Free cancellation: get a full refund up to 24 hours in advance. Learn more

Top Maui Sailing Trips

Category
Select Dates
Filter




Clear Filters
Clear Filters

12 Tours and Activities

Sort by:Default


Molokini Sail and Snorkel Adventure

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.
  • Duration: 5 hours
  • Free Cancellation
  • Duration: 5 hours
  • Free Cancellation
From  
US$117.52
From  
US$117.52
See Details

Molokini Snorkel and Performance Sail

Sail aboard a catamaran to Molokini crater, one of Maui’s best snorkel sites. The volcanic atoll off the south coast is a natural marine preserve, home to 250 species of tropical fish. Join the crew at the helm of “Paragon II” as Maui’s afternoon trade winds get the boat to this top destination.
  • Duration: 5 hours
  • Free Cancellation
  • Duration: 5 hours
  • Free Cancellation
From  
US$133.96
From  
US$133.96
See Details

Paragon Performance Sunset Sail

This sunset sail in Maui makes the perfect start or finish to your Hawaiian getaway. Not only does your guide know the perfect spot on the water to see the sunset, but you’ll also enjoy hors d’oeuvres, beer, wine, Champagne, and mai tais as you go. Unlike other cruises, this one sets off on a small boat, making it a more intimate experience for you and other cruise goers.
  • Duration: 2 hours
  • Free Cancellation
  • Duration: 2 hours
  • Free Cancellation
From  
US$80.37
From  
US$80.37
See Details

Sunset Dinner Cruise Aboard the Calypso

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.
  • Duration: 2 hours 30 minutes
  • Free Cancellation
  • Duration: 2 hours 30 minutes
  • Free Cancellation
From  
US$89.95
From  
US$89.95
See Details

Pali Coast Snorkel and Performance Sail

The Pali Coast Snorkel & Performance Sail tour cruises the Pali coastline, particularly Coral Gardens which boasts a unique blend of coral and sea life tucked into the cliffs near the West Maui Mountains. Feel the wind in your hair and the ocean spray as we set out for an adventure fueled by the afternoon trade winds.
  • Duration: 3 hours
  • Free Cancellation
  • Duration: 3 hours
  • Free Cancellation
From  
US$75.02
From  
US$75.02
See Details

Whalewatch Sail Lahaina

Keep watch for humpback whales during this top-rated 2-hour sailing catamaran cruise from Lahaina Harbor. Whether it’s aggressive males competing for mates, mothers calving or listening to whales sing underwater, you never know what this adventure will bring. Certified marine naturalists and marine biologists provide insight into the physiology and behavior of the whales — which you are guaranteed to see. Enjoy snacks and drinks on board.
  • Duration: 2 hours
  • Free Cancellation
  • Duration: 2 hours
  • Free Cancellation
From  
US$68.38
From  
US$68.38
See Details

NEW TO VIATOR

Sunset Sail Maui

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.
  • Duration: 2 hours
  • Free Cancellation
  • Duration: 2 hours
  • Free Cancellation
From  
US$89.16
From  
US$89.16
See Details

Maui Snorkeling Tour to Coral Gardens or Molokini Crater with Optional Lunch

Go snorkeling off the coast of Maui on this boat tour on board 'the Malolo,' a 55-foot (17-meter) power catamaran. You'll 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 will be 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) is available for purchase by selecting the upgrade option when booking.
  • Duration: 3 hours
  • Free Cancellation
  • Duration: 3 hours
  • Free Cancellation
From  
US$36.20
From  
US$36.20
See Details

Sunset Sailing with Live Music and Open Bar

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 2-hour sailing cruise includes an open bar with drinks and 'pupus' (appetizers).
  • Duration: 2 hours
  • Free Cancellation
  • Duration: 2 hours
  • Free Cancellation
From  
US$88.95
From  
US$88.95
See Details

Lana'i Beach Picnic Sail

A gorgeous island known for its pristine beaches and world-class snorkeling Lana’i is an incredible but sometimes difficult-to-reach destination. This Maui sailing trip offers one of the best tours for getting there. Not only is this full-day sail a great chance to check out healthy coral reefs with provided snorkeling equipment, but it’s also packed with inclusions such as breakfast, lunch, and drinks.
  • Duration: 7 hours
  • Free Cancellation
  • Duration: 7 hours
  • Free Cancellation
From  
US$195.00
From  
US$195.00
See Details

Honolua Bay Snorkel Sail

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.
  • Duration: 5 hours
  • Free Cancellation
  • Duration: 5 hours
  • Free Cancellation
From  
US$143.82
From  
US$143.82
See Details

West Maui Snorkel and Performance Sail

Nobody knows the waters of Maui better than our crew. Let us be your hosts as we explore and snorkel the incredible West Maui coast on Paragon. What’s our destination? Some of our favorites are Olowalu, Honolua, or Mokule’ia Bay, but we leave it up to our Captain to decide what’s the absolute best for the day. This adventurous excursion is offered every Saturday.
  • Duration: 5 hours
  • Free Cancellation
  • Duration: 5 hours
  • Free Cancellation
From  
US$155.39
From  
US$155.39
See Details


Book online or call
(888) 651-9785
(888) 651-9785