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Top Maui Cruises & Sailing

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109 results | All Maui Tours

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Original Sunset Sail with Open Bar from Ka’anapali Beach

Original Sunset Sail with Open Bar from Ka’anapali Beach

star-5
169
Enjoy a ‘front-row seat’ for Maui’s epic sunset accompanied by handcrafted cocktails and snacks during this sailing cruise from Kaanapali Beach. Enjoy views of nearby Lanai, Molokai, and Kahoolawe from your boat, cocktail and food in hand, as the Hawaiian sky puts on its nightly display. Snacks, unlimited alcoholic drinks, and non-alcoholic beverages are all included.
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  • 2 hours
  • Free Cancellation
  • Taking safety measures
From
$85.73
From
$85.73
Taking safety measures

Sunset Sail with Live Music and Open Bar from Ka’anapali Beach

Sunset Sail with Live Music and Open Bar from Ka’anapali Beach

star-5
35
Watch the Hawaii sunset aboard a sailing catamaran while listening to live music for a fun twist on the conventional sunset cruise. Depart from Kaanapali Beach and soak in great views of Maui as popular local performers play traditional, contemporary, and reggae versions of favorite songs. Your sailing cruise includes an open bar with drinks and 'pupus' (appetizers).
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  • 2 hours
  • Free Cancellation
  • Taking safety measures
From
$91.90
From
$91.90
Taking safety measures

Sunset Dinner Cruise Aboard the Calypso from Ma'alaea Harbor

Special Offer

Sunset Dinner Cruise Aboard the Calypso from Ma'alaea Harbor

star-4.5
67
Hawaii is a major destination for relaxation and fun times—and this Maui sunset dinner cruise allows you to let loose and enjoy yourself while visiting the island. Step aboard a ship that cruises by the Na Pali coast, and take in views during sunset as you feast on your dinner of choice. Dance to live music, sip on two free drinks from a full bar, and create your own memorable experience on the water.
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  • 2 hours 30 minutes
  • Free Cancellation
  • Taking safety measures
From
$80.05
$100.07
$20.02 savings
From
$80.05
$100.07
$20.02 savings
Taking safety measures

Maui Whale Watch Cruise from Lahaina Harbor

Maui Whale Watch Cruise from Lahaina Harbor

star-4.5
402
Catch an exciting peek at the underwater world on this whale-watching cruise in Maui. Your excursion includes narration from your captain and crew, as you learn more about these majestic creatures. Enjoy stunning views and photo opportunities while traveling along Maui’s exquisite coastline. Your family-friendly cruise comes with a guarantee that you spot a whale during your adventure.
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  • 2 hours
  • Free Cancellation
  • Taking safety measures
From
$31.74
From
$31.74
Taking safety measures

Whalewatch Sail from Lahaina

Whalewatch Sail from Lahaina

star-5
56
Maximize your chances of seeing humpback whales by embarking on a catamaran cruise from Lahaina Harbor. In the company of certified marine naturalists and marine biologists who provide insights into whale behavior, head out onto the water in search of the gentle giants. Snacks and drinks are available on board upon purchase.
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  • 2 hours
  • Free Cancellation
  • Taking safety measures
From
$68.38
From
$68.38
Taking safety measures

Champagne Sunset Sail from Lahaina Harbor

Champagne Sunset Sail from Lahaina Harbor

star-5
27
Set sail into the sunset aboard a retired racing yacht with this cruise. You'll hop aboard the Sunset Mist in Lahaiana and sail out into the Pacific, where you'll have your choice of beer, wine, or soft drinks. Best of all, group sizes are capped at 22 people so you won't have to worry about crowds.
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  • 2 hours
  • Free Cancellation
From
$73.94
From
$73.94

Sunset Dinner Cruise: Four Course Dining Experience from Lahaina

Sunset Dinner Cruise: Four Course Dining Experience from Lahaina

star-4
143
Unwind after a day of exploring Maui on a sunset cruise with a 4-course dinner. Enjoy delicious cuisine and included Mai Tais and other beverages against the stunning backdrop of the Pacific Ocean and surrounding islands of Lana'i and Moloka'i. With a limited number of guests aboard, this makes for the ideal romantic experience.
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  • 2 hours
  • Free Cancellation
  • Taking safety measures
From
$104.12
From
$104.12
Taking safety measures

Premium Sunset Cocktail Cruise from Ka’anapali Beach

Premium Sunset Cocktail Cruise from Ka’anapali Beach

star-5
33
Leave behind the crowds of Ka’anapali Beach and spend the evening on a sunset dinner 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). Plus, the buffet dinner comes with handcrafted cocktails and premium beers.
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  • 2 hours 30 minutes
  • Free Cancellation
  • Taking safety measures
From
$96.45
From
$96.45
Taking safety measures

Sunset Sail from Historic Lahaina Harbor

Sunset Sail from Historic Lahaina Harbor

star-4
21
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.
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  • 2 hours
  • Free Cancellation
  • Taking safety measures
From
$89.16
From
$89.16
Taking safety measures

Whale Watching from Lahaina Harbor

Whale Watching from Lahaina Harbor

star-4.5
268
Don’t miss one of the most popular whale-watching tours in Maui! This 2-hour catamaran cruise takes you from the historic Lahaina Harbor out to waters home to humpback whales. Using underwater hydrophones, listen to them sing, and watch males compete for mates or mother whales calving — you never know you might see on this adventure that guarantees whale sightings. Enjoy the views from the open upper deck or the shaded cabins below, and hear informative commentary from naturalist-guides on board. This family-friendly outing includes a Naturalist Program for kids.
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  • 2 hours
  • Free Cancellation
  • Taking safety measures
From
$45.22
From
$45.22
Taking safety measures

Adventure Sail from Lahaina Harbor

Adventure Sail from Lahaina Harbor

star-4
10
Our 50-foot Santa Cruz sailing yacht carries up to 22 passengers for intimate sailing excursions. The Scotch Mist is built for the Maui winds, and she was “first in class” in the prestigious Victoria-to-Maui Yacht Race besting her competitors by over 24 hours. The mast on this sailing yacht is over 65 feet tall and carries the main sail and billowing jib that moves us over the ocean waves at an exciting clip. This is a sailing vessel and we will actually sail.
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  • 2 hours
  • Free Cancellation
From
$63.23
From
$63.23

Up-Close Whale Watch Boat Tour from Lahaina

Up-Close Whale Watch Boat Tour from Lahaina

star-5
181
This tour departs from the historic Lahaina Harbor 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.
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  • 2 hours
  • Free Cancellation
  • Taking safety measures
From
$49.04
From
$49.04
Taking safety measures

Whale Watching from Ma'alaea Harbor

Whale Watching from Ma'alaea Harbor

star-4.5
172
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.
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  • 2 hours
  • Free Cancellation
  • Taking safety measures
From
$45.22
From
$45.22
Taking safety measures

Small-Group Whale Watching Adventure

Small-Group Whale Watching Adventure

star-5
168
Our small group experience takes place in a big boat atmosphere! A maximum of 12(!) guests onboard allow for as much social distancing as possible while giving our captain and crew the chance to focus on providing each guest with the very best experience possible. Our boat is really what sets us apart from other companies- we have a fast, fun, and very comfortable boat where everyone has a cushioned seat, large open platform for viewing the whales, and fast, quiet engines to help us spend the most possible time with the whales during your tour. Knowledgeable Captains who have worked amongst the whales for years will share what they know and answer your questions. Its a great photo opportunity and most people who do it come back for more!
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  • 2 hours
  • Free Cancellation
  • Taking safety measures
From
$75.60
From
$75.60
Taking safety measures

Whalewatch Sail Deluxe Tour from Lahaina

Whalewatch Sail Deluxe Tour from Lahaina

star-5
25
Get an up-close look at Hawaii’s Humpback whales during this 3-hour cruise run by a team of marine naturalists and biologists at the Pacific Whale Foundation. Each trip is different, but you’re likely to watch mothers interacting with their calves, observe mating behavior, and listen to whale songs through an underwater hydrophone. A buffet-style lunch and two complimentary drinks are also included.
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  • 3 hours
  • Free Cancellation
  • Taking safety measures
From
$95.59
From
$95.59
Taking safety measures

Private Whale Watch Boat Charters

Private Whale Watch Boat Charters

star-5
21
Charter a private boat in Maui for just your friends and family! Make your Maui vacation memorable by planning a private boat charter where you can choose the time, during, adventures, vessel and food for your ohana! Whale watch during whale migration from December - April and snorkel Lahaina, Maui, and Lanai all year-round! Our marine naturalists make educational talks fun and also provide snorkel instruction! We have 3 vessels that offer charters for groups of 1-6 passengers, up to 11 passengers, or 16 passengers. Book your private boat charter for an exclusive small group experience!We are locally owned and operated since 1982 and every ticket supports our participation in marine research projects and our role as certified first responders to whale entanglements.
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  • 2 hours
  • Free Cancellation
  • Taking safety measures
From
$535.83
From
$535.83
Taking safety measures

Whale Watching Cruise with Open Bar from Ka'anapali Beach

Whale Watching Cruise with Open Bar from Ka'anapali Beach

star-4.5
27
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.
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  • 2 hours
  • Free Cancellation
  • Taking safety measures
From
$75.02
From
$75.02
Taking safety measures

Discount Afternoon Whale Watch Tour from Lahaina Harbor

Discount Afternoon Whale Watch Tour from Lahaina Harbor

star-5
41
Get a front-row spot on a whale watching tour by booking this small-group excursion off the coast of Lahaina. While larger whale watching boats are crowded and can make it difficult to get photos of whales, this inflatable raft-style boat gets all passengers close to the water’s surface for a prime vantage point. This makes the trip ideal for photographers and families with kids.
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  • 2 hours
  • Free Cancellation
  • Taking safety measures
From
$71.80
From
$71.80
Taking safety measures

Reefdancer Semi-Sub Boat Cruise with Underwater Views from Lahaina Harbor

Reefdancer Semi-Sub Boat Cruise with Underwater Views from Lahaina Harbor

star-4.5
18
If you like sea creatures, but have no desire to scuba dive, this tour offers an alternative. Relax on board a glass bottom boat where every seat is a window seat, and prepare for an underwater show. Divers bring animals such as octopus, urchins, crabs, and starfish up to the windows for viewing, making every trip a unique experience. This is a family-friendly experience that is fun for all ages.
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  • 1 hour
  • Free Cancellation
From
$48.24
From
$48.24

Four Winds II Molokini Snorkeling Tour from Maalaea Harbor

Four Winds II Molokini Snorkeling Tour from Maalaea Harbor

star-4.5
311
Snorkeling in Molokini Crater is undeniably one of the best parts about visiting Maui. Here in this crescent, submerged volcano off Maui’s southern coastline, over 250 species of fish inhabit a world-class reef. Experience water so exceptionally clear you can see down 75 feet, and swim with schools of tropical fish while cruising the vibrant reef. You can also just sit and suntan on the deck, with sweeping views of Haleakala set just off the back of the boat.
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  • 5 hours
  • Free Cancellation
  • Taking safety measures
From
$128.24
From
$128.24
Taking safety measures

Sunset Dinner Cruise Aboard the Quicksilver from Lahaina harbor

Sunset Dinner Cruise Aboard the Quicksilver from Lahaina harbor

star-3.5
23
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 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.
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  • 2 hours
  • Free Cancellation
  • Taking safety measures
From
$89.95
From
$89.95
Taking safety measures

Whalewatch Deluxe Tour from Ma'alaea Harbor

Whalewatch Deluxe Tour from Ma'alaea Harbor

star-5
7
Ever year humpbacks whales congregate off the coast of Maui to breed, and you can see them up close from the comfort of a 65-foot double-decker catamaran. Designed to accommodate 147 people, no more than 75 are allowed on board to ensure you have a front-row seat to the show. You’ll also enjoy a delicious buffet lunch on-board. Whale sightings are guaranteed or you can go on another tour for free within a year.
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  • 3 hours
  • Free Cancellation
  • Taking safety measures
From
$95.59
From
$95.59
Taking safety measures

Lana'i Snorkeling & Dolphin Encounter Aboard the Quicksilver from Lahaina harbor

Special Offer

Lana'i Snorkeling & Dolphin Encounter Aboard the Quicksilver from Lahaina harbor

star-4.5
28
Sail to one of Hawaii's less-frequented islands on this snorkeling tour form Lahaina to Lanai, or the Pineapple Island. Snorkel beneath 300-foot tall cliffs near Shark Fin and Manele Bay, and look out for sightings of Lanai's resident pod of Spinner dolphins. This tour also includes breakfast and lunch to fuel a full day of fun.
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  • 5 hours
  • Free Cancellation
  • Taking safety measures
From
$87.96
$109.95
$21.99 savings
From
$87.96
$109.95
$21.99 savings
Taking safety measures

2-Hour Maui Whale Watching Cruise! (Ma'alaea Harbor)

2-Hour Maui Whale Watching Cruise! (Ma'alaea Harbor)

star-4.5
21
The west coast of Maui Island is one of the best places for whale watching in Hawaii and this 2-hour cruise ensures you maximize your chances of a sighting. Set sail from Maalaea Harbor aboard a high-speed catamaran, admire magnificent views along the coast, and look out for humpback whales in their natural environment.
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  • 2 hours
  • Free Cancellation
  • Taking safety measures
From
$30.99
From
$30.99
Taking safety measures

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