Taste of the Cyclades and Crete - 16 Days

Day 1: Arrive in Mykonos

Welcome to Greece! You'll start your tour of the Cyclades on Mykonos, one of the larger islands in this chain. Known for its glitzy party scene, art, and jet set crowds (it was recently home to a Gucci pop-up boutique), Mykonos will throw you headfirst into your adventure.

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 time, Ftelia Beach is known for its excellent windsurfing.
• Take a short day ferry over to the archaeological site at Delos. This entire island is full of ancient ruins and is one of the most important in the country for its history as both a sanctuary and the mythological birthplace of Apollo and Artemis.
• Stroll through Little Venice, an 18th century neighborhood where colorful former captains' mansions and seaside restaurants seem to come straight up from the sea. It's also right next to the island's famous hillside windmills.

Day 2: 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 3: Mykonos to Paros

After breakfast in Mykonos, you'll hop a ferry to the relaxed shores of Paros. This island is no less charming but significantly lower key, just waiting to lure you into a beach chair. Some of your options for exploration include:

• Hit the sea air and golden sands of popular Kolymbithres beach. The beach umbrellas are accented by towering granite rocks, resembling natural sculptures. Take in the sea breeze or take a coastal walk past the area's attractions. You'll spot antique chapels, island vines, and rustic farmhouses on your way to the hillside ruins of the Mycenean Acropolis, dating back to the 13th century BC, and the Monastery of St. John.
• Recline on the sandy beach of Molos. Lounge on the shore or visit the neighboring St. Anthony's Monastery with a walk or drive. The hiking trail also takes you through the ruins of a former Venetian castle before you reach the top, where you'll find the double-domed monastery and scenic views of both Paros and neighboring Naxos.
• Go inland to the village of Lefkes. Head up all the way towards the Byzantine architecture of the Agia Triada church, located on one of the most beautiful squares in the Cyclades.

Stick with the al fresco theme for dinner and eat on the beach, or take your pick of the traditional tavernas along the main strip of town. Listen for the ones that have live music if you're in the mood for both dinner and a bit of a show.

Day 4: Day Trip to Antiparos

Take a brief day ferry to even more petite Antiparos. This island's scenery has drawn celebrities including Tom Hanks to buy villas on its picturesque shores. Your day there could include any of these sights:

• The Venetian Castle: Set right in the heart of the old town, this castle was originally built to protect the town from pirates in the 1400s and now wraps around many of the town's central buildings.
• Kambos village: Head to the center of the island to this village with just a dozen inhabitants. Its whitewashed churches set the scene for the traditional atmosphere, as do the nearby Glyfa and Livadia beaches.
• The Cave of Antiparos: Drive roughly 10 minutes from Kambos and up Agios Ioannis Hill to visit this ancient cave, known for its stalactites and stalagmites.

Head back to Paros for the evening and explore the chic town of Naoussa. Its whitewashed cobblestone streets are home to a myriad of tiny shops, cafes, and bars and clubs that attract partiers all summer long.

Day 5: Paros to Naxos

Spend one more morning in Paros, complete with breakfast and sightseeing in Paroikia. Stroll through the island's main town, including the traditional and contemporary designs at Yria Ceramics and the famous Byzantine church of Ekantotapiliani. Also known as the Church of 100 Doors, it's worth a stop to see one of the best-preserved Christian churches in Greece.

You'll hop on the ferry to Naxos and be transferred to your hotel, with time to explore the island in the evening. 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.

Don't miss the Portara, the entrance to the former Temple of Apollo. Construction on the temple began in the 6th century BC but was never finished. 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).

If you prefer something a bit more pastoral, Naxos is also known for its rich agricultural industry. Pay a visit to a cheese-producing facility or a local distillery to sample the famous local kitron liqueur. 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 6: Cooking Class on Naxos

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 7: Beach Day on Naxos

Naxos has numerous spectacular beach options. Since the island is less famous than nearby Mykonos and Santorini, it is easy to find your own private slice of paradise. Some of the best beaches are located along the southwest coast of the island, from Plaka down through Mikri Vigra and Aliko.

Day 8: Naxos to Ios

Your next island awaits after breakfast! Ferry over to Ios, where lazy afternoons on the beach ease into a booming nighttime scene, with nightlife venues to suit your every possible interest. 

Mylopotas beach is the most popular choice for daytime. In the evenings, don't miss Far Out Village, a four-part beach club, campground, hotel, and spa, and one of the biggest hotspots on the island. It's the perfect place to meet some new friends and see where the evening goes.

Day 9: Sikinos Island Tour & Wine Tasting

Take a morning day trip to neighboring Sikinos island, whose quiet, undeveloped hills will provide the perfect break for any overindulgence headaches you may have developed. Your fully guided tour will included all of the island highlights of culture, history, and scenery. Check out the Monastery of Episkopi with a scenic hike up from the main town, central Folklore Museum, and top it off with a toast from a local winery. The island was once named the "Isle of Wine," after all.

Once you return to Ios, head back to Mylopotas beach to cool off with an afternoon swim in its deep water and stick around for a sundowner at one of its beach bars. If you partied a bit too hard previously, try the quieter Kalamos or Magganari beach.

Day 10: Ios 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 11: Santorini Tour & Wine Tasting

The morning is yours to spend as you will, whether that's browsing the boutiques of Fira or getting beachside. Don't wear yourself out too soon, though, as in the afternoon you'll take a guided tour that will show you a side of Santorini that most travelers don't see.

You'll check out hidden gems in Oia, the furthest town along the rim of the caldera. Oia's arty streets are the quintessential Santorini scene. Later, you'll take a trip up to the highest peak on the island. Bring your camera for the 360 views at the top, as well as the many stops on your way down. You'll also see medieval villages at Megalochori and Pyrgos and the Blue Dome in Firostefani before your voyage ends with a wine tasting to sample varietals dating back centuries, complete with epic caldera views as the sun goes down.

In the evening, return to Oia to wander the alleys and linger in the town's tavernas into the evening and experience a calmer vibe after the sunset crowds subside. When searching for your dinner, seek out tomato keftedes, deep-fried tomato balls that encapsulate the essence of the Mediterranean diet, and the Santorini specialty spelt pie.

Day 12: Santorini Catamaran Cruise

Enjoy a leisurely morning breakfast with time to stroll through town and scope out the small shops and boutiques. Head over to Fira, the capital of the island, which offers plenty to explore. 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 13: Santorini to Chania

After some final free time in Santorini, your journey will take you by ferry to Crete, the largest and most populous of the 230 inhabited Greek islands. Upon arrival in Heraklion port, you'll be transferred to Chania, a city (and region) on the northwest coast, and get settled into your hotel as you get ready to explore this stunning island, equipped with tips from your local specialist. 

Chania itself will be the main base of your operations during your trip. It's 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.

Depending on what time you arrive, wander around town or head for one of the western region's spectacular beaches such as Falassarna and Elafonissi. There are also plenty of deserted coves and quiet bays to enjoy total privacy. 

For dinner, wander around Chania's harbor and check out a slew of waterfront restaurants with a sunset view.

Day 14: Botanical Park Tour & Tasting

Today, you'll surround yourself with the bright tropical gardens and the shade of avocado trees at the Botanical Park and Gardens of Crete. Your trail will lead you under citrus trees and other Mediterranean flora. Learn about the different climates around the island and the produce that grows there before you enjoy a lunch in a restaurant overlooking the sweeping garden view. 

Spend the evening enjoying your return to Chania town. Head to Kikbar, located in the former 16th century Monastery of Karolos. This converted building is now home to an art gallery, theater space, and swoon-worthy open air bar.
Overnight: Chania
Meals included: Breakfast, Lunch

Day 15: 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 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, return to Chania for your final 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 16: Depart Chania

It's time to say farewell to Crete with one final breakfast in Chania. Take a sunrise stroll along the harbor or perhaps indulge in one more scoop of graviera cheese before you're transferred to the airport for your departure.