Maui Sailing Charters - 2026 Best Deals

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7-Line North Shore Zipline Canopy Tour

NorthShore Zipline - Maui • Makawao

Soar through the treetops on a 7-line zipline tour in Maui's North Shore with NorthShore Zipline Co. Glide at speeds up to 40 mph over lush eucalyptus forests, crossing suspension bridges and elevated platforms. This family-friendly adventure offers breathtaking ocean views and includes a visit to historic Camp Maui. Details

1859 Reviews

$149.00 $139.00

Total Price: $145.02 (USD)

You Save: $10.00

Maui Nui Luau

Tihati Productions • Kaanapali

Located on the beachfront along Kaanapali Beach, Maui Nui Luau at Black Rock offers an authentic Hawaiian ceremony and buffet for guests of all ages. The luau features some of the best Hawaiian and Polynesian entertainment, including an amazing fire knife dance, a Pu’u Keka’a cliff dive and more. Enjoy an all-you-can-eat feast and an open bar during the show. Details

2 Reviews

$208.19

Total Price: $217.78 (USD)

Te Au Moana Luau at The Wailea Beach Marriott Resort

Tihati Productions • Wailea

Immerse yourself in island tradition at the Te Au Moana Luau at The Wailea Beach Marriott Resort, where the ocean’s story comes alive through mesmerizing dance, live music, and blazing fire-knife performances. Savor island-inspired cuisine and genuine aloha hospitality in this unforgettable Maui evening. Details

1367 Reviews

$214.88

Total Price: $224.74 (USD)

The Feast at Mokapu Luau

The Feast at Mokapu • Wailea

Relax in ultimate luxury with an ohana-style meal at the Andaz Maui at Wailea Resort. The Feast at Mokapu Luau offers an ornately curated cultural and culinary journey on the shore of Mokapu Beach. Indulge in engaging storytelling with handcrafted cocktails and a traditional, chef-prepared Hawaiian meal while listening to traditional tales of the island. Details

234 Reviews

$283.00

Total Price: $295.80 (USD)

Royal Lahaina Myths of Maui Luau

Hawaiian Hotels Luaus • Lahaina

The Myths of Maui Luau at the Royal Lahaina Resort brings oceanfront dining and Polynesian entertainment to Kaanapali Beach. This long-running Royal Lahaina Luau pairs a traditional Hawaiian feast with sunset views and an unforgettable fire knife finale. It is a favorite for first-time Maui visitors, families, and special occasions alike. Details

2760 Reviews

$185.00

Total Price: $195.87 (USD)

The Lu'au at Grand Wailea

The Lū‘au at Grand Wailea • Wailea

Experience the Grand Wailea Luau on Maui's Wailea Beach, where Hawaiian culture comes alive through traditional cuisine, vibrant hula, and fire knife performances. Choose from Standard Seating or Ali’i Premium Seating for the best views. Enjoy pre-show activities, island legends, and a night under the stars. Details

1009 Reviews

$300.00 $280.00

Total Price: $297.23 (USD)

You Save: $20.00

Maui Luau: Gilligans' Island Luau in Kihei

Gilligans Bar & Grill • Kihei

Experience authentic Hawaiian culture and cuisine at Gilligans' Island Luau in Kihei. Enjoy panoramic ocean views, an open bar and a full Hawaiian all-you-can-eat buffet featuring Kalua Pork, Teriyaki Chicken, Mahi Mahi, and more. This intimate Maui luau at the Maui Nui Golf Club showcases hula dancers, live music and a fire dance finale. Details

593 Reviews

$159.00 $149.00

Total Price: $161.12 (USD)

You Save: $10.00

Jungle Zipline Maui Eco Tour

Makawao

Explore Maui’s lush landscapes on a Jungle Zipline Maui Eco Tour. Traverse a tropical valley on Maui’s North Shore with expert guides and state-of-the-art zipline design. Enjoy a thrilling adventure amid breathtaking scenery, and immerse in native Hawaiian plants and traditional Taro farming. Conveniently located near the Hana Highway, book your tour today! Details

1604 Reviews

$128.00 $118.00

Total Price: $125.68 (USD)

You Save: $10.00

Snorkel Tour to Lanai Half Day

Sea Maui • Kaanapali

Discover Lanai's pristine underwater world on this half-day snorkeling tour with Kaanapali Ocean Adventures. Depart from Kaanapali Beach and explore vibrant coral reefs teeming with marine life, including dolphins, turtles, and reef fish. Enjoy a continental breakfast, refreshing drinks, and a chance to connect with Hawaii's unique underwater ecosystem. Details

334 Reviews

$179.00 $169.00

Total Price: $180.89 (USD)

You Save: $10.00

Hana Rainforest Helicopter Tour

Blue Hawaiian Helicopters Maui • Kahului

Soar over Maui’s stunning eastern coastline on Blue Hawaiian Helicopters’ Hana Rainforest Tour. This 50-minute aerial adventure offers breathtaking views of lush rainforests, cascading waterfalls, and secluded beaches. With narration by your pilot, a State of Hawaii-certified tour guide, enjoy a unique perspective of Hana’s natural beauty. Details

1 Reviews

$419.00 $404.00

Total Price: $404.00 (USD)

You Save: $15.00

Majestic Maui Helicopter Tour

Blue Hawaiian Helicopters Maui • Kahului

Take your vacation to new heights with the Majestic Maui Helicopter Tour in Maui, Hawaii. Fly with Blue Hawaiian Helicopters from Kahului, HI over lush rainforests, cascading waterfalls, and the towering West Maui mountains. Marvel at the world's largest dormant volcano, Haleakala, and discover why Maui is called "The Valley Isle." Details

1867 Reviews

$419.00 $409.00

Total Price: $409.00 (USD)

You Save: $10.00

Maui & Molokai Spectacular Helicopter Tour with Remote Landing

Blue Hawaiian Helicopters Maui • Kahului

Experience the NEW! Maui and Molokai Spectacular helicopter tour with Blue Hawaiian Helicopters. This 1.5-hour adventure from Kahului offers breathtaking views of lush rainforests, dramatic coastlines, and towering sea cliffs. Enjoy an exclusive landing at Ulupalakua Ranch for refreshments and stunning vistas. Discover the islands' hidden gems from the sky! Details

1 Reviews

$559.00 $549.00

Total Price: $549.00 (USD)

You Save: $10.00

Waterfalls of West Maui and Molokai Helicopter Tour

Blue Hawaiian Helicopters Maui • Kahului

Discover Maui's stunning and diverse landscapes on a Blue Hawaiian helicopter tour in Maui. This 50-minute West Maui and Molokai helicopter tour takes you high in the air for a bird’s eye view of Molokai’s sea cliffs, towering waterfalls, and lush tropical valleys. Soar above 88 miles of untouched coastline on this epic adventure. Details

1 Reviews

$419.00 $409.00

Total Price: $409.00 (USD)

You Save: $10.00

Haleakala Sunset Tour

Polynesian Adventure Tours Maui • Kahului

The Haleakala Sunset Tour by Polynesian Adventure Tours departs from Maui hotels for a scenic journey to Haleakala's summit. Enjoy panoramic crater views, vivid skies, and expert narration. Ideal for those seeking a later start and a stress-free evening above the clouds. Details

4830 Reviews

$231.00 $211.00

Total Price: $220.62 (USD)

You Save: $20.00

Hana Rainforest Helicopter Tour with Landing

Maverick Helicopters Maui • Kahului

Get ready to embark on an immersive Hawaiian adventure! On this Hana Helicopter Tour, you’ll fly along Maui's north coast with picturesque sea cliffs, cascading waterfalls and scenic landscapes of the Road to Hana, Jurassic Rock and Jaws Surf Break. Land in the remote Hana Rainforest surrounded by native vegetation and enjoy a champagne toast. Details

1614 Reviews

$274.00 $254.00

Total Price: $400.17 (USD)

You Save: $20.00

Maui Hana Sky-Trek Half-Day Tour

Temptation Tours • Kahului

Experience the Road to Hana from the road and from above! This Road to Hana tour will take you on a half-day excursion to the world’s largest dormant volcano (Haleakala Crater), hidden waterfalls, lush rainforests, and more. Includes a delicious lunch of Pacific Rim cuisine and a 36-minute helicopter flightseeing tour that is bound to take your breath away. Details

1872 Reviews

$505.00 $475.00

Total Price: $586.77 (USD)

You Save: $30.00

Molokai Voyage Helicopter Tour

Maverick Helicopters Maui • Kahului

Hop aboard a Maverick Maui helicopter tour for a picturesque West Maui and Molokai double-island adventure. Cross the Pailolo Channel from Maui to Molakai, aka the “Friendly Isle”, and get a bird's eye view of Elephant Rock. Soar above the North Shore and Halawa Valley. Witness some of Hawaii’s tallest sea cliffs and waterfalls, ancient fishponds, and more. Details

$319.00 $289.00

Total Price: $381.01 (USD)

You Save: $30.00

Road to Hana Maui Adventure with Lunch & Pick-up

Valley Isle Excursions • Wailea

Explore the famous Road to Hana with Valley Isle Excursions. This full-day Maui Road to Hana Tour includes a continental breakfast, hot lunch, and stops at scenic locations like the Keanae Peninsula and Waianapanapa State Park's black sand beach. Hotel pickup and drop-off are provided. Details

2703 Reviews

$293.99 $273.99

Total Price: $291.29 (USD)

You Save: $20.00

Three-Island Hawaiian Odyssey Helicopter Tour

Maverick Helicopters Maui • Kahului

Join this exciting helicopter tour in Maui for triple the fun—an aerial adventure over three Hawaiian Islands on a luxury helicopter! Fly over Maui’s pristine beaches, Elephant Rock, and Molokai’s towering sea cliffs, ancient fish ponds and the longest fringing reef. Soar across Lanai to spot historic Shipwreck Beach, and return along the West Maui mountains. Details

8152 Reviews

$409.00 $379.00

Total Price: $484.21 (USD)

You Save: $30.00

Haleakala Sunrise Tour

Valley Isle Excursions • Wailea

Rise above the clouds for a dazzling Haleakalā sunrise! This tour includes transportation in a luxury cruiser with oversized viewing windows, a guided journey through Hawaiian history and legends, and a post-sunrise island-style breakfast. Witness panoramic views from the summit and Kalahaku Overlook for an unforgettable start to the day. Details

156 Reviews

$263.99 $243.99

Total Price: $259.45 (USD)

You Save: $20.00

Hana and Beyond Tour

Hana and Beyond Tours • Lahaina

Hana and Beyond Tour takes travelers through Maui’s iconic Highway, with stops at rainbow eucalyptus, dramatic lookouts, luscious fruit stands, freshwater pools and black‑sand beaches. Includes pickup, deli lunch, water, and a chance to see green sea turtles. A true local journey on one of the world's most jaw‑dropping drives. Details

599 Reviews

$210.00 $190.00

Total Price: $198.84 (USD)

You Save: $20.00

Hana Ultimate Tour

Temptation Tours • Hana

Enjoy a full day of fun-filled adventure on this ultimate Road to Hana tour, a must-see for any Maui vacation. Experience the remote Hana Coast at a leisurely, relaxed pace with numerous stops, including Kaumahina State Park, the quaint Hawaiian village of Ke'anae, Waikani Falls, and more. You'll have plenty of opportunities to capture photos of the beautiful scenery on this seacoast tour. Your helpful, state-certified tour guide will be happy to assist you in capturing the moments on your phone or camera. The tour includes a delicious breakfast, three-course lunch in Hana, and an ocean swim at a black sand beach or freshwater pool under a cascading waterfall if conditions permit. Details

1672 Reviews

$335.00 $315.00

Total Price: $418.75 (USD)

You Save: $20.00

Heavenly Hana Tour

Roberts Hawaii • Hana

The Heavenly Hana Tour takes you on a full-day excursion to East Maui! As you travel the 68-mile Hana route, get a close-up look at some of the island's most breathtaking vistas like Keanae Valley Lookout and Waianapanapa State Park (and more!), all while your expert guide explains its history and cultural significance. Details

1826 Reviews

$302.00 $282.00

Total Price: $282.00 (USD)

You Save: $20.00

Maui Hana Cave-Quest Day Tour

Temptation Tours • Hana

Maui Hana Cave-Quest Day Tour features an adventure-filled experience for guests of all ages to enjoy. Visit Ka’eleku Cavern—a giant subterranean lava tube. Includes a one-hour scenic tour of ancient volcano formations, photo opportunities, a light morning snack, a picnic lunch with vegetarian/vegan/gluten-free options available, and more. Details

1872 Reviews

$305.00 $285.00

Total Price: $372.26 (USD)

You Save: $20.00

Maui Hana Picnic Day Tour

Temptation Tours • Hana

This Maui Hana Picnic Day Tour includes a full-day adventure starting in Paia and then to the Hana Coast. Enjoy visiting the Kaumahina State Park, Keanae, and Waikani Falls, plus a delicious picnic lunch for an unforgettable Hana experience. Details

1872 Reviews

$295.00 $275.00

Total Price: $359.13 (USD)

You Save: $20.00

Road to Hana Adventure

Polynesian Adventure Tours Maui • Hana

Explore Maui's Hana coast on this expertly guided Polynesian Adventure Tours experience. Travel the legendary Hana Highway, visit landmarks like the Black Sand Beach and Pua'a Ka'a State Park, and pass iconic sights such as Paia Town and Hana Bay. With breakfast, lunch, and hotel pick-up included, this tour ensures a seamless, unforgettable adventure. Details

4831 Reviews

$249.00 $229.00

Total Price: $239.42 (USD)

You Save: $20.00

Road to Hana Waterfalls Tour with Lunch

Stardust Hawaii • Lahaina

Experience Maui's natural wonders on the Road to Hana Waterfalls Tour. Enjoy breathtaking landscapes, photo stops, and a safe journey aboard a luxury Mercedes Sprinter van with an expert driver. Swim at Waianapanapa Black Sand Beach and Pua’a Ka’a Falls, and enjoy complimentary breakfast, lunch, snacks, and drinks throughout this unforgettable adventure. Details

68 Reviews

$229.99 $209.99

Total Price: $218.48 (USD)

You Save: $20.00

Spectacular Haleakala Sunrise Tour with Breakfast

Polynesian Adventure Tours Maui • Kahului

Set out on an early morning adventure on the Haleakala Sunrise Tour. Ascend atop Mount Haleakala aboard a minibus with large side windows—perfect for viewing the scenic drive and breathtaking scenery. Watch the summit come alive with the explosion of colors as the sun rises! A delicious breakfast awaits at Cafe O'Lei at the Plantation after the descent. Details

150 Reviews

$243.00 $223.00

Total Price: $233.16 (USD)

You Save: $20.00

Maui Sailing Charters: A Scenic Ocean Escape

Imagine stepping onto a private sailing charter, with the sun warming your face and a gentle breeze in your hair. This is just a glimpse of the unforgettable experiences awaiting you with Maui sailing charters. So, what does a day on the Pacific Ocean look like? Let’s explore.

As your journey begins, you glide from the harbor into the open sea. The scent of salt air fills your lungs, and the horizon stretches endlessly ahead. Meanwhile, the waters below promise incredible encounters.

Wildlife and Ocean Wonders

You may spot playful dolphins, graceful sea turtles, and, in season, humpback whales. For example, these majestic creatures often leap above the surface during whale watch sails. As a result, each trip offers a memorable wildlife experience.

This spectacle becomes even more special aboard options like Alii Nui Sailing Charters Maui. In addition, the calm ocean setting enhances every sighting.

Sunset Sails and Evening Magic

As the day winds down, sunset sailing creates a stunning backdrop. Picture yourself raising the sails while the sun dips below the horizon. Then, the sky shifts from golden hues to a canopy of stars.

This experience reflects what a Maui dinner cruise can offer. Moreover, the peaceful setting makes it both relaxing and romantic.

Activities and Relaxation on the Water

Beyond the views, Maui sailing charters include exciting activities. For instance, you can enjoy snorkeling during the day or join an afternoon snorkel cruise. As a result, you explore Maui’s clear waters up close.

Afterward, relax with a drink from the open bar while the ocean breeze eases the day. Meanwhile, the combination of adventure and calm creates a balanced experience.

Book Your Maui Sailing Adventure

Day or night, Maui sailing charters offer a blend of adventure, relaxation, and enjoyment. In other words, they provide a unique way to connect with the ocean.

Discover your perfect sea escape by booking with Tripster today. Then, start your Hawaii adventure and create unforgettable memories on the water.