Sailing in Maui

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 all 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 (one that won't blow away), a light jacket or cover-up, sunglasses, and extra sunscreen.

Boats and Charters

America II . This onetime America's Cup contender offers an exciting, intimate alternative to crowded catamarans. For fast action, try a morning trade-wind sail. Plan to bring a change of clothes, because you will get wet. Snack and beverages are provided. No one under five years old is permitted. Lahaina Harbor Slip 6, 96761. 808/667-2195. www.sailingonmaui.com.

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 competent and friendly. Their mooring in Molokini Crater is particularly good, and they often stay after the masses have left. The Lanai trip includes a picnic lunch on the beach, snorkeling, and an afternoon blue-water swim. Extras on their trips to Lanai include mai tais and sodas, hot and cold pupu (Hawaiian tapas), and champagne. A similar spread comes with the sunset sail, which departs from Lahaina Harbor every Monday, Wednesday, and Friday. Lahaina and Maalaea harbors, 96761, 96761. 808/244-2087 or 800/441-2087. www.sailmaui.com.

Scotch Mist Charters. Follow the wind aboard this 50-foot Santa Cruz sailing yacht. Three-hour snorkeling, sunset, or whale-watching trips focus on the sail, and usually carry fewer than 25 passengers. Two-hour sunset sails start at $59.95 and include soft drinks, wine, beer, champagne, and chocolate. Lahaina Harbor, Slip 2, 96761. 808/661-0386. www.scotchmistsailingcharters.com.

Trilogy Excursions. With more than 35 years of sailing tradition and a deep commitment to Hawaiiana and the local ecosystem, Trilogy's reputation is among the best. It is one of only two companies that sail (rather than motor) to Molokini. A two-hour sail starts at $59. Alcohol is not provided on any cruise, but you can bring your choice of libation. Their sunset sail leaves in front of Kaanapali Beach Hotel. Boarding the catamaran right off the shore can be tricky. Timing is everything and getting wet is inevitable, but after that it's smooth sailing. Book online for a 10% discount. Maalaea Harbor, Slip 99, Lahaina Harbor, or by the Kaanapali Beach Hotel, 96761. 808/661-4743 or 888/225-6284. www.sailtrilogy.com.

Private Charters

Hiring a private charter for a sail will cost you more, but it's one way to avoid crowds. Although almost all sailing vessels (including those in this section) offer private charters, a few cater to them specifically. Among the top three, Shangri-La (888/855-9977. www.sailingmaui.com) is the largest and most luxurious 65-foot catamaran. Island Star (888/677-7238. www.islandstarexcursions.com) is a 57-foot Columbia offering customized trips out of Maalaea. Cinderella (808/244-0009. www.maui.net/~sailmaui) is a swift and elegant 50-foot Columbia.