Endeavor Sailing Tours
Between May and October, visitors to Nantucket can get a glimpse of the island as it was meant to be seen: from the water, and under sail. Captain Jim Genthner operates his gleaming 31-foot Friendship sloop—a reproduction of an early 1900’s single-masted craft, built by Genthner himself—out of Straight Wharf in Nantucket Town, and his informative sailing tours of the harbor and Nantucket Sound are one of the best deals to be had on the island. A one-hour morning sail (which departs every day at 11:30) costs just $15 per person; slightly longer afternoon sails (leaving at 1 and 4 p.m.) cost $25; and sunset sails (the most popular) are $35.
Tip: With a little advance time, the Endeavor can be booked for private parties; onboard musical entertainment, kids’ storytellers, and refreshments can all be arranged.