Book as soon as the hotel is confirmed
For these weeks, treat the cart like the room: Christmas–New Year, late January through March, Easter, and the first two weeks of July (Lobster Fest). 6-seaters go first. If you are a family of five landing on a Saturday in February, do not wait until the water taxi.
Shoulder and rainy months
May, early June, and late August are mixed. September and October are the softest — you can often book a few days out and negotiate a little. You can also get rained off the Secret Beach road. A cart is still useful for groceries and restaurants; it is less useful as a sunshine guarantee.
Arrival-day walk-ups
They work in quiet weeks if you are flexible on size and pickup hour. They fail when three flights dump families at the airstrip at once. If your personality is “we’ll figure it out,” still send us the dates. A no-obligation check is cheaper than a day of taxis.
How long to rent
If you need the cart more than three days, take the weekly. Extending day by day almost always costs more and risks losing the cart to the next arrival. Pickup timing tips live in airstrip vs water taxi.