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Top 10 Best Hawaii Sailing Trips

Found 108 Sailing Trips activities in Hawaii. Sort by Popularity.
 
-10% Deluxe Na Pali Sunset Tour on the Lucky Lady

Deluxe Na Pali Sunset Tour on the Lucky Lady

(4.7 of 1,440 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

Special Offer
Free Cancellation
Start From $200.57
(Saving 10% ) $222.86
 
-10% Deluxe Na Pali Sunset Tour on the Lucky Lady

Deluxe Na Pali Sunset Tour on the Lucky Lady

  • Hawaii
  • Superb1,440 reviews4.7

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

    Special Offer
    Free Cancellation
    Start From $200.57
    (Saving 10% ) $222.86
 
 

Moana’s Sunset Cocktail Sail Along Oahu's Waikiki Coast

(4.9 of 2,123 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
 
Moana’s Sunset Cocktail Sail Along Oahu's Waikiki Coast

Moana’s Sunset Cocktail Sail Along Oahu's Waikiki Coast

  • Hawaii
  • Superb2,123 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
 
 
-10% Oahu Catamaran Snorkel Tour: See Turtles 100% Guaranteed

Oahu Catamaran Snorkel Tour: See Turtles 100% Guaranteed

(4.9 of 1,214 reviews)

2025 VIATOR TOP 20 BEST EXCURSIONS award in the UNITED STATES including the TOP RATED SNORKEL EXCURSION in the US!! Best value in Waikiki! See turtles GUARANTEED or receive a FULL REFUND! Brand new PREMIUM snorkel equipment inclu... More

Special Offer
Free Cancellation
Start From $40.45
(Saving 10% ) $44.95
 
-10% Oahu Catamaran Snorkel Tour: See Turtles 100% Guaranteed

Oahu Catamaran Snorkel Tour: See Turtles 100% Guaranteed

  • Hawaii
  • Superb1,214 reviews4.9

2025 VIATOR TOP 20 BEST EXCURSIONS award in the UNITED STATES including the TOP RATED SNORKEL EXCURS....

    Special Offer
    Free Cancellation
    Start From $40.45
    (Saving 10% ) $44.95
 
 

Waikiki Turtle Snorkeling Boat Tour and Adventure

(4.7 of 1,197 reviews)

**Turtle Canyon Snorkel Adventure – Swim with Hawaiian Green Sea Turtles!** Join us for a **2-hour snorkeling adventure** at **Turtle Canyon**, one of Oahu’s top snorkeling spots! Cruise along the stunning **Waikiki coastlin... More

Free Cancellation
Start From $68.60
 
Waikiki Turtle Snorkeling Boat Tour and Adventure

Waikiki Turtle Snorkeling Boat Tour and Adventure

  • Hawaii
  • Superb1,197 reviews4.7

**Turtle Canyon Snorkel Adventure – Swim with Hawaiian Green Sea Turtles!** Join us for a **2-ho....

    Free Cancellation
    Start From $68.60
 
 

Day's End Cocktail Sunset Sail

(4.7 of 56 reviews)

Drift away aboard our 65’ luxury sailing catamaran and sail into golden hour for Maui’s most scenic cocktail hour. This isn’t a dinner cruise, it’s happy hour reimagined (a true ‘pau hana’ at sea) with handcrafted drin... More

Free Cancellation
Start From $159.00
 
Day's End Cocktail Sunset Sail

Day's End Cocktail Sunset Sail

  • Hawaii
  • Superb56 reviews4.7

Drift away aboard our 65’ luxury sailing catamaran and sail into golden hour for Maui’s most sce....

    Free Cancellation
    Start From $159.00
 
 

Waikoloa Signature Catamaran Sunset Sail

(4.7 of 382 reviews)

Explore the Waikoloa and Kohala-Kona coastline aboard The Spirit of Aloha, a 54-foot sailing catamaran. Catch the moment the sun slips below the horizon. You may even see the green flash. Board from Anaehoomalu Bay (A-Bay) to sail... More

Free Cancellation
Start From $149.00
 
Waikoloa Signature Catamaran Sunset Sail

Waikoloa Signature Catamaran Sunset Sail

  • Hawaii
  • Superb382 reviews4.7

Explore the Waikoloa and Kohala-Kona coastline aboard The Spirit of Aloha, a 54-foot sailing catamar....

    Free Cancellation
    Start From $149.00
 
 

Kona Catamaran Sunset Sail

(4.8 of 184 reviews)

Explore the beautiful Kona coastline from while aboard the Honi Olani, a 53-foot sailing catamaran. Catch the moment the sun slips below the horizon...you may even see the green flash. Enjoy the blue Pacific Ocean and maybe catch ... More

Free Cancellation
Start From $128.14
 
Kona Catamaran Sunset Sail

Kona Catamaran Sunset Sail

  • Hawaii
  • Superb184 reviews4.8

Explore the beautiful Kona coastline from while aboard the Honi Olani, a 53-foot sailing catamaran. ....

    Free Cancellation
    Start From $128.14
 
 

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

(4.9 of 773 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

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

  • Hawaii
  • Superb773 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
 
 

Turtles & Tacos Luxury Catamaran Snorkel

(4.8 of 82 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 $199.00
 
Turtles & Tacos Luxury Catamaran Snorkel

Turtles & Tacos Luxury Catamaran Snorkel

  • Hawaii
  • Superb82 reviews4.8

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

    Free Cancellation
    Start From $199.00
 
 
-8% Sunset Boat Cruise: Swim and Cruise Waikiki

Sunset Boat Cruise: Swim and Cruise Waikiki

(4.7 of 515 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

Special Offer
Free Cancellation
Start From $43.10
(Saving 8% ) $47.00
 
-8% Sunset Boat Cruise: Swim and Cruise Waikiki

Sunset Boat Cruise: Swim and Cruise Waikiki

  • Hawaii
  • Superb515 reviews4.7

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

    Special Offer
    Free Cancellation
    Start From $43.10
    (Saving 8% ) $47.00
 
 

Leila Na Pali Sunset Dinner Sail

(4.7 of 510 reviews)

Let us wine & dine you as we sail off into the sunset along Kauai’s spectacular Napali Coast. Enjoy appetizers, craft beer, wine, and Koloa Rum Mai-Tais aboard our sleek and spacious sailing catamaran, Leila. Your captain will s... More

Free Cancellation
Start From $263.82
 
Leila Na Pali Sunset Dinner Sail Likely to Sell Out

Leila Na Pali Sunset Dinner Sail

  • Hawaii
  • Superb510 reviews4.7

Let us wine & dine you as we sail off into the sunset along Kauai’s spectacular Napali Coast. Enjo....

    Free Cancellation
    Start From $263.82
 
 

Waikiki Catamaran Snorkel Sail with Lunch: Turtles Guaranteed

(4.7 of 2,106 reviews)

Welcome aboard Hawaii Nautical, you're invited to observe, learn, and experience Hawaiian Green Sea Turtles firsthand! Guests will learn about the life cycle, behaviors, and threats to the Hawaiian Sea Turtles "Honu" (Learning pr... More

Free Cancellation
Start From $109.00
 
Waikiki Catamaran Snorkel Sail with Lunch: Turtles Guaranteed Likely to Sell Out

Waikiki Catamaran Snorkel Sail with Lunch: Turtles Guaranteed

  • Hawaii
  • Superb2,106 reviews4.7

Welcome aboard Hawaii Nautical, you're invited to observe, learn, and experience Hawaiian Green Sea ....

    Free Cancellation
    Start From $109.00
 
 

Waikiki Turtle Snorkel & Sail combo on Hawea Catamaran

(4.8 of 1,586 reviews)

This is the best way to start your day on Oahu! Complimentary cold brew coffee from Honolulu’s local favorite ARVO Café, served with a selection of Anahola Granola bars—Original, Chocolate Chip, Tropical, and Mango & Ginger. ... More

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

Waikiki Turtle Snorkel & Sail combo on Hawea Catamaran

  • Hawaii
  • Superb1,586 reviews4.8

This is the best way to start your day on Oahu! Complimentary cold brew coffee from Honolulu’s loc....

    Free Cancellation
    Start From $89.56
 
 

Na Pali Coast Kauai Snorkel and Sail

(4.8 of 530 reviews)

Families and groups-- say YES to an action-packed, five-hour ocean adventure aboard our gorgeous and comfortable 50’ Kauai-built sailing catamaran, Leila. Let’s explore the cliffs, valleys, sea caves and wildlife of the Napali... More

Free Cancellation
Start From $292.48
 
Na Pali Coast Kauai Snorkel and Sail Likely to Sell Out

Na Pali Coast Kauai Snorkel and Sail

  • Hawaii
  • Superb530 reviews4.8

Families and groups-- say YES to an action-packed, five-hour ocean adventure aboard our gorgeous and....

    Free Cancellation
    Start From $292.48
 
 

Waikiki Sunset Cocktail Sail with Open Bar

(4.8 of 527 reviews)

This is our most popular sail for the fun-loving crowd! All drinks are included on this lively cruise! Strangers become fast friends on this one regardless if your cruising solo or with a crew! We provide juice, soda, bottled wate... More

Free Cancellation
Start From $84.77
 
Waikiki Sunset Cocktail Sail with Open Bar Likely to Sell Out

Waikiki Sunset Cocktail Sail with Open Bar

  • Hawaii
  • Superb527 reviews4.8

This is our most popular sail for the fun-loving crowd! All drinks are included on this lively cruis....

    Free Cancellation
    Start From $84.77
 
 

Snorkel Sail Adventure off Ka'anapali Beach, Maui

(4.9 of 35 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 $183.08
 
Snorkel Sail Adventure off Ka'anapali Beach, Maui Likely to Sell Out

Snorkel Sail Adventure off Ka'anapali Beach, Maui

  • Hawaii
  • Superb35 reviews4.9

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

    Free Cancellation
    Start From $183.08
 
 

'Alihilani Sunset Sail

(4.9 of 83 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 while wa... More

Free Cancellation
Start From $113.51
 
'Alihilani Sunset Sail Likely to Sell Out

'Alihilani Sunset Sail

  • Hawaii
  • Superb83 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 $113.51
 
 

Best Waikiki Snorkel Tour: Guaranteed Turtles at Turtle Canyon

(4.8 of 278 reviews)

-Guaranteed Hawaiian sea turtles at Turtle Canyon -Ample shade and seating on board -Premium snorkel equipment -Fun, friendly, lifeguard certified crew -BYOB (Bring your own Beverage. No glass bottles)... More

Special Offer
Free Cancellation
Start From $83.16
(Saving 16% ) $99.00
 
-16% Best Waikiki Snorkel Tour: Guaranteed Turtles at Turtle Canyon Likely to Sell Out

Best Waikiki Snorkel Tour: Guaranteed Turtles at Turtle Canyon

  • Hawaii
  • Superb278 reviews4.8

-Guaranteed Hawaiian sea turtles at Turtle Canyon -Ample shade and seating on board -Premium snorkel....

    Special Offer
    Free Cancellation
    Start From $83.16
    (Saving 16% ) $99.00
 
 

Deluxe Sail & Snorkel to the Captain Cook Monument

(4.9 of 519 reviews)

Set Sail down the Majestic Kona Coastline with breathtaking views of landscaped ledges of ancient lava flows. As you arrive at the "World Famous Captain Cook Monument" your snorkeling adventure will begin in the turquoise waters a... More

Free Cancellation
Start From $177.73
 
Deluxe Sail & Snorkel to the Captain Cook Monument Likely to Sell Out

Deluxe Sail & Snorkel to the Captain Cook Monument

  • Hawaii
  • Superb519 reviews4.9

Set Sail down the Majestic Kona Coastline with breathtaking views of landscaped ledges of ancient la....

    Free Cancellation
    Start From $177.73
 
 

Luxury Catamaran Royal Sunset Dinner Sail (Adults-Only)

(4.8 of 39 reviews)

Picture yourself boarding Alii's newest and most elegant catamaran as the golden hues of the Maui sunset begin to paint the sky. As you step aboard, you're greeted by the friendly crew who welcome you with warm aloha spirit. The c... More

Free Cancellation
Start From $289.00
 
Luxury Catamaran Royal Sunset Dinner Sail (Adults-Only) Likely to Sell Out

Luxury Catamaran Royal Sunset Dinner Sail (Adults-Only)

  • Hawaii
  • Superb39 reviews4.8

Picture yourself boarding Alii's newest and most elegant catamaran as the golden hues of the Maui su....

    Free Cancellation
    Start From $289.00
 
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