Boating in Santorini with Caldera Yachting

Each of the Cycladic islands has its unique attractions: Milos has its otherworldly landscapes, Mykonos has its international nightlife, Paros has its luxe harbor and shopping edge, Naxos has its agriculture and authentic quality, and Santorini… well, it’s Santorini. For many travelers, Santorini is what comes to mind when we speak of the Cycladic islands or the Greek islands generally. Its iconic landscape with colorful buildings cascading down the island’s edge is virtually a universal honeymoon dream locale on an island known for its romantic tilt. But to appreciate Santorini means going beyond the classic postcard-perfect snapshot in Oia (though that’s understandably a draw unto itself). Once upon a time, Santorini was quite literally a volcano. The main island as we know it curves around from Oia to Akrotiri in a narrow crescent shape but then continues on with other islands that make up pieces of the once circular volcanic rim. The center of the volcano is now occupied by the Aegean, going down 3000+ feet. You can – and should – rent an ATV (or car) to explore the island from top to bottom, but boating in Santorini is a must-do for virtually every visitor to the island. A sunset cruise around Santorini was the most recommended thing to do by previous visitors but our itinerary called for a daytime excursion which suited us perfectly. With friends joining us on the island, we ventured out with Caldera Yachting on a private charter to explore Santorini’s coast and neighboring islets. While the sunset cruise gets two thumbs up from past visitors, we found our daytime excursion the perfect fit for us: a way to explore beaches by day, take intermittent dips, have lunch on board, and get a bit more perspective as we worked our way around the island.

Boating in SantoriniBoating in Santorini

The Caldera Yachting team picked us up at our hotel in Oia and transported us to the south of the island where we would start our adventure. While Santorini isn’t a big island, it takes about 30 – 40 minutes to transit from Oia down to Vlychada in the south, possibly longer during Santorini’s peak season. Caldera Yachting has a fleet of catamarans available for daytime excursions, sunset cruises, and even charters for longer experiences (e.g. an island-hopping week in the Cyclades staying on board). After our introduction to the tour and itinerary, we promptly propped ourselves on the front of the boat, comfortably perched to take in the scenery along the way. We visited in September 2020 while COVID-related precautions were still in full effect. For us, that meant masks while getting off and on the boat but we were free to lounge sans masks while exploring by water.

Boating in SantoriniBoating in Santorini

We started our trip venturing by Santorini’s iconic red beach, white beach (reminiscent of Milos’ Kleftiko with the bright white formations), and finally a black sand beach. The island is arguably most famous for its black sand beaches, a product of its volcanic make up, so we stopped to enjoy the views and take a dip. For snorkelers, masks are available on board if you’re so inclined and the water is perfectly clear for those that like to spend time under the water (check out my video to see the snorkeling!). For those like me that prefer a noodle and a bit of time to float and enjoy the scenery, that’s an option, too. Whether you’re on a shared excursion or a private charter, you’ll have options for wine, beer, and soft drinks available throughout the day and the crew was beyond generous with keeping our glasses full.

Boating in Santorini

The roughest patch of the sea is around the outer edge of Santorini as you enter the inside of the caldera. For anyone that worries about getting seasick, the catamarans make for an extra smooth journey that helps mitigate any seasickness issues. Even in choppy waters, we glided through with just a few welcomed splashes that cooled us down during the mid-day sun. Once we entered the inside part of the volcano it was smooth sailing once again.

Boating in SantoriniBoating in Santorini

We ventured first to the thermal baths, an area near the small islets in the center of the caldera. Our skipper explained the history of Santorini and its famous historic volcanic eruption. The islets dotting the sea around Santorini’s main body are pieces of the volcano that broke during the Minoan Eruption. In the center, we pulled up to a small volcanic formation to see the thermal waters. You can jump in if you’re so inclined but the sulfuric water is a bit murky so for anyone in white or light bathing suits, either bring a dark-colored backup or refrain from jumping in if you don’t feel like getting stained. Thermal springs are probably expected in the center of a volcano where there’s still some regular activity under the sea. More interesting perhaps is the small home perched on the volcanic islet, where a population of ONE resides. The story has become part of modern-day Santorini’s lore: a middle-aged man has resided on the island for 25+ years, now a hermit who calls this spit of land home after heartbreak left him wanting isolation. (The cruel irony of course is that many boats plop down right in front of his house each day on summer excursions.)

Continuing around by water with Oia in the distance, we approached Thirasia. After the volcanic eruption (about 1500BC), Santorini split into seven pieces, and while we’re most familiar with the main crescent-shaped hub, a second island, Thirasia, sits across from Oia and is home to a small population of its own. With about 150 residents there are some basic facilities, accommodation options on the island for anyone wanting total seclusion, and boats that transit for residents from Thirasia to Santorini.

It was here that we pulled up our boat for lunch with views of Thirasia and Oia for a picture-perfect stop. How the crew managed to whip up a mega-meal on board still blows my mind but sure enough, we were seated around the outdoor table with a family-style presentation of salads, freshly grilled meats, seafood, rice, and dips. It was arguably our favorite meal in Santorini, a traditional Greek offering with traditional flavors paired with local vino.

Boating in Santorini
Lunch on board. 🥗

Our final stretch took us into Ammoudi Bay, just a few minutes’ drive from Oia, per our request. Your charter is flexible but with a few time constraints on our end, we chose to end closer to our hotel to limit our drive time home. And while we based ourselves in Oia, walking the town streets each night for dinners and shopping, seeing it by water gave us an entirely different perspective as we approached the shoreline.

Santorini is an interesting phenomenon. For Americans, it’s probably the best-known Greek island, which has become both a blessing and a curse for the island. Tourism has brought wealth and opportunities but the 2 million visitors that come to the island each year also color most people’s experiences. Many people we spoke with talked about their memories of a crowded island, overrun in the summer months. As we pulled into Oia and sailed along the iconic coastline, it was hard to not understand what’s made Santorini such a draw for visitors though. It’s uniquely beautiful in the Cyclades with its shape, its cascading architecture, and its history. We felt incredibly lucky to be visiting during a year with minimal tourism, walking the streets virtually by ourselves as we’d come home from dinners in the evenings. But if you’re visiting Santorini during busy months and busy years where crowds seem to descend on the island, boating is a beautiful reprieve from the masses. On the water, whether it’s daytime or sunset, there’s peace and freedom while you get the iconic vistas sans crowds. And while I 100% think everyone should explore by car or ATV, there’s a lot of Santorini’s landscape that simply must be seen by water to really appreciate the island and its history.

Boating in SantoriniBoating in Santorini

If you’re traveling in a group (6+ people), look at a private charter with Caldera Yachting if you can swing it. For couples who want company (or don’t want to splurge on the private charter), look at options for shared experiences. Whether daytime or nighttime, private or shared, I’m echoing everyone else’s recommendation: boating in Santorini is a must for your to-do list.

Have you been boating in Santorini? Would you recommend daytime or nighttime for an outing?

Shannon Kircher, The Wanderlust Effect

More about Shannon Kircher

Shannon Kircher is the founder and editor of The Wanderlust Effect. Founded in 2009, she has continued to document her international escapes as an expat in Europe and the Caribbean. Additionally, Shannon is the founder of Compass & Vine, a luxury boutique travel design firm, and is the Director of Marketing for the Frangipani Beach Resort. Shannon holds an MSc in Social Policy and Development from the London School of Economics and is a current candidate for WSET Level 3 in Wines & Spirits.