From December into May, whale-watching becomes one of the most popular activities on Maui. During the season, all outfitters offer whale-watching in addition to their regular activities, and most do an excellent job. Boats leave the wharves at Lahaina and Maalaea in search of humpbacks, allowing you to enjoy the awe-inspiring size of these creatures in closer proximity. From November through May, the Pacific Whale Foundation sponsors the Maui Whale Festival, a variety of whale-related events for locals and visitors; check the calendar at www.mauiwhalefestival.org.
As it's almost impossible not to see whales in winter on Maui, you'll want to prioritize: is adventure or comfort your aim? If close encounters with the giants of the deep are your desire, pick a smaller boat that promises sightings. Those who think "green" usually prefer the smaller, quieter vessels that produce the least amount of negative impact to the whales' natural environment. For those wanting to sip mai tais as whales cruise calmly by, stick with a sunset cruise ($40 and up) on a boat with an open bar and pupu (Hawaiian tapas). Afternoon trips are generally rougher because the wind picks up, but some say this is when the most surface action occurs.
Every captain aims to please during whale season, getting as close as legally possible (100 yards). Crew members know when a whale is about to dive (after several waves of its heart-shape tail) but rarely can predict breaches (when the whale hurls itself up and almost entirely out of the water). Prime viewing space (on the upper and lower decks, around the railings) is limited, so boats can feel crowded even when half full. If you don't want to squeeze in beside strangers, opt for a smaller boat with fewer bookings. Don't forget to bring sunscreen, sunglasses, a light long-sleeve cover-up, and a hat you can secure. Winter weather is less predictable and at times can be extreme, especially as the wind picks up. Arrive early to find parking.
Keawakapu Beach. The northern end of Keawakapu Beach on the South Shore seems to be a whale magnet. Situate yourself on the sand or at the nearby restaurant and watch mamas and calves. S. Kihei Rd., near Kilohana Dr., Kihei, HI, 96753.
Papawai Point Lookout. From December 15 to May 1, the Pacific Whale Foundation has naturalists in two places—on the rooftop of its headquarters and at the scenic viewpoint at Papawai Point Lookout. Like the commuting traffic, whales cruise along the pali, or cliff side, of West Maui's Honoapiilani Highway all day long. Make sure to park safely before craning your neck out to see them. Rte. 30, 3 mi west of Maalaea Harbor, Maalaea, HI, 96793.
Gemini Sailing Charters. Morning and afternoon whale-watching trips off the Kaanapali coast are available on this well-maintained catamaran staffed by an experienced and fun crew. The cost is $60 per person for the morning trip and $70 for the afternoon trip. You can find Gemini on Kaanapali Beach near the Westin Maui resort's activity desk. Westin Maui Resort & Spa, 2365 Kaanapali Pkwy., Lahaina, HI, 96761. PHONE: 800/820-7245 or 808/669-0508. www.geminicharters.com..
Pacific Whale Foundation. With a fleet of nine boats, this nonprofit organization pioneered whale-watching back in 1979. The crew (including a certified marine biologist) offers insights into whale behavior and suggests ways for you to help save marine life worldwide. One of the best things about these trips is the underwater hydrophone that allows you to listen to the whales sing. Trips meet at the organization's store, which sells whale paraphernalia. You'll be sharing the boat with about 100 people in stadium-style seating, but once you catch sight of the wildlife up close, you can't help but be thrilled. 612 Front St., Lahaina, HI, 96793. PHONE: 808/249-8811. www.pacificwhale.org.
Trilogy Excursions. Whale-watching trips with Trilogy Excursions consist of smaller groups of about 20 to 36 passengers and include beverages and snacks, an onboard marine naturalist, and hydrophones that detect underwater sound waves. Trips are $39, and you load at West Maui's Kaanapali Beach Hotel. Kaanapali Beach Hotel, 2525 Kaanapali Pkwy., Lahaina, HI, 96761. PHONE: 808/874-5649 or 888/225-6284. www.sailtrilogy.com.