Get away from the hustle and bustle of everyday life with laid-back visits to some of the Mediterranean's best beaches and coastal towns. In Italy, explore the cliffside fishing villages of Positano and Amalfi and enjoy Sorrento's sunny coast, making time for a day trip to the nearby resort island of Capri. Then, catch a flight to the Greek archipelago where you'll go wine tasting in Santorini, explore 3,000-year-old Greek history near Heraklion, and relax on Crete's famed beaches.


  • Experience the dramatic scenery and charming villages of the Amalfi Coast
  • Eat an authentic Neopolitan pizza and try fresh-pressed olive oil
  • See Santorini's caldera on a full-day catamaran tour
  • Tour Bronze Age ruins in Knossos, possibly Europe's oldest city
  • Relax on the sands and crystal waters of Elafonissi Beach

Brief Itinerary

Day Highlights Overnight
Day 1 Welcome to Naples! Naples
Day 2 Naples to the Amalfi Coast — Pompeii & Mount Vesuvius Amalfi Coast
Day 3 Tour of Amalfi, Positano, & Ravello Amalfi Coast
Day 4 Kayak Tour of the Amalfi Coast Amalfi Coast
Day 5 From the Amalfi Coast to Sorrento, Food Tour Sorrento
Day 6 Capri & Anacapri Day Trip from Sorrento Sorrento
Day 7 Sorrento to Santorini & Sunset Wine Tasting Santorini
Day 8 Santorini Tour & Sunset in Oia Santorini
Day 9 Catamaran Cruise in the Caldera Lagoon Santorini
Day 10 Free Day in Santorini & Ferry to Crete Heraklion
Day 11 Tour of Knossos & Rethymno, Travel to Chania Chania
Day 12 Chania Beach Day & Afternoon Walking Tour Chania
Day 13 Day Trip to Elafonissi Beach Chania
Day 14 Depart Chania  

Detailed Itinerary

Day 1: Welcome to Naples!

Backlit street in Quartieri Spagnoli
Backlit street in Quartieri Spagnoli

Welcome to Italy! You'll arrive at Naples Airport and transfer to your accommodation in the city center. Naples sits on a bay near the still-active Mount Vesuvius, which buried nearby Pompeii in 79 CE. There's a lot to see and do here, so make the most of your time with these suggested activities: 

  • Visit the Naples Archaeological Museum to see Roman, Greek, and Renaissance-era ruins, including artifacts from nearby Pompeii.
  • Tour the Castel dell'Ovo, a seaside castle located on the former island of Megaride.
  • See the 16th-century Museo Cappella Sansevero, which houses thousands of veiled sculptures. 
  • Go underground to see the network of tunnels and passageways built under the city streets. 
  • Get outside and see the dormant Solfatara volcano, located a half-hour drive west of Naples.

In the evening, go for a stroll along the Caracciolo e Lungomare di Napoli, a waterfront promenade, then head to the Quartieri Spagnoli, a lively commercial hub, for dinner at a trattoria. On the way, stop at the Toledo Metro station, the Stazione della Metropolitana dell'Arte, to see beautiful mosaic inlays.

Day 2: Naples to the Amalfi Coast — Pompeii & Mount Vesuvius

Ancient street in Pompeii
Ancient street in Pompeii

In the morning you'll leave Naples and head south to the Amalfi Coast. Along the way, stop to visit the area's most notable attractions, Pompeii and nearby Mount Vesuvius.

Start with a visit to the ruins of Pompeii, once a flourishing Roman coastal city that was famously buried under ash and volcanic debris after the eruption of Mount Vesuvius in 79 CE. The ash, which killed many of Pompeii's residents, acted as an archaeological time capsule by preserving many of the city's original buildings completely intact. You'll stroll the remains of Pompeii's ancient streets, which are lined with well-preserved villas, shops, public buildings, and plazas. 

Afterward, visit Mount Vesuvius, which is designated as a UNESCO Biosphere World Reserve. It's a brisk 30-minute hike up a trail to the top, where you'll be rewarded with stunning views inside the crater as well as panoramic views of the surrounding landscapes and the Tyrrhenian Sea

After the excursion to Vesuvius, you'll continue on to the Amalfi Coast, where you'll check into your hotel and settle in for the evening.

Day 3: Tour of Amalfi, Positano, & Ravello

Positano in the evening
Positano in the evening

Start your morning with a coffee along a quiet lane, then go for a walk through the village of Amalfi to see the sights and soak up the atmosphere. Stop by La Piazzetta di Sant'Andrea—the square at the heart of the city—to see the Duomo and the Romanesque-baroque Cattedrale di Sant'Andrea. Once one of the four main Maritime Republics of Italy, Amalfi is now primarily a resort town. Stop by the Paper Museum to learn about the local flourishing paper industry, which brought a stream of wealth and skilled craftsmen to the area. 

From Amalfi, enjoy a nice 3-hour walk to the village of Ravello, above the Amalfi Coast. Reward yourself with lunch and a coffee at a cafe in the main piazza, then head to Positano, a colorful and romantic seaside town. Explore the city and its narrow streets, shop for souvenirs and the local fashion—flowy bohemian flower-print dresses—then walk down the hill to a small beach for a quiet sunset, followed by dinner in the village of your choice. 

Day 4: Kayak Tour of the Amalfi Coast

Kayak amid crystalline waters
Kayak amid crystalline waters

The Amalfi Coast is too beautiful to simply admire from the land. To really experience this region you need to take a half-day kayak tour around the coast. Doing so will allow you to visit all the hidden coves, grottoes, and secluded pebbly beaches you wouldn't otherwise get to see.

After getting your paddle and strapping on your life vest, you'll hop in the kayak and embark. Not only will you get a workout during this 3 to 4-hour excursion, but you'll also be treated to one-of-a-kind views looking back at the coast from the water. You'll pass by colorful seaside towns like Positano, plus kayak into sea caves, pass through grottoes, and even visit fjords. 

After the tour, you'll return to the beach and drop off your kayak, then have the rest of the day free to relax on the beach.

Day 5: From the Amalfi Coast to Sorrento, Food Tour

Hotel along the Sorrento waterfront
Hotel along the Sorrento waterfront

After a leisurely breakfast, say goodbye to the Amalfi Coast and head north to Sorrento. This city is a long-time favorite with Italian and international vacationers for its beautiful views, tranquil atmosphere, and terraced lemon groves. After checking in to your hotel, take a quick stroll around town.

The city's focal point is the Piazza Tasso, a central square built over a gorge that splits the city. Other notable sights in and around Sorrento include the nearby bay of Marina Piccola, the ruins of Villa Pollio in Capo di Sorrento, the church monastery San Francesco d'Assisi, the 11th-century Duomo, and the Basilica di Sant'Antonino. The latter houses the remains of Saint Anthony, Sorrento's patron saint, who died in the 7th century.

Spend the afternoon exploring the city through the Italian love language: food. Visit the local food market and stop in small family shops to learn about local cuisine on a small-group food tour. Kick things off with a strong cup of cappuccino or espresso as you enjoy the sounds of the city around you and chat with your guide about local food culture and regional traditions. From here, make your way through the market stalls as you rub shoulders with locals shopping for fresh dinner ingredients, from fresh-caught fish to seasonal produce. Explore the stands selling cheeses, fresh bread, cured meats, and other delicacies as you learn first-hand why the Mediterranean diet is one of the world's most renowned. 

Once the market portion of your tour is done, head to lunch with your tour guide. Afterward, enjoy a gelato tasting at the neighborhood family-run gelateria where you'll sample a variety of flavors.

Spend the rest of the day exploring the town's historical sites and browsing small shops for gifts and souvenirs.

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Day 6: Capri & Anacapri Day Trip from Sorrento

Colorful street cafes, Capri
Colorful street cafes, Capri

Spend the whole day enjoying the sunshine and clear blue waters of the island of Capri. Known locally as the "Pearl of the Mediterranean," the ancient Greeks called it the "Isle of Sirens." Capri sits on the south side of the Gulf of Naples and has been a popular vacation destination for millennia. The ancient Romans, in fact, built summer villas here for the Empire's VIPs.

In the morning, you'll catch a hydrofoil to Capri. From here you'll enjoy a guided walking tour of the island's attractions. Visit the Marina Grande and Marina Piccola harbors, walk along the Belvedere of Tragara (a villa-lined promenade with panoramic views), and explore the ruins of ancient Roman villas.

For lunch, try Caprese salad with vine-ripened tomatoes, milky mozzarella, aromatic basil leaves, and a drizzle of sharply flavored olive oil while you take in the views. 

Then, head up the hill to Anacapri see the Piazzetta and Augustus' Garden, and enjoy the best views of the Faraglioni Rocks. Should you choose, you can later return to the water and explore the Grotta Azzurra, the famous "Blue Grotto," which is located inside a hollowed sea cave. Afterward, perhaps spend the remainder of the afternoon soaking in the sunshine on the beach, then return to Sorrento for the night.

Day 7: Sorrento to Santorini & Sunset Wine Tasting

Kamari Beach
Kamari Beach

After breakfast at your hotel, you'll head back to the airport and get an early flight to Santorini. Nothing says "good morning" like watching the sun shining down on the island's iconic cubic architecture. As you arrive, take in views of the island's central caldera—the site of one of the largest volcanic eruptions in history. 

The island's volcanic history has led to the formation of some of the more unique beaches in the Greek Islands, like Kamari, with a stretch of black sand against the clear blue water. The beach is backed by the town of its namesake, a popular area with hotels, restaurants, beachside bars, and shops. 

In the evening, enjoy a laid-back wine tasting tour to the wineries of Santorini.

Your first stop is to a small family-owned winery, which uses centuries of tradition to cultivate vines in the poor volcanic soil. Taste three different ancient varietals along with local snacks as you learn about the winery's ancient growing techniques. Unique to this region, the red-colored Santorinian Vinsanto (holy wine) is Santorini's sun-dried dessert wine made from overripe white grapes — you'll taste this wine and many others this evening. 

Round out the experience with drinks on a balcony with breathtaking sunset views. For dinner, make your way to one of the island's numerous restaurants or tavernas along the waterfront.

Day 8: Santorini Tour & Sunset in Oia

Views of Oia
Views of Oia

In the morning, you’ll be picked up from your hotel for a half-day guided tour. After a short excursion of the area, you'll head to the village of Oia, the furthest town along the rim of the caldera. Oia's arty streets, white-washed facades, and pastel-hued homes are the quintessential Santorini scene. 

From here, you'll take a trip up to Prophet Elias Monastery, which stands atop the highest peak on the island. Bring your camera for the 360-degree views at the top, as well as the many stops on your way down. You'll also see the lesser-known medieval villages of Megalochori and Pyrgos and the Blue Dome in Firostefani.

After the tour, return to Oia to wander the alleys and linger in the town's tavernas into the afternoon. When searching for your meal, seek out tomato keftedes, deep-fried tomato balls that encapsulate the essence of the Mediterranean diet, and a Santorini specialty — spelt pie.

Oia is also the perfect place to catch sunset views. Stake out your viewing platform over the panorama, then stick around to enjoy the town's tavernas into the evening.

Day 9: Catamaran Cruise in the Caldera Lagoon

Santorini's Red Beach
Santorini's Red Beach

Enjoy a leisurely breakfast before taking some time to stroll around and scope out small shops and boutiques. Explore the many attractions of Fira, the capital of the island. History buffs will be delighted by the Archaeological Museum of Santorini, the Museum of Prehistoric Thera, the Folklore Museum of Emmanuel Lignos, and the Church of Hypapante.

In the late afternoon, head to Vlychada Port to board your semi-private catamaran for a cruise around the island. Your first stop will be at Red Beach to swim and enjoy the sun, followed by a second stop at White Beach.

Enjoy a barbecue dinner on board as you sail past landmarks at Aspronisi, the Ancient Lighthouse, Indian Rock, and the ancient 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 BCE. Top off your day 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 Day in Santorini & Ferry to Crete

Santorini coast
Santorini coast

The day is yours to explore as you wish before your afternoon ferry to Crete. If you're in the mood for archaeology, scope out Santorini's main historical attraction and one of the Aegean's most significant prehistoric settlements, the excavated city at Akrotiri. Walk through its well-preserved streets and envision the once-bustling city life that filled them.

The Museum of Prehistoric Thera and Archaeological Museum of Thera complement your visit, with findings including murals preserved from Akrotiri and the settlement of ancient Thera once found on the eastern part of the island. If you'd rather see it for yourself, hike up to where ancient Thera once sat to see the ruins and get a sense of why its location was so strategic.

If you would rather spend the day on a beach, you've got plenty to choose from:

  • Kamari Beach: The most upscale and touristy of the beach towns, with plenty of family-friendly options
  • Perissa and Perivolos Beach: Essentially one very long beach that caters to the backpacker crowd and party scene (beach style, not clubs) but still has a wide range of accommodations and restaurants
  • Red Beach: The pebbly sand here is red and the backdrop is stunning
  • Monolithos Beach: The nicest sand and the most family-friendly beach on Santorini. It's quiet, with a small collection of hotels and restaurants.

Another option is to visit some of the other beautiful villages of Santorini, such as Emporio, where locals built their houses extremely close to each other to prevent piracy. 

Once you've wrapped up, catch a ferry over to Crete, the largest and most populous of the 230 inhabited Greek islands.

Day 11: Tour of Knossos & Rethymno, Travel to Chania


After breakfast at your hotel, you'll explore Heraklion and the archaeological site at Knossos before heading to Chania, roughly two hours' drive away. Start by visiting Heraklion's Archaeological Museum, home to one of the largest collections of Minoan artifacts in the world. This is an excellent crash course for the next stop, located just outside of town: the 3,500-year-old Minoan palace of Knossos, a sprawling maze of royal chambers, grand staircases, storerooms, and workshops. This evocative Bronze Age site is believed to be Europe's oldest city, and you'll learn all about its history and mythology with your guide.

You'll then head to the western part of Crete, visiting the aristocratic seaside town of Rethymno—the island’s intellectual and cultural capital. Wander around the town's lively Venetian harbor, check out its 19th-century lighthouse, or take a sunset stroll along the sandy Rethymno beach, before continuing on to Chania for the night.

Day 12: Chania Beach Day & Afternoon Walking Tour

Chania Old Town
Chania Old Town

Spend a free day exploring the beaches around Chania. Some of your options include:

  • Make a full day of it and head to the western shore of Crete to visit Falassarna and Elafonissi, along with deserted coves and quiet bays for a more solitary experience.
  • Stay closer to the city at petite Seitan Limania or on the expansive sands of Kiani.
  • Head south to where the water is warmest and visit Agia Roumeli or Loutro Sfakion, coastal villages only accessible by foot or boat.
  • Take the whole family to Almyrida, with clear, shallow waters and plenty of facilities to fulfill your needs.

In the afternoon, learn about the city's history on a walking tour of the old town. Walk the stone paths where the Venetians, the Ottomans, and older generations of Cretans used to live and work, admiring the flower-decorated neighborhoods. You'll learn about Cretan history, mythology, and traditions as you wander.

Visit the neighborhoods of Topanas, Splantzia, Kolombo, and Kasteli, along with high spots to admire the panoramic view of the harbor. You'll also see the ruins of the great Minoan city of Kydonia and the high walls of former Venetian moats, which are now integrated into the city.

When hunger strikes, visit the Municipal Market of Chania and the neighboring Municipal Garden to enjoy coffee and a later lunch amid the shade of the trees or garden clocktower. Then, top it off with a sunset drink on the rooftop at trendy Pallas.

Day 13: Day Trip to Elafonissi Beach

Ready for a swim?
Ready for a swim?

Spend your day on the pink sands of some of the most beautiful beaches in the world. Head to Elafonissi Beach, 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. 

Elafonissi is set in the southwestern part of the island. It's one of the most beautiful and beloved beaches in Greece, featuring shallow water and a small island so close to the beach that you can walk there from the shore. To top it off, the crystal-clear, turquoise waters in combination with the white-and-coral-hued sand create a landscape of unparalleled beauty. 

Along the way, you'll drive through small, traditional villages and cross the Topolian Gorge before stopping at the cave of Agia Sofia. The cave features incredible stalactites, stalagmites, and a small chapel at its entrance.

Upon arriving in Elafonissi, you're free to relax on the beach and enjoy the lovely scenery surrounding you. On your way back you'll make a stop at the village Elos, where you get the chance to dine at a traditional tavern and try the local Cretan dishes.

After you've sunned and swum to your heart's content, 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 14: Depart Chania

Trot off into the sunset
Trot off into the sunset

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.

Written by Tasos M., updated Feb 18, 2021