Sailing off Maui is among the better ways to spend a day there. The channel between Maui, Lanai and Molokai is sheltered enough to be pleasant and open enough to be real sailing, and the marine life is genuinely exceptional.
Skippered or bareboat
For most visitors the answer is skippered, and not only for the obvious reason.
Hawaiian waters are demanding. The channels accelerate the trade winds considerably, conditions build through the day, and local knowledge of where it is safe to anchor is not something you acquire from a chart. Many operators will not bareboat charter here at all.
A skippered charter also solves the problem that somebody has to sail the boat rather than look at the water.
If you do want to bareboat, expect to demonstrate real experience and expect a thorough checkout.
What the sailing is like
Trade winds blow reliably, typically freshening through the day. Mornings are calmer, afternoons livelier — which is why most trips leave early.
The leeward side of the island is protected and comfortable. Going round the ends, where the channels funnel the wind, is a different proposition.
What to check before booking
Group size and boat size. A shared charter on a large catamaran is a very different day from six people on a monohull. Neither is wrong; they are not the same product.
What is included. Snorkel gear, food, drinks, and whether there is a head on board. Half-day trips frequently include less than you assume.
Departure time. Morning trips get calmer water and better visibility for snorkelling. Afternoon trips get better sailing and more wind.
Cancellation terms for weather. Trips are cancelled for conditions with some regularity, and you want that to be a refund rather than a credit.
Seasickness
Worth taking seriously — the channels are choppier than the flat water near shore suggests, and a bad day on a small boat is a long one.
Take something before you leave rather than when you start to feel it. Stay on deck, look at the horizon, and eat something beforehand.
Whales
Between roughly December and April the humpbacks are there in numbers, and seeing them from a small boat is the reason a lot of people book.
Operators must keep a legal distance. A boat that offers to get closer than that is telling you something about how it operates.
