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Top 10 Best Hawaii Sailing Trips

Found 107 Sailing Trips activities in Hawaii. Sort by Popularity.
 

Waikiki Turtle Snorkeling & 6-in-1 Adventure with Free Pickup

(4.9 of 559 reviews)

Experience a special turtle snorkeling adventure in Waikiki aboard a smooth and comfortable catamaran. This all-in-one 6-in-1 ocean tour includes snorkeling, kayaking, stand-up paddleboarding (SUP), sea scooters, and more—offeri... More

Free Cancellation
Start From $90.00
 
Waikiki Turtle Snorkeling & 6-in-1 Adventure with Free Pickup

Waikiki Turtle Snorkeling & 6-in-1 Adventure with Free Pickup

  • Hawaii
  • Superb559 reviews4.9

Experience a special turtle snorkeling adventure in Waikiki aboard a smooth and comfortable catamara....

    Free Cancellation
    Start From $90.00
 
 

Kona Signature Catamaran Sunset Sail

(4.8 of 374 reviews)

End your day in paradise with a sunset sail along the beautiful Kona Coast aboard the Spirit of Aloha. Enjoy panoramic views of the ocean and coastline as the sky transforms with vibrant hues of orange, pink and gold. Relax on d... More

Free Cancellation
Start From $109.00
 
Kona Signature Catamaran Sunset Sail

Kona Signature Catamaran Sunset Sail

  • Hawaii
  • Superb374 reviews4.8

End your day in paradise with a sunset sail along the beautiful Kona Coast aboard the Spirit of Aloh....

    Free Cancellation
    Start From $109.00
 
 

Maui Romantic Sunset Sail for Couples with Open Bar & Appetizers

(4.9 of 45 reviews)

Experience a romantic Maui sunset together aboard Akialoa, a luxury 55-foot sailing catamaran. This two-hour evening sail takes you into the picturesque ʻAuʻau Channel, where you can unwind together as the sun sets over the Paci... More

Free Cancellation
Start From $126.82
 
Maui Romantic Sunset Sail for Couples with Open Bar & Appetizers

Maui Romantic Sunset Sail for Couples with Open Bar & Appetizers

  • Hawaii
  • Superb45 reviews4.9

Experience a romantic Maui sunset together aboard Akialoa, a luxury 55-foot sailing catamaran. This ....

    Free Cancellation
    Start From $126.82
 
 

Turtles & Tacos Luxury Catamaran Snorkel

(4.7 of 170 reviews)

Laid-back, fresh, and full of fun, this mid-morning snorkel sail is all about good vibes and island flavor. Cruise aboard our spacious 65’ catamaran and snorkel alongside Hawaiian green sea turtles and colorful tropical fish at ... More

Free Cancellation
Start From $169.00
 
Turtles & Tacos Luxury Catamaran Snorkel

Turtles & Tacos Luxury Catamaran Snorkel

  • Hawaii
  • Superb170 reviews4.7

Laid-back, fresh, and full of fun, this mid-morning snorkel sail is all about good vibes and island ....

    Free Cancellation
    Start From $169.00
 
 

Kauai: Deluxe Na Pali Sunset Cruise aboard Lucky Lady

(4.7 of 1,615 reviews)

Tour the Na Pali coast aboard a Luxury Catamaran, Lucky Lady for an afternoon that features incredible scenery topped off with a spectacular sunset. Look for dolphins, whales, and other marine critters as you sip a drink, snap som... More

Free Cancellation
Start From $222.86
 
Kauai: Deluxe Na Pali Sunset Cruise aboard Lucky Lady Likely to Sell Out

Kauai: Deluxe Na Pali Sunset Cruise aboard Lucky Lady

  • Hawaii
  • Superb1,615 reviews4.7

Tour the Na Pali coast aboard a Luxury Catamaran, Lucky Lady for an afternoon that features incredib....

    Free Cancellation
    Start From $222.86
 
 

Lahaina Maui Romantic Lanai Snorkel Sail | Meals & Full Open Bar

(5 of 88 reviews)

Experience the flexibility of a true ocean adventure aboard our premium Gold Coast catamaran, where our experienced crew selects the day’s best snorkel destination based on weather, tides, and ocean conditions. • Explore Lana... More

Free Cancellation
Start From $242.60
 
Lahaina Maui Romantic Lanai Snorkel Sail | Meals & Full Open Bar Likely to Sell Out

Lahaina Maui Romantic Lanai Snorkel Sail | Meals & Full Open Bar

  • Hawaii
  • Superb88 reviews5

Experience the flexibility of a true ocean adventure aboard our premium Gold Coast catamaran, where ....

    Free Cancellation
    Start From $242.60
 
 

Waikiki Sunset Cocktail Sail on the Moana Catamaran

(4.9 of 2,451 reviews)

All aboard! There is no better place to be during Oahu’s magnificent golden sunsets than on our Waikiki Sunset Cruise, an unmatched experience complete with premium drinks, indescribable views, and music. As we sail alongside Oa... More

Free Cancellation
Start From $89.99
 
Waikiki Sunset Cocktail Sail on the Moana Catamaran Likely to Sell Out

Waikiki Sunset Cocktail Sail on the Moana Catamaran

  • Hawaii
  • Superb2,451 reviews4.9

All aboard! There is no better place to be during Oahu’s magnificent golden sunsets than on our Wa....

    Free Cancellation
    Start From $89.99
 
 

Oahu Catamaran Snorkel Tour: See Turtles 100% Guaranteed

(4.9 of 1,811 reviews)

Experience one Viator's 2025 Top 20 Best Excursions in the country. This Oahu Catamaran snorkel tour offers unbeatable value and family-friendly fun from Waikiki. Swim alongside Hawaiian green sea turtles and vibrant tropical fis... More

Free Cancellation
Start From $49.99
 
Oahu Catamaran Snorkel Tour: See Turtles 100% Guaranteed Likely to Sell Out

Oahu Catamaran Snorkel Tour: See Turtles 100% Guaranteed

  • Hawaii
  • Superb1,811 reviews4.9

Experience one Viator's 2025 Top 20 Best Excursions in the country. This Oahu Catamaran snorkel tour....

    Free Cancellation
    Start From $49.99
 
 

Waikiki 2 Hour Sunset Cruise Catamaran Swim Adventure

(4.7 of 625 reviews)

There’s no better place to take a dip than the crystal-clear waters of Waikiki—and no better way to experience a Hawaiian sunset than from the ocean, with the iconic Waikiki coastline as your backdrop. As the sun begins to se... More

Free Cancellation
Start From $58.64
 
Waikiki 2 Hour Sunset Cruise Catamaran Swim Adventure Likely to Sell Out

Waikiki 2 Hour Sunset Cruise Catamaran Swim Adventure

  • Hawaii
  • Superb625 reviews4.7

There’s no better place to take a dip than the crystal-clear waters of Waikiki—and no better way....

    Free Cancellation
    Start From $58.64
 
 

Waikiki Sunset Boat Cruise

(4.9 of 262 reviews)

No vacation is complete without experiencing a vibrant Hawaiian sunset from the water. Unobstructed views create the best photo opportunities! Listen to great music as we cruise the Waikiki coastline with views of Diamond head cra... More

Free Cancellation
Start From $50.00
 
Waikiki Sunset Boat Cruise Likely to Sell Out

Waikiki Sunset Boat Cruise

  • Hawaii
  • Superb262 reviews4.9

No vacation is complete without experiencing a vibrant Hawaiian sunset from the water. Unobstructed ....

    Free Cancellation
    Start From $50.00
 
 

Lahaina Maui Sunset Sail on 'Alihilani

(4.9 of 212 reviews)

We pride ourselves on sailing, so enjoy the natural sounds as we turn of our motors and raise our sails. Our spacious catamarans make for a luxurious experience, allowing for incredible views of Maui and the inter islands from the... More

Free Cancellation
Start From $126.82
 
Lahaina Maui Sunset Sail on 'Alihilani Likely to Sell Out

Lahaina Maui Sunset Sail on 'Alihilani

  • Hawaii
  • Superb212 reviews4.9

We pride ourselves on sailing, so enjoy the natural sounds as we turn of our motors and raise our sa....

    Free Cancellation
    Start From $126.82
 
 

Ka'anapali Luxury Sunset Cocktail Sail with Open Bar in Maui

(4.6 of 88 reviews)

Set sail on a luxurious journey along West Maui's stunning coastline with the Holo Holo Sunset Cocktail Sail. Departing from Ka’anapali Beach, this 2-hour experience offers breathtaking views of the sunset complemented by deligh... More

Free Cancellation
Start From $141.98
 
Ka'anapali Luxury Sunset Cocktail Sail with Open Bar in Maui Likely to Sell Out

Ka'anapali Luxury Sunset Cocktail Sail with Open Bar in Maui

  • Hawaii
  • Superb88 reviews4.6

Set sail on a luxurious journey along West Maui's stunning coastline with the Holo Holo Sunset Cockt....

    Free Cancellation
    Start From $141.98
 
 

Snorkel Sail Adventure off Ka'anapali Beach in Maui

(5 of 53 reviews)

While snorkeling along West Maui’s coastline, experience warm waters abundant with sea life. You will see a variety of tropical fish, and if you’re lucky, an endangered Hawaiian Green Sea turtle called a ‘Honu’. A hot buff... More

Free Cancellation
Start From $193.17
 
Snorkel Sail Adventure off Ka'anapali Beach in Maui Likely to Sell Out

Snorkel Sail Adventure off Ka'anapali Beach in Maui

  • Hawaii
  • Superb53 reviews5

While snorkeling along West Maui’s coastline, experience warm waters abundant with sea life. You w....

    Free Cancellation
    Start From $193.17
 
 

Waikiki 2 hour Turtle Canyon Snorkeling Adventure

(4.7 of 1,518 reviews)

Join us for a 2-hour snorkeling adventure at Turtle Canyon, one of Oahu’s top snorkeling spots! Cruise along the stunning Waikiki coastline aboard the either 55-ft open-style catamaran or 50-ft double-decker power catamaran and ... More

Free Cancellation
Start From $80.71
 
Waikiki 2 hour Turtle Canyon Snorkeling Adventure Likely to Sell Out

Waikiki 2 hour Turtle Canyon Snorkeling Adventure

  • Hawaii
  • Superb1,518 reviews4.7

Join us for a 2-hour snorkeling adventure at Turtle Canyon, one of Oahu’s top snorkeling spots! Cr....

    Free Cancellation
    Start From $80.71
 
 

Waikiki Turtle Snorkel and Sail on Hawea Catamaran

(4.8 of 1,786 reviews)

Experience the best of Waikiki on a Turtle Snorkel & Sail combo aboard the Hawea Catamaran. This popular Oahu tour blends marine exploration and island relaxation in one extraordinary outing. Swim among sea turtles and tropical fi... More

Free Cancellation
Start From $89.56
 
Waikiki Turtle Snorkel and Sail on Hawea Catamaran Likely to Sell Out

Waikiki Turtle Snorkel and Sail on Hawea Catamaran

  • Hawaii
  • Superb1,786 reviews4.8

Experience the best of Waikiki on a Turtle Snorkel & Sail combo aboard the Hawea Catamaran. This pop....

    Free Cancellation
    Start From $89.56
 
 

Oahu Catamaran Waikiki Sunset on 40 Foot Catamaran: Food and BYOB

(4.9 of 1,014 reviews)

2025 VIATOR TOP 10 award for WATER EXPERIENCES in the UNITED STATES including the TOP SUNSET CRUISE in the US! Join us for a beautiful Hawaiian sunset!! We have been sailing the Pacific waters off of the Island of Oahu since 1985... More

Free Cancellation
Start From $54.99
 
Oahu Catamaran Waikiki Sunset on 40 Foot Catamaran: Food and BYOB Likely to Sell Out

Oahu Catamaran Waikiki Sunset on 40 Foot Catamaran: Food and BYOB

  • Hawaii
  • Superb1,014 reviews4.9

2025 VIATOR TOP 10 award for WATER EXPERIENCES in the UNITED STATES including the TOP SUNSET CRUISE ....

    Free Cancellation
    Start From $54.99
 
 

Waikiki: Sunset Cruise from Beach & Cocktail Open Bar | Oahu

(4.7 of 625 reviews)

-Open bar fully included: beer, wine, cocktails, and more -21+ only on Fridays! -Direct beach boarding — no harbor shuttle, no bus, no wasted time -Spacious 45-foot catamaran with near 360 degree view -Families welcome: Keiki ra... More

Free Cancellation
Start From $84.77
 
Waikiki: Sunset Cruise from Beach & Cocktail Open Bar | Oahu Likely to Sell Out

Waikiki: Sunset Cruise from Beach & Cocktail Open Bar | Oahu

  • Hawaii
  • Superb625 reviews4.7

-Open bar fully included: beer, wine, cocktails, and more -21+ only on Fridays! -Direct beach boardi....

    Free Cancellation
    Start From $84.77
 
 

Lahaina Maui | Romantic Luxury Sunset Sail | Motors Off Sailing

(4.9 of 44 reviews)

Experience a romantic Maui evening aboard Paragon, Sail Maui's flagship 47-foot performance sailing catamaran. Settle in together and experience the peace and serenity of sailing the beautiful ʻAuʻau Channel, surrounded by the s... More

Free Cancellation
Start From $126.82
 
Lahaina Maui | Romantic Luxury Sunset Sail | Motors Off Sailing Likely to Sell Out

Lahaina Maui | Romantic Luxury Sunset Sail | Motors Off Sailing

  • Hawaii
  • Superb44 reviews4.9

Experience a romantic Maui evening aboard Paragon, Sail Maui's flagship 47-foot performance sailing ....

    Free Cancellation
    Start From $126.82
 
 

Honolulu Sunset Sail from Kewalo Harbor Including Drinks

(4.8 of 217 reviews)

Our Sunset Sail tour is a fun and wild 90-minute sail where all drinks are complimentary! (Must be 21+ with valid ID to consume alcoholic beverages). Sail the south shore from Kaka'ako Waterfront to Waikiki, with beautiful views ... More

Free Cancellation
Start From $61.50
 
Honolulu Sunset Sail from Kewalo Harbor Including Drinks Likely to Sell Out

Honolulu Sunset Sail from Kewalo Harbor Including Drinks

  • Hawaii
  • Superb217 reviews4.8

Our Sunset Sail tour is a fun and wild 90-minute sail where all drinks are complimentary! (Must be 2....

    Free Cancellation
    Start From $61.50
 
 

Four Winds Molokini Snorkeling Tour from Maalaea Harbor

(4.7 of 862 reviews)

Cruise to Molokini and snorkel into a crescent-shaped submerged volcanic crater! Discover the beautiful coral reefs and tropical fish underneath the water, or bask in the warmth of paradise. From the experienced snorkeler to those... More

Free Cancellation
Start From $213.41
 
Four Winds Molokini Snorkeling Tour from Maalaea Harbor Likely to Sell Out

Four Winds Molokini Snorkeling Tour from Maalaea Harbor

  • Hawaii
  • Superb862 reviews4.7

Cruise to Molokini and snorkel into a crescent-shaped submerged volcanic crater! Discover the beauti....

    Free Cancellation
    Start From $213.41
 
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