Top Maui Sailing
Saved to wishlist!
Select Dates
When are you traveling?
Popular
Search experiences that may have limited interaction with crowds.
Search experiences with increased health and safety practices.
Search tours and activities you can do from home.
You are viewing Virtual Experiences in Maui. See more Virtual Experiences around the globe. 🌎
Dolphin Watching
Whale Watching
Wildlife Watching
Glass Bottom Boat Tours
Water Tours
Adventure Tours
Sightseeing Cruises
Whale Watching
Day Trips
Full-day Tours
Half-day Tours
Price
Duration
Time of Day
RatingClear
Specials
18 results | All Maui Tours

From Ma'alaea Harbor: Sunset Dinner Cruise Aboard Calypso
588
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.
…More
From
$129.95
From
$129.95

Adventure Sail from Lahaina Harbor
96
Enjoy stunning coastal views only available from the water during this sailing tour down Hawaii's Au'au Channel. Relax onboard a comfortable, well-equipped sailing yacht with a full captain and crew, enjoying complimentary beverages such as wine, local beer, or soft drinks.
…More
From
$79.30
From
$79.30

Champagne Sunset Sail from Lahaina Harbor
203
Set sail into the sunset aboard a sailing yacht with this cruise. You'll hop aboard the Scotch Mist in Lahaina and sail out into the Pacific, where you'll have your choice of champagne, local beers, white wine, soda, juices, and bottled water. Best of all, group sizes are capped at 22 people so you won't have to worry about crowds.
…More
From
$90.02
From
$90.02

From Ma'alaea Harbor, Maui: Afternoon (PM) Snorkel Aboard Malolo
318
Go snorkeling off the coast of Maui on this boat tour on board 'the Malolo,' a 55-foot (17-meter) power catamaran. Cruise to one of two snorkeling sites—either Molokini Crater or Coral Gardens—where you can swim along the reef system to watch for colorful fish and other marine life. The location is selected by the captain depending on the daily conditions. If you're lucky, you may spot turtles or whales, too. Equipment and instructions are provided by the crew. Lunch (hot dog and soda) by selecting the upgrade option when booking.
…More
From
$89.95
From
$89.95

Four Winds II Molokini Snorkeling Tour from Maalaea Harbor
532
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.
…More
From
$178.47
From
$178.47

Original Sunset Cruise with Open Bar from Ka’anapali Beach
517
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.
…More
From
$91.09
From
$91.09

Reefdancer Semi-Sub Boat Cruise with Underwater Views from Lahaina Harbor
248
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.
…More
From
$53.60
From
$53.60

Maui Whale Watch Cruise from Lahaina Harbor
948
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.
…More
From
$74.25
From
$74.25

Premium Sunset Dinner Cruise from Ka’anapali Beach
134
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
From
$132.89
From
$132.89

Maui Sunset Luau Dinner Cruise from Ma'alaea Harbor aboard Pride of Maui
245
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.
…More
From
$185.40
From
$185.40

Morning Snorkel Sail from Lahaina Harbor
25
Start your day off with an exciting adventure aboard this snorkel tour from Lahaina. Join a small group and set out onto the seas for a sail along Maui's west coast. Your captain chooses a location for the day, depending on weather conditions, for the chance to see green sea turtles and other aquatic species that hang around the coral reefs.
…More
From
$138.24
From
$138.24

Sunset Cruise with Live Music and Open Bar from Ka’anapali Beach
119
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).
…More
From
$96.45
From
$96.45

Hawaiian Canoe Sailing Experience in Maui
21
Partake in a time-honored Hawaiian tradition during this private, outrigger canoe sailing experience along Maui's stunning Wailea coast. Learn about Hawaiian culture and history, including the ancient art of canoe construction, sailing, and navigation. Launch the boat from the beach using traditional methods. Spot sea turtles, reef fish, and seasonal humpback whales, with snorkeling equipment provided.
…More
From
$179.00
From
$179.00

Whalewatch Sail from Lahaina
73
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.
…More
From
$104.55
From
$104.55

Honolua Bay Snorkel Sail from Lahaina
32
Dive beneath the waves to explore Maui’s colorful fish, vibrant coral, and graceful sea turtles on this 6-hour snorkel excursion to Honolua Bay. Experience one of the island’s most popular snorkel spots with the help of a certified marine naturalist before heading to a second site for more underwater adventure. An included breakfast, barbecue lunch, and periodic sightings of wild dolphins help add to the experience.
…More
From
$169.95
From
$169.95

Sunset Sail from Historic Lahaina Harbor
29
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
From
$129.95
From
$129.95

Private Charter 4-hour Morning Snorkel Sail
Private Charters.
No other passengers.
4-hours on the water, sailing with time to swim and snorkel.
Personal Service is our trademark and tradition.
Let our experienced captains and crew do all the work.
Come Sail Away.
Scotch Mist is a 50-foot Santa Cruz sailing yacht carrying up to 22 passengers.
Tropical treat breakfast, local fruits and breads.
Turkey (or veggie) wrap, local fruit, chips and cookies for lunch.
Your choice of sodas, juices and bottled water available throughout the trip.
Champagne, local beer and white wine available after swimming.
…More
From
$2,089.74
per group
From
$2,089.74
per group

Private Charter, 2-hour Adventure Sail
Private Charters.
No other passengers.
2-hours on the water, sailing.
Personal Service is our trademark and tradition.
Let our experienced captains and crew do all the work.
Come Sail Away.
Scotch Mist is a 50-foot Santa Cruz sailing yacht carrying up to 22 passengers.
Your choice of champagne, local beer, white wine, sodas, juices and bottled water are complimentary and included.
…More
From
$1,232.41
per group
From
$1,232.41
per group
- Art & Culture
- Food & Drink
- Kid-Friendly
- Likely To Sell Out
- Outdoor Activities
- Nature and Wildlife Tours
- On the Water
- Catamaran Cruises
- Dinner Cruises
- Freediving
- Glass Bottom Boat Tours
- Kayaking Tours
- Lunch Cruises
- Sailing
- Sightseeing Cruises
- Snorkeling
- Swimming
- Seasonal & Special Occasions
- Tickets & Passes
- Tours, Sightseeing & Cruises
- Cruises & Sailing
- Day Cruises
- Ports of Call Tours
- Shore Excursions
- Sunset Cruises
- Whale Watching
- How to Get Around
- Private and Luxury
- Sightseeing Tours
- Tours by Duration
- Travel & Transportation Services
- Classes & Workshops
- Unique Experiences
- Wailuku Tours & Tickets
- Makawao Tours & Tickets
- Bailey House Museum Tours & Tickets
- Kaʻanapali Tours & Tickets
- Kalaupapa National Historical Park Tours & Tickets
- Surfing Goat Dairy Tours & Tickets
- ʻIao Valley State Monument Tours & Tickets
- Lahaina Jodo Mission Tours & Tickets
- Waiʻanapanapa State Park Tours & Tickets
- Ocean Vodka Organic Farm and Distillery Tours & Tickets
- Waihee Ridge Trail Tours & Tickets
- Kapalua Tours & Tickets
- Puaʻa Kaʻa State Wayside Park Tours & Tickets
- Haleakala National Park Tours & Tickets
- Pipiwai Trail Tours & Tickets
- Kahului Tours & Tickets
- Kaumahina State Wayside Park Tours & Tickets
- Kaʻanapali Beach Tours & Tickets
- Maui Tropical Plantation Tours & Tickets
- Wailea Tours & Tickets
Trending attractions
Popular on Viator
- Statue of Liberty Tours and Tickets
- The White House Tours and Tickets
- Antelope Canyon Tours and Tickets
- Hoover Dam Tours and Tickets
- Alcatraz Tours and Tickets
- Stonehenge Tours and Tickets
- Auschwitz-Birkenau Memorial and Museum Tours and Tickets
- Beverly Hills Tours and Tickets
- Colosseum Tours and Tickets
- Washington Monument Tours and Tickets
- San Diego Zoo Tours and Tickets
- Space Needle Tours and Tickets
- Eiffel Tower Tours and Tickets
- Pearl Harbor National Memorial Tours and Tickets
- Empire State Building Tours and Tickets
- Art Institute of Chicago Tours and Tickets
- Aquarium of the Pacific Tours and Tickets
- Blue Lagoon Tours and Tickets
- Burj Khalifa Tours and Tickets
- Metropolitan Museum of Art (The Met) Tours and Tickets