Cape Cod Sailing Charters & Tours

Cape Cod Sailing Charters Have Historic Origins

From the first Viking and European explorers to schooners setting out to fish Georges Bank, the whaling ships of Nantucket, and the Pilgrims landfall on the Cape on a crisp autumn day, sailing has been integral to the growth and development of the Cape region. (Nathaniel Philbrick notes in Mayflower that after a nasty encounter with Pollock Rip south of Chatham, the Pilgrims gave up their Hudson River destination, turning to sail back up the Backside of the Cape to land in Provincetown.)

 Cape Cod Sailing Charters

For hundreds of years, sailors and mariners have used the sea breeze to propel them through the blue-green waters around Cape Cod and the Islands, first out of necessity, and then for pleasure. Visitors to the area have a wealth of choices for sailing Cape Cod boat charters, from historic schooners to smaller boats, and from day sails around the harbor to multi-day trips. Many friendly and seasoned captains are ready to get you out on the water!

Scenic Cape Cod Sailing Charters

Leave the crowds behind and experience the peace and freedom of sailing past dunes, lighthouses, and beaches. Lots of Cape Cod sailing charters also offer sunset tours where guests enjoy spectacular colors and epic sunsets while sharing a drink with friends aboard a gently rocking vessel.

From classic schooners like the Bay Lady II and Liberte, in Provincetown, to small sailboat tours like those offered by Outer Cape Sailing in Wellfleet and many in between, there’s a boat for every group’s needs.

If you’re looking to celebrate a big event like a wedding or family birthday with guests of all ages you may want to opt for a larger, steadier vessel with more space to spread out. Some Cape Cod sailing charters offer multi-course meals and beverages, others offer cheese plates or charcuterie boards, and still others allow you to bring your own coolers with food and beverages.

Adventurous Cape Cod Sailing Charters

Those looking to get out on the water for a more adventurous sail may enjoy cutting along the waves at a good clip in a smaller boat. A smaller boat charter is perfect for those looking for a cozy outing, and not minding the possibility of sea spray from a good heel or tack! Some of the small boat charters take visitors to secluded beaches that would be hard to reach otherwise. Bring a picnic lunch, a cooler of drinks, and a camera. Wildlife abounds, with birds, seals, and maybe even whale sightings!

Whether it’s a day sail, a tour of the harbor, a sunset cruise, or a multi-day trip, sailing boat charters are a wonderful way to enjoy the rich maritime history the Cape and the Islands offer. Sailing boat charters offer visitors a chance to get back to the Age of Sail, touring harbors, bays, coastlines, and the open waters  propelled by a steady wind, without the loud drone of an engine. Learn from experienced captains who have sailed these waters for years, enjoy friendly crews, and relax on the water. You won’t regret the time spent soaking in the sun and sea!