Cancel

    Open app

    Search

    Calypso Charters

    4.5 (416 reviews)
    Closed 6:00 am - 8:00 pm

    Calypso Charters Photos

    Recommended Reviews - Calypso Charters

    Your trust is our priority, so businesses can't pay to alter or remove their reviews. Learn more about reviews.
    Yelp app icon
    Browse more easily on the app
    Review Feed Illustration

    Reviews With Photos

    starboard view approaching Molokini
    Angelina L.

    Calypso is the only Maui snorkeling boat that is wheelchair accessible with ADA restroom. Highly recommend for other wheelchair users! The crew is very professional, helpful, kind, humorous, and efficient. The boat also supplies optical prescription snorkel masks, included with the tour fee...super amazing as I forgot to pack my contact lenses. Amazing clear waters snorkeling at Molokini with various beautiful fish, and saw 3 large turtles at Turtle Bay. Worth every penny!

    Michelle S.

    I had a lovely time snorkeling at molokini crater and turtle town while aboard the Calypso. I got a bit sea sick because of the waves but Corinne took great care of me! I also want to thank the lovely lady who helped my mom when she got nervous in the water. The other staff were also fabulous as well and you can tell they have been doing this awhile. The captain was also very funny and kept everyone engaged the entire time. I am also participating in the maui dinner cruise so will circle back on my review for that!

    Sunset on the ocean!
    Roman B.

    Booked a Sunset Dinner cruise and it was spectacular! From the beginning till the end of the cruise, that staff was amazing. The water was a little bumpy with all the ups and downs on the boat, but the captain said it might be and he would try to make as smooth as possible. Absolutely worth the price. Included 3 course dinner and 2 alcohol drinks, as well as soft drinks. Staff is very attentive and treats you so well. If you are thinking about doing the dinner cruise, well we highly recommend doing it!!

    It's of pretty fish
    Alyce S.

    Fantastic experience, very organized, food was good, snorkeling was exactly what we were looking for. Very friendly staff.

    Surpassed my expectations. Great organization/ service food drinks as soon as you board , amazing music , views and a comfortable ride ! 15/10 The only feedback would be a barcode to tip ! We felt bad Because we didnt have cash!

    Watching for flying fish.
    Beau F.

    My family had a GREAT time with Captain Kiwi and crew! John and Erica were especially friendly and helpful. Erica was very patient and attentive to my 82 year old mom, who actually went snorkeling. The boat ride was very smooth, and my wife didn't feel sea sick at all, and she usually always feels nauseous on a boat. When the water did get a little choppy, the captain was able to steer to lessen the rocking. This is an ideal boat for first timers as the whole crew was very accommodating and friendly. Ryan, the cameraman, took great care to get a lot of pictures of each group on board. We loved the slides, jumping platform, breakfast, lunch, and probably my favorite part, standing at the front of the boat while cruising and seeing the flying fish jump out and fly in front of us. We all had a really fun time and made memories that were still talking about.

    Brionna K.

    This was our first time snorkeling and what better way to kick off our honeymoon with this experience. Breakfast, lunch and small bites are served. Staff was very friendly and informative. It makes two stops molokini crater and turtle town. We had such a great time!

    Roure B.

    The experience was great and staff was very accommodating and attentive to your needs! I absolutely recommend using them. They rent out go-pros for you to create your own snorkeling experience! So much fun! One thing I do want to mention, has nothing to do with the boat itself, but with the parking to get on the boat. The app only allows you to pay up to three hours, the experience is a total Of 5-6 hours!!! Make sure you pay attention and pay for the entirety of your trip! My car got towed for failing to pay an extra $2. Cost me $200 to get it back! Highway robbery' they are waiting for you to not pay attention!

    Sunset dinner cruise.

    We did the sunset dinner cruise and had a great experience. Good food, strong drinks, and beautiful views of the sunset. It's a very windy harbor so be prepared for that but otherwise a wonderful experience.

    Trying out my gear before we got in the water.
    Donna S.

    Fabulous company; went out of their way to give us a great experience. Awesome time, fun crew, clean, quality gear. Appreciated the hot coffee and breakfast at the beginning of the trip, the fruit, veggies, and lunch on board. My travel partner had a mai tai or two after we were done snorkeling, which he enjoyed. It was fun with the slides and the jump off deck. I would have loved to have had an opportunity to wear a wet suit top, but Calypso only offers on one piece, short sleeve top and shorts combination. Having three working restrooms was great as well. My travel partner and I have snorkeled with another company in Maui in the past (who canceled our originally booked trip this time) and agreed that we enjoyed our time with Calypso even though it was a little more expensive.

    Fearless Captain
    Marshall G.

    This is a strong yes. Top to bottom, more steps to go in water. Fully supplied snorkel gear , full breakfast, eggs and sausage and lunch, pulled pork on buns with potato salad and mixed beans. No towels. Deck showers, slides and a dive step 30 feet off the water. Most jumped. Some did not want to get wet, or went below for glass bottom views. Something for all abilities. They had a lifeguard in the water to observe and enforce not getting up on the dry land. The Bar was at 2.00 per, and a helpful crew male and female full of aloha. Thank you Patrick, crew, ex real estate, for the extra ice cream treats. Yum. We had whale watching both directions, but a dead stop on return leg. At least 10-15 minutes to watch a mother and baby and escort cavort. A real show at the bow, no moving on till they do. We did a generous crew tip at the end. Painless..... Thanks to the Fearless Captain. Pic in cabin provided below. He was full of whale information and jokes. We all had padded seats everywhere, some other watch trips didn't. And a final body count at both snorkel stops, both announced with jokes before we moved the boat. Can't be left behind that way.... A great 5 or 6 hours with other visitors that wanted to be there and showed it. First time on Calypso, not first to the Crater dive spot. We would come again. Mahalo

    Over all best experience! Highly recommend! Very family friendly and first timer friendly too! Captain took the time to give a lesson to those of of us first-timers to help us feel more comfortable and enjoy the experience which absolutely helped. They have little boat floats with with clear windows into water.for little kids which my 4yr old.really enjoyed. recommend and would book again!

    We saw migrating humpback whales

    See all

    9 years ago

    Business owner information

    Photo of Chris K.

    Chris K.

    Thanks for booking your Calypso trip at Boss Frog's!

    Helpful 0
    Thanks 0
    Love this 0
    Oh no 0

    9 years ago

    Staff was super helpful. Water slide was fun. Plenty of time for snorkeling.Great pictures!

    Business owner information

    Photo of Chris K.

    Chris K.

    Thanks for letting everyone know you had a great time on the Calypso!

    Helpful 0
    Thanks 0
    Love this 0
    Oh no 0
    Photo of M M.
    1
    23
    18

    9 years ago

    Business owner information

    Photo of Chris K.

    Chris K.

    Helpful 0
    Thanks 0
    Love this 0
    Oh no 0

    8 years ago

    Business owner information

    Photo of Chris K.

    Chris K.

    Thanks for recommending the tour, glad you had so much fun!

    Helpful 0
    Thanks 0
    Love this 0
    Oh no 0
    Photo of Jen H.
    1
    73
    9

    9 years ago

    Business owner information

    Photo of Chris K.

    Chris K.

    Helpful 0
    Thanks 0
    Love this 0
    Oh no 0

    9 years ago

    Helpful 0
    Thanks 0
    Love this 0
    Oh no 0

    9 years ago

    Business owner information

    Photo of Chris K.

    Chris K.

    Helpful 0
    Thanks 0
    Love this 0
    Oh no 0

    9 years ago

    Business owner information

    Photo of Chris K.

    Chris K.

    Helpful 0
    Thanks 0
    Love this 0
    Oh no 0

    9 years ago

    Business owner information

    Photo of Chris K.

    Chris K.

    Helpful 0
    Thanks 0
    Love this 0
    Oh no 0

    8 years ago

    Business owner information

    Photo of Chris K.

    Chris K.

    Helpful 0
    Thanks 0
    Love this 0
    Oh no 0
    Photo of V R.
    27
    59
    25

    8 years ago

    Business owner information

    Photo of Chris K.

    Chris K.

    Helpful 0
    Thanks 0
    Love this 0
    Oh no 0

    9 years ago

    Helpful 0
    Thanks 0
    Love this 0
    Oh no 0

    7 years ago

    Business owner information

    Photo of Chris K.

    Chris K.

    Helpful 0
    Thanks 0
    Love this 0
    Oh no 0

    9 years ago

    Helpful 0
    Thanks 0
    Love this 0
    Oh no 0

    9 years ago

    Business owner information

    Photo of Chris K.

    Chris K.

    Helpful 0
    Thanks 0
    Love this 0
    Oh no 0

    9 years ago

    Business owner information

    Photo of Chris K.

    Chris K.

    Helpful 0
    Thanks 0
    Love this 0
    Oh no 0

    Page 11 of 11

    Ask the Community - Calypso Charters

    Would this be suitable to take a 2 1/2 year old and 8 month old on (and stay on the boat obviously) while the rest of the family snorkels?

    Family members of all ages take our cruises. Adults are responsible for watching children. There is about 45 minutes of actual snorkel time so you can make a judgment! Please contact Reservations for more info - 808-661-9937. Mahalo

    How much is the scuba option for 8 years olds? Or is that included in the ticket?

    Aloha! Please call our live reservations agent and have your question answered and book directly 808-661-3333! Mahalo!

    Don’t See Your Question? Ask Away!

    Review Highlights - Calypso Charters

    Didn't feel that was worth it for just one image :( We loved going to both the Molokini Crater and Turtle Town!

    Mentioned in 71 reviews

    Read more highlights

    Trilogy Excursions - Captain Michael

    Trilogy Excursions

    4.9(2.4k reviews)
    12.5 mi

    Captain Michael and crew who led our "Discover Lanai" day were awesome! Super attentive, the food…read morewas abundant, the boat was very clean, and I felt safe out snorkeling even with a pretty big swell shift from the Hurricane. The details: Our tour started by meeting at tree at the Sheraton, which sounds awkward but for us was super convenient and it was fun boarding the sailboat from the beach but you will get a little wet! Captain Michael walks you though the day and then you are off for about ~90 minutes to Lanai. During that time you are served (not a buffet) two meals. The cinnamon rolls were great and the breakfast croissants are now something I make at home. There was also a photographer on board so we took advantage and took some family photos (you buy at the end and I found them a whole lot cheaper and less stress than an actual family shoot). Once you get to the Island you can take a golf cart or take a short walk to the beach where they have all the gear you need. After the safety briefing you have about 2 hours to snorkel with the crew serving as lifeguards in the water. It is VERY easy to lose where you are when you've got your head underwater. I appreciated how attentive the crew was to where the four of us were at since there were a few times we needed some gentle guidance out of a harms way (shoreline rocks). The photographer also captures your snorkel sesh. After snorkeling, you're treated to another full meal of noodles and chicken. Followed by anything you might need for a little seasickness to prep for the journey back . My 12 yo son was pretty full at this point and had befriended the captain who let him help get the boat ready for the return trip. That was very cool! The ride home was a bit bumpy (Hurricane Lowell was coming) but Captain Michael did a great job avoiding anything major and even found a pod of dolphins. We also enjoyed the mai tais! Great experience! We will book more tours in the future. I would have booked another snorkeling or sunset tour during this trip but the water quality really deteriorated with the upcoming storm.

    The crew on our Trilogy sunset dinner cruise--Kayden, Kevin, Michelle, and Captain Kukii--did an…read moreamazing job making the evening unforgettable. The level of service exceeded our expectations from beginning to end. Everyone was friendly, attentive, and made us feel incredibly well taken care of throughout the cruise. The four-course meal was stellar and much better than we expected from food served on a boat. Everything was fresh, beautifully prepared, and delicious. Between the incredible crew, exceptional service, wonderful food, beautiful ocean views, and Maui sunset, this was the perfect way to end our time in Maui. We couldn't have asked for a better final evening on the island.

    Photos
    Trilogy Excursions - Justin BEING A FREAKING BOSS

    Justin BEING A FREAKING BOSS

    Trilogy Excursions - MY EPIC WIFE VIBING DURING SUNRISE!!!

    MY EPIC WIFE VIBING DURING SUNRISE!!!

    Trilogy Excursions - Whale watching

    See all

    Whale watching

    Four Winds Molokini Maui Snorkel Tour - Molokini Crater

    Four Winds Molokini Maui Snorkel Tour

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

    Because of winds / choppy waters at the crater we had to detour to a different area. It was still…read morean amazing trip. Snorkeling experience was amazing but the differentiator was the staff and the food....just an awesome staff all around, so helpful and they actually cared / went out of their way to help the people that paid for the trip. The breakfast was hard boiled eggs, fruit, muffins, croissants....sounds basic but it was really quality - not crap food. Lunch was fantastic - fish tacos, pork tacos, vegetarian tacos or hot dog - grilled it right on the boat. Toppings were great - it was just good fresh food. Super impressed with the whole experience

    Had an awesome experience on Four Winds snorkeling Molokini Crater. The staff was super down to…read moreearth and friendly. When you get on board they have a light breakfast with fruit, croissants and muffins that you can snack on, as well as fruit juice. The ride out, they explain some safety stuff and how the day is going to run. There are 2 floors to the boat with the upstairs being much more open. There were only about 30 people the day we went but I believe they have up to 100, so a more crowded day may have a different experience. Despite being in November, we ended up seeing several whales coming to the surface (apparently they are in abundance come January). They provide snorkel gear and fins, but you are more than welcome to bring your own (we borrow fins only as we brought our own masks). They provide a simple anti fog spray which worked great. They let us snorkel for about 2 hours in the surrounding area asking us to stay within 50 yards of the boat with a buddy. The staff answered all our questions about what fish we were seeing and recommendation for how to see the best fish. There is also a glass bottom that you can climb down a ladder in the boat to see the fish without going in the water. They served lunch while docked so you could eat while you took a break from snorkeling. It was fish tacos with a selection of fish, pork or being burger meat. They had a slaw and quinoa side and some chips. Nothing fancy but o found it delicious after working up an appetite snorkeling. They had cameras for rent (extremely expensive so I'd bring your own), a photographer that took picture you could purchase for a fee ($80 for all the pictures she took of us, again a little pricey), wet suit tops for rent ($10 each) and special snorkel masks if you are near sighted (I believe this had no additional charge). The boat was pretty new, clean and open which was nice. I would 100% go out with this company again.

    Photos
    Four Winds Molokini Maui Snorkel Tour - 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!

    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!

    Four Winds Molokini Maui Snorkel Tour
    Four Winds Molokini Maui Snorkel Tour

    See all

    Sea Maui - Memorable sunsets

    Sea Maui

    4.9(1.2k reviews)
    15.0 mi

    Sea Maui's cocktail sunset cruise was easily one of the highlights of our trip. Nick, Luke and…read moreJames were absolute rock stars. And when they say open bar... they mean it. Beers, cocktails, spirits, pretty much whatever you wanted and the crew constantly walked around asking if anyone needed another drink. The heavy appetizers were also way better than I expected for "boat food", chicken katsu, Chinese chicken salad, pasta salad and kalua pork sliders, everything was really good. (No pictures cause I mopped it lol) The cruise itself was around 1.5 to 2 hours and our ride was incredibly smooth, although obviously that'll depend on the weather. They also offer a kamaʻāina discount if you call to book, which brought it to around $100 per person for us. Between the views, legit open bar, surprisingly good food and an awesome crew, I thought it was absolutely worth it. Would do this again in a heartbeat.

    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 !!

    Photos
    Sea Maui - Mai tai time

    Mai tai time

    Sea Maui - Sunset cruise

    Sunset cruise

    Sea Maui - Whale tail

    See all

    Whale tail

    Pride of Maui - The Pride of Maui returning from Molokini

    Pride of Maui

    4.3(849 reviews)
    0.2 mi
    43 years in business
    Locally owned & operated

    While on our Babymoon, I booked a reservation for my husband and I to go snorkeling on the Pride of…read moreMaui. I chose this particular tour because it was a smaller group size and I did not want to feel crowded or overwhelmed on a boat with strangers. It was the perfect amount of people, and my husband and I ended up chatting with most of the other passengers, having lots in common. Our captain was Caiden, who was extremely kind, informative, and entertaining. We also had crewmates Sienna, Diego, and Jim looking out for us and making sure that we were comfortable and had all of our wants and needs met. I felt completely safe and comfortable the entire trip and I appreciated having a certified lifeguard on boat with us. The snorkeling experience was phenomenal and being pregnant, it made me feel so calm and relaxed. I appreciated learning the history of the two various locations we snorkeled at and the opportunity to see a sea turtle. The ship itself was pristine, and the restrooms were some of the cleanest I have ever experienced on a boat. The breakfast and lunch that they served us was tasty, and the macadamia nut cookies at the end were the perfect sweet treat. I appreciated that they were able to offer me mocktails since I cannot drink at this time, and those were tasty as well. This experience was worth every penny and I would definitely come back and do it again.

    I snorkeled with Pride of Maui twice. We visited the crater, Turtle Town and Coral Garden. The…read morecrater was super cool but the Coral Garden had the best snorkeling experience. The cost of the trips were worth it because we got four things. 1) Meals, 2) open bar, "ongoing" beverages like passion fruit juice and ginger drink, 3) the boat ride itself and 4) snorkeling, snorkel support and equipment. I was surprised that 130 were on the trip both times yet it did not seem crowded at all. The old school metal slide was extremely popular. I learned on these trips that you can't guess the calmness of the upcoming snorkeling spot. It might be white caps in the middle of the harbor while Coral Garden could be super calm. The staff members were nice, professional and smart. I would go a third time!

    Photos
    Pride of Maui - Starboard side of the Pride of Maui

    Starboard side of the Pride of Maui

    Pride of Maui - Guests jumping into the water to snorkel

    Guests jumping into the water to snorkel

    Pride of Maui - Guest enjoys Maui SNUBA diving, one of the most incredible ocean activities

    See all

    Guest enjoys Maui SNUBA diving, one of the most incredible ocean activities

    Hawaii Nautical - Maalaea - Whale breaching, these visitors are seen March-December.

    Hawaii Nautical - Maalaea

    4.5(8 reviews)
    0.1 mi

    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.

    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.

    Photos
    Hawaii Nautical - Maalaea - Off we go ! Good tunes and a sunny day

    Off we go ! Good tunes and a sunny day

    Hawaii Nautical - Maalaea - Snorkeling near turtles

    Snorkeling near turtles

    Hawaii Nautical - Maalaea

    See all

    Maui Magic Snorkel - BRAND -NEW Maui Magic

    Maui Magic Snorkel

    4.8(270 reviews)
    0.1 mi

    1. I had previously went snorkeling on the big island company and had a very poor experience. I was…read moreterrified of open water but the staff on Maui magic were very flotation device friendly. They were more concerned about my overall experience, not shaming me for my fear but rather making sure I enjoyed myself by being as accommodating as possible. And it wasn't just one person, it was all of them. Making this an extremely special and cathartic experience. 2. The food. Ok, I mean the eggs, muffins and croissants were awesome but can we talk about the tacos!!! Bro! The pork tacos were incredible. The mahi mahi tacos were also very good. The pineapple salsa was a must have! And this was all before I had 2 mai Tais... so this isn't my taste buds under the influence. 3. The charter itself was wonderful. The boat was comfortable, there was plenty of space. We went to 2 different spots and were given plenty of time to explore. The music was on point, a little Fleetwood Mac, Green Day, etc. it was eclectic alt chill. Legit they could make their own Spotify playlist, 4. It's not the cheapest, or the most expensive. But I don't know how it gets better than this and I think it was 100% worth the money. So a huge thank you to the crew of Maui magic. Maybe saying it was a magical experience seems kind of cheesy but go head and call me a big ole cheese ball, because I'm here for it!

    Amazing snorkel trip with the family. The captain and crew were great. Really accommodating and…read moremade sure everyone had a safe, good time. Started off with a light breakfast and saw some dolphins on the way for our first stop in Molokini. Lunch was far better than expected which I had the grilled fish tacos and was probably better than I've had at one of the restaurants we've eaten at in Wailea. The slide was fun and grandson had a blast. Saw some turtles on the way back as the captain stopped so we could all check out. Only thing I thought probably shouldn't do is charge $10 for a wet suit top. It's not the amount but if they fell they need to charge, raise adult price up $5 bucks to cover since seems would be better to include as part of the total cost. I would highly recommend since we have done snorkel trips on other boats and this is was by far the best.

    Photos
    Maui Magic Snorkel
    Maui Magic Snorkel
    Maui Magic Snorkel

    See all

    Calypso Charters - snorkeling - Updated September 2026

    Loading...
    Loading...
    Loading...