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Hawaii Sailing: 2024 Best Deals

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Experience a morning of diving in and exploring Hawaii's pristine waters in this Big Island snorkeling tour! This highly acclaimed Spirit of Aloha catamaran adventure features a leisurely trip out to the open ocean to see marine animals such as dolphins, turtles, exotic fishes – and even whales. Truly a great experience from start to finish! Details
TripAdvisor user rating 4.50 out of 5
2600 Reviews
$159.00 $157.79
Total Price: $175.31 (USD)
You Save: $1.21
A four-hour deluxe sightseeing dinner cruise in Kauai, the Kauai Sea Tours Na Pali Sightsee Sunset Dinner Cruise Aboard the Lucky Lady offers an afternoon filled with playful dolphins, abundant marine life, humpback whale watching (seasonal), narration about the Na Pali history, and more. Guests of all ages can enjoy a casual, local-style dinner with sodas and select alcoholic beverages. Details
TripAdvisor user rating 4.50 out of 5
3426 Reviews
$215.00 $211.99
Total Price: $234.60 (USD)
You Save: $3.01
Enjoy a Kona sunset cruise that guarantees a leisurely and romantic experience along the Kohala Coast! Getting a Catamaran Sunset Sail ticket promises you a sunset cocktail cruise that highlights wildlife encounters along the journey and relaxing views of the open ocean horizon. Drinks and snacks are served onboard! Details
TripAdvisor user rating 4.50 out of 5
2600 Reviews
$139.16
Total Price: $154.76 (USD)
The Kauai Sea Tours Deluxe Na Pali Snorkel Cruise Aboard the Lucky Lady features snorkeling, sailing, and more. The cruises also offer stunning views of sea cliffs, waterfalls, sea caves, beaches and lush rainforest, as well as spinner dolphins, sea turtles, and humpback whales (seasonally). A continental breakfast and deli lunch are included, plus a variety of alcoholic beverages. Details
TripAdvisor user rating 4.50 out of 5
3426 Reviews
$222.86
Total Price: $243.95 (USD)
A deluxe five-hour snorkel cruise offered on select dates between May and September, Kauai Sea Tours Na Pali Snorkel & Sunset Dinner Cruise Aboard the Lucky Lady combines the adventure of snorkeling with the romance of a sunset dinner cruise. Guests can enjoy learning about Kauai’s history and culture from professional narrators, as well as an early dinner of local-style casual menu items. Details
TripAdvisor user rating 4.50 out of 5
3426 Reviews
$222.86
Total Price: $246.62 (USD)
Enjoy a boat cruise along the sea cliffs and sandy sceneries of the Kona Coast. Kona is known for its beautiful seaside views, pristine crystal clear blue waters, fresh sea breeze and abundance of aquatic wildlife for you to spot! Six back and relax as you set sail for the morning, sunbathing under the Hawaiian sun or taking in the natural beauty of Kona! Details
TripAdvisor user rating 4.50 out of 5
2600 Reviews
$159.00 $157.79
Total Price: $175.31 (USD)
You Save: $1.21
Sail off into the sunset with Pink Sails Waikiki on this relaxing Friday Night Fireworks Cruise and enjoy a spectacular fireworks’ show from the water! Take a front-row seat as the world explodes in color between the calm seas and starry sky. Spend the night dancing and singing along to the music that accompanies you throughout the evening! Details
1 Reviews
$75.00
Total Price: $79.95 (USD)
Spirit of Aloha Catamaran Adventure Sail from Hilton Pier offers an exciting expedition to Waikiki’s Diamond Head aboard a smooth-sailing catamaran. Experience breathtaking sights of Oahu’s natural and city scenery, as well as marine wildlife, tropical rainforests, and more along your journey. Complimentary snacks and non-alcoholic beverages are included. Details
TripAdvisor user rating 4.50 out of 5
1165 Reviews
$48.82
Total Price: $55.17 (USD)
Soak up the sun and sea on Pink Sail's unforgettable Waikiki Sunset Cruise - Swim & Sail! As you travel through the water, taking in the sky's colors and swimming in the pristine ocean, this family-friendly excursion assures you a safe and relaxing experience. If you're lucky, you could even meet some friendly dolphins or turtles along the way! Details
1 Reviews
$47.00
Total Price: $50.10 (USD)
Ready for a relaxing time seeing the best views of Oahu? Aboard this 53-foot catamaran “Honi Olani”, you’ll sail through and see the Kewalo-Kakaako district, Ala Mona Beach shoreline, Waikiki beach and head toward Diamond Head! Enjoy the breeze and see the friendly wildlife out in the ocean as you sail along! Details
TripAdvisor user rating 4.50 out of 5
2600 Reviews
$75.00 $74.00
Total Price: $82.90 (USD)
You Save: $1.00
Set sail on this Hawaii Nautical West Oahu dolphin snorkeling cruise along the Leeward Coast for views of dolphins, sea turtles, and whales (in season). When the catamaran anchors, jump into the clear waters and snorkel with colorful tropical fish and corals. Tour includes a deli lunch, unlimited non-alcohol drinks and two free bar dinks per adult ticket. Details
TripAdvisor user rating 4.50 out of 5
2600 Reviews
$149.00 $147.87
Total Price: $164.37 (USD)
You Save: $1.13
Offered by Hawaii Nautical, the two-hour Whale Watch West Oahu trip allows guests of all ages to enjoy an eco-friendly adventure to spot the majestic humpback whales that roam the Hawaiian waters. Each catamaran tour departs from the Waianae boat harbor daily at 1:30 pm (except on Mondays and Wednesdays) and guarantees a whale sighting or a second tour will be given! Details
TripAdvisor user rating 4.50 out of 5
2600 Reviews
$98.25
Total Price: $109.64 (USD)

Fancy the wind in your hair and salt spray on your skin? Imagine you're gliding over the emerald waters of the stunning Kohala Coast and Kalakekua Bay and sailing Hawaii. As you embark on your sailboat, the vibration from the waves beneath melds harmoniously with the soothing tropical breeze. The captivating sight of playful sea turtles or breaching whales is not rare in these beautiful Hawaiian Island waters.

A range of experiences unwraps itself before you while sailing along Big Island and West Maui coasts - serene sunsets painting a watercolor palette against an azure horizon, forbidden coves nesting along dramatic cliffs, and remote beaches that coax you into dreams of undiscovered retreats. The islands of Hawaii, Maui, Oahu, Kauai, Lanai, and Molokai, each promising a unique voyage, sparkle like sapphire gems within sweeping ocean expanses and beckon adventurers with their allure.

Hawaii's year-round sailing conditions and steady trade winds make it a magnet for novice and seasoned sailors. The diverse water conditions, from glassy calm lagoons to challenging open ocean waves, reward each sailor's palate. And when night falls, stars twinkle bright above, unpolluted and luminous, guiding you along your sailing route over the undulating ocean.

Throughout their sailing tours, voyagers can bask in the tranquillity of the sea, interspersed with moments of sheer thrill when slicing through waters at significant speed. An authentic Hawaiian sailing experience is a symphony of sounds, sensations, and stunning visuals.

Sailing to Hawaii is more than just a sunset sail adventure. It is an immersive journey through time, exploring the beauty of untouched nature, a harmonious blend of turquoise waves, lush green mountains, vibrant rainbows, and a vibrant marine life that echoes the Spirit of Aloha. A sailing trip to Diamond Head West or Diamond Head South Shore is bound to fill your heart with unforgettable memories.

Discover Hawaii's Timeless Beauty: Book Your Unforgettable Sailing Adventure with Tripster Today!


Don't just dream about soaking up the endless beauty of Hawaii - make it a reality! Tripster's tickets to various sailing adventures lets you harness the captivating breeze of Hawaiian waters, immersing you in nature's grandeur. Experiencing this iconic paradise from a sailing charter promises lasting memories. So why wait? When you could be plotting your course through those magical blue tides. Book your trip to Hawaii with Tripster today. And say 'Aloha' to the voyage of a lifetime! Let us help turn your travel dreams into the most unforgettable adventure!