Setting Sail on Cape Cod

Explore wildlife in its natural habitat, or perhaps just sip some bubbly while watching the sun go down.

“Sailing takes me away to where I’ve always heard it could be
Just a dream and the wind to carry me
And soon I will be free.”

—    Christopher Cross


On Cape Cod, Christopher Cross’s words could not ring truer. Whether you’re on a sunset sail with the wind at your back and a glass of champagne in your hand, or you’re exploring the wildlife, the beaches and the lighthouses across this idyllic peninsula, taking a sail is a relaxing, educational and invigorating way to spend the day.

With the Ship’s Knees Inn as your base, you are ideally situated close to day sails that depart from Harwich Port, Provincetown, Wellfleet and Hyannis. You can choose from two- to six-hour tours, while even taking over the tiller while cruising through an estuary, spying on seals or perhaps encountering a whale. Or you can just sit back in gilded luxury.

Cape Sail offers a three-hour cruise that departs from Saquatucket Harbor in Harwich Port on Sabbatical, a rugged Southern Cross sailboat. Day trips normally sail to the National Wildlife Sanctuary at Chatham’s Monomoy Island, where birding enthusiasts will find plenty to see while passing the seven-mile strip of barrier beach. You can personally take part in the sailing or just enjoy the scenery. There is a six-person maximum, but groups up to 12 can charter a second boat and take a tandem sail.

Nearby is Cape Charters & Boat Rentals in Pleasant Bay, where you can board the luxury daysailer, Maria, for a private chartered sunset excursion.

At Outer Cape Sailing in Wellfleet you’ll depart from Wellfleet Harbor and tack upwind toward Jeremy Point on Great Island, where you can stop for a peaceful picnic on a secluded sandbar. This is also a great spot for watching seals as they jump and play in the water. If you’re lucky, you might glimpse a Humpback whale or a Basking Shark, but you won’t have to fret about encountering a Great White Shark, for they stick to the ocean side.

You can also take a romantic sunset sail to Blackfish Creek, which forms an inlet between Lieutenants Island and Indian Neck and can be seen from the South Wellfleet General Store. Tide permitting, you’ll cruise through the Herring River estuary and watch the sun go down over the sand dunes where Great Island connects to Chequessett Neck. On the way home, they’ll even let you drop a fishing line into the water if the wind is low and maybe you’ll catch a bluefish to enjoy for dinner.

Feel like pampering yourself for the day? Moment Sailing Adventures in Provincetown defines elegance. The 47-foot Moment features three staterooms, two heads and a full galley, and will accommodate up to six passengers on a day or evening sail. You’ll be aboard a boat that once circumnavigated the globe and underwent an extensive refit a few years ago. Sails of two, four and six hours will take you around Provincetown Harbor and Cape Cod Bay. The longer sails will venture to Race Point or Wellfleet, where you can dinghy ashore to Long Pond and Herring Cove Beach.

Finally, Catboat Rides of Hyannis will give you spectacular scenery and a history lesson, courtesy of 40-year sailing veteran Marcus Sherman, who regularly regales his visitors with colorful stories while pointing out areas of interest during dazzling sunset cruises and tours to Hyannisport.

Orleans Vacation Guide

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