How do I schedule a sail?

The Endeavor and its Captain are very traditional, and so is our reservation process. We like to take the time to talk with our guests and design the best experience for them – a chance to connect and start a conversation. Give us a call at (508) 228-5585 or stop by our Slip #1015 on Straight Wharf, directly across from the Hyline ticket office. You can also drop us a line to get started. We require payment in full with a credit card or cash when you make the reservation. The fare is fully refundable with a 30-day notice or if it is raining at the time of departure. We can't wait to plan your adventure!

What types of trips do you offer?

Our most popular option is a private charter. We are Coast Guard certified to carry 14 passengers. Please be certain to count everyone in your party, including infants.

The 1 ½-hour sail is perfect for most groups, but we do have a 3-hour option as well. We sail at 10am, 11:45am, 1:30pm, 3:30pm, 5:15pm and sunset (time varies).

You can choose to join others with our per-person fare. This is a great way to meet new people and share the Endeavor experience. Trips depart at 10am, 1:30pm, 3:30pm, and sunset (time varies). Give us a call or contact us to check on availability for a specific date and time.

Where do we sail?

The simple answer is: wherever the wind takes us! The prevailing wind is southwest during the season, which takes us past Brant Point lighthouse, through the jetties, and into Nantucket Sound. The deck of the Endeavor is a terrific vantage point to see the boats in the Boat Basin and mooring field as well as the homes and beaches along the waterfront. A variety of birds can be seen on the rock jetties and in the shoulder season we can be lucky enough to see some seals. If the winds allow, we can sail up the head of the harbor along the Coatue Wildlife Refuge.

What do I wear to meet Captain Jim?

The weather can vary greatly on the island from day to day or even hour to hour. It's best to dress in layers, even in the summer. You can always store your extra gear down below if you don't need it. Step outside your house or hotel and however you might dress for that day – add a layer. It's always cooler on the water! Comfortable shoes, a hat, sunscreen, and a windbreaker for that splash over the bow, and you are set to sail.

What if we get hungry or thirsty?

You are welcome to bring aboard food and beverages. We suggest a simple picnic lunch, snacks, or charcuterie. You may pack and bring your own cooler or we have a cooler with ice onboard, as well as openers and paper cups. If you prefer, we can suggest places to pick up food on your way to the wharf or have it delivered to the Endeavor in time for your sail.

Where do we get on board, and what do I do with the car I shouldn't have brought?

We have occupied the same Slip #1015 on Straight Wharf in the center of downtown since 1982. Walk down Main Street and onto Straight Wharf. We are on the right side directly across from the Hyline ferry ticket office. Parking is extremely limited. If possible, plan to walk, bike, take a cab, or the NRTA shuttle to the wharf. If you do bring a car, take advantage of the valet parking located at 5 Candle Street, directly across from the Lobster Trap Restaurant. If you must drive, plan on coming into town at least 1 hour prior to your sail.

Are there restrooms available?

We strongly urge you to arrive at the wharf 30 minutes prior to your sail to leave time to use the public restrooms at the end of Straight Wharf. There is a head on board the Endeavor for emergency use only. It is smaller than you can imagine and not an easy maneuver while under sail.

Should we bring Jr. and Gramma?

There are no age limitations on the Endeavor! We welcome the young and young at heart. Some of our favorite trips are grandparents sharing the wonder of a sail with their grandchildren. Private charters are a great choice for multigenerational trips. For the youngest sailors, sometimes morning is a good choice when they are ready for the day and not worn out from a day at the beach.

Can I bring my four-legged friend?

Captain Jim has a golden retriever, Tucker, and loves four-legged sailors. We do require that you choose the private charter option if you would like to share the experience with your pup.

I've changed my mind or my app says it's going to rain a week from Tuesday. What now?

There is a high demand to secure a reservation on the Endeavor so in order to be fair to everyone trying to make a reservation, we adhere to a firm cancellation policy. When making a reservation, you pay in full for your trip. The fare is fully refundable only with a 30-day notice or if it is raining at the time of departure. The weather on the island is predictably unpredictable, so we do not cancel for a forecast of rain. There are no refunds or credits outside of our policy and the reservations are not changeable.

Should we tip the crew?

If you’ve had a great sail, gratuities are always appreciated by the crew.