Maui
Sunset Tours

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Our most recommended Maui Sunset Tours

From Lahaina: Sunset Dinner Cruise with Live Music

1. From Lahaina: Sunset Dinner Cruise with Live Music

Departing from Pier One in Lahaina Harbor, enjoy a relaxing sunset cruise with a delicious three course meal, listen to island-style music, and watch the sun go down while cruising the waves on a state-of-the-art catamaran. Once aboard you will be seated by our crew to tables assigned based on the size of your party. Once you’ve settled in, our table side service will begin, and the crew will bring you warm breadsticks and water. Your dinner cruise includes two free drinks, once the catamaran has motored out of the harbor, we will take your drink order. We typically serve local beers from Maui Brewing Company, Cabernet and Chardonnay wine, cocktails such as Mai-Tai's, Pina Colada's, Margarita's, Tequila Sunrise, etc., soda, juice, and water. Your meal begins with a crisp Caesar salad, homemade buttery croutons, shredded parmesan cheese, and warm breadsticks. For the main course, your options are rosemary garlic roasted prime rib, fresh Mahi-Mahi with lemon buttery caper sauce, or penne pasta with fresh Thai basil marinara sauce. On the side, enjoy freshly sourced vegetables sautéed and steamed white rice with shoyu sauce. For dessert delight in homemade double layer chocolate cake or New York-style cheesecake. Relax as the sun sets behind the distant Maui mountains, and keep an eye out for humpback whales while you enjoy your delicious dinner cruise.

Maui: Deluxe Sunset Sail from Lahaina

2. Maui: Deluxe Sunset Sail from Lahaina

Enjoy stunning sunset on the coast of Maui on a catamaran cruise from Lahaina. Lay back on the forward trampolines or sit under the covered cabin space while savoring mouth-watering cold hors d’oeuvres and sipping on chilled drinks. Keep an eye out for whales as you sail.  Depart from Lahaina and set sail in the waters of Maui. Admire breathtaking views of the verdant and dynamic shores as the sunset paints the sea in a golden glow. Have a refreshing cocktail or snack on a delicious selection of hors d’oeuvres.  From December to May, enjoy the thrill of watching the humpback whales as they make their yearly journey to Hawaii. During the rest of the year, keep your eyes peeled for graceful seabirds and the black-finned Māui dolphin.  Return to your meeting point in Lahaina at the end of your cruise. 

From Ma'alaea Harbor: Sunset Dinner Cruise with Live Music

3. From Ma'alaea Harbor: Sunset Dinner Cruise with Live Music

Depart from the Ma’alaea Harbor and set off into the waves on a deluxe, 3-story catamaran. After exiting the harbor, enjoy a complimentary drink before the dinner service kicks off. Explore the alcoves of the boat, gaze out over the ocean, and snap photos. While soaking up the tropical views, listen to island-style music. For dinner, chef Keoni will serve the succulent Hawaiian prime rib, Mahi Mahi, teriyaki chicken, ribs, steamed vegetables, white rice with soy sauce, and more. As you dine, take in views of Kaho’olawe and Lanai in the distance, as well as the top snorkeling location, Molokini Crater. Gaze out at the Kahalawai Mountains of Maui extending toward the sky. You are likely to see humpback whales visiting the islands from Alaska along with other marine mammals.

Maui: Sunset Sailing Cruise with Champagne from Lahaina

4. Maui: Sunset Sailing Cruise with Champagne from Lahaina

A perfect Maui experience is not complete without witnessing the beauty of a sunset while out on the ocean. Board Paragon to experience a sunset sailing cruise and watch the sun dip below the horizon as you glide along the picturesque west cost of Maui. Beverages, including locally brewed beer, mai tais, wine, and champagne, are served as well as pupus (appetizers). This is as close as you can get to yachting, but make no mistake — when the wind is up it can be quite an exhilarating sail. During season from December to May, enjoy the thrill of watching the humpback whales that make their way to Hawaii each year.

Maui: Self-Drive Sightseeing Road Trip

5. Maui: Self-Drive Sightseeing Road Trip

Embark on a self-driving road trip with a guide in your pocket. Skip the crowded tour buses and experience Maui independently, at your own pace. See historic sites, popular attractions, world-class beaches, and scenic hikes. Listen to local stories, legends, and fun facts about the places you’re visiting as well as unique Hawaiian music to entertain and relax you along the way. Experiences you can have on the tour are: • Hike to Twin Falls • Explore Wai'anapanapa State Park to visit a black sand beach • Hike to Maui’s Red Sand Beach • Swim at Oheo Gulch (Seven Sacred Falls)  • Explore a lava tube • Explore the Backside to Hana • Visit scenic waterfalls • Watch the sunrise atop Mt. Haleakala • Hike the Hosmer Grove or Sliding Sands trails • Visit a lavender or dairy farm • Walk through historic Makawao Town

From Ka'anapali Beach: 2-Hour Sunset Sail with Live Music

6. From Ka'anapali Beach: 2-Hour Sunset Sail with Live Music

Setting off from Ka'anapali Beach, start your adventurous sunset cruise by boarding your luxurious Catamaran. Once aboard, enjoy a pleasant meet-and-greet with the friendly staff before embarking on this 2-hour cruise. Relax and take in the breathtaking views as you listen to popular local musicians performing live on the Catamaran. Enjoy a mixture of traditional, contemporary and reggae covers of the popular songs you know and love as you take advantage of the delicious beverages at the open bar and tasty pupus appetisers. These conditions create the perfect setting to witness the stunning views of the sunset over the horizon. For participants on the cruise during the period of December 15th to April the 15th, whale watching is also a great possibility.

Maui: Haleakalā National Park Sunset Tour

7. Maui: Haleakalā National Park Sunset Tour

Take a fantastic tour in the twilight hours to witness a sunset from atop Haleakalā, a dormant crater in Haleakalā National Park. View Maui on the ascent from the safety and comfort of your bus. Catch a glimpse of the endemic Hawaiian Nene goose and the Silversword plant on your ascent. Watch the sunset with an incredible view from 9,740 feet elevation. Listen to your driver tell Hawaiian legends and learn about the history and culture of Maui. Descend from the crater and note the changes in topography and weather. Pass through Kula town in upcountry Maui on your return and see flourishing farmland and stunning views of the land below.

Maui: Haleakala and Ia'o Valley Tour

8. Maui: Haleakala and Ia'o Valley Tour

Take in the breathtaking sights and catch the highlights of upcountry Maui on this guided day tour.  Start your day with a journey to Haleakala National Park to see famous dormant volcano Halekalalā, the “House of the Sun”.  This National Park showcases the best of Maui in its truest and most natural form. Covering 33,000 acres of volcanic wilderness, witness the unforgettable sweeping views from what seems to be the top of the world.  Discover native plants and wildlife including the rare silversword plant which only grows on the slopes of Haleakala. You will also have time to check out the Haleakalā Visitor Center’s educational exhibits. On the next part of your adventure, head to Wailuku Town in central Maui. This is the capital of Maui County and a historic plantation town. Your guide will share their insights about the local culture and history of this vibrant town. After that, don't miss out on scenic ‘Iao Valley and marvel at the famed ʻIao Needle in its towering glory.  Learn about the site of a great battle between King Kamehameha I and Maui's army in an effort to unite the Hawaiian Islands. Finish off your day by climbing 133 steps to the top the ‘Iao Valley lookout where you will be rewarded by mesmerizing 360-degree views.  

Maui: Private Haleakala Sunset Tour with Dinner

9. Maui: Private Haleakala Sunset Tour with Dinner

Travel to the central Upcountry region of Maui, the site of the imposing Haleakala volcano, on a guided tour in a luxury vehicle. Enjoy stops at several locations, including the beach at Ho'okipa and the charming town of Makawao, before enjoying dinner on the slopes of Haleakala. Start with pickup from your hotel and first travel to Ho'okipa beach, known for its stunning views, high waves, and giant turtles who often lie on its golden sands. Have a photo stop here and take the amazing vistas of crashing waves on the beach. Continue with a short photo stop at Old Paia High School. Then, head to the heart of the Upcountry at the town of Makawao. Take some time here to do a bit of shopping as you explore its charming streets. After exploring the town for a bit, travel along the Kula Highway, enjoying the panoramic views all around you. Make a stop at Harold W Rice Memorial Park for a brief photo stop to take in your surroundings. Finally, arrive at a scenic private location on the slopes of the Haleakala volcano. Enjoy a private dinner surrounded by stunning scenery and tranquil nature, with the possibility of seeing birds and paragliders soaring overhead. Admire a beautiful and tranquil sunset as you enjoy your meal. Afterward, relax on your journey back to your hotel in Maui.

Maui: Kaanapali Shore Sunset Segway Tour

10. Maui: Kaanapali Shore Sunset Segway Tour

End your day in paradise on a perfect note with this sunset Segway tour. After a brief orientation and training covering Segway safety protocols, explore Hanakoo Beach Park and Wahikuli State Park (also known as Canoe Park). Follow the long, uninterrupted stretch of golden sand between Kaanapali and Lahaina. Glide along the walking path through both beach parks, both of which are known for great swimming and snorkeling. You will pass grassy picnic areas and shady Kiawe and palm tree groves. Stop for pictures whenever and wherever you like. Bask in the glow of the setting sun from the seashore.

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What people are saying about Maui

Overall rating

4.6 / 5

based on 18 reviews

Amazing experience! The crew was wonderful and the captain did a spectacular job narrating our cruise. He knew SO much about the area. Live music was a major bonus-can’t get that anywhere else. Food was delicious. This was the highlight of our trip to Hawaii!!

It was a great time with Sail Maui. The all female crew were fun and engaging. There were plenty of drinks and some food. It was cloudy and we weren’t sure we would get much of a sunset but it ended up being stunning. I would recommend it.

The crew was great we had a all female crew they were on top of making sure everyone was having a good time bringing drinks.

Elly Milani & Nicholas were amazing. This was one the best sunset cruises I have been on. Nice drinks & service. Cheers

The sis set dinner cruise was a fantastic time! The crew members were great and provided exceptional service!