Cape Cod Multi-Day Sail

Take two or more days to explore New England waters!

Quick Details

Clock Departure Time: 1 p.m.

Location Depart/Return: Provincetown, Cape Cod

Calendar Availability: Late May – Late September

Users Number of Guests:  Up to four

Food Food/Beverage: We provide customized chef-prepared meals and beverages.

Multi-Day Sailing Details

During the summer months, let’s set sail aboard Moment on our two-day classic tour of Cape Cod Bay or take more time to explore further beyond to other New England gems.

For our Cape Cod two-day charters, we can welcome up to four guests within two cabins. We’ll sail to Plymouth and Wellfleet harbors and experience their towns’ history and dining while staying aboard the Moment on anchor. Enjoy chef-prepared breakfasts, lunches, and snacks. If you have any food or beverage requests or limitations, we are happy to accommodate your needs! Linens and bath towels are included. The captain treats you like family as you enjoy the sailing adventure of a lifetime!

Interested in additional New England destinations such as Nantucket, Boston, Martha’s Vineyard, Cuttyhunk, Marblehead, Sandwich, New Bedford, and more? Extend your trip to experience these sought after locales. Contact us for more information.

Considering a sailing charter during the winter? Join us in an international location of your choice for a custom sailing adventure that best suits your group’s desires.

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


  • Chevron down Directions to Dock
  • Provincetown
    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 four guests of all ages for multi-day sails. All children up to and including 12 years old must come supplied with their own life jackets and count as one of the guests. We apologize that Moment is not very handicap-friendly. Sorry, no pets.

  • Chevron down What to Bring
  • Clothes

    You can bring a waterproof jacket in case we get rain or sea spray. Pack a couple of layers like a light long sleeve and a sweater or fleece as some days and evenings can get cool on the water. Don’t forget sunglasses, hats, bathing suits, beach towels, and sunscreen to make your sail more enjoyable. Please bring non-spray/non-bronzer sunscreen to use while on board. Bath towels and linens are provided. We recommend packing your things in duffel bags, not roller-board suitcases, as they are easier to stow and do not bang around as the boat moves.


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

    Food and beverages

    You can create a customized chef-prepared menu with your captain. You are welcome to pack your own favorite beverages (please, no red wine or staining beverages!) You have the option of dining in town or onboard each night.

    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 Multi-Day Destinations
  • If you are taking our two-day classic tour of Cape Cod Bay aboard Moment, we sail to Plymouth and Wellfleet harbors to experience the towns’ dining and history while staying aboard Moment on anchor.

    If you’re interested in exploring other New England destinations such as Nantucket, Boston, Martha’s Vineyard, Cuttyhunk, Marblehead, Sandwich, New Bedford, and more, you can add on more days and destinations by extending your trip! Please email [email protected] to inquire and reserve.

    Day 1
    After boarding the boat at 1 p.m. on the first day of your charter, we get you settled and then discuss the weather forecast. In most cases, we then quickly set sail for Plymouth Harbor (or a previously discussed first destination). The sail is typically four to five hours. We anchor off of Plymouth Harbor unless you would like to request a slip or mooring (at your expense), which is closer to shore. We get you to shore to walk around and have dinner.

    Day 2
    The next day, we review the weather and see if there is time for you to go into town again or if we should depart for Wellfleet Harbor first thing. With good winds, Wellfleet is five to six hours away. This requires us anchoring and taking a dinghy ashore for you to explore this quaint town with some fantastic seafood options. We return to the mooring by noon of the last day and call for the launch to return you to Flyer’s.

  • 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 unfavorable or severe weather, we continue the charter but make sailing decisions on an hour-by-hour basis to make the best of your experience.

  • Chevron down Guest Involvement
  • You are welcome to participate, learn, or simply soak up the sailing and enjoy the Moment. There are some tasks that are helpful to have an extra hand with, and we gladly welcome your support. Otherwise, only in special circumstances may you be asked to assist with the vessel.

  • 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 & Additional Expenses
  • 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!

    The price does not include onboard meals, launch/dockage fees, diesel surcharge exceeding four hours a day, or gratuity.