Santorini & Crete: Two Greek Islands That Stole Our Hearts

Joan and I recently had the pleasure of returning to two of our favorite destinations in Greece--Santorini and Crete. Every visit reminds us why these islands continue to rank among our favorite places in the world.
We traveled from late April through the first 10 days of May, an ideal time to experience Greece before the summer crowds arrive. Early spring in Santorini can bring temperatures in the low 60s, along with strong, chilly winds. Our first couple of days were certainly cooler and windier than we had hoped.
Fortunately, we were staying on the cliffside in Oia, where our suite was sheltered from much of the wind while providing breathtaking views of the caldera. It quickly became our own private oasis—and our hot tub certainly helped make those cooler evenings even more enjoyable.

Why We Love Visiting Santorini in the Early Season
The greatest advantage of visiting Santorini in early May is the absence of the overwhelming summer crowds. Wandering the charming streets of Oia was peaceful and relaxed, and Joan had plenty of time to browse the local boutiques for handmade dresses, scarves, and artisan gifts without feeling rushed.
Each day began with what may have been our favorite experience of the trip—breakfast on our private terrace overlooking the sea and the spectacular caldera as the morning sun warmed the island.

Sunset Dining You'll Never Forget
Watching the sunset in Oia is something every traveler should experience at least once.
During our stay, we enjoyed two unforgettable sunset dinners—one overlooking the caldera from a cliffside restaurant and another down in Ammoudi Bay. While both were exceptional, I would recommend the cliffside restaurants for the panoramic views and much easier access.
If you choose Ammoudi Bay, consider taking a taxi. Walking down is manageable, but the climb back up is long and steep. The scenery is absolutely worth it, though—just keep an eye out for the resident donkeys...and where they've been! 😊

Hidden Gems Around Oia
One of the unexpected highlights of our stay was walking from our hotel to Domaine Sigalas Winery. The trail wound through fields filled with colorful wildflowers, and because it was still early in the season, we had much of it to ourselves.
The vineyard tour, wine tasting, and expertly paired local cuisine made for one of our favorite afternoons on the island.
Another must-do is the famous cliff walk from Oia to Fira. We happened to tackle it on a day with 30 mph winds—not exactly ideal—but it was still one of the most spectacular hikes we've experienced.
It does require good mobility, but the incredible views make every step worthwhile. And after arriving in Fira, I can honestly say that pizza and a cold beer have never tasted so good! 😊

Exploring the Rest of Santorini
Renting a car for a day allowed us to experience a completely different side of Santorini.
Our day included visits to:

• Red Beach
• White Beach
• Black Beach
• The fascinating Akrotiri Archaeological Site
• Lunch in the beautiful village of Megalochori
• A wonderful wine tasting hosted by the owner of Gavalas Winery

Megalochori, in particular, is a hidden gem that deserves a spot on every Santorini itinerary.

Crossing to Crete
From Santorini, we boarded a high-speed ferry to Crete—one of my personal retirement dream destinations.
For this visit, we stayed near Elounda, conveniently located between Elounda and Agios Nikolaos. Having a rental car for our entire stay allowed us the freedom to explore this incredible island at our own pace.

Why Crete Captured Our Hearts
Crete offers an entirely different experience from Santorini.
Here, the journey becomes about discovering authentic villages, meeting welcoming locals, and immersing yourself in everyday Cretan life.
During our stay we were able to:

• Make our own olive oil at a local farm.
• Drive through the breathtaking mountain roads surrounding Kritsa Gorge.
• Cross the island for an unforgettable farm tour and cooking class with Cretan Vibes.
• Visit charming mountain villages.
• Explore the stunning Virgin Mary Kalyviani Convent, which looks like something straight out of a movie.
• Admire the snow-capped mountains that provide a dramatic backdrop to the island.

Every day felt like a new adventure.

Agios Nikolaos – One of Greece's Most Charming Towns
Agios Nikolaos perfectly blends tourism with authentic Cretan culture.
Its picturesque harbor, unique inland lake, waterfront cafés, boutique shopping, and outstanding restaurants make it a destination where you can easily spend several relaxing days simply wandering and soaking in the atmosphere.
Food lovers, in particular, will have no shortage of excellent dining options.
One of our favorite unexpected discoveries was Spiridi Olive Oil Farm. We hadn't planned to stop, but on a whim, we pulled in—and we're so glad we did.
The tour was outstanding, and yes...I even got to play the role of the donkey during the traditional olive oil-making demonstration!

Elounda, Plaka & Spinalonga
The waterfront village of Elounda is another delightful place to explore, but for me, the true stars are the secluded beaches with their unbelievably crystal-clear water. They're the perfect place to relax and simply lose track of time.
Just beyond Elounda lies Spinalonga, the former leper colony that can be reached by boat from Agios Nikolaos, Elounda, or the charming fishing village of Plaka, which is our favorite departure point.
Plaka itself is another picturesque waterfront village filled with excellent restaurants, inviting cafés, and local shops. The mountain road above the village also provided one of the most scenic drives of our trip as we made our way toward Heraklion for our final night in Greece.

Why We Love Crete
Crete is one of those rare destinations where it's easy to move beyond being a tourist and truly feel connected to the local culture.
The island offers:

• Crystal-clear water
• Outstanding food
• Friendly, welcoming people
• Beautiful beaches
• Dramatic mountains
• Traditional villages
• Ancient history
• Incredible driving routes

Because Crete is such a large island, you can experience completely different landscapes and cultures within just a couple of hours of driving.
With excellent ferry connections and air service, it's the perfect addition to a classic Athens, Mykonos, and Santorini itinerary.

Santorini Deserves More Than a Cruise Stop
Many travelers only experience Santorini as a port of call on a cruise.
While that's certainly better than missing it altogether, staying on the island for several nights transforms the experience completely.
You'll enjoy peaceful mornings, magical evenings after the cruise crowds depart, leisurely dinners, hidden villages, wineries, scenic hikes, and countless unforgettable moments that simply aren't possible during a few rushed hours ashore.
And yes—for those looking for those iconic Instagram photos—staying in Oia gives you the time and flexibility to capture those famous views without battling thousands of day visitors.

Our Final Thoughts
One of the greatest joys of travel is slowing down long enough to truly experience a destination.
That's exactly what our Expressly 4U itineraries are designed to do.
Rather than simply checking famous sights off a list, we help our travelers discover the places, people, food, and experiences that create lifelong memories.

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