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Santorini Kayak Circumnavigation

Santorini Kayak Circumnavigation
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 create memories that will last a lifetime.
Family Owned Inns
8 Days, 7 Nights
Skill Rating
Van Supported
Single Supplement


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

Upcoming Dates:

June 10-17, 2024
September 22-29, 2024
June 10-17, 2025
June 18-25, 2025
September 10-17, 2025
September 18-25, 2025


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.
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