• Part 1: Planning & Pre-Cruise Athens - September 28-October 1, 2022
• Part 2: Embarking Norwegian Jade, Ephesus & Patmos - October 2-3, 2022
• Part 3: Rhodes & Mykonos - October 4-5, 2022
• Part 4: Argostoli & Corfu - October 6-7, 2022
• Part 5: Santorini & Disembarkation - October 8-9, 2022
• Part 6: Prague: Arrival, The Augustine & Old Town - October 9-10, 2022
• Part 7: Prague Castle, Cold War History, & Musical Evenings - October 11-14, 2022
• Part 8: Barcelona: From the Vltava to the Mediterranean - October 14-15, 2022
• Part 9: Embarking Valiant Lady, Ibiza & Day at Sea - October 16-18, 2022
• Part 10: Virgin Voyages: Malaga Heights & Madeira Green - October 19-21, 2022
• Part 11: Virgin Voyages: Crossing the Atlantic & Miami Arrival - October 22-30, 2022 (Coming Soon)

Santorini: The Jewel of the Aegean

Waking Up in the Caldera

Our penultimate day brought us to the most recognizable stop of the cruise: Santorini. As the ship maneuvered into the massive volcanic caldera, the sight of the whitewashed villages clinging to the dark, jagged cliffs offered a striking contrast. The scale of the caldera is notable when viewed from the water, a quiet reminder of the island’s violent volcanic history.

We prepared for a day of exploring the island, starting with the logistics of getting from the pier up to the clifftops.

The Climb to Fira

Around midday, the Norwegian Jade anchored in the blue waters off the coast of Santorini, directly across from the capital, Fira. Seeing the town perched precariously atop the caldera rim is a classic sight, with the white buildings appearing almost like a dusting of snow on the dark volcanic rock.

Because there is no deep-water pier, we had to take a tender to reach the small harbor at the base of the cliffs. Once on shore, you are faced with a choice to reach the town: pay for the cable car, navigate the steep switchback path on foot, or hire a mule to carry you up.

Having read that the animals are often poorly cared for, we opted to skip the mules as well as the long queue for the cable car. Instead, we decided to make a hike of it. The climb was notably steep and the Aegean sun was unforgiving. There were moments where the exertion made me almost regret the decision, but reaching the summit provided a great sense of accomplishment and some excellent exercise.

A Serendipitous Ride to Oia

Our plan for the day was to take a bus to the northern village of Oia and then hike back to Fira along the caldera rim trail. We found the bus stop, but the schedule was confusing and it was unclear when the next one would arrive.

While we were waiting, a local driver pulled up and asked where we were headed. He claimed the bus wouldn’t be coming and offered to take us to Oia for 30 euro—a slight discount from his usual rate, as his original passengers had failed to show. We decided not to risk the wait and got in the car.

During the drive, the rim trail occasionally paralleled the main road, and our driver laughed as he pointed out the hikers, calling them “crazy” for walking in the heat. We just smiled, not revealing that we intended to be those “crazy” people in just a few hours. As we neared Oia, a massive traffic jam had stalled the narrow two-lane road. The driver had to let us out on the outskirts, as the center of town was completely gridlocked.

The Whitewashed Charm of Oia

Oia is the Santorini of the postcards, famous for its labyrinth of whitewashed buildings and iconic blue-domed churches. The view as you enter the village is undeniable, with the bright structures tumbling down the cliffside toward the sea.

Finding the perfect vantage point for photos was a bit of a challenge, as many of the best paths are actually private entrances to luxury villas and hotels. However, we were still able to capture some of the classic blue dome vistas that make the island so famous.

The narrow walkways were filled with a bustling mix of sightseers and shoppers. The storefronts offered local art, clothing, and the ubiquitous Blue Eye souvenirs we’d seen throughout the islands.

The Rim Trail: Oia to Fira

Before the trip, I had read several reviews of the famous rim trail suggesting that hiking from Oia to Fira was the better choice. Even though this direction is technically uphill, it allowed us to see Oia earlier in the day when it was slightly less crowded. More importantly, it put us in control of our own timing to get back to the ship. After witnessing the gridlock on the main road, we didn’t want to risk being stuck in Oia hoping for a bus or taxi that might never arrive.

Kaleb used the AllTrails app to locate the trailhead within the village, and we set off toward Fira. The hike was estimated to take anywhere from three to five hours depending on pace and how often we stopped for photos.

The initial stretch led us past some of Santorini’s most beautiful whitewashed villas. Seeing the private infinity pools overlooking the Aegean Sea was quite the view as we left the village behind.

Along the Cliffside

Eventually, the residential paths gave way to more rugged terrain along the cliff edge. The uphill portions proved to be a bit challenging, particularly with the afternoon sun reflecting off the volcanic rock, but the perspective of the caldera changed with every bend in the trail.

At one point, we came across a small refreshment stand. It was a simple setup, but finding a cold drink in the middle of that heat was most welcomed.

A Quiet Supper

By around 4:00 PM, we were hungry and decided to stop at a restaurant called Steki Tou Nikou located just below the trail. We were the only patrons in the place at that hour, which made for a very relaxing experience. Despite the lack of a crowd, the food was excellent—exactly the kind of fuel we needed to finish the trek.

As a kind gesture, the owner even brought us some complimentary ice cream bars for dessert. It was a small detail, but a perfect end to our mid-hike meal.

The Golden Hour on the Rim Trail

As we continued our trek, the sun began its descent toward the horizon. The low angle of the light completely changed the landscape, illuminating the volcanic cliffs and the Aegean Sea in a quiet, almost mystic light.

Returning to Fira

Eventually, the rugged, dusty terrain of the rim trail gave way to paved paths as we reached the outskirts of Fira. The transition back into the village was marked by the reappearance of the iconic whitewashed architecture, which seemed to glow against the darkening sky.

This final stretch offered numerous photo opportunities. The blue and white color palette is a sight that never quite gets old, no matter how many times you see it.

Passing Skaros Rock

Along the way, we passed the turnoff for the side trail leading to Skaros Rock. This prominent headland was once the site of a medieval fortress and the island’s capital. It looked like a fascinating place to explore, but with the light fading and the need to get back to Fira to catch a tender, we didn’t have the time to make the detour.

Navigating the Fira Alleys

As we drew closer to the center of Fira, the maze of walkways became more complex. Much of the cliffside is carved into private terraces, but we managed to find a few side alleys and stairwells not marked “Private.” These offered some of the best perspectives of the town’s tiered architecture without intruding on the local villas.

We successfully made it into the heart of town just before the sun dipped below the horizon. Looking out from the balcony of the caldera, we could see the Norwegian Jade resting at anchor below.

The Descent and the Departure

With the light fading, we began our journey back down to the water. We chose to walk the switchback path again; as expected, the descent was much easier on the legs than the climb had been earlier in the day. By the time we reached the tender pier, we joined a considerable queue of passengers waiting to return to the ship.

While the wait was long, it gave us a chance to look back up at the cliffs. Fira lit up at night is quite striking, with thousands of lights shimmering along the dark volcanic rim like a gemstone necklace. It was a fitting final image of Santorini as we boarded our tender and headed back to the Jade for our last night on board.

A Quiet Final Night

We didn’t have anything elaborate planned for our last evening on the ship. Between the long hike from Oia and the need to get our luggage sorted, we spent the night packing and reflecting on the week. It was a low-key end to a very busy itinerary, allowing us to rest before the next leg of our journey.

Returning to Piraeus

A Familiar Face at the Pier

The following morning, the Norwegian Jade returned to the port of Piraeus, bringing our Greek Isles loop to a close. Disembarkation was quicker than embarkation the week prior, and we were off the ship and through the terminal in no time.

For our ride to the airport, we had booked through Welcome Pickups again, and in a pleasant stroke of luck, Theo was there—the same driver throughout our time in Greece. He was genuinely happy to see us again, and we spent the ride catching him up on our favorite stops. While tipping isn’t strictly required in Greece, we insisted Theo take ten euros for a coffee as a thank you for his careful driving and friendly personality.

Reflecting on Norwegian Jade

Looking back on the week, the Norwegian Jade served us well. While she is an older vessel in the NCL fleet, the age of the ship was never an issue for us. Because our itinerary was so port-intensive with no days at sea, we primarily used the ship as a floating hotel.

We were quite pleased with the meals onboard and the overall value of the trip. Between the post-pandemic air/cruise deal and the various AMEX offers we utilized on our credit cards, the final cost was very reasonable for the experience we had.

Final Thoughts on the Greek Isles

A cruise is an excellent way to see a variety of islands in a short amount of time. That said, the brief port stays in places like Argostoli and Santorini definitely left us wanting more. The views and the coastal atmosphere of those islands specifically are enough to make us consider a longer, land-based stay in the future. I curiously looked up prices for the cute little hotel we passed along the way to Fira (Afroessa) and it was decently affordable!

For now, however, our time in Greece has come to an end. We are traded the Aegean blue for the gothic spires of the Czech Republic. We’re heading to the airport for our flight to Prague, where we’ll be staying five nights at The Augustine.

Stay tuned for our adventures in the “City of a Hundred Spires!”