Laidback Athens, Tinos, Mykonos, Santorini, and Crete - 14 Days

Day 1: Arrive in Athens

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. 

Spend your evening exploring the up-and-coming Pangrati neighborhood or amid the nightlife and mezze of the Psyrri district.

Day 2: Athens Food Tour

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

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: Ferry to Tinos

Take an early ferry to Tinos, one of the most overlooked islands of the Cyclades. Tinos has remained under the radar for many years, overshadowed by its celebrity neighbor of Mykonos and seen mainly as a religious destination. Those who continue to believe that, however, are missing out on an island with fascinating history and culture, winding streets, great outdoor activities, and glittering beaches.

The imposing Panagia Evangelistria should not be overlooked, as Tinos is also known as the island of the Virgin Mary. Its icon is believed to have healing powers, and the annual August pilgrimage is a key part of the island's identity as churchgoers crawl on their knees toward the temple as a sign of piety.

If pilgrimage isn't quite your scene, there are also nearly 80 windmills to be explored, Venetian ruins, hiking at Exomvourgo mountain, and beaches for any moods. Try the island's craft beer from Nissos brewery or sample the cheeses at the shop belonging to the Cheese Cooperative of Tinos. Keep an eye out for the many painted dovecotes around the island as well, small white pigeon homes dotting the countryside of which there are nearly 1,000.

Day 5: Follow the Marble Route

Tinos is known for its marble crafting, and you'll see why as you follow this route from raw materials to artists' workshops.

Start at the Museum of Marble Arts. In its halls, you'll learn how Tinian craftsmen start with slabs of stone and craft them into artful statues and other works from fountains and altarpieces to tower bells, palaces, and stadiums. See that work in practice as you walk through the cemetery of Pyrgos, also an open-air sculpture museum, on your way to Pyrgos Square. Take a break in the square for some coffee or ouzo along with an afternoon snack or sweet. 

Your next stop is the home of sculptor Yannoulis Chalepas and the Museum of Tinian Artists. You'll make your way through the workshops of the village, where you can meet a sculptor who will introduce you to the raw marble along with their tools and tricks of the trade. 

Cap it off with a swim at Agia Thalassa beach and dinner in the fishing village of Panormos.

Day 6: Ferry to Mykonos

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 7: Explore Mykonos, Traditional Dinner and Optional Cooking Class

You've got two options for your early day today. Independent types can continue their island explorations on their own or head to a beach to lounge. Stroll through the cosmopolitan streets, scoping out the boutiques that draw the island's stylish crowd season after season.

If you'd prefer a more guided experience, opt for a cooking class to learn about Greek cooking techniques and ingredients. You'll master strategic deployment of olive oil, fresh produce, seafood, and more with your master instructor.

Either way, as the sun begins to set, you'll sit down to a traditional dinner, either cooked by you or your fellow travelers. 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 8: Mykonos to Santorini

After breakfast at your hotel, you'll get an early 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 9: Santorini Catamaran Cruise

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 Lighthouse, Indian 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 10: Free Morning in Santorini, Travel to Chania

Spend one more morning in Santorini to explore however you like, whether that's a morning on the beach or getting in some last-minute souvenir shopping.

In the late afternoon, you'll continue onward to Chania, a city (and region) on the northwest coast of Crete. Chania itself is the second largest city in Crete and one of the most scenic spots on an island with stiff competition for that title. Life in this former Venetian city revolves around its charming 14th-century harbor, narrow streets with winding alleys, and colorful architecture influenced by past Ottoman and Egyptian eras.

While you're exploring the area, don't miss some of these spots:

• The elevated neighborhoods of Topanas, Splantzia, Kolombo, and Kasteli for panoramic harbor views, Cretan taverns, and architectural history. You can see the ruins of the Minoan city of Kydonia and high walls of former Venetian moats integrated into the city.
• The Municipal Market of Chania and neighboring Municipal Garden to enjoy a coffee amid the shade of the trees or garden clocktower. 
• The Botanical Parks and Gardens of Crete to enjoy Cretan nature at its finest. The special micro-climate formed at this specific area allows plants from three different climate zones to grow in the park.
• The olive-oil-producing region of Vouves, to the west of the city, complete with a museum and one of the oldest olive trees in existence.
• Falassarna and Elafonissi beaches, also to the west, where you can find solitude on the sands.

Top it all off with a sunset drink on the rooftop at trendy Pallas or visit Cafe Koukouvaya for a pastry and a view of Chania town and harbor.

Day 11: Gramvousa and Balos Beaches

Spend your day on the pink sands of some of the most beautiful beaches in the world. You'll be transported by boat to Balos and Gramvousa beaches, where crystal-clear turquoise waters are home to stellar swimming, sunshine, and protected animal and plant species. If you're lucky, you may even spot a Mediterranean seal. 

In Gramvousa, you can also choose to hike up to a former Venetian castle or a shipwreck along the beach. Nearby Balos is a shallow, more protected lagoon, home to placid waters.

After you've sunned and swum to your heart's content, you'll return to Chania for a night on the town. Visit the graves of the Eleftherios Venizelos family, one of Greece's most notable political figures, for spectacular panoramic views.

Day 12: Explore the Villages of Apokoronas

Today, you'll have a chance to hear some of the island's history firsthand during a guided tour through nearby Apokoronas. The region's villages—seven of them—are home to a number of sites including an Ottoman fort, historic churches, and a folklore museum. But most interesting will be the conversations you and your guide will have with the local residents of the area.

Some potential highlights include:

• The hillside ruins at ancient Aptera, one of the largest city-states in Crete until it was destroyed by an earthquake in the seventh century, including a Minoan tomb believed to date back to roughly the 13th century BCE.
• Two-aisled churches in Stilos village from the 13th and 15th centuries, along with a limestone fossil once believed to be a fossilized sea siren and a walk along the Kiliaris river to a Venetian watermill.
• A glassblowing factory in Kokkino Chorio.
• The old square of  Gavolochori, where you can visit the women's cooperative and see hand-knit lace created using a Byzantine technique or the neighboring Folklore Museum of Gavalochori.

In the evening, check out Chania's waterfront districts of Halepa and Tabakaria. Wander among former tanneries and factories in these off-the-beaten-track parts of town, just past the end of the main promenade.

Day 13: Return to Athens, Sunset at Cape Sounion

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

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