What a fantastic time! Let me clear it up front. It's a boat. And if you've never been on a boat before it's a little intimidating. Maybe a lot intimidating. And I was intimidated. But I went ahead on the cruise. The dinner cruise? Was amazing! The staff was so nice (as are most of the wonderful folks of Maui). The drinks were very tasty and the food was delicious! How good could food be on a boat? Turns out very good! Juicy prime rib, tasty salad, delicious veggies and the rice was actually solid! Dessert was a chocolate cake for us and was very moist with great frosting. But the reason you came on the cruise? The vibes. The views. The atmosphere! And let me tell you the views, vibes and atmosphere were amazing. Boat takes off at golden hour so the photos you take (take photos please) will look immaculate. Over all? Amazing experience. Pull the trigger on this fantastic dinner cruise! Next time we're in town we'll be taking the dinner cruise once more. read more

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Had a very nice time and thoroughly enjoyed our romantic sunset cruise! Food was good and drinks were strong (a good thing!). All staff was super friendly and appreciated such a nice evening! read more

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The servers were awesome- right on top of our continual needs. The food was delicious. We had the prime rib- holy smokes! It was so so good! Big portions! The whole experience was amazing- saw whales and dolphins which was a huge treat. The sunset was gorgeous! read more

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Travel mate and I ventured out for a dinner cruise on 1/23/26. The weather cooperated and the captain said, "it's whale season, so we may see a few". Even though whale watching wasn't the prime motivation, we saw plenty of action. All the crew was outstanding, helpful and informative. Food was maybe 7-8/10. Food service and follow-up drink service were superlative. We would do this trip again in a heartbeat. Aloha read more

Just a lovely experience all around. Knowledgable, attentive, friendly staff. Surprisingly good food- and our crew spanned fish, chicken, and prime rib - and yummy cocktails. Views can't be beat, and we saw a small spunky pod of whales at the end. Highly recommend! read more

Wife and I did this dinner cruise for our anniversary. It was very fun, the whole crew was top notch, dinner was amazing,and the cocktails were on point....and the best part was the Maui sunset. We booked this cruise through one of the local snorkeling shops and saved a lot vs booking online. read more

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. read more

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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. read more

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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. read more

Calypso Sunset Dinner Cruise - Tim McDill provided the musical entertainment. Great song selection, good guitar playing, and what a voice! - Boat Tours Near Me - Wailuku, Hawaii

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The service was impeccable, particularly from Lionel, with delicious dinner and drinks. We really appreciated the captain's expertise and enthusiastic conversation. He navigated us to a gorgeous whale display nearly at molokini. The ride was smooth and very comfortable. Mahalos all around! read more

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! read more

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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. read more

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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 . read more

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Calypso sunset dinner cruise was not what my trip advisor explained it to be. There was nothing romantic about the cruise. The seats were beach chairs. The drinks were watered down served with plastic clear cups. The food tasted like it was frozen food and Luke warm like they heated it up in the microwave for 45 seconds. The price we paid $250 was not worth the plastic cups microwaveable food and beach chairs. Word from the locals do not book here. It was windy and we didn't see any wildlife read more

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. read more

Calypso Sunset Dinner Cruise - Boat Tours Near Me - Wailuku, Hawaii

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. read more

Calypso Sunset Dinner Cruise - Salad with soggy croutons and a hot as rock bread stick. - Boat Tours Near Me - Wailuku, Hawaii

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This was a great dinner cruise! The food was delicious and plenty of it. Five different dinner choices and our group loved them all. Good choices of drinks also. The service was great. Always making sure you had everything you needed. There was also good entertainment. I would definitely do this cruise again! read more

What a great experience! The crew is excellent. The size of the boat makes it a very calm trip, and easy to enjoy your meal. The sunset was beautiful. My wife and I will absolutely go again on our next trip to Maui. I highly recommend this cruse. read more

Food not edible! Served cold and over cooked! Captain not friendly! Our sever G was amazing 5 stars for him! Music was great! Not much whale activity due to captain not following them! 2 other boats out amazing whale show as we know both captains! This was a Christmas present from our children and I truly wish we just would not have gone! We are a local family and will never recommend this dinner cruise! read more

Updated review on customer service! They reached out to me to rectify the situation. I would for sure give them another try based on their customer service! The fact that they reached out to me to make it right and were so polite in doing so, leaves me with a better feeling! If a company has great customer service that is gold these days! Thank you so much!!! read more

We took the cruise Jan. 23rd to celebrate my girl friends 70th birthday. We lined up early and Meagan was the photographer and very knowledgeable and friendly. Danielle, the tour guide, assisted with our check in and through out the entire cruise. The capt. came out and gave instructions and warned about the rough water but stated he would make things as calm as possible. The entire crew was enthusiastic and friendly throughout the entire cruise. We had mahi mahi and prime rib for dinner. Very good. The entertainer on board sang happy birthday to my girlfriend. We even saw whales next to the boat. I would recommend this sunset dinner cruise to anyone. It's an experience my girlfriend will treasure. Larry G Washington State read more

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. read more

Calypso Sunset Dinner Cruise - View from Cruise - Boat Tours Near Me - Wailuku, Hawaii

The first hour was a 2-3 star experience. After that it was 4-5 stars. To compromise, I'm giving this 4 stars. Here's the rundown: The notes said there would be a prompt 5pm departure. We arrived and didn't board until about 5:10. Then we didn't leave the dock until around 5:45. The waitresses started to come around and get drink and food orders, and they took everyone's order around us and then skipped us. A couple arrived around 5:30 and was still allowed to board the boat, and they took a seat right next to us (literally about 5 inches away, our seats were right next to each other). A waitress came up and took their order and STILL skipped us. We tried to get their attention with no luck. Eventually we got someone to come by, but at that point we'd been sitting on the boat for almost an hour. Fast forward to the meal. The Mahi Mahi was good, as were the mashed potatoes and veggies. There was a hair in my mashed potatoes but that didn't really bother me - it was insanely windy and hairs happen, but if that bothers you then be warned because it seriously was VERY windy. Drinks were also just ok. Keep in mind this is a boat, not a bar, so you're not going to get the best piña colada you've ever had. However, given the price of this experience, I would have liked the drinks to have been a bit better. Now to the better parts - the views were amazing. It was an incredible view of the sunset and a romantic cruise on the water. Our captain also pulled up near the coast so we could see an endangered monk seal sleeping on the rocks. The view of the night sky was also incredible and we could see a million stars and the milky way, which is an unforgettable experience. The other two best parts - the Captain and the musician, Tim McDill. The captain was so nice and funny, and Tim played the best music. This cruise is very lucky to have found such a talented musician to play on the boat! It really made the night a lot better. All in all, if you're looking for a 100% perfect dinner cruise experience, this might not be it. But it did have amazing views, a great captain, and great music. It's a bit overpriced, but it's probably one of the better sunset cruises you'll find in Maui. If you have long hair, I recommend pulling it back or into a braid, because the wind will whip it around and you'll have a mess of a time brushing it out later. Our captain said this is one of the windiest harbors in the world, and having now experienced it, I believe it. read more

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First of all...the food....if you opt for that.. is ONO!!!!!! My boyfriend had the prime rib...my 8 year old the fish..and me... LOBSTER TAIL....of course you know I tried it all...lol. Adults have 2....yes 2 complimentary adult beverages to as soon as your out of the harbor. Just keep your food cards out visible so that the waitresses/waiters will bring your meals... I assumed everyone was having dinners but nope..we didn't know and everyone else was served fast...SO KEEP YOUR CARD VISIBLE! The views AMAZING The seating AMAZING The staff AMAZING The captain Amazing The ride AMAZING the sunset well you need to go see....it was whale season so we had a very big bonus before the sun went down...a mama whale and baby whale breaching!!!!! NEEDLESS TO SAY AMAZING!!!!!!!! read more

Calypso Sunset Dinner Cruise - Boat Tours Near Me - Wailuku, Hawaii

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Excellent sunset cruise to take. We had live music that we thought was Jack Johnson. Our crew were amazing (all of them). The names I recall are Melissa and Tiffany as they had name tags :) The food was awesome, we had prime rib. We saw a turtle and some flying fish, birds nestled into the cliffs. Our captain did a great job getting us a bit of shade early on and making note of the wild life we could see. I would do this again. Gorgeous views. read more

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The prime rib was not edible! The food was not hot, Luke warm at best. I feel sorry for the staff because it seemed like they tried really hard to make it better but there was no helping this food. The captain let us rock and roll in relatively calm seas on the way out, as if he was trying to conserve fuel by not planeing the boat. On the contrary when returning to shore he motored up a few nots and we had a smooth ride back. In summary the sunset was nice, but I guess if you go on a dinner cruise you at least want Denny's or hamburger quality. This charter needs to either fire there food services or stop offering dinner cruises and just call it sunset cruise. By the way, it seemed like the Captain was either tired or just didn't care about connecting or informing his passengers about the ride. Although I give him credit for the one whale sighting, which was the highlight of the trip. read more

We had an awesome time tonight with Captain Karl and crew. Food was good. Drinks were great and the views and commentary were outstanding! read more

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We had a great time! We saw a ton of wales and had a great meal. Covid sucks and makes everything difficult but the crew did a great job in spite of it. We will be making this a spot for us each visit. Recommended for sure. read more

Calypso Sunset Dinner Cruise - people boarding a boat at night - Boat Tours Near Me - Wailuku, Hawaii

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For those of you taking this dinner cruise keep in mind if you sit on the 3rd deck you will be served last. The crew made an announcement prior to setting sail and stated our waitress would instruct us when to go down stairs to get our food. Never once did this happened. We went down on our own and sure enough they were down to just about nothing. Potatoes cold, prime rib was so over cooked and not smoked like we were told it would be. The crew tried to make up to us by giving us chicken instead of prime rib! They tried, but obviously not well prepared and chicken is not what we paid for. Overall this dinner cruise was a huge let down. I gave them a 2 star review just because the singer/musician was good. Drinks were subpar as well read more

Calypso Sunset Dinner Cruise - Boat Tours Near Me - Wailuku, Hawaii

We scheduled this a few days out and the day we went it was overcast so we did not get the Sunset we were expecting, but it was a very nice evening and we did enjoy ourselves. The food was great and the crew was very nice and very attentive. The music was great too. read more

Calypso Sunset Dinner Cruise - Great dinner - Boat Tours Near Me - Wailuku, Hawaii

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These people don't have a clue on how to treat customers. I had reservations for seven people. When I entered the boat there were two empty tables. Both tables had a plate with the last name of the party. Angela, took the plates off the tables and told me she was sorry but someone must have taken my table and my party would have to split up or use a chair at the end of the table. I tried the chair it didn't work there was no way we could fit. I don't understand why they think the other group that took or was given our table would think that was OK. What makes the other party more important than mine? Why would Angela (staff)take the plates with the names of the people that should've been sitting there and then proceed to ask me if I was enjoying the music and the whales? I looked at her & asked her does it look like I'm having fun? Later the captain came over to talk to me. I told him exactly what happened and how upset I was at the fact that his staff would do something like that. I explained the $700.00 I paid was to unsure we had a table for 7 not to hear excesses about the virus. Athe night continued I discovered my table was given to the other party because they claimed they had just gotten married and did not want to split up their friends. Well I wanted to be with my family and I didn't want to be split either. They should have just been honest with me from the very beginning instead of trying to hide what they did. read more

The dinner cruise was outstanding. I would do it again. The servers were wonderful, food was amazing and the ambiance was breath taking. I loved it. read more

The main highlight of this dinner cruise was the sunset. It was very beautiful, and despite the windy conditions in the beginning, throughout the trip it slowed down during our dinner! However, we were unable to sit on the first and second levels since we were on of the last ones to board. Hence, we sat on the third floor and were one of the last ones to get our food. We originally ordered two prime rib and two fish dinners, but they ran out of fish. This also happened to two ladies in front of me, who both ordered lobster but were unable to get it. We got alternatives instead, and I choose the prime rib. I don't think the food was worth the price - prime rib was over cooked (since I got the 'last slice'), vegetables were soggy, and potatoes were salty. Dessert (cheesecake) was okay. However, the staff was kind, as they asked if we wanted and took pictures and let us know what was going on despite being on the third level. The music was a very nice touch as well! read more

The sunset was beautiful and the cheese cake and chocolate cake was pretty good. I did not like the dinner much at all for the price. Skimpy portions also. No flavor to the fish or prime rib. Service was great though. Special shout out to Kiki for letting me try something else since the fish was not good! read more

Calypso Sunset Dinner Cruise - Fish dinner - Boat Tours Near Me - Wailuku, Hawaii

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First off I want to mention that WEATHER will have a HUGE impact on your cruising experience. This is something the boat owner and crew have no control over, so it's a shame so many negative reviews are actually based on weather. My advice is wait to make reservations for dates when weather cooperates, and then you will have a WONDERFUL ride!! Now, regarding this BOAT, it is really great! It's new and has many great features and facilities (the snorkel trips should be wonderful too! Fun slides for water fun, great easy access ladders to get you back on the boat again). For the dinner part, seating is awesome and was comfortable and you can tell they tried to maximize your viewing experience. I like the drink holder in the table, that was a nice touch. My husband and I both had the lobster dinner and we really enjoyed our dinner. The boat ride and views on our night were gentile and perfect! The sunset, the views of Maui from the water, and being SURROUNDED by visiting humpback whales is just simply amazing! This was absolutely a highlight of our trip, and we WILL be back again! This is the boat we will choose! We prefer the top deck with the best views and fresh air, but that is the area you'd get tossed around most on if weather isn't the greatest. The lower levels have less sway and where you want to be if you are motion sensitive. (I've been on a lot of boats, can you tell?) I also want to offer a little advice for those prone to seasickness... Alcohol helps! It seems counter intuitive, but it really works. Don't get sloppy drunk or anything, but just get a little tipsy (quickly drink your first drink, then slow down and sip/enjoy a 2nd) and you won't notice the boat rocking or won't care anymore and you'll have more fun . I learned this many years ago because my grandmother taught me that. And it really does help. When I see someone feeling motion sickness (on a boat, plane, whatever) if they follow my advice (age appropriate of course!) they always thank me later and feel better. So that's my little secret for dealing with less than perfect weather while on a boat. read more

My boyfriend and I did the cruise and we will definitely do it again! I booked our tour through boss frogs- we had prime rib which was amazinnnnng!!! Live music on deck and we even saw whales!! Honestly it was the best thing we did during our whole trip! read more

Calypso Sunset Dinner Cruise - Prime rib - Boat Tours Near Me - Wailuku, Hawaii

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Food was a bit mediocre, but the staff was awesome and the view of the sunset was amazing. Plenty of room on this boat, and lots of fun. I would do it again, and just might...the next time I'm on the island. read more

First off a special thanks to Capital Karl... he was the sweetest and most helpful person. He called us from our car to make sure that my family and I were able to get on the boat even though our book agency was not helpful and our reservation was canceled. Our booking company "get your guide" messed up and didn't give us a refund or a proper email showing our trip was sold out when we booked. We showed up on time for the cruise and our name wasn't on the list. Obviously we were frustrated, but they worked around it. They made room for us on the boat as they had some no shows! Extremely, kind even tho we were frustrated. All the staff was extremely helpful and kind. NEVER BOOK THROUGH get your guide!!! Book directly through Calypso! But never the less, they were extremely helpful and allowed us on their dinner cruise. Ended up having a great night with good food and drinks!! THANK YOU STAFF OF CALYPSO!!! read more

Food was not good, drinks were very watered down. Staff was friendly but the service was poor. Boat is multi-use for snorkeling trips during the day and dinner cruise in the afternoon so it does not have a fancy dinner if that is what you are looking for. Staff encouraged walking around the boat, but there wasn't anywhere to go because the boat is fairly crammed with seating tables so most everyone sat in their seats through the entire ride. Would not recommend this at all. Not sure where so many positive reviews are coming from, maybe for the snorkeling? read more

The views, crew, service was top notch. The entertainment was also great One area which needs serious improvement is food choices and quality/taste. It tasted straight out of a hospital cafe or cash and carry frozen section(and heated poorly), with the exception of dessert The vegetarian food was basically raw veggies and i edible ravioli. Fish was smelly. Bbq chicken was bland and tasteless read more