Maui Cruises & Sailing

Top Maui Cruises & Sailing

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183 results

Best Seller
Original Sunset Cruise with Open Bar from Ka’anapali Beach
4.8
(1,043)

Original Sunset Cruise with Open Bar from Ka’anapali Beach

Enjoy a ‘front-row seat’ for Maui’s epic sunset accompanied by cocktails and snacks during this sailing cruise from Ka’anapali Beach. Enjoy views of nearby Lanai, Molokai, and Kahoolawe from your boat, drink and food in hand, as the Hawaiian sky puts on its nightly display. Plus, keep your eyes peeled for local marine life, including whales from mid-December to mid-April. Snacks, unlimited alcoholic drinks, and non-alcoholic beverages are all included.
... More
  • 2 hours
  • Free Cancellation
from
$115
From Maalaea Harbor: Whale Watching Tour Aboard the Quicksilver
4.6
(953)

From Maalaea Harbor: Whale Watching Tour Aboard the Quicksilver

Observe humpback whales in their natural habitat during their return migration to Maui’s waters December–April. This whale watching adventure by high-speed catamaran provides a front row seat to fin slaps, flukes, and breaches. Underwater hydrophones help you hear whale songs, while the captain and crew provide the commentary. Juices and sodas are available on board to keep passengers hydrated.
... More
  • 2 hours
  • Free Cancellation
from
$50
Whale Watching Cruise with Open Bar from Ka'anapali Beach
4.8
(571)

Whale Watching Cruise with Open Bar from Ka'anapali Beach

Set sail into one of the world’s most active winter whale playgrounds on a whale-watching tour from Maui’s Ka’anapali Beach. Head offshore directly from the beach and, with the help of a naturalist guide, look for pods of humpback whales making their winter home in Maui’s warm waters. Get comfortable aboard a spacious catamaran with plenty of seating—including bean bags on open nets that get you close to the action—and enjoy unlimited drinks from an open bar as you cruise alongside spectacular marine mammals.
... More
  • 2 hours
  • Free Cancellation
from
$103
Premium Sunset Dinner Cruise from Ka’anapali Beach
4.8
(536)

Premium Sunset Dinner Cruise from Ka’anapali Beach

Leave behind the crowds of Ka’anapali Beach and spend the evening on a sunset cruise off the coast of Maui. The perfect romantic evening out, this sunset cruise offers unmatched island views, photo opportunities, and even the chance to spot whales (December–April).
... More
  • 2 hours 30 minutes
  • Free Cancellation
from
$154
Sunset Sail from Ma'alaea Harbor
4.6
(193)

Sunset Sail from Ma'alaea Harbor

Eat, drink, and be merry on a sunset cruise aboard a luxury catamaran. Sail the waters off Maui as you experience the ho’okipa (hospitality) of the crew and panoramic views. Enjoy an array of premium appetizers and a full bar—three alcoholic drinks are included in the price. There’s also a marine biologist on board to comment on any wildlife you may encounter or answer questions about the local flora and fauna.
... More
  • 2 hours
  • Free Cancellation
from
$125
Molokini and Turtle Town Snorkeling Adventure Aboard the Malolo
4.4
(1,913)

Molokini and Turtle Town Snorkeling Adventure Aboard the Malolo

Imagine swimming in a sunken volcano that teems with thousands of fish, while splashing in crystal clear water. On this Molokini snorkeling tour, cruise out to the crater, before jumping in the crystalline waters and scouring the colorful reef. Make a second stop dependent upon conditions, and search for turtles at Turtle Town or a spot named Coral Gardens. This family-friendly Maui activity is one of the island's most popular, and an unforgettable day of exploring the underwater world.
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  • 5 hours 30 minutes
  • Free Cancellation
from
$160
Ma'alaea Harbor: Sunset Prime Rib or Mahi Mahi Dinner Cruise
4.5
(316)

Ma'alaea Harbor: Sunset Prime Rib or Mahi Mahi Dinner Cruise

This Maalaea Harbor Sunset Dinner Cruise from Wailuku is perfect for couples or anyone looking to add a beautiful, sunset experience to their trip while in Maui. When booking, choose from multiple dinner options such as prime rib, baby back ribs, and a vegetarian penne pasta. During your cruise, sit back with tableside service and drinks included as your captain and crew take care of the rest and you take in the sunset with island-style music playing in the background.
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  • 2 hours
  • Free Cancellation
from
$150
Maui Sunset Luau Dinner Cruise Pride of Maui
4.6
(540)

Maui Sunset Luau Dinner Cruise Pride of Maui

Board the beautiful and spacious Pride of Maui catamaran for a sunset cruise near the Molokini crater. Enjoy an open bar including craft beer and blended drinks, plus a generous buffet featuring barbecued ribs, honey-glazed chicken, stir fried vegetables, and more. Watch the sun set, take in a live hula show and if you’re lucky, you may even see humpback whales during mating season.
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  • 2 hours
  • Free Cancellation
from
$168
Eye-Level Whale Watching Eco-Raft Tour from Lahaina
4.9
(1,518)

Eye-Level Whale Watching Eco-Raft Tour from Lahaina

This tour departs from Lahaina, Maui to find the majestic humpback whales that frequent the waters surrounding Maui in the winter months. Traveling in a small raft creates an intimate whale watching experience not found on the larger vessels commonly used on whale watching tours. Plus, the raft travels quickly, letting you spend more time whale watching and less time in transit. -Enjoy a small group whale watching tour off the coast of Maui. -You can choose from a morning or afternoon tour so it doesn’t interfere with other plans -In the event of cancellation due to weather, you are offered an alternate outing or a full refund -Prepare for the chance to photograph whales in their natural habitat
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  • 2 hours
  • Free Cancellation
from
$79
From Ma'alaea Harbor: Sunset Dinner Cruise Aboard the Quicksilver
4.3
(752)

From Ma'alaea Harbor: Sunset Dinner Cruise Aboard the Quicksilver

Rather than spending the most magical time of day inside a restaurant or hotel, treat yourself to this sunset dinner cruise aboard a catamaran. Enjoy included drinks and watch the sun go down behind the island of Lanai as you cruise along the Lahaina coastline. Then, indulge in a delicious 3-course dinner accompanied by the sounds of a local musician. Depending on the time of year, you might even spot humpback whales.
... More
  • 2 hours
  • Free Cancellation
from
$140
Likely to Sell Out
Maui Snorkeling Molokini Crater and Turtle Town
4.7
(832)

Maui Snorkeling Molokini Crater and Turtle Town

A trip to Molokini Crater grants visitors the chance to take in scenic ocean views from a catamaran and discover the world below the surface while snorkeling at the underwater lava formations of Turtle Town. The calm water and bountiful marine life make this an ideal snorkeling spot for everyone from first-timers to long-time snorkeling enthusiasts. Plus, a guide provides security and instruction for beginners.
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  • 5 hours
  • Free Cancellation
from
$198
Molokini Snorkeling Adventure Aboard Calypso From Ma'alaea Harbor
4.6
(1,566)

Molokini Snorkeling Adventure Aboard Calypso From Ma'alaea Harbor

Over 200 different species of fish inhabit Molokini Crater, and you have the chance to search for them all aboard this Maui snorkeling tour. Inside this ancient volcanic caldera that rises up out of the sea, you might also find manta rays, sea urchins, eels, or even a harmless shark. This tour also stops at a spot called Turtle Town along the Maui coastline, where you have the chance to swim alongside enormous Hawaiian Green sea turtles. Enjoy amenities like a glass-bottom viewing room and snorkeling equipment as well as a buffet lunch on the triple-decker catamaran.
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  • 5 hours 30 minutes
  • Free Cancellation
from
$180
Small-Group Whale Watching Adventure
4.9
(786)

Small-Group Whale Watching Adventure

Our small group experience takes place in a big boat atmosphere! A maximum of 20 guests onboard allows our captain and crew the chance to focus on providing each guest with the very best experience. Our boat is really what sets us apart from other companies- we have a fast, fun and extremely comfortable boat where everyone has a cushioned seat, large open platform for viewing the whales and fast, quiet engines to help us maximize our time with the whales during your tour. Knowledgeable captains and crew who have worked among the whales for years will share whale facts and answer your questions. It's a great photo opportunity and most people who do it come back for more!
... More
  • 2 hours
  • Free Cancellation
from
$91
Whale Watching from Ma'alaea Harbor
4.7
(406)

Whale Watching from Ma'alaea Harbor

Experience the magic of whale watching off the coast of Maui with this incredible tour from Ma'alaea Harbor. Spend two-hours cruising the waters with a team of certified marine naturalists and listen in as they unlock the secretes of humpback whales. You'll have the chance to hear whale songs through underwater hydrophones and learn about interactions between these giant marine mammals. Travelers are guaranteed to see whales on this is a once-in-a-lifetime tour or the next trip is free.
... More
  • 2 hours
  • Free Cancellation
from
$83
Molokini Crater Snorkeling Adventure
4.8
(609)

Molokini Crater Snorkeling Adventure

The offshore crater of Molokini has some of the best snorkeling spots in Maui—if you can reach them. Thankfully, this half-day snorkeling tour heads straight for Molokini and Turtle Town nearby on a 53-foot (16 meters) Lani Kai II boat with a 20-foot (6 meters) waterslide. Visit two snorkeling locations, get the chance to spot whales, and enjoy onboard breakfast and lunch. Whales sightings are seasonal in nature, from November through April.
... More
  • 5 hours
  • Free Cancellation
from
$197
Likely to Sell Out
From Maalaea Harbor: Whale Watching Tours Aboard Winona Catamaran
4.8
(91)

From Maalaea Harbor: Whale Watching Tours Aboard Winona Catamaran

Check out the whales in the Molokini Crater on this group tour in Maui. You’ll keep costs down by booking this group gour, but you’ll still have a fantastic chance of seeing the gorgeous whales. You’ll also have commentary by a biologist who knows all about the humpback whales. Just make your way to the starting point, board your vessel, and relax until you find the whales.
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  • 2 hours 30 minutes
  • Free Cancellation
from
$70
Maui Nui Luau at the Sheraton Maui Resort & Spa
4.4
(1,251)

Maui Nui Luau at the Sheraton Maui Resort & Spa

At this oceanfront, Kaanapali luau on the island of Maui, feel the rhythmic beat of the drums as the sun sinks low in the sky, and experience the magic of Polynesian dance as tiki torches flicker in the night. Here at one of Maui’s best luaus, smell the fragrant tropical lei you’re given upon arrival. This Kaanapali sunset luau is full of exotic dances, as well as a filling, flavorful all-you-can-eat buffet featuring traditional Hawaiian cooking.
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  • 3 hours
  • Free Cancellation
from
$198
Maui Snorkel & Slide
4.6
(312)

Maui Snorkel & Slide

The Maui Afternoon Tour is ideal for those that seek a less congested snorkeling experience. We snorkel & slide at the Coral Gardens or Turtle Town on most afternoons. On rare occasions, we will snorkel only (no water sliding) at the Molokini Crater. You'll have the opportunity to experience many tropical fish and sea turtles, that lie within a naturally protected ocean bay. On this tour, you will head out on the Lani Kai II, a 53-foot boat (16 meters) with a 20-foot waterslide (6 meters) for several hours of snorkeling. Get the chance to see whales from November through April.
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  • 3 hours
  • Free Cancellation
from
$131
Maui Zipline Eco Adventure: 8 Lines through the Jungle
4.9
(1,044)

Maui Zipline Eco Adventure: 8 Lines through the Jungle

Fly through the treetops on a zipline course through the jungle environment of Haiku with this thrilling tour. Cross eight ziplines, three tree platforms, two swinging bridges, and a suspension bridge all in a couple of hours. This is a great activity to enjoy if you're taking a day trip on Maui's Hana Highway or visiting area waterfalls.
... More
  • 2 hours
  • Free Cancellation
from
$155
Maui Whale-Watching Tour by Raft from Kihei
4.9
(490)

Maui Whale-Watching Tour by Raft from Kihei

Spot humpbacks as they travel through Maui’s warm waters on this 1.5-hour whale-watching excursion. Hop aboard a sturdy raft in Kihei with an expert naturalist as your guide, and jet to the southern coastline, which hosts one of the highest whale populations in Hawaii. Your guide will provide commentary about these fascinating creatures as you see them spout and slap the water. To keep this whale-watching tour intimate, your group is limited to a small group.
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  • 1 hour 30 minutes
  • Free Cancellation
from
$84
Molokini and Turtle Arches Snorkeling Trip from Ma'alaea Harbor
4.6
(791)

Molokini and Turtle Arches Snorkeling Trip from Ma'alaea Harbor

Get off the beaten path to explore the wild side of Molokini on this half-day adventure from Maui. The small, crescent-shaped island of Molokini is an extinct volcanic crater with a thriving coral reef, home to more than 250 species of fish and 38 species of coral. Hop aboard a 54-foot, single-deck catamaran and jump in the water for a snorkel at the Turtle Arches reef. Then, cruise around Molokini's rugged, red rock back wall, home to a variety of seabirds. Snorkeling equipment plus a continental breakfast, buffet lunch, and refreshments are included.
... More
  • 5 hours
  • Free Cancellation
from
$210
West Maui Half Day Snorkel from Ka’anapali Beach
4.9
(916)

West Maui Half Day Snorkel from Ka’anapali Beach

Dive in to explore West Maui's underwater world during this half-day snorkeling excursion from Ka'anapali Beach. Under the guidance of your experienced captain, travel to some of the island's best snorkel locations to see green sea turtles (honu), schools of colorful tropical fish and maybe spinner dolphins, bottlenose dolphins, or even humpback whales (seasonal). After snorkeling, enjoy a delicious lunch onboard the boat, accompanied by nonalcoholic refreshments and beer and cocktails for purchase. Breakfast, lunch, and use of snorkel equipment are included.
... More
  • 4 hours
  • Free Cancellation
from
$176
Whale Watching Maui: 2-Hour Small Group Raft Tour from Lahaina
4.9
(355)

Whale Watching Maui: 2-Hour Small Group Raft Tour from Lahaina

Head out to sea for the chance to see migrating whales with this two-hour excursion from Lahaina. Your group will sail off to the waters of the Maui Nui whale sanctuary, a mating and birthing destination for humpback whales. Best of all, you're guaranteed to see the gargantuan sea mammals or you'll get to go on another trip for free.
... More
  • 2 hours
  • Free Cancellation
from
$81
Price varies by group size
Maui Pineapple Farm Tour in Haliimaile
4.8
(2,480)

Maui Pineapple Farm Tour in Haliimaile

Hawaii has a rich history of pineapple farming and this tour puts it all into perspective. Head to the historic plantation town of Hali'imaile to walk around a working pineapple field. Learn about pineapple growing cycles and cultivation from your guide and sample the fruit at its different stages. Best of all, each guest receives an 'airport-ready,' fresh pineapple at the end of the tour.
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  • 1 hour 30 minutes
  • Free Cancellation
from
$95
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