The Aeolian Islands are truly a sight to be seen. This UNESCO World Heritage sight is a small cluster of islands located off the Northeastern coast of Sicily. These islands are famous for their spectacular scenery, rich history, pure Mediterranean water, and Italian charm. We invite you to join us on this kayak adventure weaving through the Aeolian Islands and exploring the best of what Italy has to offer.

With world-class kayaking along a dazzling coastline, local cuisine, fascinating culture, warm hospitality and incredibly comfortable climate, it’s easy to see why this award-winning trip has been our most popular year after year.

Join us for an unforgettable plein air retreat infused with optional adventures in the coastal haven of Matala, Crete where ancient caves meet the cerulean sea, and creativity flows as freely as the Mediterranean breeze. Over six inspiring days you'll explore your artistic voice during open air sessions in a variety of captivating environments alongside your plein air host, Kathie Wheeler. Kathie is a lifelong student of painting and loves to share her passion with others. She is a signature member of Oil Painters of America, American Impressionist Society, and American Women Artists. She serves as the the vice chair of the board of the American Impressionist Society and is both a member and the Wisconsin State Ambassador for the Portrait Society of America. (See some of her work in the carousel below.) You'll also have the opportunity to take inspiration from adventure along the wild and vibrant Cretan coastline with Northwest Passage founder, Rick Sweitzer. Engage with the sea as you kayak beneath towering bluffs and into caves. Hike scenic trails amongst the seaside hills, and explore palace ruins of the fascinating ancient Minoans. Discover the magical south coast of Crete as few others can.

Folegandros is a stark contrast from the crowded party scene of Greek Isles like Mykonos. This 8-mile long island with a mere 650 permanent residents is a haven for travelers wishing to experience traditional Greece.

The summit of Kilimanjaro reaches nearly 20,000 feet above the Moshi plains making it the tallest freestanding mountain in the world, the tallest peak on the African continent, and an ideal spot for a panoramic view! Join us on a trek up the most scenic and adventurous - yet little used - Lemosho-Glades route. Instead of rushing for the summit while following a Spartan daily regimen, we prefer to enjoy every minute of our the adventure up this totally unique natural treasure.

Delight your senses with the scenery, hospitality and mouthwatering culinary delights of Crete. Spend 8 days walking from the Highlands of Omalos to the Libyan Sea. You'll explore Minoan ruins, venture into the territory of the native kri-kri (mountain goat), and bask in the warm turquoise waters of the sea.

"Go for it! Great experience, even for beginners. This was one of the best vacations I have ever been on. The guides, Ryan and Chris, were AMAZING! Very helpful in difficult situations and always there for a good laugh. Great guys!" - Ashley D.

Try your hand at rock climbing and kayaking on a weekend camping adventure.

You’ll learn why the Galapagos have been called an open-air zoo, and after each day’s guided adventures, you’ll retire to the most comfortable accommodations the islands have to offer.

Spend eight days climbing on the famous islands of Santorini and Crete. Indulge in their amazing food, warm hospitality, grand vistas, and refreshing beaches. All while climbing in high-walled canyons and on sea side cliffs.