarded with quieter sands and scenic surroundings.

Day 10: Ferry to Mykonos

Bright balconies of Little Venice
Bright balconies of Little Venice

You'll take a ferry in the morning to Mykonos, one of the most famous islands in the Cyclades. Known for its glitzy restaurants and nightlife, art scene, and jet set crowds (it was recently home to a Gucci pop-up boutique), Mykonos is one of the most quintessential Greek isles.

Your first day's itinerary is up to you. You'll receive a personalized list of tips for exploration, but some highlights include:

  • If you need to get your toes in the sand immediately, head to remote Agios Sostis beach to find your own isolated paradise.
  • For a more active experience, Ftelia Beach is known for its excellent windsurfing.
  • Stroll through Little Venice, an 18th-century neighborhood where colorful former captains' mansions and seaside restaurants seem to sprout straight from the sea. It's also right next to the island's famous hillside windmills for great photo ops.

Day 11: Farm Visit and Mykonian Dinner

A mealtime spread
A mealtime spread

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 a traditional farm. Talk to the farm's caretakers to learn about how vegetables are grown on the islands and how the livestock are raised, and even say hi to the animals.

As the sun begins to set, you'll sit down to a traditional dinner. You'll be welcomed into a local Mykonian household for the meal, where you'll experience the traditional Greek way of life, culture, and cooking. Hear all about their stories of the island's culture and history as well as their own family history, over authentic dishes and free-flowing local wine (for the older crowd).

Day 12: Mykonos Beach Day

Join the lines
Join the lines

Spend a relaxing day filled with sea and sun! Choose from one of Mykonos's many lovely beaches, such as:

  • Agios Sostis, full of island residents and travelers who prefer tranquility to amenities, with just sand and a nearby taverna.
  • Fokos, a quiet beach on the northeastern end of the island, with no distractions but a single taverna serving up local favorites and organic white wine produced on the island.
  • Elia, considered one of Mykonos's most beautiful beaches. This beach has one of the longest stretches of sand on the island and plenty of sunbeds and umbrellas to keep you fed and serviced.
  • Kalo Livadi, a petite pebbled beach on eastern Mykonos. This is one of the best spots for swimming, with plenty of people enjoying the beach along with you.
  • Platis Gialos, a popular beach lined with hotels and restaurants with music drifting out of their patios.
  • Kalafatis, a quiet beach ideal for family relaxation.
  • Ftelia on the northern side of the island, known for windsurfing and sailing when the winds are blowing and tavernas along the bay.

Day 13: Return to Athens, Sunset at Cape Sounion

Temple of Poseidon
Temple of Poseidon

Return to Athens in the morning.

In the afternoon, you'll be transferred down to the Athenian Riviera, full of both history and stunning island views. Your adventure will take you along the coast to visit the Temple of Poseidon, while being provided with historical background on the way. The views overlook the Saronic Gulf, with one of the best sunset views Greece has to offer. Sip a complimentary beverage and take in the sunset while you listen to music and immortalize the moment with a Polaroid-style photo.

You'll be transferred back to your lodging in the evening just in time for a late (Greek-style) dinner. Or, if you're not ready to call it a night, you can request a drop-off at some of the most popular beach bars to dance until the sun comes up.

Day 14: Depart Athens

Wave to the city
Wave to the city

Time to say farewell to Greece. Enjoy your final Athenian breakfast before your transfer to the airport.

Map

Map of Relaxed Athens, Santorini, Naxos & Mykonos - 14 Days
Map of Relaxed Athens, Santorini, Naxos & Mykonos - 14 Days