Santorini Kayak Circumnavigation

Thira, Santorini

Based on double occupancy. Single supplement applies $975.


8 Days, 7 Nights

8 Days, 7 Nights

Skill Rating
Van Supported

Thira, Santorini

Family Owned Inns


Based on double occupancy. Single supplement applies $975.


Guides, ground transportation, support vehicle, lodging (based on double occupancy, single supplement applies), most meals per itinerary (noted as (B), (L), and (D) below), all kayaking equipment, all instruction, and entry fees into archaeological sites and the National Geological Park of New Kameni (the volcano).
Not Included
Air or ferry to Santorini, lunches, drinks and one dinner, personal clothing and accessories, full medical, baggage and trip cancellation insurance, airport taxes and gratuities. Single Supplement: $975
“This was a fabulous experience. The water, the sea and cliffs are remarkable and beautiful. The route around Santorini and Thirassia was unforgettable.” -Peter C.

The fabled islands of Santorini and Therassia has inspired travelers for thousands of years, and these days is renowned as the most romantic of all the Greek islands. Is it the lost Atlantis? Many believe it is, but there is no doubt that it's super cool.  

On this one-of-a-kind adventure, you'll learn its secret coves, remote volcanic black sand beaches, and undersea hot springs in a way few ever do - by kayak. During the days, we'll paddle the waters, hike the still-active volcano which is the centerpiece of the caldera, and enjoy the dramatic seascapes topped by white towns on top of the cliffs that combine to make Santorini one of the most beautiful locations on earth.

At night, we'll share splendid world-class Greek cuisine, taste the special wines that this dry volcanic terroir produces and even have time to explore shopping opportunities in the towns of Thira and Oia.

These indulgences will pale however to the centerpiece of our adventure - two nights on the little visited island of Thirassia, where we will stay perched high above the sea, overlooking volcanic islets and the quaint port of Korfos.

During this unforgettable trip, we will circumnavigate both the island of Santorini itself and Thirassia, observe the legendary sunsets - and a few sunrises, too, for the early-birds among us - and bask in the vast history of Cycladic civilizations.

Day 1: Our trip officially  begins at 5:00pm at the Sea Sound Hotel with welcome drinks and our first fabulous sunset to inaugurate our first night together. Guests who arrive early in the day may choose to hike the scenic and historic footpath overlooking the caldera from Firostefani to the famous town of Oia. D

Day 2: After a delicious breakfast we will commence our circumnavigation of Santorini beginning at beautiful Caldera Beach on the southwest coast. First we paddle west toward the point of Faros, enjoying a breathtaking caldera view with the cliffs of Santorini on our left and the smaller islands of Thirasia and Nea Kameni on our right. We’ll see the colorful doors of traditional Greek boat houses carved right into the seaside cliff walls. We’ll turn back east along the coast to our cappuccino stop at Pigadia Beach. Our lunch stop is at the historic Akrotiri Beach where we will take some time to visit the ruins of Akrotiri. Our destination for the night is near the southernmost tip of the island of Fira, where our friendly hosts await us in their beautiful villas. After a swim and shower we will visit a fine Santorini winery, perched atop one of the many picturesque cliffs, for wine tasting and one of many caldera sunsets. Afterwards we'll head back to a seaside taverna for dinner. B, D

Day 3: After a hearty breakfast by the pool at our hotel, we’ll take to the sea once again paddling north to the world-famous black volcanic sand beach of Kamares, where we'll enjoy a cappuccino stop before ascending by van to the ancient Roman-era site of Thira. We'll explore this fascinating and well-preserved ruin. Tonight we stay in the outskirts of Oia.   In this famous cliff-dwelling town where we will stay for two nights, you will have the opportunity to have the quintessential Santorini experience: sunset viewing, jewelry and art shopping, fine food and drink. The white-washed houses and blue church domes we’ll see here have been captured in countless travel photos of Santorini. B, D

Day 4: After enjoying breakfast, we will return to the boats to round the northern tip of Santorini. Our destination is charming and energetic Ammoudi Bay, which sits just below our beautiful cliffside hotel in Oia. Walk or ride up to your room for yet another amazing sunset. Tonight you are on your own for dinner and have the opportunity to explore the town, visit the castle, and enjoy the numerous artisan shops and cafes.  B

Day 5: After breakfast we’ll walk down to Ammoudi Bay and begin our day’s journey into the spectacular Santorini caldera. Our first stop is historic Armeni Bay for our morning cappuccino. We’ll admire the intense contrasting colors of the banded cliffs that show the different layers of volcanic materials. The impossibly warm, luminescent sea against the caldera’s sheer cliffs creates an inviting stage for photographs and swimming. We’ll paddle along the interior of the caldera to the Port of Thira for our lunch stop, which provides opportunities for quick shopping and people watching. After lunch we will cross the caldera to the island of Thirassia, a time-capsule of the Greek islands from decades ago. Tonight we stay at the only inn on the island, where our worldly and charming host extends his heartfelt Greek hospitality. From here we can enjoy the glimmering lights of Oia and Thira on the “big” island, and enjoy unique traditional cuisine at a local taverna. B, D

Day 6: We’ll circumnavigate Thirassia and have a picnic lunch along the shore. Tonight our sunset hike takes us to the site of a historic monastery with one of the most spectacular views in the Greek Islands! B, D

Day 7: We’ll say good bye to Thirassia and make our final crossing back to Santorini. On the way, we’ll explore the "new" volcanic islands which have recently arisen in the caldera. The youngest of these, Nea Kameni, or “New Burnt Island” is only 300 years old and is surrounded by hot springs. After a swim in the volcanic springs that empty directly into the sea, we’ll hike to the core of the volcanic crater and have a hearty picnic lunch overlooking the sea. At last, we’ll make our final crossing back to our launching place at Santorini’s Caldera Beach and enjoy a well-deserved celebratory dinner. B, D

Day 8: Breakfast ends our stay on this beautiful and enchanting island. Final partings and transfers to flights or ferries round out our final day. B

This itinerary is subject to change. As with all adventure travel, some activities are dependent on appropriate wind and water conditions. In the case of unfavorable weather, we have other activities available.

“This was a fabulous experience. The water, the sea and cliffs are remarkable and beautiful. The route around Santorini and Thirassia was unforgettable.” -Peter C.

“Excellent trip! Fun meter was spinning the whole time – never expected to come home with my own Greek phone number...!” -Cindy L., Sauk Rapids, Minnesota

"Incredible paddling & a rare insight into Greece that few people see, Thank you! The first thing I will do when I get home, after my laundry, is buy a kayak. I'm hooked and ready to train for the next trip!"- Margo M., Ottawa, Ontario, Canada 

"Rick, Ryan, Elena, You did a wonderful job of rolling with the "windy punches". Without hesitation, I'd recommend you to those who trust me. Warmest regards,"  -Don R., Ottawa, Ontario, Canada

"Great trip! Thanks for the many ways you met our needs and desires to make it so." -Bud M., Golden, Colorado

"Dear friends, Thanks for all your great leadership and for introducing us to this marvelous place. We appreciate your flexibility and helping us be so successful with this adventure! Best,"  -BJ M., Golden, Colorado

"Wendy, Matthew and Rick, So many special memories. Each day brought a newness to the trip experience. Your expertise, humor and excellent flexibility are beyond reproach. Thank you for an excellent trip." -Norby and Harold P., Littleton, Colorado

“Sun, sand, surf, serenity, solace, serendipity and some social sipping with special sea-going souls. A surprising surfeit of super times.” -Michael W., Goderich, Ontario, Canada

“Geological Evolution" – Michael Watts

“Undeniably, irrevocably, irretrievably, definitely, certainly, quite the best kayak trip I’ve ever been on -- just like the other Northwest Passage trips.” -Michael W., Goderich, Ontario, Canada

The dramatic cliffs rising up from the Aegean sea tell a story like no other in the Greek islands.  Santorini is what remains of a volcanic island located in the Aegean Sea, about 120 miles from Greece's mainland. While its ancient name of Thera or Thira came back into use during the 19th Century, Santorini remains its colloquial name, a remnant of the Venetian occupation of many of the Greek islands.

The earliest evidence of habitation on the island of Santorini dates to the Cycladic culture of  the early Bronze Age (3000-2000 BC).  During this time, close ties were made with the Minoan civilization based on the large island of Crete less than a hundred miles away.  The buried ancient city of Akrotiri shows an advanced town blending Cycladic and Minoan features, which may have given rise to the rumors that this island was the home of lost Atlantis.  The ancient inhabitants lived in multilevel buildings with the earliest known plumbing systems that carried both hot and cold water into homes. Santorini is a volcanic island, and so it is most likely that the Minoans utilized the thermal heat for their access to hot water.  Experts still debate when this came to an abrupt end when the sleeping volcano awoke,  erupting so vigorously that much of the island was literally vaporized and a civilization-ending tsunami swept high up into the hills of eastern Crete and wreaking havoc elsewhere in the Aegean. The entombed city reveals a wealthy society with merchant warehouses, textile weaving, and beautiful, hand-painted murals.

After the destruction of the Minoans, the island remained uninhabited for hundreds of years. The Phoenicians, an enterprising maritime trade culture that flourished in the Mediterranean between 1550BC and 300BC, were next to settle on Santorini. Not long after the time of the Phoenicians, during the 9thCentury BC, an ancient tribe of Greeks called the Dorians settled on Santorini, now known as Kalliste, or the "Beautiful Island". The Dorians founded a city called Mesa Vouno. Later taken over by the Romans and rebuilt, the remains of this city, now known as Ancient Thera, can still be visited today. The city was used as a trading and military port, but slowly declined in importance. It remained inhabited until 726 AD, when a small eruption covered the city in a layer of pumice and it was finally given up.

The island was settled and renamed after “Saint Irene” by the Venetians during the 13th Century Crusades and later fell into Ottoman hands. From 1579 until 1821, Santorini remained under the control of the Ottoman Empire. It gained its independence, along with most of the rest of Greece during the Greek War of Independence. In 1830, Santorini was united as a part of Greece under the Treaty of London.

In 1954, a strong earthquake struck Greece and many of the buildings on Santorini were demolished. The present-day buildings date from after the earthquake. The volcano of Santorini is still active and the islands in the center of the caldera emit a small amount of steam. A second active volcano has been recently discovered just outside the crescent of Santorini, and will eventually create a new island offshore.

Today, Santorini's relies primarily on tourism during the summer months. The view over the caldera entices visitors from around the world, and the island is popular for weddings and honeymoons. Its rich volcanic soils and indigenous grapes support a small, but flourishing, wine industry with a number of new wineries opening to the public for tastings. The traditional wine the island produces is called Vinsanto, which in Italian means “holy wine”. The sweet and strong wine is made from the best sun-dried grapes and is then aged in barrels, sometimes for as long as  for twenty to twenty-five years. The result is a sweet, dark amber-orange dessert wine with aromas of citrus and minerals, layered with overtones of nuts, raisins, figs, honey and tea. Other wines include the distinctive dry white wines called Asyrtiko which retain a taste of the volcanic terroir, and  rich local red wines. All of the grapes are grown using a unique low "basket" method of viticulture which makes the most of the sparse moisture the island receives as the volcanic mists condense over the porous soil. The renowned "Santorini Tomato" is grown the same way, along with a small and intensely flavored local fava bean and a special form of cucumber.