Sailing


HAWAII

15 Best Sailing Tours In Hawaii

Hawaii’s best days out.

The 15 sailing tours travellers book most across Oahu and Maui, with what each one costs, how long it runs and the operator behind it.

15 Best Sailing Tours In Hawaii

Ma'alaea Harbor: Whale Watching Tour Aboard Power Catamaran - The Captain’s Whale Notes: What the Narration Helps You Spot
Cruises & Boat Tours, Maui, Sailing, Tour Reviews, Tours, Whale Watching, Whale Watching Tours

Ma’alaea Harbor: Whale Watching Tour Aboard Power Catamaran

/

1.Ma’alaea Harbor: Whale Watching Tour Aboard Power Catamaran

Hear humpback songs on a narrated 2-hour Maui catamaran cruise from Ma'alaea Harbor. Watch breaches, tail slaps, and more.

Most Popular★ 4.7

“Captain Carlos had the best narration! He has a lot of knowledge and wasn’t afraid to go past time in order for us to see as many whales as possible. I went in March at 3:30pm- we saw a lot of mamas and their calf’s. Lots of “male competition” sightings as well. “Cheapest drinks in…”

827 reviewsFrom $50by Quicksilver Charters

Check Availability →Read the review →

Maui: Molokini and Turtles Luxury Yacht Snorkel - Molokini Crater snorkeling: clearer water, classic reef energy
Cruises & Boat Tours, Maui, Molokini & Turtle Town Snorkeling, Sailing, Snorkeling Tours, Tour Reviews, VIP

Maui: Molokini and Turtles Luxury Yacht Snorkel

/
Oahu: Waikiki Sunset Catamaran Sail and Swim - How the boarding works at Pink Sails Waikiki (and how to avoid stress)
Cruises & Boat Tours, Evening Experiences, Honolulu, Sailing, Sunset & Dinner Cruises, Tour Reviews

Oahu: Waikiki Sunset Catamaran Sail and Swim

/
Maalaea: West Maui Snorkeling & Sailing Day Trip with Lunch - The catamaran ride along West Maui: comfort, scenery, and real weather
1-Day Tours, Cruises & Boat Tours, Lunch Experiences, Maui, Sailing, Snorkeling, Snorkeling Tours, Tour Reviews

Maalaea: West Maui Snorkeling & Sailing Day Trip with Lunch

/

4.Maalaea: West Maui Snorkeling & Sailing Day Trip with Lunch

Sail West Maui on a luxury catamaran with included breakfast, lunch, snorkel gear, and an open bar, with flexible reef stops.

★ 4.8

“It was outstanding and worth every dollar. Especially the guides were great. They explained everything very well and gave insights into everything. From our perspective, it was the best sail trip you can book in Maui. Best regards, Mahalo, the Swiss. It could not be better 🤙”

210 reviewsFrom $200by Sail Maui

Check Availability →Read the review →

Whale Watching Tour on a Charming Hawaiian Catamaran From Maalaea - Finding the Winona at 233 Maalaea Rd (and getting oriented fast)
Cruises & Boat Tours, Maui, Sailing, Tour Reviews, Tours, Whale Watching, Whale Watching Tours

Whale Watching Tour on a Charming Hawaiian Catamaran From Maalaea

/

5.Whale Watching Tour on a Charming Hawaiian Catamaran From Maalaea

Whale-watch from Maui’s Hawaiian-built catamaran Winona in Maalaea with snacks, drinks, and underwater hydrophones for humpback songs.

★ 5.0

“Excellent fun adventure reasonably priced compared to others. We were right up near the Whales. The captian turned off the engines and we drifted then the whales came to us so close. Great crew very knowable and attentive.”

194 reviews2 hours 30 minutes (approx.)From $85.00by Makena Coast Charters

Check Availability →Read the review →

Luxury Catamaran Whale Watch - Comfort and motion: decks, shaded cabin, restrooms, and the step onto the boat
Cruises & Boat Tours, Maui, Sailing, Tour Reviews, VIP, Whale Watching, Whale Watching Tours

Luxury Catamaran Whale Watch

/

9.Luxury Catamaran Whale Watch

Luxury catamaran whale watch from West Maui with marine naturalist, premium open bar, and hydrophone whale songs.

★ 5.0

“Excellent customer service, staff was very friendly. Did not see alot of whales or any quite close but the experience was delightful”

66 reviews2 hours (approx.)From $119.00by Alii Nui Sailing Charters

Check Availability →Read the review →

Hawaiian Canoe Sailing Experience in Maui - Snorkeling in Maui’s Secret Spots: What You Can Actually See
Canoes & Kayaks, Cruises & Boat Tours, Maui, Sailing, Tour Reviews

Hawaiian Canoe Sailing Experience in Maui

/

11.Hawaiian Canoe Sailing Experience in Maui

Sail Maui’s Wailea coast on a private outrigger canoe with snorkeling gear included, chasing sea turtles and possible humpback whales.

★ 4.5

“Amazing experience. Super fun on a handmade Hawaiian Canoe. Complete with snorkeling gear, crystal clear waters made for an awesome adventure! Thank you!”

59 reviews2 hours (approx.)by Hawaiian Sailing Canoe Adventures

Check Availability →Read the review →

Luxury Catamaran Royal Sunset Dinner Sail (Adults-Only) - The Open Bar Reality: What You’re Really Buying
Cruises & Boat Tours, Dining Experiences, Dinner Experiences, Evening Experiences, Maui, Sailing, Sunset & Dinner Cruises, Tour Reviews, VIP

Luxury Catamaran Royal Sunset Dinner Sail (Adults-Only)

/

13.Luxury Catamaran Royal Sunset Dinner Sail (Adults-Only)

Adults-only Maui sunset dinner cruise on a luxury catamaran with a top-shelf open bar, five-course plated meal, and photo option.

★ 5.0

“Very swanky experience. Great food, great crew, excellent food and drinks. Onboard photographer (extra fee) took some nice photos of us. The boat was pristine. I would do it again if I return to Maui!”

43 reviews2 hours 30 minutes (approx.)From $289.00by Alii Nui Sailing Charters

Check Availability →Read the review →

From Maalaea: Whale Watching Catamaran Cruise with Drinks - Hydrophones and the Marine Biologist Talk: What You’ll Learn Beyond Sightings
Cruises & Boat Tours, Maui, Sailing, Tour Reviews, Whale Watching, Whale Watching Tours

From Maalaea: Whale Watching Catamaran Cruise with Drinks

/

14.From Maalaea: Whale Watching Catamaran Cruise with Drinks

See humpback whales off Maalaea on a small catamaran with ice-cold drinks, a marine biologist talk, and hydrophones to hear whale songs.

★ 4.7

“The crew was great, friendly and helpful. We got free fruit, chips and soft drinks on the boat. The boat was clean and they were available at the restrooms. The trip was flawless and even though it was the very end of the season, we did encounter whales! The crew knew what they were doing…”

21 reviewsFrom $69by Makena Coast Charters

Check Availability →Read the review →

Maui: Ma'alaea Catamaran Sunset Sail with Appetizers - The onboard layout: open deck, trampoline, and covered seating
Cruises & Boat Tours, Evening Experiences, Maui, Sailing, Sunset & Dinner Cruises, Tour Reviews

Maui: Ma’alaea Catamaran Sunset Sail with Appetizers

/

15.Maui: Ma’alaea Catamaran Sunset Sail with Appetizers

Maui sunset catamaran with appetizers and unlimited drinks, plus marine naturalists and whale-spotting chances. 2 hours.

★ 4.7

“The sunset cruise was a perfect evening! The crew was very professional. The appetizers and beverages were flavorful. A professional photographer took photos during the evening. Good music and conversation among the guests. Highly recommend!”

16 reviews2 hoursFrom $137by PWF Eco Adventures

Check Availability →Read the review →

More Sailing Tours In Hawaii

Scroll to Top

Explore Hawaii

Both islands, and every way to see them.

Oahu

Maui

Snorkel & Reefs

Boats & Whales

Luau & Nights