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    Calypso Sunset Dinner Cruise

    3.8 (75 reviews)
    Closed 6:00 am - 8:00 pm

    Calypso Sunset Dinner Cruise Photos

    CALYPSO SUNSET DINNER CRUISE ATMOSPHERE

    What's the vibe?
    Classy
    Good for kids

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    Just a stairwell backdrop. Not much views.
    Clarissa T.

    I booked this event for my family for the cruise on 10/16/21 to celebrate my brother's. I had gone to a sunset dinner cruise in Oahu and was thinking this would be somewhat the same, and to my disappointment, it wasn't at all. First off, the boarding experience should be improved. The staff had us line up at the side of the boat, and said we would check in a half hour early and board promptly at 5pm. Due to this, several of us were standing around by 4:30pm, but the check in process started late. We then also boarded late...around 5:15pm'ish. Once inside, the views around the boat were not too good. The only clear view was on the top outside deck. The food was also just okay for me. The staff was friendly, but didn't seem to really have anything to engage the guests. There was also nothing special they added for celebrations, (birthdays, anniversaries, etc). In the future, I would suggest to book any dinner cruises in Oahu. The cruises there have more of an all you can eat crab leg buffet style cruise with a polynesian dance show and dancing for the guests as well. They also allow add-on's like a bottle of wine, or a cake to celebrate any special occasions.

    The Calypso dinner Cruise boat
    Kathy D.

    Was ok, not the best Mahi-mahi. A bit over cooked, disappointing. Nice cruise, cheap made drinks but nice staff. I guess the others loved their prime rib and chicken though. Sat inside so missed the sunset but got good photos of the after sky. Music was awesome! Tim McDill check him out on Facebook! A very relaxing cruise. Just expected great Mahi Mahi in Maui... for the cruise price.

    Tim McDill provided the musical entertainment. Great song selection, good guitar playing, and what a voice!
    Rob M.

    Great whale watching and sunset dinner cruise. Easy check-in, with seating on three levels. We sat on the middle deck, open air, and near the live entertainment-Tim McDill, playing guitar and singing. What a great voice! Two drinks per person were included. Generous wine pours and a good selection of canned beers. Our friends tried the cocktails, but they were not really good. The Dark and Stormy did not have real ginger beer (that's how they should be made) but they used several different flavors from the soft drink dispenser. Yuck. The tequila mixes were bad, too. Get cocktails at a good bar or restaurant, not on a boat! Our friendly server replaced the Stormy with a glass of Chardonnay-good job! Salad and a dinner roll, followed by the entree and then brownies for dessert. I thought the ribs were the best dinner choice. My wife tried them and wished she had ordered them, too. Prime rib, fish and chicken were all OK. Saw lots of whales, great sunset, and got back to Maalea Harbor in the dusk. Big, comfortable boat. Our favorite dinner cruise on Maui.

    Cocktails at sunset
    Jasmin Nina S.

    So beautiful! Make sure you get there a little early to pay parking at the dock. The parking pay machines are a little finicky so bring cash just in case it decides not to take card that day lol. They have you wait in a line before boarding, and a photographer takes your picture in front of the boat (they are printed and sold at the end after you get off the boat - my husband and I decided not to purchase the pictures). The seats are assigned (as of November 2021), not sure if this was because of COVID or if that was how it always has been, but I am so glad they were pre-assigned. It made the entire boarding process and overall experience very seamless. My husband and I were seated toward the front of the boat and shortly after, a waitress came by to take our drink orders. They give you drink tickets to use for alcoholic beverages. Pina coladas were yummy! The meal included bread, salad, mahi mahi, mashed potatoes, veggies, and dessert (choice of cheesecake and chocolate cake). The food was good and very filling! The servers forgot us from time to time, we had to remind them about our drinks a couple times. It's the ocean breeze, live music, and sunset that really sell this cruise for me. It was all so beautiful and romantic! Also, make sure to bring a light sweater/jacket, it got chilly on the way back to the dock. This was such a wonderful experience for my husband and I, a great way to kick off our Maui vacation. I would definitely recommend this excursion!

    Mahi option
    Renz L.

    Needed a fun, semi-casual activity for 5 adults + 4 kids under 5 and this was perfect! I was weary bc we get seasick easily but the boat was a 3 level snorkeling catamaran and they take you to the calm bays along Maui's west coast. Parking was free on the dock. Each adult gets 2 alcoholic drink coupons, unlimited non-alcoholic drinks. Food was solid banquet style (not a gourmet made to order kitchen): ceasar salad, dinner roll, mashed potatoes, vegetables and either mahi or prime rib with cheesecake or chocolate cake for dessert. Live music was pleasant, guy on guitar with synthetic pedals and played generational top 40 hits. Crew went out of their way to serve you! Captain explained geography and had sense of humor. Been on cruise ships and fancy dinner river cruises, but this one was hit all the checkpoints for what we needed. Lasts 5:30pm to ~ 8pm.

    the sun setting over the ocean

    It was a nice experience , however for 250$ for two people I expected a lot more for the money . I was sold by a event coordinator he said it was a luxury dinner with live music , which def wasn't live music and basic dinner . Food was okay, was a nice experience but don't think I'd be back, staff was friendly and nice .

    Just completed Calypso dinner cruise, couldn't have been more pleased with the quality of the dinner the mahi was incredible. The crew couldn't have been any nicer, it was a great evening.

    Salad with soggy croutons and a hot as rock bread stick.

    The food was horrible. Two glasses of warm water and a salad with soggy croutons were on all the tables. The bread stick we didn't dare eat. Hard, cold, and looked like fake food for child play. My pasta was so dry I asked for some marinara sauce on the side. The waiter said they didn't have any pasta sauce onboard so I pushed my plate away. It was too dry to choke down. The music was terrible and sleepy time music. Save your money go eat at Mama's Fish house. Two stars are for the staff 0 stars for food and ambience. The views will just as great on a different cruise.

    View from Cruise
    Luanda L.

    Ehh, if you're just looking for a cruise to get pictures of the sunset and possibly see some whales and dolphins, sure. Then book it. I wasn't really impressed with their food. They told us from the get go that they're using a new catering company... the fish was not well seasoned.. the sauce barely saved it. The drinks were watered down.

    Sunset view from Calypso - moon showing.

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    Page 1 of 2

    Ask the Community - Calypso Sunset Dinner Cruise

    How long is the cruise?

    Roughly 5pm to 8pm

    Do you have to pay to park?

    There is paid parking and also free parking between the Maui Ocean Center and 76 Gas Station.

    Don’t See Your Question? Ask Away!

    Review Highlights - Calypso Sunset Dinner Cruise

    Being that it was whale season, we did in fact encounter MANY whales during our dinner cruise.

    Mentioned in 4 reviews

    Read more highlights

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    My wife and I booked the voyage as our 22 year anniversary and it did not disappoint…read more The entire tour (Lahaina to Lanai) was spectacular. Captain Riley explained much of what the islands in the past (before Captain Cook) and to today. The boat (Trilogy VI) was brand new and beautiful. When we arrived on Lana'i we went to a beautiful white sand beach with great snorkeling, and a hike to see some amazing views. The food...! It almost never stopped with breakfast, a big and delicious lunch. Got back on the boat and saw dolphins, flying fish, and other tropical sea life. The crew were amazing from start to finish. Friendly, helpful, and great crew members. The photographer was friendly and knowledgeable about the best shots. They provide the photos electronically via a very reasonable $85 (nice as a keep sake of the photos of the two of us that the photographer placed us in.) Cannot recommend Trilogy enough. They've been around since 1973 and really have it figured out. Our 18 year old son loved it too. It's great for any age.

    My wife's and my Trilogy Turtle Snorkeling tour was amazing: 10 / 10 in every respect…read more First Mate Zach met us in the parking lot and had us laughing and enjoying ourselves before we even boarded Trilogy We saw many fish and turtles, and toward the end of the tour Captain Justin found (and the crew pointed out) dozens of dolphins, both Bottlenose and Hawaiian Spinner The entire crew, Captain Justin, Zach, Bex, Lilly, and photographer Julia, were tremendous! My wife and I had some special needs, and Zach accommodated us far beyond our expectations The food and beverages were delicious and provided in generous amount We felt very comfortable with the detailed safety instruction, equipment, and practices Trilogy is obviously a firm that is dedicated to delighting its customers, and today we became permanent Trilogy fans

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    Four Winds Molokini Maui Snorkel Tour

    Four Winds Molokini Maui Snorkel Tour

    4.6
    (803 reviews)
    0.1 mi
    Locally owned & operated
    Kid friendly

    My friend is going to be leaving the islands after 25 years. He also wanted to visit my family on…read moreMaui. I thought I would make his departure very special with a Molokini snorkel trip. We could not have been more lucky. I called to make sure there was vegan options for food and also the person that I spoke with made it easy to purchase 4 tickets for my father and stepmother as well as for my friend and I. We arrived early and found parking. There is also easy parking on the pier for a dollar an hour. I booked these tickets about a month in advance. Why I say we were very fortunate is because the weather although cloudy on the way to Molokai cleared up twice while we were in the water. The breakfast was fresh there was croissants small corn muffins and fresh fruit as well as deviled eggs. My parents enjoyed the devil eggs tremendously. The croissants were very fresh tasting. There were plenty of fish to snorkel and see. The crew was spectacular the captain pointed out different formations and shared interesting history 2 and from the island. What made the trip spectacular was the incredible amount of whales we saw. At 1 point the captain cut the engine because whales played around our boat going underneath several times. It was a trip of a lifetime.

    They hide the fact that you have a 50% chance of not going to the crater…read more... I am writing this review while on the boat because instead of going to the crater, they took us to a spot easily accessible from the road with little fish/diversity. Snorkeling off the beach from our hotel has much more fish and diversity than the spot they took us to. Waste of money and more importantly precious vacation time as you might be stuck at an awful spot for 5 hours. The day is not particularly windy either so I suspect it was due to the amount of children on the boat is why they neglected to deliver on going to the crater and instead went somewhere utterly useless.

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    Snuba, no experience necessary.  Allows you to float at any level using air just like the pros who dive.  Lots of fun, be sure to try it!
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    Four Winds Molokini Maui Snorkel Tour
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    We've sailed with Sea Maui 8 or 9 times on their Sunset Dinner, Sunset Cocktail and Whale watching…read morecruises. For us, we prefer the Sunset Cocktail cruise as it's the perfect amount of food and drinks. This last trip, we took the whole family for the express snorkel trip. It's a shorter trip, which worked perfectly for the younger kids and didn't tie up a big amount of island time. Captain Nick and his crew was all about making sure all had a great time while keeping safety at the top of mind. They guaranteed we'd see turtles... we did! Immediately. I accused them of being remote controlled because they were there right on cue! I'm not a big snorkel guy, but I had a blast. We'll keep returning to Sea Maui. Greatest crew on Maui !!

    On our vacation to Maui last week, we took trips out to the sea with Sea Maui twice. Our first trip…read moreout was an adults-only family excursion while the kids hung out with their grandma and auntie. The catamaran was pretty sweet, with some really comfy bean bags overlooking the edge out to the ocean. While we did occasionally get splashed in this area, it was worth the unobstructed view of the sunset and the breeze in my hair. The crew was especially sweet and treated all of us like absolute royalty. A note to those who are prone to motion sickness: do not try to be brave and only wear sea bands thinking you'll be okay. Take your Dramamine an hour before you board the catamaran. While the first half of our dinner cruise was fine with my motion sickness, the second half of the trip left me feeling really queasy around dinner service time. This made me very sad. This was no fault of the crew, and 100% my fault for thinking I could tough it out. If you are ill-prepared, the crew has ginger ale, club soda and ginger chews to help. Speaking of dinner, the few bites I was able to eat on our first trip were fantastic: a full dinner buffet prepared by Cafe Jai. The salmon was perfectly tender, as was the short rib. The caesar salad was just the right amount of tangy (and the extra dressing was really great on the salmon as well.) I'm not sure what kind of sauce was on the crispy seasoned potatoes but they were absolutely delightful. And of course, the crown on top of a delicious meal was the mini brownie cup we were served for dessert before we wrapped up the trip. Our second trip (where I was prepared with some Dramamine) was a memorial for our grandparents, where we released their cremains at sea with eco-urns. I must say that the crew handled everything wonderfully. We had the full bar, another beautiful buffet spread including some delicious crispy chicken, a pesto pasta salad, pulled beef sliders, and rolls. After we said our emotional goodbyes, we were given rose petals to release into the ocean. We even received certificates after the trip that gave us the coordinates of where my grandparents cremains were released. I seriously cannot thank Sea Maui enough for giving my family a truly memorable experience on our trip to Maui. They made our trip so special. A million thanks for the kindness!

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    Maui Reef Adventures

    Maui Reef Adventures

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    A snorkeling trip to Molokini Atoll with a side trip to swim with the green sea turtles right off…read morethe beach from the homes of Tiger Woods, Michael Jordan, and a house once owned by David Bowie, was a must for our family Christmas Vacation on Maui. We selected this company due to their excellent reviews, and we're sure glad we did! Captain Ryan and deckhands Jade and Chloe were friendly, funny, knowledgeable and accommodating. And even though the tour was for snorkeling only, Ryan decided to throw in some dolphins and whale watching we hadn't expected! Lunch and snacks were very good, too. The 60' Rigid Hull Inflatable Boat (RHIB) was maneuverable, comfortable, and with FOUR 350 HP Yamaha outboards (that's 1,400 HP), VERY fast! Just an outstanding day for the whole family. First rate all the way!

    We booked a whale watching activity at 1pm. There was probable about 10 people in the boat (small…read moregroup, which I like better). The captain and naturalist were nice, friendly and knowledgeable. We saw a lot of whales, sea turte, and we also heard the whales sing! The captain has a hyrophone and that's when we heard the whales sing. Towards the end of our tour, I heard the whale sounds with just my ear and without the hydrophone. It was a really cool and memorable experience. I highly recommend Maui Reef Adventure.

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    Whale splashing
    Beautiful and close to our boat. This company respected the ocean and its guests
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    Pride of Maui

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    Staff were excellent! The ride was smooth. I have been on their snorkeling numerous times and I was…read moreimpressed every time. I went on the sunset dinner cruise this time and it was also amazing!

    We did the deluxe Molokini Crater and Turtle Town tour. The boat experience was excellent though…read moresomehow my boyfriend and I ended up getting on last and getting the leftovers for seating. The staff was all fantastic--Kayden, Sienna, Carly and Jim. The weather was great and we got to circle around Molokini. The clarity as Molokini is every bit as amazing as they say. The downsize is you are corralled into a virtual pen so you can't really drift away from the crowd to explore. You'll need to watch for human feet while you are watching the sea-life. Turtle Town was nice, but the visibility was not as good. We saw more turtles off Ka'anapali Beach and one of the wayside beaches. Still, the other part of the experience was the snorkeling and... the drinks! And the food! The watermelon mojito was our favorite, though all the drinks were great and the food likewise was excellent. I would highly recommend this experience. While it wasn't our favorite snorkeling experience, the overall experience was one of the highlights of our trip!

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    Hawaii Nautical - Maalaea

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    4.5
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    Spencer and Sam made our engagement absolutely unforgettable. What I didn't realize at the time was…read morethat they had been secretly coordinating with my now fiancé to create such a magical, perfectly planned experience. Every detail felt so thoughtful and special. They not only guided us to the most beautiful spots, but also took amazing photos and made sure we fully enjoyed every moment. Their energy, professionalism, and genuine excitement for us made the whole experience even better. If you're in Maui, I cannot recommend booking with them enough. And if you can request a captain; definitely ask for Spencer and Sam. They're the best.

    I booked a snorkeling tour for one person in March 2026. Both my booking confirmation through…read moreGetYourGuide and the confirmation from Hawaii Nautical clearly reflected that the reservation was for one guest. The evening before my tour, I called to confirm everything. During that call, the representative noticed what appeared to be a duplicate reservation and assured me she would cancel the duplicate booking. She also recommended that I contact GetYourGuide to verify I would not be double charged. GetYourGuide confirmed that my reservation had always been for only one person and that I had only been charged once. Despite this, approximately two hours before my scheduled departure, I received a call informing me that my tour was being canceled because there were not enough passengers. I even offered to purchase a second seat so the tour could proceed, but that offer was declined. What is most frustrating is not simply that the tour was canceled, but that this issue could have been communicated much earlier. If the company knew they were unlikely to meet their minimum passenger requirement, there was no reason to wait until two hours before departure. By that point, I had already arranged transportation, incurred cancellation fees on my ride, and lost the opportunity to book another snorkeling excursion during my vacation. Yes, I was refunded, but a refund is the bare minimum when a company cancels a service for reasons entirely within its control. The last-minute cancellation created unnecessary inconvenience and wasted valuable vacation time. If you're booking with Hawaii Nautical, especially as a solo traveler, be aware that your reservation may be canceled at the last minute if they don't have enough passengers. I would have appreciated more transparency and significantly more notice.

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    Off we go ! Good tunes and a sunny day
    Off we go ! Good tunes and a sunny day
    Snorkeling near turtles
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    Maui Magic Snorkel

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    Such a memorable experience!! We snorkeled mid December and it was still great weather with amazing…read moreviews. We saw plenty of fish at the reef near the bird sanctuary. Plenty many swimming around us, we even saw a baby shark and a stingray! They provide snorkeling gear, floaties, boogie boards, and a water slide for those interested. The service was amazing and super helpful. They're always checking up on you and making sure all is well. They provide drinks (alcohol for 21 and above) light breakfast, and delicious lunch. They do rent weather swim jackets for $10 incase the water is cold. We got them but there was no need.

    We had a great time going snorkling with Maui Magic. We were welcomed with breakfast. The crew was…read moresuper helpful, and they have great instructions, while also explaining things about Hawaii's history, culture and the different islands. We went to Molokini first. When we went into the water, the first thing we saw was a baby blacktip reef shark, so we were super excited. We stayed in that location for about an hour and saw many tropical fish in the reef. We then went to Oneuli, where we saw a green seaturtle and plenty more fish. They served a great lunch on the boat (fish and BBQ pork tacos) and had a cocktail. We then went back to the harbor. Check-in was at 630am and we were back around noon. These snorkel trips are expensive but the one with Maui Magic is around the same price points as other good providers (~$225 per person). I would highly recommend Maui Magic!

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    Maui Magic Snorkel
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    Calypso Sunset Dinner Cruise - boattours - Updated July 2026

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