Naxos-Santorini Crossing Elite Kayak Adventure


*Special First year Price Based On Double Occupany. Single Supplement Applies.

6 Days, 5 Nights

Upcoming dates


6 Days, 5 Nights

Skill Rating
Van Supported


Family Owned Inns


*Special First year Price Based On Double Occupany. Single Supplement Applies.

Guides, ground transportation, lodging, meals per itinerary (B, L, D), all kayaking equipment, and instruction.
Not Included
Air or ferry to Naxos, ferry tickets if necessary during the program and from your ending island to your next destination, lunches, drinks and one dinner, personal clothing and accessories, full medical, baggage and trip cancellation insurance, airport taxes and gratuities. Single Supplement: $475.

Looking for a new twist in your Mediterranean travels? We continue our tradition of exploring the gorgeous Greek islands by kayak as we island-hop through the Cycladic islands. Come ready for challenging paddling as we comb the shores of Naxos, weave through the Small Cyclades islands, pause on the shores of Ios and conclude with a demanding day-long open water crossing to what maybe Atlantis itself-the famed island of Santorini. Designed for only the strong, experienced and confident kayaker, we will travel light, carrying all gear in our kayaks as we paddle these beautiful and remote coasts. This trip will include open-sea crossings in variable and unpredictable conditions; applicants subject to approval.

Day 1: Arriving by ferry or plane to Naxos, Northwest Passage guides will meet you at the airport or port. We ask that you arrive before the afternoon. As our time together begins, we will introduce our fleet of kayaks and paddling equipment. Depending on the weather, we will then paddle in the bay. During our first evening together the group will discuss the route and plans for the week, and review weather reports. D

Day 2: We will start off the day by paddling down the western shore of Naxos as we make our way to the first open water crossing of the trip. After our lunch stop we will go over crossing strategy and then begin the five mile stretch of open water. Weather permitting after the crossing, we will circumnavigate the island of Schinoussa before heading to our home for the night on the island of Irakleia B,D

Day 3: From the island of Iraklia we plan to spend the day working our way along the shores and crossing open water to Ios. We’ll then paddle south along the shoreline of Ios to the beautiful beach at Manganari. As we paddle south along Ios’ shoreline we’ll catch our first glimpse of Santorini—the endpoint of our most ambitious open water crossing. B,D

Day 4: Weather permitting, today is the big day! If conditions are favorable, we’ll paddle south through 12 miles of open water to Santorini, and watch the island expand in size and detail as we go. Upon reaching the island, only a short paddle to the protected bay below Oia remains. We stow our boats and walk up the caldera hillside to our spectacular hostel for the night, overlooking the incredible caldera and promising a world class sunset to remember. Dinner is on your own tonight to give you a choice of the numerous restaurant possibilities in town as well as a chance to set you own schedule for the evening.

However, if weather conditions preclude open water paddling, we’ll fill the day with scenic hikes on Ios and paddling practice around Manganari. B, D

Day 5: To celebrate yesterday’s successful crossing; we’ll explore the very cool and usually protected caldera, checkout Santorini’s island neighbors to the west, Nea Kameni and Thirassia, or maybe even go for a partial circumnavigation of Santorini itself. However, if the previous day’s weather didn’t allow for open water paddling, we’ll embark on the audacious crossing today. Regardless of the day’s activities we plan to enjoy a celebratory dinner reflecting on the week’s adventure. B, D

Day 6: After breakfast, we’ll have a few hours to walk the streets of Thira and purchase any last minute keepsakes or gifts. For those interested in one last adventure, consider paddling from our hotel to the other side of the island before heading to the airport. We will then transport you to the Santorini airport** by 11:00am allowing you to make necessary connections. B


Note I : This is our intended itinerary. As with any adventure travel, the forces of nature can be unpredictable, causing us to make adjustments and changes to the itinerary, especially since this elite trip involves extended open-sea crossings. Rest assured that our many years of exploring have provided us with numerous options if changes need to be made. If it is too windy to paddle, various hiking, cultural and historical options will make you glad for the winds.

**Note II: Special attention needs to be paid to travel arrangements. This trip does not begin and end on the same island. Weather delays put your departure location and date at risk. Our office staff is happy to help discuss the ideal travel options to meet your specific needs. Please call or email for additional information.

Trip details: Our planned accommodations for the week may include inns, rent rooms, windmills or deluxe tent camping. Our trip is only partially supported by van and ferry. You should plan to pack your kayak with all of your luggage. As noted above, you will be ending the trip on a different island from where you started.

**This itinerary is subject to change.


Naxos is truly a Greek island of the gods. According to mythology, Zeus, king of all the Greek gods, grew up on Naxos. His mother kept him hidden on Naxos, away from the ferocity of his father, Cronus. The son of Zeus, Dionysus, is also said to have been born and raised on Naxos. Dionysus was the god of wine and feast, and loved the island of Naxos so much that he ensured it would always have fertile lands, full of vineyards know for their excellent wine.

One legend tells the tale of the princess Ariadne of Crete, who after helping Theseus kill the Minotaur and escape from the Labyrinth, was abandoned on Naxos. Dionysus found her on the island, fell in love with the young princess, and took her to Mount Drios where, from there union, Oinopion (Wine Drinker), Staphylos (Grape) and Evanthi (Lovely Flower) were born.

Historically, Naxos was the center of civilization for the Cyclade Islands. Naxos was first inhabited by the Thracians. Their ancient culture thrived on Naxos for two centuries, until the Careans settled on the island, replacing the Thracians. It is from the Carean leader, known simply as Naxos, that the island got its name.

In the 7th Century BC, the Ionians came to Naxos, bringing with them the concept of sea trade. During this period Naxos became wealthy and one of the more developed civilizations in the region.


Santorini is a volcanic island located in the Aegean Sea, about 120 miles from Greece's mainland. While it's ancient Minoan name of Thera came back into use during the 19th Century, Santorini remains as its colloquial name.

The earliest evidence of habitation on the island of Santorini dates back to the Bronze Age (3000-2000 BC) when an impressively advanced civilization, known as the Minoans, flourished. Excavations of the island show that the Minoans lived in multilevel buildings with the earliest know 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. Around 1450 BC, however, a volcanic eruption demolished the Minoan civilization on Santorini. While unable to recover from this disaster, much of our knowledge about the ancient Minoans is due to the city preserved underneath layers of volcanic ash and pumice. 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 the remainder of the Bronze Age. It was hundreds of years before Santorini was occupied once again. 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 9th Century BC, an ancient tribe of Greeks called the Dorians settled on the Santorini. The Dorians founded a city called Mesa Vouno, 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 Franks during the 13th Century Crusades. From 1579 until 1821, Santorini remained under the control of the Ottoman Empire. It gained its independence, along with the rest of Greece during the Greek War of independence. In 1830, Santorini was was united as a part of Greece under the Treaty of London.

Today, Sanotrini's industy relies primarily on tourism during the summer months. Its rich volcanic soils and indigenous grapes, however, support a small, but flourishing, wine industry. The unique and prized 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 ages in barrels 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.