Maalaea is a fantastic hub for sailing because it offers a prime location with easy access to both the calm waters of Maalaea Bay and the vibrant marine life just offshore. Unlike busier ports, Maalaea Harbor tends to be quieter and less crowded—making it a more relaxed setting for your ocean adventures. We are particularly fond of the Sunset Sail on a Charming Hawaiian Catamaran because it combines intimacy with breathtaking views and personalized service. Plus, the chance to spot whales (Dec-Apr) and enjoy Hawaiian pupu with an open bar makes it a memorable experience. If you’re after a more upscale evening, the Luxury Catamaran Royal Sunset 5-Course Dinner Cruise offers a refined, adult-only setting with gourmet food and top-shelf drinks, perfect for a romantic or special celebration. For those who love snorkeling and wildlife, the Turtles & Tacos Snorkel trip blends underwater exploration, fresh local flavors, and guaranteed turtle sightings.
We’ve put together a list below highlighting the top sailing options in Maalaea, each with its own charm, so you can pick the perfect match for your trip.
1. Maalaea Harbor: Sunset Sail on a Charming Hawaiian Catamaran
For around $129 per person, this Sunset Sail offers a more personal and relaxed way to enjoy Maalaea’s stunning evenings. The tour features a small, charming Hawaiian catamaran that limits groups to just 30-40 passengers, avoiding the overcrowded feeling of larger boats. It’s ideal if you value comfort and space to move around while watching the sun dip behind the islands. The cruise also includes whale watching from December through April—making it a seasonal highlight—and Hawaiian pupu alongside an open bar serving locally brewed beer, seltzers, and Hawaiian cocktails.
What makes this trip stand out is its emphasis on personalized service and a laid-back atmosphere. Unlike the massive boats that can feel like a cattle call, this experience offers a cozy setting with plenty of opportunities to chat with the crew and fellow travelers. The crew’s friendly attitude and the chance for whale sightings make it a solid choice for travelers seeking a genuine, intimate sailing experience. The two-hour cruise is perfect for an evening escape, especially if you prefer a more relaxed pace.
Bottom Line: If you want a small-group, personable sunset cruise with whale watching and a relaxed vibe, this catamaran cruise offers great value and a memorable experience.
2. Maui: Luxury Catamaran Royal Sunset 5-Course Dinner Cruise
At number two, the Luxury Catamaran Royal Sunset 5-Course Dinner Cruise combines the beauty of Maui’s sunset with a gourmet dining experience. Priced at $290 per person, it’s a more indulgent way to enjoy your evening. This cruise includes a beautifully plated five-course dinner prepared by a top chef, paired with an open bar featuring signature wines, premium spirits, and beers. The focus here is on creating a refined, adults-only atmosphere that’s perfect for celebrating or enjoying a romantic night out.
The boat itself is a luxury vessel, with an elegant setting that emphasizes comfort and style. During the cruise, you’ll witness Maui’s famous sunset views while savoring expertly prepared food and drinks. The reviews highlight its “intimate, refined atmosphere,” making it ideal for couples or travelers looking for a sophisticated evening. The only potential downside is the higher price point, which reflects the quality and exclusivity of the experience.
Bottom Line: For travelers seeking a luxurious, dinner-focused cruise with exceptional food and drinks, this Maui sunset cruise offers a memorable, upscale evening.
3. Maui: Turtles & Tacos Snorkel
Priced at $159 per person, the Turtles & Tacos Snorkel trip is perfect if you want to combine underwater adventure with local flavor. This 2.5-hour sail on a luxurious catamaran includes premium snorkel gear, reef-safe sunscreen, and easy ocean access. The highlight is the guaranteed turtle sightings—an exciting highlight for wildlife lovers—and the chance to swim in vibrant coral reefs. After snorkeling, you’ll indulge in fresh, island-inspired tacos served onboard, alongside a premium open bar with specialty margaritas and local craft brews.
This tour is highly rated, even with only one review, which notes the well-organized nature of the snorkel trip and the fun of spotting turtles in their natural habitat. The boat’s amenities include warm freshwater showers and spacious restrooms, making it comfortable for everyone. The combination of wildlife, snorkeling, and tasty food makes it a great choice for active travelers who want a bit of everything in their day on the water.
Bottom Line: If snorkeling with turtles and enjoying fresh tacos sounds appealing, this trip offers a lively, wildlife-focused experience with a laid-back vibe.
$159 per person
How to Choose
When deciding between these sailing options, consider your budget, interests, and the kind of atmosphere you prefer. The Sunset Sail on a Charming Hawaiian Catamaran suits travelers wanting a relaxed, small-group experience with whale watching. If you’re after a romantic or special evening, the Luxury Catamaran Dinner Cruise provides an upscale, gourmet setting. For those who want a mix of underwater adventure and local flavors, the Turtles & Tacos Snorkel combines wildlife viewing with fun, casual dining.
Booking early is especially important for the luxury dinner cruise, which tends to fill up fast, and for seasonal whale watching cruises from December through April. Each offers a different way to experience Maalaea’s waters, so think about what excites you most—whether it’s the intimacy, the luxury, or the wildlife.
Maalaea’s sailing scene offers a wide range of options, from relaxed sunset cruises to gourmet dinners and snorkeling adventures. For a small-group, personalized experience with whale watching, the Sunset Sail on a Charming Hawaiian Catamaran is a fantastic choice. If you’re celebrating a special occasion or want to indulge, the Luxury Maui Catamaran Dinner will not disappoint. And for active explorers eager to see turtles in their natural habitat, the Turtles & Tacos Snorkel offers both fun and relaxation.
Whatever your style, booking early and choosing the right experience will ensure you get the most out of your time on the water in Maalaea. Happy sailing!