Big Island
Kauai
Maui
Oahu
All Islands
Hawaii Sailing Adventures

Hawaii Sailing Adventures

Enjoy picturesque Hawaiian sunsets, sightseeing, and marine life encounters when you book your Hawaii sailing trip with ReserveHawaii.com. Sailing in Kauai and other islands are available, with music, food, beverages, and the most breathtaking scenery on every trip. Enjoy a relaxing evening in Hawaii or set out for a morning snorkeling and sailing combo. The choice is yours when you book your Hawaii sailing tour with Reserve Hawaii.

Sort by:
When you purchase a Go Oahu Card, you’ll receive 55% off admission for 32+ of Oahu’s most popular attractions, activities, and tours. From Pearl Harbor to snorkeling, kayaking to paddle boarding, and so much more, you’ll explore Oahu the right way and save money at the same time. All 3, 5, or 7-day passes include free admission to a bonus Oahu attraction! Details
$69.00
per person
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
1046 Reviews
$105.00
per person
Featured in Maui, Hawaii, Molokini Snorkel Trip Aboard the Four Winds II offers an exciting family-friendly experience. Guests can explore premium destinations like Molokini Crater and Coral Gardens to see spinner and Pacific bottlenose dolphins, reefs, fish and other aquatic life while enjoying free use of snorkel equipment and optical masks, a waterslide, an onboard daily movie, and more. Details
TripAdvisor user rating 4.50 out of 5
776 Reviews
$95.00
per person
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
1046 Reviews
$146.00
per person
Featuring five and a half hours aboard a 55-foot luxury sailing catamaran, Capt. Andy’s Na Pali Snorkel Picnic Sail offers an up-close view of the Na Pali coast, complete with a variety of marine life, waterfalls, sea caves, cliffs and more. Each four-hour tour offers narrated guides of the area’s history, snorkeling (with gear provided), a continental breakfast, a deli-style lunch, and more. Details
TripAdvisor user rating 5.00 out of 5
4150 Reviews
$149.00 $139.00
per person
You Save: $10.00
With a variety of exciting tours for guests of all ages, the Kualoa Ranch Experience Tours offer unforgettable experiences while vacationing in Hawaii. Guests can enjoy their choice of: The Valley – Movie Site and Ranch Tour; The Mountains – Jungle Expedition Tour; The Ocean – Ocean Voyage & Hawaiian Fishpond and Garden Tour; and The Secret – Private Beach at Kualoa. Details
TripAdvisor user rating 4.50 out of 5
2396 Reviews
$119.95
per person
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
1046 Reviews
$146.00 $136.00
per person
You Save: $10.00
A four-hour sunset dinner cruise and tour, Capt. Andy's Na Pali Sunset Dinner Sail offers a narrated history and legends of the beautiful island of Kauai, as well as views of exotic marine life, including flying fish, sea turtles, dolphins, whales (seasonal), and more. Plus, guests can enjoy a full Hawaiian-style dinner, and an open bar, unlimited soft drinks, and water. Details
TripAdvisor user rating 5.00 out of 5
4150 Reviews
$119.00 $109.00
per person
You Save: $10.00
A five-and-a-half-hour experience aboard a 65-foot luxury catamaran, Capt. Andy’s Star Na Pali Snorkel BBQ Sail offers a private charter tour along one of the world’s most scenic coastlines. Guests can enjoy a continental breakfast, a barbecue lunch, provided snorkel gear and beverages, while getting up-close views of dolphins, lava tubes, steep valleys and more in Niihau, Polihale, and Kokee. Details
TripAdvisor user rating 5.00 out of 5
4150 Reviews
$169.00 $159.00
per person
You Save: $10.00
Presented by the Pacific Whale Foundation, Ocean Spirit Honolua Bay Snorkel & Sail offers a scenic view of Maui and Honolua Bay. Guests will board the luxury catamaran Ocean Spirit and cruise to one of the island’s top snorkel spots, then experience a guided reef tour, led by certified marine naturalists. The tour often offers up-close views of wild spinner, spotted, and bottlenose dolphins. Details
TripAdvisor user rating 4.50 out of 5
5234 Reviews
$125.00 $120.00
per person
You Save: $5.00
Offered by Capt. Andy’s Sailing Adventures, the Southern Star Na Pali Dinner Sunset Sail features four hours of unforgettable sailing aboard a 65-foot luxury catamaran, complete with a delicious dinner and stunning views of the coastline from Haena to Milolii. Guests can enjoy cocktails, sodas, and water included with the cruise, as well as a breathtaking sunset in the distance. Details
TripAdvisor user rating 5.00 out of 5
4150 Reviews
$149.00 $139.00
per person
You Save: $10.00
Offered by Hawaii Nautical, Adventure Sail Waikiki lets guests experience an exciting expedition to Waikiki’s Diamond Head. Each excursion offers breathtaking sights of Oahu’s natural and city scenery, and guests can get great views of marine wildlife, tropical rainforests and more along the way. Guests receive two free alcoholic drinks, and bar snacks and non-alcoholic beverages are unlimited. Details
TripAdvisor user rating 5.00 out of 5
998 Reviews
$49.00
per person
Experience the legendary Oahu sunsets from out on the ocean. Guests will marvel at the changing colors of the sky reflecting off of the ocean while peering through the glass bottom of the smooth sailing boat. Relax as the Haleiwa Queen cruises through the ocean, granting you exclusive access to views rarely seen. Trust us, a Hawaiian sunset from out on the ocean is a memory you’ll never forget. Details
TripAdvisor user rating 4.50 out of 5
108 Reviews
$55.00 $50.00
per person
You Save: $5.00
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. The sail includes bar snacks, unlimited non-alcoholic drinks, and two bar drinks (21+). The experience departs from Kewalo Basin Harbor daily. Details
TripAdvisor user rating 5.00 out of 5
998 Reviews
$65.00
per person
A two-hour sunset excursion at sea (available Saturdays only), Capt. Andy's Poipu Sunset Sail offers live Hawaiian music, pupus (appetizers), alcoholic beverages, and more while heading toward Maha’ulepu and Kipu Kai. Guests can also enjoy sightseeing (included), featuring up-close views of beautiful marine life, such as dolphins, humpback whales (if in season), and other aquatic creatures. Details
TripAdvisor user rating 5.00 out of 5
4150 Reviews
$69.00
per person