With the islands of Molokai, Lanai, Kahoolawe, and Molokini a stone's throw away, Maui waters offer visually arresting backdrops for sailing adventures. Sailing conditions can be fickle, so some operations throw in snorkeling or whale-watching, and others offer sunset cruises. Winds are consistent in summer but variable in winter, and afternoons are generally windier throughout the year. Prices range from around $40 for two-hour trips to $80 for half-day excursions. You won't be sheltered from the elements on the trim racing boats, so be sure to bring a hat that won't blow away, a light jacket, sunglasses, and sunscreen.
Paragon. If you want to snorkel and sail, this is your boat. Many snorkel cruises claim to sail but actually motor most of the way; Paragon is an exception. Both Paragon vessels (one catamaran in Lahaina, the other in Maalaea) are ship-shape, and crews are accommodating and friendly. Its mooring in Molokini Crater is particularly good, and tours will often stay after the masses have left. The Lanai trip includes a picnic lunch on Manele Bay, snorkeling, and a quick afternoon blue-water swim. Extras on the trips to Lanai include mai tais, sodas, dessert, and champagne. Hot and cold appetizers come with the sunset sail, which departs from Lahaina Harbor every Monday, Wednesday, and Friday. Maalaea Harbor, Maalaea, HI, 96793. 808/244–2087 or 800/441–2087. www.sailmaui.com.
Scotch Mist Charters. Follow the wind aboard this 50-foot Santa Cruz sailing yacht. The sunset sail, four-hour snorkeling excursion, and two-hour whale-watching trips usually carry fewer than 18 passengers. Two-hour sunset sails start at $59.95 and include soft drinks, wine, beer, champagne, and chocolate-covered macadamia nuts. Lahaina Harbor, Slip 2, Lahaina, HI, 96761. 808/661–0386. www.scotchmistsailingcharters.com.
Trilogy Excursions. With more than 40 years of experience and some good karma from their reef-cleaning campaigns, Trilogy has a great reputation in the community. It's one of only two companies that sail, rather than motor, to Molokini Crater. A two-hour sail starts at $69. The sunset trip includes appetizers, beer, wine, champagne, margaritas, and mai tais. Boarding the catamaran from shore can be tricky—timing is everything and getting wet is inevitable, but after that it's smooth sailing. Tours depart from Lahaina Harbor; Maalaea Harbor; and, in West Maui, in front of the Kaanapali Beach Hotel. 207 Kuopohi St., Lahaina, HI, 96761. 808/874–5649 or 888/225–6284. www.sailtrilogy.com.
Hiring a private charter for a sail will cost you more, but it's one way to avoid crowds. Although almost all sailing vessels offer private charters, a few cater to them specifically.
Cinderella. This swift and elegant 51-foot Peterson costs $400 per hour for regular charter and includes beverages and light appetizers (two-hour minimum), while a snorkel sail with lunch is $1,800 per hour. Sunset sails run at an hourly rate of $800. The yacht takes up to six passengers. HI. 808/244–0009. www.cinderellasailing.com.
Island Star. This 57-foot Columbia offers customized trips out of Maalaea. It's equipped with a galley for on-board food preparation and a master stateroom with a king-size bed. The rate is $600 per hour with a minimum of two hours. Maalaea Harbor, Slip 42, Lahaina, HI, 96767. 888/677–7238. www.islandstarexcursions.com.
Shangri-La. A 65-foot catamaran, Shangri-La is the largest and most luxurious boat catering to private charters. This gorgeous yacht can accommodate up to 49 guests, with a starting hourly rate of $1,533 for a group of 24 or less. A chef and premium alcohol are available for additional fees. Lahaina, HI, 96761. 888/855–9977. www.sailingmaui.com.