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Ios-Sikinos Kayak Circumnavigation

Ios-Sikinos Kayak Circumnavigation
Join us as we explore the overlooked islands of the Cyclades! On this adventure, we will circumnavigate Ios and Sikinos, sister islands off the coast of Santorini. Ios has what every Greek island should; unspoiled beaches, turquoise waters, ancient ruins, and crystal blue waters.
Family Owned Inns
8 Days, 7 Nights
Skill Rating
Van Supported
Single Supplement


Guides, ground transportation, support vehicle, lodging, meals per itinerary (B, D), all kayaking equipment, instruction, and entry fee into the archaeological sites.

Not Included

Air to Greece and ferry to Ios, drinks and lunches, personal clothing and accessories, full medical, baggage and trip cancellation insurance, airport taxes and gratuities. Single Supplement: $550.

Upcoming Dates:

June 26 - July 3, 2025
September 2-9, 2025
September 26 - October 3, 2025


Day 1: Your Northwest Passage Guides will meet you on the beautiful island of Ios. As there is no airport on the island, it can be accessed by ferry from various places, but most frequently Santorini. We will meet you at the port and transport you to our hotel outside the village of Chora. After we settle into our accommodations there will be time in the afternoon to explore the village or beach, and possibly get out on the water to conduct our introductory sea kayaking clinic. As evening falls, we will get to know one another and discuss the planned itinerary over sunset drinks and a delicious dinner on the coast. (D) Day 2: After an energizing breakfast, we will hop into our kayaks for our first day out on the water. We begin our circumnavigation of Ios by heading southeast along the coast. As we pass numerous isolated and pristine beaches we will have our choice of where to stop for a picnic lunch and a dip in the Aegean Sea. Our destination for the day is the small fishing village of Manganari, located on the southern point of Ios. We will return to our hotel and regroup later to enjoy a hardy dinner of fresh, local cuisine. (B, D) Day 3: We will round the southern point of Ios and continue up the coast of the island. Along this portion of the coast there are many inlets to explore. We will glide past long stretches of white sand beaches, as well as smaller beaches isolated by rock formations. We will spend the day exploring the best of them, enjoying a picnic lunch along the way. We will end our day of paddling at Agia Theodoti beach, where our van will meet us and transport us back to our inn. As usual, we will spend the evening at leisure, enjoying the Greek culture, food, and hospitality. (B, D) Day 4: Today we launch our kayaks with a renewed enthusiasm, for today is the day we complete our circumnavigation of Ios! We will launch from Agia Theodoti beach, and paddle the remainder of the island. Another sublime day of picnics, secluded beaches, swimming, and paddling awaits us. At the end of our day, we will paddle right into Chora, and celebrate our speedy circumnavigation in the appropriate Ios fashion - on the beach! Dinner is on your own tonight, giving you a choice of the numerous restaurant possibilities in town, as well as a chance to set your own schedule for the evening. (B) Day 5: Heading out from Chora Bay, we will cross the six miles of open water to Sikinos to launch our second island circumnavigation. Once we have reached the eastern tip of Sikinos, we will follow the southern coast of the island to the main port of Alopronia. As this is one of our shortest days, there will surely be time to investigate this quiet and unspoiled island. We will perhaps enjoy a traditional wine tasting at sunset followed with dinner in Alopronia, enjoying the unique pace of life on unspoiled Sikinos. (B, D) Day 6: Today is sure to be a long, but rewarding day. Due to the steep nature of the terrain in this last leg, there are fewer resting points, but strengthened and rejuvenated from the past week, we will endeavor to circle the island! On the north coast of the island, we will stop for a picnic lunch. By the end of the day, we will have completed our circumnavigation of Sikinos, and have become familiar with its remote beauty. Back in the Port of Alopronia a well-earned shower, dinner, and bed awaits us all... (B, D) Day 7: Our last full day, we will return to Ios. Once again paddling the six-mile stretch of open water back to Chora, we will end our week of exploration and kayaking. As this is a shorter day, people will have the option to continue kayaking in the area, stay in town to sight-see and shop, or simply relax on the beach. In the evening we will enjoy our celebratory dinner and reminisce on our favorite memories from our adventure in the Cyclades. (B, D) Day 8: After breakfast, we gather our belongings and bid farewell to this incredible island. We transfer you to the ferry port so that you can make it back to Santorini (Thira) for any connecting flights. (B) * Note: 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. 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.
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