Provincetown Day Sails

Choose from a two, four, or six-hour sail!


Quick Facts

Clock Departure times: 8:30 a.m. – 7:30 p.m. Check schedule for departure times.

Location Location: Provincetown, Cape Cod

Calendar Availability: Late May-Late September

Users Number of guests: Up to six.

Food Food/beverages: You are more than welcome to bring your own food and non-staining beverages.

Day Sailing Details

Bring up to six guests aboard the Moment for an unforgettable day of sailing around Provincetown Harbor, and enjoy the beautiful sights of beaches, lighthouses, and wildlife.

Our day sails are perfect for exploring Cape Cod, celebrating a special occasion, or just enjoying a day out with your family and friends. For all of our sailing charters, you are more than welcome to bring your own food and beverages of choice (please, no red wine or staining beverages). Choose from two, four, or six hours on the water and get ready for a perfect day of sailing.

Two-Hour Sail – Our Most Popular Option!

Set sail, tour the harbor, and enjoy the Moment! Get a taste of the sailing life on this brief trip. Our two-hour sailing charter is one of our most popular options.

Four-Hour Sail

Enjoy a half-day of sailing and sunning aboard the Moment! We set sail near Provincetown’s West End and then sail around the Harbor, Long Point, and into Cape Cod Bay. Time and weather permitting, we have the option to anchor off Long Point Beach or Herring Cove Beach and go swimming.

Six-Hour Sail

Spend a glorious six hours sailing, snacking, and sunning. We set sail near Provincetown’s West End and then sail around the Harbor, Long Point, and into Cape Cod Bay. If time and the weather allow, we have the option to anchor off Long Point Beach or Herring Cove Beach for a refreshing swim. Take some extra time to enjoy the surrounding beaches and maybe take a peaceful nap.

Please read our below FAQ section for further specifics about our multi-day sails.


  • Chevron down Directions
  • Depart from Flyer’s Boat Rentals located at 131 Commercial St, Provincetown. Note there is no parking onsite at Flyer’s. View Parking options for Provincetown. Walk to the end of their pier and ask the launch attendant to bring you to Moment’s mooring. The launch is $10 cash each way for the group.

    Note that, on low tides, you may have to get your feet wet in order to get on board the launch, so please dress accordingly.

    Map to dock and harbor in Provincetown, Massachusetts

  • Chevron down Guests & Accessibility
  • Moment can take up to six guests of all ages for day sails. All children up to and including 12 years old must wear a life jacket and count toward the six-person capacity of the boat. We do our best to provide life jackets, but please announce children 12 and under in advance. We apologize that Moment is not very handicap-friendly as all guests must be able to step up the equivalent of a three-step ladder. Sorry, no pets.

  • Chevron down What to Bring
  • Clothes

    You can bring a light waterproof jacket in case we get a sprinkle or sea spray. Some evenings get cool, so an additional sweater or sweatshirt isn’t a bad idea either. Don’t forget sunglasses, hats, bathing suits, beach towels, and non-spray/non-bronzer sunscreen to make your sail more enjoyable. We request that you apply spray sun-screen onshore prior to boarding and not use it while on board.


    We like to keep our white decks white, so the first rule on shoes is no black marking soles. Shoes and sandals with gum soles like Converse and white-soled boat shoes and deck shoes are best. Boots and sneakers, while seeming like they would have good grip, often don’t and mark the decks with their dark soles. You are welcome to go shoe-less as well if you prefer.

    Food and beverages

    We provide water for all sails, and you are welcome to pack a picnic and your own favorite beverages (please, no red wine or staining beverages!). Please otherwise let us know if you would like any special accommodations.

    For fine wine and spirits, we recommend Perry’s. With advanced notice, we can arrange to pick up your purchased beverages and have them chilled and awaiting your arrival.

  • Chevron down Cape Cod Destinations & Activities
  • While each day’s winds and weather dictate the course of our sail, here are some possibilities of how our sail might go:

    After boarding the boat, we set sail and go out around Provincetown Harbor and Long Point for our two-hour sails.

    Four to six-hour sails allow us to go further into Cape Cod Bay to Wood End Light and possibly to Race Point or towards Wellfleet. With time and conditions permitting, we can anchor the boat, swim, or take a dinghy ashore to explore Long Point or Herring Cove Beach. We often see wildlife, including seals, birds, and sometimes dolphins or whales.

    Evening sails enjoy Provincetown’s beautiful golden light and the setting sun. At the end of each sail, we call Flyer’s launch to return you to shore.

  • Chevron down Cancellation Policy & Severe Weather
  • If you contact us and cancel 14 days or more prior to your departure date, you receive a full credit to book another trip within one year or an 85% refund.

    If you give us less than 14 days notice, you receive a 50% refund. If you must cancel less than 48 hours before your trip, there is no refund. No-shows are charged the full price.

    If we have to cancel due to unforeseen circumstances, we do our best to reschedule or give you a full refund. If there is severe weather, we work with you to reschedule.

  • Chevron down Guest Involvement
  • You are welcome to participate, learn, or simply soak up the sailing and enjoy the Moment. Only in special circumstances would you be asked to assist with the vessel while onboard the Moment.

  • Chevron down Motion Sickness
  • It is very normal for guests to not be accustomed to the motion of the boat at sea. Recommendations for preventing sickness include proper rest and hydration, Bonine (take one hour before boarding), ginger gum and chews, motion sickness wristbands, always looking at the horizon, and refraining from discussing the topic at length.

  • Chevron down Gratuity
  • It is customary to tip the captain/crew 15-25% of the cost of the sail when chartering a sailboat. Like any hospitality position, this is a large part of our compensation. Did you have fun? Please show us here!