Sailing
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.
Boats and Charters
Paragon Sailing Charters. 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 shipshape, 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 at 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 through Saturday. Sunset sail starts at $75, snorkel at $125. Maalaea Harbor, Maalaea, Hawaii, 96793. 808/419-3422; www.sailmaui.com.
Scotch Mist Charters. Follow the wind aboard this 50-foot Santa Cruz sailing yacht. The four-hour snorkeling excursion, and two-hour whale-watching and sunset sail trips usually carry fewer than 18 passengers. Two-hour sunset sails are $70 and include soft drinks, wine, beer, champagne, and chocolate. Lahaina Harbor, Slip 2, Lahaina, Hawaii, 96761. 808/661–0386; www.scotchmistsailingcharters.com.
Trilogy Excursions. With more than four decades 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 $60. The sunset trip includes appetizers, beer, wine, champagne, margaritas, and mai tais. Tours depart from Lahaina Harbor; Maalaea Harbor; and, in West Maui, in front of the Kaanapali Beach Hotel. Lahaina Harbor, 675 Wharf St. , Lahaina, Hawaii, 96761. 808/874–5649; 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 offer private charters, a few cater to them specifically.
Cinderella Sailing Charters. This swift and elegant 51-foot Peterson costs $400 per hour for regular charter of up to six people and includes beverages and light appetizers (two-hour minimum), while a snorkel sail with lunch is $1,900 for the day, roughly five hours. Sunset sails run at $800 for two hours. Discounts available for multiple trips booked. Maalaea Harbor, 101 Maalaea Rd. , Slip 41, Hawaii. 808/344--3906; www.cinderellasailing.com.
Island Star. This 60-foot Columbia offers customized trips out of Maalaea. It's equipped with a galley for onboard food preparation and a master stateroom with a king-size bed. The rate is $700 per hour with a minimum of two hours. Maalaea Harbor, Slip 42, Maalaea, Hawaii, 96753. 808/669--7827; www.islandstarmaui.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 20 or less. A chef and premium alcohol are available for additional fees. Kaanapali Beach, Lahaina, Hawaii, 96761. 808/665–0077; www.sailingmaui.com.
