Maui · EVENING EXPERIENCES

The 15 Evening Experiences in Maui That Earn the Price

44 tours  ·  from $50 a head

The good evening experiences fill up weeks ahead in high season. Below: the 15 to book early, what each includes and how they differ.

Maui: Original Sunset Cruise with Open Bar from Ka’anapali Beach - The sunset and the island views
Drinking Tours, Evening Experiences, Maui Boat Tours, Maui Sunset Cruises, Maui Tours, Tour Reviews, West Maui Tours

Maui: Original Sunset Cruise with Open Bar from Ka’anapali Beach

1.Original Sunset Cruise with Open Bar from Ka’anapali Beach

★★★★★★★★★★5.0 · 1,422 reviews · 2 hours (approx.) · from $127Our pick

Board a barefoot catamaran from Ka’anapali Beach for a roughly two-hour sunset sail. Expect an open bar, substantial pupus, coastal views toward Lanai, Molokai, and Kahoolawe, and possible dolphins or winter whales. The crew handles drinks and safety; beach boarding means you will wade through water, and shoes come off before you board.

“We had a great time on the sunset cruise. The drinks and food were great and plentiful. The crew was fun and kept our drinks full. We plan on doing it again next time we're in Maui!”

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Maui Premium Sunset Dinner Cruise from Ka’anapali Beach - Sunset views, dinner, and an open bar
Dining Experiences, Dinner Experiences, Evening Experiences, Maui Boat Tours, Maui Dinner Cruises, Maui Sunset Cruises, Maui Tours, Tour Reviews, West Maui Tours

Maui Premium Sunset Dinner Cruise from Ka’anapali Beach

2.Maui Premium Sunset Dinner Cruise from Ka’anapali Beach

★★★★★★★★★★5.0 · 903 reviews · 2 hours 30 minutes (approx.) · from $166

Sea Maui’s 65-foot catamaran departs directly from Ka’anapali Beach for a 2.5-hour sunset sail with a buffet dinner and open bar. From December 15 to April 15, you may also see humpback whales. Expect to board from the sand, and plan for wet feet. Live music is offered Wednesdays and Saturdays.

“Exceptional experience. The whale watching was off the charts. Multiple whales breaching and frolicking near the boat. Crew was friendly engaging and professional. Truly a bucket list effort!”

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From Ma'alaea Harbor: Sunset Dinner Cruise Aboard the Quicksilver - Dinner: five mains and a full three-course meal
Dining Experiences, Dinner Experiences, Evening Experiences, Maui Boat Tours, Maui Dinner Cruises, Maui Sunset Cruises, Maui Tours, South Maui Tours, Tour Reviews

From Ma’alaea Harbor: Sunset Dinner Cruise Aboard the Quicksilver

3.From Ma’alaea Harbor: Sunset Dinner Cruise Aboard the Quicksilver

★★★★★★★★★★4.5 · 826 reviews · 2 hours (approx.) · from $139

Board a double-decker catamaran at Ma’alaea Harbor for a two-hour sunset cruise with island-style music, table-side service, and a three-course dinner. Choose prime rib, mahi-mahi, chicken, ribs, or a vegetarian pasta, plus two included alcoholic drinks. In winter, keep watch for humpback whales. Check in 30 minutes early at Boss Frog’s.

“We had such a fun time on this trip! Easy boarding, beautiful sunset and music, good food, service was amazing”

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Maui Sunset Dinner Cruise - A Hawaiian Hula Experience - Dinner is generous, but it is not a restaurant meal
Dining Experiences, Dinner Experiences, Evening Experiences, Maui Boat Tours, Maui Dinner Cruises, Maui Sunset Cruises, Maui Tours, Tour Reviews

Maui Sunset Dinner Cruise – A Hawaiian Hula Experience

4.Maui Sunset Dinner Cruise – A Hawaiian Hula Experience

★★★★★★★★★★4.5 · 703 reviews · 2 hours (approx.) · from $158

Board the Pride of Maui for a two-hour coastal cruise near Molokini, starting at 5:00 pm. Dinner, an open bar, live Hawaiian slack-key music, and hula are included. During humpback whale season, the captain may pause near whales in the area. Check in 30 minutes early at Maalaea Harbor.

“Great experience excellent food whale watching and entertainment. Crew was 5 star and I would highly recommend it for a relaxing evening.”

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Maui Ma'alaea Sunset Prime Rib or Fresh Island Fish Dinner Cruise - Dinner choices and what the meal is like
Dining Experiences, Dinner Experiences, Evening Experiences, Maui Boat Tours, Maui Dinner Cruises, Maui Sunset Cruises, Maui Tours, South Maui Tours, Tour Reviews

Maui Ma’alaea Sunset Prime Rib or Fresh Island Fish Dinner Cruise

5.Maui Ma’alaea Sunset Prime Rib or Fresh Island Fish Dinner Cruise

★★★★★★★★★★4.5 · 533 reviews · 2 hours (approx.) · from $149

Board the three-story Calypso at Maalaea Harbor for a two-hour sunset cruise with table-side dinner service, Hawaiian-style music, and a full bar. Choose a main course such as prime rib, fresh fish, ribs, chicken, or penne pasta. The captain may spot whales along the way, but sightings depend on conditions.

“Always good food, drinks and hospitality. Our trip this time was rough but crew made the best of it.”

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Maui Premium Sunset Dinner Cruise & Whale Watch - Whale watching with a naturalist on board
Dining Experiences, Dinner Experiences, Evening Experiences, Maui Boat Tours, Maui Dinner Cruises, Maui Sunset Cruises, Maui Tours, Maui Whale Watching Tours, Tour Reviews

Maui Premium Sunset Dinner Cruise & Whale Watch

6.Maui Premium Sunset Dinner Cruise & Whale Watch

★★★★★★★★★★4.5 · 504 reviews · 3 hours (approx.) · from $189

Leave Maalaea Harbor on a roughly three-hour sunset cruise with a four-course dinner, alcoholic beverages, and live naturalist commentary as you look for migrating whales. The route includes views of McGregor Point Lighthouse and the Pacific, with Lana‘i and Moloka‘i on the horizon. Whale sightings and activity vary.

“We had an excellent experience. It could not have been better. We saw a mother whale teaching her calf how to breech, a single whale decided to hang out beside and under our boat for an incredible amount of time showing off for everyone on board. We also saw many other whales within the 2 hours plus hearing them sing through the hydrophone. I was so looking forward to this excursion and my expectations were beyond met. I’m not sure what I was expecting but the number of whales we saw was incredible. Add in the close up viewing of a whale checking us out, it just could not have…”

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From Ma'alaea: 'Alihilani Sunset Sail Catamaran Tour - A catamaran built for lounging
Evening Experiences, Maui Boat Tours, Maui Sunset Cruises, Maui Tours, South Maui Tours, Tour Reviews, Tours

From Ma’alaea: ‘Alihilani Sunset Sail Catamaran Tour

7.‘Alihilani Sunset Sail Catamaran Tour

★★★★★★★★★★4.8 · 348 reviews · from $114

Sail Maui’s English-speaking crew takes you from Ma’alaea Harbor into the Au’au Channel for a two-hour sunset sail aboard the catamaran ‘Alihilani. Settle on the forward trampoline or in covered seating, enjoy cold hors d’oeuvres and drinks, and watch for dolphins, seabirds, and, from December to March, humpback whales.

“This was a wonderful experience. The staff (Nicholas, Aly, & 2 others whose name I didn’t catch) were fun, helpful & provided great service. They let the guests help choose the playlist. The views & sunset were lovely. Highly recommend!”

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Romantic Sunset Champagne -Private- Maui Air Tour: Intimate & Spectacular! - Practical details before you book
Evening Experiences, Maui Private Tours, Maui Sunset Cruises, Maui Tours, Tour Reviews, Tours, Wine Tours

Romantic Sunset Champagne -Private- Maui Air Tour: Intimate & Spectacular!

8.Romantic Sunset Champagne -Private- Maui Air Tour: Intimate & Spectacular!

★★★★★★★★★★5.0 · 264 reviews · 1 hour (approx.) · from $420

Take an approximately one-hour private air tour from Kahului, with room for up to three people. Your pilot provides live commentary through a headset as you fly over Maui’s coasts, Molokini Crater and Kahoʻolawe. The flight ends with a glass of champagne after landing. Past passengers mention pilots named Steve and Eric, but your pilot may vary.

“Great views. Unique approach. Knowledge pilot. This is a once in a lifetime your that is worth the investment”

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South Maui: Sunset Prime Rib or Island Fish Dinner Cruise - Watching the Sun Set Across Maui’s Coast
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South Maui: Sunset Prime Rib or Island Fish Dinner Cruise

9.Sunset Prime Rib or Island Fish Dinner Cruise

★★★★★★★★★★4.7 · 242 reviews · 2 hours · from $149

Sail Ma’alaea Bay aboard a three-deck catamaran as the sun sets behind Maui’s Kahalawai Mountains, with views toward Lanai, Kaho’olawe, and Molokini. You’ll get dinner, live music, and two alcoholic drinks. Choose your entrée when booking, and watch for humpback whales from December through April.

“The sunset was amazing. There was a rainbow over the mountains. The dinner was excellent. Well worth the trip.”

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Haleakala Maui Sunset Twilight Tour with Dinner - The crater overlook at sunset
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Haleakala Maui Sunset Twilight Tour with Dinner

10.Haleakala Maui Sunset Twilight Tour with Dinner

★★★★★★★★★★4.5 · 240 reviews · 7 hours (approx.) · from $256

Ride an air-conditioned coach from a participating Maui hotel to Haleakalā National Park, stopping at Kula Lodge Marketplace and the visitor center before reaching a crater overlook at 9,740 feet. Park admission and a Kula Bistro dinner to go are included. Guides have included Mitchell, Randall, and Dino, though your driver may differ.

“This was an last minute plan for us and we didn't regret it. Randall (I hope i got your name right) was a great host. He drove us to the top skillfully while sharing his knowledge and his personal experiences of growing up in Maui. We enjoyed the sunset at 10,000 ft atop haleakala while having dinner. The crater wasn't visible due to cloud/ fog but we enjoyed the views despite that.”

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From Ma'alaea: Sunset Dinner Cruise Aboard the Quicksilver - Sailing into the sunset
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From Ma’alaea: Sunset Dinner Cruise Aboard the Quicksilver

11.Sunset Dinner Cruise Aboard the Quicksilver

★★★★★★★★★★4.5 · 218 reviews · 2 hours · from $139

Board the Quicksilver at Maalaea for a two-hour sunset cruise with a three-course dinner served table-side, island-style music, and views from a double-deck catamaran. Choose a main course such as prime rib, island fish, ribs, chicken, or vegetarian pasta. Two alcoholic drinks are included, and wildlife sightings are possible but never guaranteed.

“The crew was very accommodating, friendly, provided good service, and good people skills!”

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Sunset Sail from Ma'alaea Harbor - Sunset, island music, and the Ocean Spirit
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Sunset Sail from Ma’alaea Harbor

12.Sunset Sail from Ma’alaea Harbor

★★★★★★★★★★4.5 · 207 reviews · from $151

Sail for about two hours aboard the Ocean Spirit, a luxury catamaran departing from Ma'alaea Harbor. The crew serves appetizers, non-alcoholic drinks, coffee, and tea as you watch the sunset over the Pacific. Humpback whales may appear in season. Alcohol availability has been inconsistent, so confirm the current policy with Pacific Whale Foundation before you go.

“Our sunset cruise turned into an unforgettable adventure. It was windy out there, but the crew managed to keep their feet on the deck, serve the delicious appetizers, answer all the questions the kids had and guarantee us a great sunset experience. We even saw some whales. I would highly recommend this sunset cruise for kids and adults alike.”

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Maui: Ka'anapali Luxury Sunset Cocktail Sail with Open Bar - Two hours for sea air and a Maui sunset
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Maui: Ka’anapali Luxury Sunset Cocktail Sail with Open Bar

13.Ka’anapali Luxury Sunset Cocktail Sail with Open Bar

★★★★★★★★★★4.7 · 150 reviews · 2 hours · from $134

Set out from Ka'anapali Beach on a two-hour sunset sail aboard a Teralani catamaran. Expect ocean and West Maui Mountain views, an open bar, and pupus such as coconut-crusted shrimp and caprese skewers. You’ll wade through shallow water to board. Humpbacks may appear from November to April, but this is a sunset cruise, not a whale-watching tour.

“Great fun! Captain Julia and First Mates Anna and Nico were fabulous. Felt warmly welcomed, had a wonderful sail with the spectacular sunset and avoided the rain showers. Cocktails and pupus were perfect. Mahalo!”

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Night-Time Snorkel at TurtleTown with Stars, Lights, and Photos - The sea can be bumpy, even near shore
Evening Experiences, Maui Photo Shoots, Maui Snorkeling Tours, Maui Tours, Tour Reviews

Night-Time Snorkel at TurtleTown with Stars, Lights, and Photos

14.Night-Time Snorkel at TurtleTown with Stars, Lights, and Photos

★★★★★★★★★★5.0 · 126 reviews · 1 hour 30 minutes (approx.) · from $119

Swim from Makena Landing toward Turtle Town with a guide such as Robbie, Payson, Joe, Alec, or Jon. The small-group outing starts before sunset, then uses personal flashlights and a powerful colored light to spot turtles and other sea life. Gear is included, photos may cost extra, and you must be able to swim.

“Amazing experience with lots of turtle action! Payson was a fantastic tour guide. The sunset in the water was gorgeous and swimming with the turtles was even better. Highly recommend!!”

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Maui: Ka'anapali Luxury Sunset Dinner Sail - Wildlife is a bonus, not the itinerary
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Maui: Ka’anapali Luxury Sunset Dinner Sail

15.Ka’anapali Luxury Sunset Dinner Sail

★★★★★★★★★★4.8 · 123 reviews · 2h 30m · from $169

Set sail from Ka'anapali Beach aboard a luxury catamaran for a 150-minute sunset cruise with an assisted buffet and open bar. Expect ocean views, the West Maui Mountains and, if wildlife appears, a chance to spot whales or dolphins. Boarding is directly from the beach, so plan for sand and shallow surf. Check in at the Aqualani kiosk by the Outrigger Ka'anapali Beach Resort.

“Fabulous crew and great dinner and cocktails!! The perfect boat for a large group with plenty of room to relax and stretch out. Tanner, Freddie, Ian and Sammie were knowledgeable and a lot of fun!!”

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New in Evening Experiences

★ 4.5Maui Snorkel and Sunset SailFrom $12710 reviews
★ 4.0Haleakala Sunset and Stargazing Audio Tour10 reviews
★ 5.0Haleakalā Sunset Spectacle Private Tour: Maui’s Heavenly EveningFrom $2,0003 reviews
★ 5.0Haleakala Sunset and Astronomy TourFrom $23533 reviews
★ 4.0Haleakala’s Best Sunset Tour with DinnerFrom $31416 reviews
★ 3.5Clear Kayak Sunset and Glow Tour in MauiFrom $1253 reviews
★ 5.0Luxury Catamaran Royal Sunset Dinner Sail (Adults-Only)From $28943 reviews
★ 4.5Ka’anapali Luxury Sunset Cocktail Sail with Open BarFrom $1415 reviews
★ 5.02-Hour Maalaea Luxury Powerboat Sunset Cruise for up to 6 GuestsFrom $27916 reviews
★ 5.0Haleakala Sunset Open Air Jeep Private Tour3 reviews
★ 4.7South Maui Sunset & Celestial CruiseFrom $1324 reviews
★ 4.9Night Time Snorkel At Turtle Town With Lights And StarsFrom $1296 reviews
★ 5.0Luxury Catamaran Royal Sunset 5-Course Dinner CruiseFrom $2894 reviews
★ 4.7Ma’alaea Catamaran Sunset Sail with AppetizersFrom $13716 reviews
★ 4.5Haleakala Sunset and Stargazing Tour with DinnerFrom $29930 reviews

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