Jeff Cooper, owner of Maine-based kayak experts H2Outfitters, has a degree in classical archaeology and a serious affinity for Vernaccia, panzanella, and other Tuscan culinary specialties. The logical extension of his interests is a sea kayaking/cooking/archaeology trip in Tuscany—the first of its kind. The journey begins in the village of Impruneta, where clients apprentice themselves to chef Cristophe Becucci, whose family has owned the Casa Bellavista Inn since World War II. You’ll perfect Tuscan stews, fried rabbit, and bread salad and, in September, take part in the local grape harvest festival (the town’s white Vernaccia wine is world famous) before boarding a ferry to the island of Elba, in the Tuscan Archipelago. The mountainous isle houses red-tile villages and leftover fortifications against the Vikings, Swiss, and Germans. "Coastal Italy has been invaded by everybody—it was a battlefield for centuries," says Cooper. "During World War II the Germans constructed defensive positions made of rebar; Italians created works of art." Those masterpieces—stairways etched into cliffs leading to tiled archways and canons—are visible only from the sea. As you paddle around the island (its clear waters protected by Tuscan Archipelago National Park), the coastline alternates between wide, sandy beaches and hidden harbors tucked into rocky cliffs.

Outfitter: H2Outfitters; h2outfitters.com
Price: $4,550
Length: 10 days
Departs: May, September

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