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Trilogy – Captain’s Sunset Dinner Sail

by Trilogy

$145.00 BOOK NOW

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Aboard the Trilogy Captain’s Sunset Dinner Sail you will feel like you are at a 5-star restaurant…on the water! All of the tables are arranged for a private restaurant feel without the crowds, aboard Maui’s newest sailing catamaran. The evening begins with your choice of cocktail and a sail along the Pali sea cliffs. Trilogy will take you to a beautiful and secluded location to anchor, where the first course is served. The next two courses will then be served, including an entrée of your choice that our onboard chef is preparing in the galley. Set sail in style! Chef Bailey has thoughtfully incorporated fresh local ingredients into each course that will make your meal a memorable one for sure. Not to mention the service of the staff and crew that will be taking care of your every need.

Lahaina Harbor Available Days:
Thursday, Saturday

Maalaea Harbor Available Days:
Monday, Wednesday, Friday

Both Locations Closed on ALL Major Holidays

Other Activity Options by Trilogy: Trilogy – Discover Molokini, Trilogy – Discover Lanai,

Maui Activities: Departing Lahaina, Departing Maalaea Harbor, Maui Dinner Cruises, Maui Ocean Activities, Maui Sunset Cruises. Locations: Blog,

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Trilogy Captain's Sunset Dinner Cruise

Best Price Guarantee
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Free Cancellation

per Adult $145.00

Date *

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Adult - $145.00

Ages 18 and Up (7.25 Fuel Surcharged Added in Checkout)

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Meet in Lahaina Harbor public loading dock
GPS: Lahaina Harbor, 675 Wharf Street. Lahaina, Hawaii 96761

Use Republic Parking Lot on Dickenson Street in Lahaina. Look for the “Trilogy Parking” sign. Parking is $10.00 for the day. A Trilogy crew member will meet you & help with parking & directions to Lahaina Harbor where Trilogy will check you in.

2 Premium Drinks Free. Cash Bar After.
Reschedule fees within 24 hours apply: $30.00 = Pay Direct

Maui Tickets For Less Cancelation Policy:
A 72 hours notice is required for a refund. Only exception is a note from a local doctor.
No-shows” will be charged full.

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(808) 856-3500

Trilogy - Captain's Sunset Dinner Sail

5.0

Based on 1914 reviews

Trilogy Excursions

4.9

Based on 171 reviews

Trilogy Excursions

5.0

Based on 1743 reviews

Cathy R L.

Awesome company - super organized and so much fun! The captain was awesome as well as the crew! We did the molikini snorkeling trip and could not have had a...

Holly F.

We had the best time on a molokini snorkel trip and a sunset cruise out of Lahaina. The crews on both boats were so friendly and work hard to give you the...

Kathy K.

There isn't much that I can add to the other hundreds of 5 star reviews Trilogy has earned.Only to say that they provided an amazing sailing and snorkeling...

Michelle S.

Perfect for families! We had two families with 6 kids total (ages 2, 3, 6, 8, 8, 10) and the Trilogy crew catered to our every need. Endless POG juice for...

Vidyun S.

Went for a sunset sail cruise from the Lahaina harbor and it was a really fun experience. Captain Rachael and her crew were super fun, attentive, gave us a...

Candice C.

Trilogy 3 was a fantastic crew and Captain! They were extremely hospitable, helpful, and made the experience stress free. They also played awesome music!...

Ron D.

We had a great time on Trilogy 6, the crew was great. Capt. Turtle was was great, very fun and informative with facts and safety. The crew was very...

Jacqueline K.

Wow, I can honestly say this is the best excursion I've ever taken. To start was the sail over to Lanai, first we were treated with a story from the...

Patti R.

Yesterday we went out with Turtle, Chris, Kenzie, and Katie on the Lanai catamaran trip.This group of folks are really wonderful. They are fun to be with...

Magan P.

Captain Turtle, Zach, and Clay did a wonderful job on our trip to Lanai! this was our second time to experience this excursion and have Captian Turtle as...

Eren L.

This is a must do every time I visit!The people and the environment are the perfect half day trip you're looking for.Plenty of honestly delicious food...

Carol T.

We went on a sunset cruise out of Maalaea harbor with Trilogy and booked through a third party called Veltra. Everything from booking to hopping off the...

Katy M.

Absolutely amazing! My husband and I did snorkeling at Kaanapali and the sunset sail. Mario, Claire, Kenzie, bella, and zach did fabulous with both.

Julia F.

We did the snorkeling trip and i have no complaints!! Staff was super friendly and attentive and the food / drinks were delicious. They all made sure we had...

David C.

Amazing. Thank you Triology team led by Captain Turtle. We took the day trip to Lanai. Captain Turtle is the most friendly Cap we have met on these tours....

Kelley B.

My family took the Discover Lanai tour with Trilogy a few days ago and I was a bit hesitant about booking because of the price, but it was worth every penny...

Pam D.

Turtle and crew did awesome job. enjoyed the ride and had an excellent meal with good drinks. Go on this one!

Courtney D.

Our trip to Molokini was definitely one of the highlights of our trip. Capt Dani, Siera, Rocco and Jason were all awesome. The food was great (kiddos LOVED...

Sam H.

My wife and I went on the sunset sail. It was a beautiful night, nice breeze, the ship was well taken care of and the Staff was very nice. Unfortunately the...

Stephanie C.

I'm here to add to the overflowing pile of 5 star reviews for Trilogy, because they are just THAT GOOD.My fiancé and I signed up for the 5-hour Discover...

Lisa C.

We had a GREAT time on the sunset sail from Kaanapali beach on Trilogy III. The beach loading was tough but the crew did a great job. You WILL get wet...

Evelyn C.

We took the snorkeling tour to Lanai coast. The tour starts at 7:30 and the parking situation is a little bit tricky (10 min walk to the Lahaina Harbor and...

Dinah R.

We had such a great experience with trilogy for our snorkel trip to Lanai! We had an all lady crew that were absolutely amazing! The food was good, the...

Ajanaa J.

This was my first time sailing and it was an unforgettable experience. The girls that work on the sail boat were so sweet and friendly. The views were...

Amanda L.

Enjoyed the snorkeling excursion! The crew members were amazing and very attentive. Customer service was 100%. I will book with them again!

Tara R.

My family and I went on a snorkel excursion today with Trilogy on the Trilogy III. The day was amazing! All communication with booking was very clear and...

Trina H.

We booked the day trip with snorkeling for 3 and enjoyed every moment of it. Very covid social distancing friendly!The staff were very fun, very...

Charmian M.

The absolute highlight of our amazing trip to Maui! We were onboard with Captain Casey and crew for the most wonderful morning sailing along the Auau...

Lulu M.

Our adventure with Trilogy was whale watching and it was amazing! We embarked on the Trilogy VI- the newest boat in their fleet that i believe holds about...

Nina F.

Post Covid review- feb 2021Came on this tour for our honeymoon at the recommendation of our travel agentthey did not disappoint!! All the crew learned...

Ryan G.

Great crew for Lahaina catamaran whale watch! Very fun, knowledgeable and courteous! Highly recommend for everyone! Great for all ages. We saw many...

QBar A.

This is not the first time we used Trilogy while in Maui. We did the Molokini trip with 5 of us. Top notch service... especially during COVID. They are...

Michelle M.

The folks at Trilogy NEVER disappoint. We took friends on a snorkel trip and Captain Katie and crew did an outstanding job. Winds were too strong for...

Nicole J.

Hands down, the best boat tour we've taken in a long time. We typically choose a smaller outfit to avoid a large crowd, but thought we would try this...

Meloni K.

We loved captain turtle and his crew. They were very helpful and was able to entertain us through the whole trip. The boat was pretty and it was spacious....

Craig N.

My wife and I, and two other couples in my family, had an amazing evening on board with Sail Trilogy for their Sunset Cruise out of Kaanapali Beach! The...

Terry C.

This is one of the best snorkeling trips I've been on ever! The boat is beautiful and clean, the crew Covid sensitive. Our crew was Captains Turtle &...

Sarah C.

Soooo phenomenal . We loved everything about this experience. Amazing crew of courteous, professional, fun people. They jumped to do anything any everything...

Diane C.

Traveled out with Trilogy yesterday. Great trip, excellent crew, friendly, and very safe. COVID guidelines very well delineated and followed. Great...

Julia T.

Just got back from the Lahaina Sunset Sail -- 10/10 HIGHLY RECOMMEND.Crew: the crew was AMAZING! We were greeted at check in by Captain Turtle who...

Michelle R.

My family and I had such a nice time on a sunset Trilogy cruise Friday night. Riley and crew were incredibly good hosts - we enjoyed the food and cocktails...

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.

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...

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.

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....

Zach S.

We have been to Hawaii 5 times now, and have gone on many excursions. Trilogy does it the best. Great crew, friendly and helpful. Boat is the nicest we have been on. Can't say enough about them. Well worth the money!

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....

SuzyQ1962

Terrific way to watch whales! Smaller boat, great crew (all female this time). Very knowledgeable and we saw 12 whales all in a pod? Bathroom on board. No views blocked, and drinks/snack included. Best adventure ever.

Lisa J.

First of all, the CPT & crew were OUTSTANDING!! The snorkeling, whale watching, snacks, and service is top notch! Everyone has a good vibe/attitude, very friendly and professional. High energy, family friendly, very informed & informative. This was just a really great experience! Get on board/in line ahead of the throng for the best seats. The cook-out was superb! Everyone was really friendly & fun to be around, very accommodating, and knew exactly how to be there for everyone. I would recommend to one and all! Don't forget to give 'em a tip before you disembark...these people deserve it. Mahalo!!

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...

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,...

Howard B.

We just finished the 8 hour sailing/snorkeling / whale watching trip to Lanai. It was fantastic ! Crew and food were great. We saw a number of whales.Highly recommended trip. A shout out to Eric, the new guy, who did a great job.

Angela G.

We did a whale watching excursion with Trilogy on one of their catamarans. It was a great excursion staffed by a very nice crew. Although we didn’t get any close up views of the whales the captain did all he could to hunt for them. After all, it is January; early in the season for humpbacks. I wish we could come back in February! We did see several blows and two whales breaching. Braden served us fruit, cocktails (as much as we wanted....we drank cokes. ), turkey pesto sliders and a chocolate chip cookie. Jenny, the co-captain did a nice job educating us about humpback whales. Kevin, the captain, was very friendly.

Nicci W.

We loved our special birthday trip on the Trilogy, especially the time we spent with Amanda. She was in the water with us when we were snorkeling and she taught us so much about the wildlife we saw and even pointed out a few things we would have missed. Once back on board, she took great care of us as well! Great day!

Veronica M.

We did the day trip to Lanai and let me tell you it was absolutely worth it . Captain Turtle was hilarious and a such a fun person to be around. The boat we sailed is one of the newest boats the island of Maui has it was such an awesome experience.They give you so much good food and I took great pictures while there. I had read some bad reviews and was hoping for the best but so glad I went through Trilogy. Me and my boyfriend had such a good time thanks to Captain Turtle and his team !!