Kaanapali Deluxe Sunset Sail

Trilogy - Kaanapali Deluxe Sunset Sail (Crew)Trilogy - Kaanapali Deluxe Sunset Sail (Trilogy Boat)Maui Trilogy activity 221Trilogy - Kaanapali Deluxe Sunset Sail (Sunset Sailing)Trilogy - Kaanapali Deluxe Sunset Sail (Departure)
Trilogy - Kaanapali Deluxe Sunset Sail (Couple)
Trilogy - Kaanapali Deluxe Sunset Sail (Crew)
Trilogy - Kaanapali Deluxe Sunset Sail (Trilogy Boat)
Maui Trilogy activity 221
Trilogy - Kaanapali Deluxe Sunset Sail (Sunset Sailing)
Trilogy - Kaanapali Deluxe Sunset Sail (Departure)

Trilogy – Kaanapali Deluxe Sunset Sail

$89.00 BOOK NOW

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Trilogy has been sailing the coast of Maui and Lanai since 1973 and the Trilogy Kaanapali Deluxe Sunset Sail is their marquee trip. They are the longest running sailing charter on Maui and that’s because they do it right. The Trilogy Kaanapali Deluxe Sunset Sail is a perfectly imagined evening sailing off the coast of Kaanapali enjoying the famous Maui sunsets. Food and drinks are included and have been carefully considered as well. On a brilliant evening, the colors of the sky will reflect on the water, bringing to life a sea of colors. Sunsets on Maui are magical. Trilogy is owned by the Coon Family. They have shaped Maui sea activities into what it represents today. Since founded, Trilogy has expanded their offering to include just about everything you can imagine. From whale watches, Lanai and Molokini snorkeling and Maui sunset sails, Trilogy has an adventure for everyone. Trilogy has the largest fleet of sailing catamarans on Maui, each one represents their name – excellence. Trilogy regularly gives back to the community. Each year they sponsor events on Lanai and Maui for the less fortunate and ocean clean up. Through the years Trilogy has demonstrated a standard of excellence that few other companies can live up too.

During the whale watching season, Trilogy will lower its sails to provide a whale watching tour for their guests. The whale watching season on Maui runs from December 15th to April 15th. It’s a treat to be out on the water during sunset and have a whale watch at the same time. The photos are priceless.
Our agents on Front Street regularly schedule Trilogy’s sunset sail. Our guests always seem to enjoy it. After experiencing a Maui sunset sail with trilogy, we would have to agree with them.

Tip of the Day:
Ladies should wear a wrap for after dark in the winter months.
Boarding is from the beach
it’s a barefoot sail
Chef prepared appetizers.
Juice, soda, and chilled filtered water.
Molokai Mule, Lanai Tai, Maui Brew Co.’s Bikini Blonde Lager, Kona Brewing Company’s Big Wave Golden Ale, Prosecco, Sauvignon Blanc, & Pinot Noir.
Valid photo ID required to consume alcohol.
No handicap access

Other Activity Options by TrilogyTrilogy – Captain’S Sunset Dinner Sail, Trilogy – Discover LanaiTrilogy – Discover Molokini



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  • E-Ticket Delivery
  • Free Cancellation
per Adult $89.00

Ages 21 and Up (4.45 Fuel Charge Applied in Checkout)

Ages 13-20 (3.75 Fuel Charge applied in Checkout)

Ages 3-12 (2.50 Fuel Charge Applied in Checkout)

Ages 0-2

Total $0.00

Location: Kaanapali: In front of Kaanapali Beach Hotel.
GPS: 2525 Kaanapali Park Way Lahaina Hawaii 96761.

Days Available:
Tuesday, Thursday, Saturday Only
Closed on 4th of July, Halloween, Thanksgiving, Christmas Eve & Day, New Year’s Night & Day

48 Hour Cancellation Policy

April 16th – August 31st: Check-in 4:30pm. Departs at 5:00pm.
Return 7:00pm
September 1st – September 30th: Check-in 4:00pm. Departs at 4:30pm.
Return 6:30pm
October 1st – January 31st: Check-in 3:30pm. Departs at 4:00pm.
Return 6:00pm
February 1st – April 15th: Check-in 4:00pm. Departs at 4:30pm.
Return 6:30pm

Check-in 30 minutes prior to activity start time.

Total Duration: 2 hours.

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Trilogy Excursions: Office + Store
Based on 1887 reviews
Trilogy Excursions
Based on 1545 reviews
Dani F.
Dani F.
Thank you for not canceling our reservation during these unpredictable times! We did the Molokini Express Snorkle. It was so much fun! Their photographer...
Myles F.
Myles F.
This review is incredibly overdue, but I have to thank Captain Jeff & Crew! My wife and I purchased the Discover Molokini tour and it turned out to be an...
Dave Baglee
Dave B.
Had an awesome whale watching trip today on Trilogy 5. Fantastic that we got the all women crew too! They made the trip fun, and we got to see SO MANY whales! We also got to enjoy a couple of beverages and some snacks. There was plenty of space to move about and the two hours flew past. One of the best excursions we’ve ever done ! Will do it again, next visit!
Jim Lincoln
Jim L.
We went on the sunset cruise and it was such a delight. We had gone on another catamaran cruise with another company, but Trilogy seemed much more professional and took pride in what they were doing. We were lucky enough to have Captain Katie, who was great, raise the sail and move around without the engines. The other three staff members on board, Shannon, Jason, and Brandon worked their butts off to make sure that everyone had drinks and food while always remaining friendly. We were also lucky enough to see some whales.
Lola J.
Lola J.
I don't like boat cruises. They're crowded and cheesy. Trilogy excursions redefines the boating experience. **Room to sit and watch the water in peace....
Traci Church
Traci C.
This tour was literally the BEST excursion we have ever done! Everything was so well done down to each detail. All of the food that was served was fresh and yummy! And they fed us all day long. The private beach was wonderful and the snorkeling was some of the best we have seen in Maui! All of the staff on the boat were friendly and so attentive! Can’ say enough good about this day of fun:) it was amazing!!
Beth H.
Beth H.
The reviews are spot on. This is the best tour on the island. We had such a great time. The staff was amazing. The boat was perfect. Not too many people....
Scott Nakao
Scott N.
Happily greeted by crew member Sidney's big smile for Trilogy III Sunset Tour. From the beach, she safely boarded all passengers on to their super clean Catamaran. More awesome crew members Lindsey, Kobe, Eric served 1st class yummy bites and tasty beverages. Captain Michael navigated us towards great whale watching opportunities. The ocean breeze filled the sails while taking in Maui's majestic sunset. A Must See aboard the Trilogy III. Thank you Captain and Crew for creating a wonderful life memory for us to take home. Planning our return visit 😉
Roger Coon
Roger C.
Had a truly great experience today on the Lanai trip with Captain Seth, Kristyn, Seth, Sierra, and Leo. From the check-in to the disembarking in Lahaina it was a joy. The service, the attention to our needs, the food, the attention to detail and concern for our safety was top notch! Great professionals working hard to make our experience the best it could be! I would also like to complement the company on the vessel (Trilogy IV) we sailed on! Very well appointed and in beautiful shape! It’s obvious the company wants the highest quality experience for its customers! I would highly recommend Trilogy cruises, and in particular this trip to anyone! Thanks for a wonderful day!
Kate Rowbotham
Kate R.
Highly recommend! We loved our day with Captain Katie and her crew! It was an early start but we had a great morning sail with breakfast (loved the cinnamon rolls!). Made it to Lanai for a few hours of snorkeling and a fabulous lunch. The trip back was fantastic - tons of whales, great cocktails, and ice cream for the kids. It was a fabulous day all around. We have been to Maui several times and even to Lanai; this was our first trip with Trilogy, and we would definitely do another trip!
Kelly K.
Kelly K.
THE BEST! We had so much fun on our whale watch tour on 01/29/2020. We departed from Ka'anapali Beach and did the early tour. It was very convenient for...
Susan deHoll
Susan D.
This was by far the best thing we could have done! Looking around at the other boats at the harbor, I knew that we had been guided correctly to Trilogy. Captain Emily was fabulous as was her crew... Sydney, etc. My mother and I saw so many whale AND learned so much! The breakfast and mimosas were a fabulous surprise. They do not pack these boats. Plenty of room. Best most beautiful boats in the harbor and they know exactly what they are doing. Don't miss out on Trilogy.
Dawn Fries
Dawn F.
Went on Trilogies morning Whale watch and had a phenomenal trip. Saw a mother her calf and her male escort swim right close beside us. We also saw a adult breech and a calf breech. We could not have had a better experience. The crew was knowledgeable and the refreshments were delicious. I would recommend this tour for whale watching in Maui! Captain Raquel and her crew were amazing.
Taryn S.
Taryn S.
Trust in all the 5-star reviews! Fantastic!We did the Deluxe Sunset Sail that leaves from Kaanapali Beach and had the best time. January is whale season,...
Heidi Rhome
Heidi R.
This tour was spectacular! We’ve been on many tours and usually other tours are oversold and too many people gathered on their boats - this tour was the opposite and everyone has a seat. The Captain and crew were amazing and watched out for whales and dolphins. The food was also wonderful. Diverse drink menu as well - unlimited. If you are looking for a high class sail catamaran - this is it! We opted for the sunset sail and it was incredible! Coming from someone that books private tours and travels well I highly recommend Trilogy!
Cheryl Sanford
Cheryl S.
Such a great experience! I highly recommend this excursion to anyone interested in checking out the island of Lanai! We had our young kids with us and they loved it. The staff was super friendly and accommodating and the boat was really nice and clean. They pretty much take care of everything for you from snacks and drinks on the boat, to chairs, sand mats, sand toys and snorkeling gear at the beach on Lanai. They provide lunch on the island and it was awesome! We also saw several whales and dolphins.Overall, one of the best excursions I’ve done!

Questions? Call Maui Tickets for Less (Toll Free) 855-268-0387