This active island-hopping itinerary visits two gems in the Aegean Sea—both world-famous for different reasons. You'll start in Crete, largest of the Greek islands and home of ancient Minoan palaces and striking landscapes like canyons, gorges, mountains, and beautiful beaches. You'll then ferry over to the smaller volcanic island of Santorini and have three days to explore its whitewashed cliff-side villages with hiking, swimming, sea kayaking, and, of course, romantic sunsets.


  • Visit the 3,500-year-old palace of Knossos, believed to be Europe's oldest city
  • Stay four nights in Crete's intellectual and cultural capital with a Venetian harbor
  • Take numerous hikes on both islands, including the rim of Santorini's caldera
  • Enjoy plenty of opportunities to swim and snorkel in the cobalt blue Aegean Sea

Brief Itinerary

Day Highlights Overnight
Day 1 Arrival in Heraklion Heraklion
Day 2 Explore Heraklion, Drive to Rethymno Rethymno
Day 3 Hike Ancient Eleutherna Rethymno
Day 4 Hike Aradena Gorge Rethymno
Day 5 Explore Cretan Cuisine & Chania Rethymno
Day 6 Ferry from Crete to Santorini Kamari
Day 7 Akrotiri Archaeological Site & Sea Kayaking Kamari
Day 8 Hike from Pyrgos to Kamari Kamari
Day 9 Depart Santorini  

Day 1: Arrival in Heraklion

Heraklion harbor on the northern coast

Welcome to Greece! Your journey starts in Crete—the largest and most populous of the 230 inhabited Greek islands. Upon arrival at Heraklion International Airport, you will be transferred to your hotel in the city center. The rest of the afternoon is free time to explore Crete's capital, which sits along the northern coast where many of the best-known archaeological sites on the entire island are just steps away. 

Spend the afternoon walking around the old city's medieval streets with architecture representing the island's Venetian past. Highlights include the elegant arches of the Loggia, now in use as the town hall, and the Koules Venetian fortress along the harbor walls.

From here, you can take a break in a traditional café or head to the more modern boutique shops on Daedalou Street. Finish the first day with dinner in a traditional Cretan restaurant.

Overnight: Heraklion

Day 2: Explore Heraklion, Drive to Rethymno

Rethymno's Venetian harbor with nearby beaches

After breakfast at your hotel, you'll start the day by visiting Heraklion's Archaeological Museum with 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.

From here, you'll head toward Heraklion's surrounding vineyards, where locals believe wine has been produced for several centuries. You'll then continue driving west on the island, ending the day in the aristocratic seaside town of Rethymno—the island’s intellectual and cultural capital, and also your base for the remaining days in Crete.

Wander around the town's lively Venetian harbor after dinner. If there's time, check out the town's 19th-century lighthouse or take a sunset stroll along the sandy Rethymno beach. 

Overnight: Rethymno

Day 3: Hike Ancient Eleutherna

Picturesque exteriors in Margarites

After breakfast in Rethymno, you'll take a morning hike through ancient Eleutherna. This Dorian-built settlement lies in the foothills of Psiloritis, the highest mountain of Crete. In fact, the Archaeological Institute of America declared its grave sites one of their top discoveries in 2009, and now you can explore the site for yourself. The hike starts at the ancient Acropolis (not to be confused with the one in Athens), and you'll pass Roman cisterns carved into the side of the hill, the necropolis at Orthi Petra, and a bridge built in the third century BC.

The trail eventually leads to the village of Margarites, known for its pottery. Here you can learn about the traditional techniques from a local potter who derives inspiration for his ceramics from Minoan and Byzantine originals, much like the ones you saw in the museum. 

Return to Rethymno to spend the afternoon exploring its historic quarter, where accents of Venetian and Ottoman influence are still felt. Mosques and churches mingle together creating an enchanting old town that leads into the Venetian harbor.

Overnight: Rethymno

Day 4: Hike Aradena Gorge

A trail along Crete's coast

Get ready for another beautiful hike in Crete! After breakfast, you'll head to the southern slopes of the White Mountains to find one of the most fascinating gorges on the island. Aradena Gorge isn't quite as well-known as fellow island resident the Samaria Gorge, but it's no less impressive and boasts significantly fewer crowds. 

You'll start in the abandoned village of Aradena as you trek past the gorge's high, colorful walls and cliff-dwelling flowers all the way down to the Libyan Sea. Once you've conquered the descent, the sandy beach of Marmara awaits you for sunbathing, swimming, and a well-deserved lunch break. You'll then hike the coastal path toward the quiet seaside village of Loutro. Scope out the rocky views and keep an eye out for the many seabird species that call these remote beaches home.

Overnight: Rethymno

Day 5: Explore Cretan Cuisine & Chania

Learn to cook Cretan cuisine from a local expert

This morning, you'll get to learn about Cretan cuisine from the experts. The local food scene has a special place within its culture, with an identity separating it from other Greek cooking. Try not to eat too much at breakfast, as you'll spend your morning in the village of Vamos seeing food prepared hands-on. You'll participate in a cooking class in an old olive press built in 1846, as you learn all about the fresh ingredients, local herbs and greens, and, of course, essential olive oil of island cooking. 

After you've sampled the spread, you'll drive to the town of Chania, 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 Turkish and Venetian city revolves around its harbor. A guided walking tour will take you through the history of the area, which dates all the way back to the Neolithic era.

Overnight: Rethymno

Day 6: Ferry from Crete to Santorini

Santorini's hiking trail to Oia

After an early breakfast in Crete, you'll return to Heraklion and catch a morning ferry to Santorini. Nothing says "good morning" like watching the sun coming up over the island's iconic cubic architecture. Upon arrival, take note of the island's central caldera—the site of one of the largest volcanic eruptions in history—rising above you. 

Spend some time relaxing on the black sand beaches of Kamari, where you'll spend the night. Later in the day, you'll transfer to the buzzing island capital of Fira where you'll start a hike around the rim of the famous caldera to picturesque Oia, passing white stone houses and stunning views along the way. Linger on Oia's artsy streets until evening for the best sunset views on the island.

Overnight: Kamari

Day 7: Akrotiri Archaeological Site & Sea Kayaking

Take a sea kayaking tour off the south coast

After breakfast in Kamari, you'll visit the prehistoric city at Akrotiri, hidden away at the southern tip of Santorini. These ruins are the site 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. You'll have the morning to explore its streets alongside a local guide who will share its stories.  

In the afternoon, you'll head to the beach for a sea kayaking tour on the lesser-known south side of the island. Get a new perspective on the shores while you paddle past the Red and White beaches, named for their distinctly-colored sands, with plenty of time to stop for swimming and snorkeling in the Aegean's clear water.

Overnight: Kamari

Day 8: Hike from Pyrgos to Kamari

Walk from Pyrgos to Kamari

Today, you'll explore medieval Santorini in the village of Pyrgos, the island's former capital. The Venetian manors and old markets of this well-preserved settlement sit at one of the highest points on the island. You'll take in panoramic views on your hike from Pyrgos to the ruins of ancient Thera. Wind through the ruins of buildings that once housed Doric colonists or Ptolemaic soldiers, seated on the headland between the beaches of Kamari and Perissa.

To end the visit, descend from the mountainside back down toward Kamari, taking in the dramatic cliff views and blue water en route. There will be time to walk around Kamari village or relax on the beach once you've completed your trek.

Late in the evening, you'll wrap up your Greek island adventure in Fira, with a farewell dinner overlooking the island's caldera as the sun goes down.

Overnight: Kamari

Day 9: Depart Santorini

Memorable views to say the least

It's time to say farewell to Greece! Today, you'll savor one more breakfast in Santorini before your transfer to the airport for your flight home.


Map of Crete & Santorini - 9 Days
Map of Crete & Santorini - 9 Days