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Hawaii Sailing Trips

103 Results
Molokini Crater Deluxe Snorkel and Sail - Half Day Excursion

Begin your morning with a chef-prepared buffet breakfast as we cruise to Molokini Crater, a world-renowned marine preserve home to over 400 species of tropical …More

Maui, USA

Begin your morning with a chef-prepared buffet breakfast as we cruise to Molokini Crater, a world-renowned marine preserve home to over 400 species of tropical...

5 hours Free Cancellation
5.0 (135)
from
$269
Nāpali Sunset Dinner Sail

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 …More

Likely to Sell Out
Likely to Sell Out
Kauai, USA

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...

4 to 5 hours Free Cancellation
4.8 (563)
from
$264
Polynesian Canoe Sunset Sail

Kamoauli is a locally owned, all-wood, double-hulled, traditional sailing vessel (wa’a kaulua) offering a one-of-a-kind native Hawaiian cultural and educational experience. Come sail along the …More

Likely to Sell Out
Likely to Sell Out
Oahu, USA

Kamoauli is a locally owned, all-wood, double-hulled, traditional sailing vessel (wa’a kaulua) offering a one-of-a-kind native Hawaiian cultural and educational experience. Come sail along the...

2 hours Free Cancellation
5.0 (128)
from
$250
Moana’s VIP Waikiki Turtle Snorkeling Experience on Nalu

Enjoy the Hawaiian Ocean, your way! The “MOANA” (moh-AH-nah), the Hawaiian word meaning Ocean, will be showcased in this customizable experience. From November to May, …More

Oahu, USA

Enjoy the Hawaiian Ocean, your way! The “MOANA” (moh-AH-nah), the Hawaiian word meaning Ocean, will be showcased in this customizable experience. From November to May,...

2 hours Free Cancellation
4.8 (37)
from
$250
Luxury Catamaran Royal Sunset Dinner at Sea (Adults-Only)

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 …More

Maui, USA

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...

2 hours 30 minutes Free Cancellation
4.8 (63)
from
$249
Lahaina Maui Romantic Lanai Snorkel Sail | Meals & Full Open Bar

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 …More

Maui, USA

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...

5 hours Free Cancellation
5.0 (95)
from
$243
Kauai: Deluxe Na Pali Sunset Cruise aboard Lucky Lady

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 …More

Kauai, USA

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...

5 hours Free Cancellation
4.8 (1,559)
from
$223
Maui Molokini Snorkeling Sailing Adventure with Breakfast & Lunch

Sail Maui is proud to offer a destination snorkel sail to Molokini, one of Maui’s most incredible snorkeling destinations. The unique, crescent shaped crater is a natural marine preserve, …More

Maui, USA

Sail Maui is proud to offer a destination snorkel sail to Molokini, one of Maui’s most incredible snorkeling destinations. The unique, crescent shaped crater is a natural marine preserve,...

5 hours Free Cancellation
4.9 (218)
from
$221
Maui: 5-hour Snorkel w/ BBQ Lunch & Open Bar from Kaanapali

5-hour, two-spot snorkel is unlike any other on Ka'anapali Beach as it's aboard Ka'anapali's newest luxury custom built catamarans and includes breakfast, lunch, dessert and …More

Likely to Sell Out
Likely to Sell Out
Maui, USA

5-hour, two-spot snorkel is unlike any other on Ka'anapali Beach as it's aboard Ka'anapali's newest luxury custom built catamarans and includes breakfast, lunch, dessert and...

5 hours Free Cancellation
5.0 (40)
from
$214
Four Winds Molokini Snorkeling Tour from Maalaea Harbor

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 …More

Maui, USA

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...

5 hours Free Cancellation
4.8 (836)
from
$213
Half Day Oahu Combo Adventure: Bike, Sail and Snorkel

Join our Honolulu bike tour on the Bike, Sail & Snorkel adventure. This exhilarating Oahu combo tour from rainforest to reef combines views high above …More

Honolulu, USA

Join our Honolulu bike tour on the Bike, Sail & Snorkel adventure. This exhilarating Oahu combo tour from rainforest to reef combines views high above...

5 hours 30 minutes Hotel pickup offered Free Cancellation
4.7 (67)
from
$197
Snorkel Sail Adventure off Ka'anapali Beach in Maui aboard Gemini

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, …More

Likely to Sell Out
Likely to Sell Out
Lahaina, USA

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,...

4 hours Free Cancellation
5.0 (55)
from
$193
Lahaina Maui Sea Turtle Snorkel Sail Adventure w/Lunch & Open Bar

Ready for an unforgettable day of sailing, snorkeling, island lunch, and open bar aboard our luxury sailing catamaran? Perfect for families, couples, kids, first-time snorkelers, …More

Maui, USA

Ready for an unforgettable day of sailing, snorkeling, island lunch, and open bar aboard our luxury sailing catamaran? Perfect for families, couples, kids, first-time snorkelers,...

5 hours Free Cancellation
5.0 (140)
from
$193
Kealakekua Bay (Captain Cook Monument) Snorkel and Sail Adventure

Join us aboard our luxurious 50’ catamaran “Kona Style”, as we sail the Kona coast. Scan the horizon for dolphins and whales (seasonal) from our …More

Likely to Sell Out
Likely to Sell Out
Big Island of Hawaii, USA

Join us aboard our luxurious 50’ catamaran “Kona Style”, as we sail the Kona coast. Scan the horizon for dolphins and whales (seasonal) from our...

4 hours Free Cancellation
5.0 (713)
from
$189
Waikoloa Catamaran Snorkel Sail Including Lunch

Set sail from Anaeho‘omalu Bay on a 3-hour snorkel and cruise adventure along Waikoloa’s beautiful Kohala Coast. Aboard the spacious Spirit of Aloha catamaran, enjoy …More

Big Island of Hawaii, USA

Set sail from Anaeho‘omalu Bay on a 3-hour snorkel and cruise adventure along Waikoloa’s beautiful Kohala Coast. Aboard the spacious Spirit of Aloha catamaran, enjoy...

3 hours Free Cancellation
4.8 (108)
from
$189
Maui: Catamaran Sunset Whale Watch with Cocktails

Experience the best of whale season at sunset! Watch humpbacks breach and play from the deck of a 65' luxury catamaran as the sun sets …More

Maui, USA

Experience the best of whale season at sunset! Watch humpbacks breach and play from the deck of a 65' luxury catamaran as the sun sets...

2 hours Free Cancellation
5.0 (2)
from
$189

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