Small Group Waikiki Sunset Sailing Tour

Great experience! Must do! 10/10

Hands down the most incredible sailing experience I’ve ever had! Captain Tony was wonderful. Experienced, personable, and genuinely passionate about sailing. With decades of experience on the water and travels to 110 countries, he had fascinating stories to share and made the entire experience feel personal and unforgettable. Tony invited my girlfriend and I to relax at the bow of the sailboat, giving us the opportunity to enjoy the beautiful sunset together in complete serenity. The combination of wonderful views, great conversation, and Tony’s thoughtful hospitality made this an experience Lex and I will never forget. Worth every penny and then some. I truly cannot recommend it enough. 🤙🏼🤙🏼🤙🏼

Fabulous evening with Captain Tony who made is feel so welcome and able do share a few yarns with a fellow seafarer. Only 6 onboard as 2 got held up by the Pride Parade. Rainbow over Diamond Heads was magical.

We had such a wonderful experience on our sunset cruise off the coast of Waikiki with Captain Tony! We booked through Viator, and it was such a fun surprise to realize that Captain Tony had actually taken my friends and me out on a cruise back in 2023 as well, although we had booked through a different company at the time. Captain Tony was incredibly sweet, personable, and professional. He pointed out different sights along the coast, took photos of us, gave us great recommendations for things to do and places to visit, and was genuinely so kind and polite throughout the entire experience. The ride itself was peaceful and relaxing, and watching the sunset from the water was absolutely beautiful. We had such a great time and would definitely book with Captain Tony again. Highly recommend!

We had such a wonderful experience on our sunset cruise off the coast of Waikiki with Captain Tony! We booked through Viator, and it was such a fun surprise to realize that Captain Tony had actually taken my friends and me out on a cruise back in 2023 as well, although we had booked through a different company at the time. Captain Tony was incredibly sweet, personable, and professional. He pointed out different sights along the coast, took photos of us, gave us great recommendations for things to do and places to visit, and was genuinely so kind and polite throughout the entire experience. The ride itself was peaceful and relaxing, and watching the sunset from the water was absolutely beautiful. We had such a great time and would definitely book with Captain Tony again. Highly recommend!

A magical sailboat experience to say the least. From the views to the vessel itself- sunset was absolutely beautiful on the water & Tony treated us like family. Not only is he 100% the expert in his profession - he’s been sailing for 40+ years and has the best stories. Thank you for a beautiful experience Tony, we’ll be back soon :)

Stunning views. Incredibly relaxing. We can't wait to sail with Captain Tony again. He deserves all the credit for an ultra smooth sail on a very windy day. He's a great conversationalist and respects silence--a wonderful combo.

Tony took us for a wonderful evening sail out to Diamond Head and back. He was fun, courteous, and interesting, and also no-nonsense and easy to talk to. The boat was comfortable, and we enjoyed having it to ourselves for a short amount of time. Highly recommend a private tour with Captain Tony!

Captain Tony was great! Very friendly and the boat and sunset sail was perfect. Will definitely be a repeat for us.

Very chill experience as Captain Tony took us off Waikiki Beach and (mostly) floated as we watched the city lights or the setting sun.

This was a terrible experience. It's the worst service I've ever seen on Earth. I left my phone number and email address when I booked, but no one contacted me. When I arrived at the navigation point and couldn't find the boat, no one called me to contact the operator, ultimately causing me to miss my boat. When I finally got through to the operator, he arrogantly told me, "It's all your fault." Please, get your act together. I paid you; you're obligated to provide excellent service, not just shift blame onto the customer when problems arise. We're not paying to be humiliated. You need to remember that you owe your mortgage and credit card payments to these customers; they owe you nothing. Honestly, I don't care about the few hundred dollars; I'll just consider it gone. But if you continue with this arrogant attitude, you'll get your comeuppance sooner or later. If other potential customers see this review, please think twice. If you want to pay for a terrible experience, go ahead and book this operator. If you want good service, you'd better look elsewhere.

Captain Tony took us out a beautiful sail to watch the sunset. He’s an incredible man with lots of life to share. Highly recommend. Romantic and fun!

Captain Tony was simply outstanding! From the moment we arrived, he was warm, welcoming, and made us feel completely at ease. He has a fascinating background and many years of experience, which really shine through in theway he runs his tours. We had our grandson with us, and Captain Tony immediately made a connection with him—clearly explaining that on his boat, he’s the “boss.” He showed us our seating options and went over safety instructions before we got underway, making sure everyone felt comfortable. Once we were out on the water, the sail was raised and off we went. We were treated to two beautiful rainbows arching over the mountains and could even see where it was raining in the valley. As the sun began to set, the glow reflecting off the water and the Waikiki shoreline was absolutely stunning. It’s very evident that Captain Tony loves where he lives. He shared many lesser-known spots around the island that give visitors a more unique perspective of Oahu. He also offered excellent restaurant recommendations— we went to Nico’s Pier 38 based on his suggestion, and it turned out to be one of our favorite meals of the entire trip. If you’re looking for a personable, knowledgeable captain and an unforgettable sailing experience, look no further than Captain Tony!

Well worth it! Our family young adults 18, 21 and 23 all loved the sunset cruise. Captain Tony is very knowledgeable and interesting. Would highly recommend!

Our sunset cruise was perfect!! Communication before hand was great! Stunning views and perfect weather. The highlight of the cruise was getting to know capatain tony and hearing of his adventures and his knowledge of Hawaii. He did an amazing job of making our 4 year old feel comfortable and apart of everything!! Couldn’t have asked for a better experience!! Thank you Captain Tony!! Enjoy your time with your sister and nephew!!!

We had a great experience with Captain Tony. He was incredibly friendly and knowledgeable about the area. The smaller, intimate sailing was just what we were looking for whilst on our honeymoon and we ended up sailing as the only passengers. The pictures don’t do the sunset justice, it was incredible to see from the boat. At the end, Tony provided multiple suggestions of how to best explore the island and places to visit, including a car rental and scenic route recommendation. This also includes his small group turtle snorkelling excursion which we have reviewed separately.

We had a wonderful time on the sunset cruise! Captain Tony was friendly, knowledgeable, and easy-going, which made the trip even more enjoyable. The scenery was breathtaking and the whole experience was very relaxing. We also loved learning about Hawaiian history from Captain Tony—he shared so much interesting information. Highly recommend this sunset cruise!!

Girls trip - The night before we left we booked this sunset sail. We were so glad we did. It was just the 3 of us as the other couple cancelled. Captain Tony was personable and very knowledgeable. We enjoyed sitting on the front of the sailboat as we headed towards Diamond Head. It was a gorgeous night. Other party boats were out and they were crowded and very noisy. If that’s your vibe this is not the sail for you. If you want a quiet, relaxing, zen sail then don’t hesitate to book this. It is well worth it. As we turned around and headed back we were able to watch the colorful sunset and moved to the back of the boat where Captain Tony talked about the landscape and Hawaii itself to us. This is a must if you love the ocean and watching sunsets.

Tony knows the seas and the ropes as well. Had a wonderful time riding and talking. Gave us several recommendations for our remaining days on the island. The time went by to quickly. Thanks again Captain Tony.

Captain Tony is a wonderfully knowledgeable guide, with a wealth of information about the Hawaiian islands. The sailing was smooth and relaxing

Been on the larger boats for a sunset cruise but this was much more intimate and peaceful. Captain Tony was absolutely amazing. Accommodating, helpful, responsive. Thank you, Tony!

We were able to book this cruise on short notice and it ended up being a great decision. With a maximum of six passengers, we weren’t fighting for space or a seat or a view. This was in stark contrast to the numerous boats we saw underway that had dozens of people on them fighting to get the best view. I don’t know if he drinks dose of keys, but Captain Tony would certainly be in the running for one of the most interesting men in the world. In addition to a comprehensive knowledge of Hawaii, he had stories from his travels and adventures around the world to share with the boat. It was a great cruise and we book it again in a heartbeat.

Excellent experience. Captain Tony was a great host and outstanding narrator. Highly recommended. Boat was clean and in great condition.

This was a fantastic sunset sail. Way more laid back and intimate than the crowded cruises we saw. There was a max of 6 people and the other group scheduled cancelled, but Capt Tony kept the reservation and took just us 2. The slip was pretty easy to find and the boat was well maintained and comfortable. The cruise was extremely enjoyable along the Waikiki waterfront. If you’re looking for a true sailing experience with a personal touch, I would highly recommend booking with Captain Tony.

There are so many reasons to choose this charter over others, but my top two were: Captain Tony and the intimate small-group setting (no more than six guests). It’s rare to find an experience that isn’t packed with dozens of people—which can be fun, but we were looking for something more peaceful and personal. Captain Tony was incredibly professional, friendly, and clearly an expert sailor. His knowledge and laid-back vibe made our time on the water truly relaxing and memorable. We had some great conversations, and even ended up visiting a few of the spots he recommended around the island. We’re so glad we booked this sail—it was exactly what we were hoping for. We’ll definitely be back on our next trip. Mahalo, Captain Tony!

It was really awesome to see Waikiki from the oceans perspective. And it was not on a big noisy crowded catamaran!! Very private and exclusive, Captain Tony was fantastic. Highly recommend. Kids loved it too! Take Dramamine :) we took it and had no problem!

The rhythm of the waves felt like a gentle, low-frequency massage from Mother Nature herself. It was such a relaxing trip to the beautiful Waikiki Beach. Many thanks to Captain Tony—he kindly hosted only our family of four, making the experience even more special. His warmth and generosity made the day truly unforgettable!

Private sailboat tour, easy walk from our Waikiki hotel. Quiet and relaxing with just my family. Nice captain & beautiful sunset.

Nice, intimate sail with a very experienced and knowledgeable owner/captain. It’s rare to find a sailing where the captain is also the owner of the vessel.

Tony is a fantastic captain. He has a lot of knowledge of Hawaii. This is a perfect trip for families and couples. The sunset was amazing.

We have such an unforgettable experience even though we booked last minute via call center with Viator We were to see the beautiful Sunset and the captain was very nice and also helped us when locating the boat since we were kind of lost at the Marina We were able to take amazing photos and play our favorites songs and playlists since this is an experience for few people onboard 🛥️

Capt Tony was awesome, very knowledgeable and friendly! Great sunset sailing with spectacular views of diamond head and Waikiki from the water!

Thank you so much Capt Tony! My cousin and I were looking for an on-the-water experience during our stay in Oahu. As a sailor hobbyist, I was more interested in getting to experience the sailing aspect of a sunset cruise than just a commercial catamaran being pushed out by the local companies with crowds of tourists. I am SO glad I happened upon Tony's excursion. He has a beautiful 45' monohull in which he's put a lot of love in repairing and sailing around Hawaii. He was a great host and there were only 4 guests aboard so it was exactly the level of intimate I was looking for! The winds were up earlier in the day and I was concerned our excursion getting cancelled but he responded quickly to texts and assured us of the time, location (with photos) and confirmation it would be great. He was absolutely right! We had a great sunset, beautiful sailing winds and nice easy water, and we even saw dolphins and whales. Capt Tony is a 'relaxed' captain, really demonstrating the sailor lifestyle through his stories, but also exercises textbook safety protocol. He isn't overly chatty or "professional" but just a down to earth guy you want to hang out with for a few hours and ask a bunch of questions about his experience. We are so thankful for the sunset cruise experience we had - and absolutely would recommend going with a local sailor (of course Capt Tony is our top recommendation) if you are looking for the sunset and water experience.

Captain Tony was communicative before we arrived, giving us great parking information and clear directions to find his sailboat. We left right on time, and he got us under sail as quickly as possible. He shared lots of interesting points about the area, and gave us time just to chill and enjoy the peaceful time on the water. We would 100% book with Captain Tony again!

Great evening cruse. Highly enjoyable, a very nice way to spend a few hours before dinner. Thank you Capt Tony.

This sunset boat ride was a top highlight of our trip. Captain Tony is very nice and makes sure to include and talk to everyone. Tony made the ride special by taking pictures for everyone at the perfect time and angle for sunset. If you’re looking for a more intimate sunset boat experience instead of being crammed on a boat with 60 other people, then this is the experience to book. You may sit on seats on the back of the boat, inside, or at the front and each provide great views of Waikiki beach & the sunset. Tony also mentioned he does private Turtle snorkeling, & creates special moments for those planning to propose and will keep it a secret to make it be perfect! We celebrated our honeymoon for this ride and it couldn’t have been any more perfect.

Clean boat, Captain Tony is very knowledgeable and chatty, beautiful scenery - better than the "cattle" boats

Sailing with Captain Tony was an unforgettable experience! From the moment we stepped on board, he made us feel welcome and at ease. With only four people on the sail, it felt personal—perfect for soaking in the stunning sunset views. He was not only a skilled sailor but also a fantastic guide. He shared interesting stories about the area, offered great insights, and even knew the best times and angles for capturing beautiful photos. He was more than happy to take pictures for us, making sure we had great memories to take home. The peaceful, small-group setting combined with Captain Tony’s hospitality made this sunset sail truly special. If you’re looking for a relaxed yet informative sailing experience with breathtaking views, this is definitely the way to go! Highly recommend!

Captain Tony was superb! My parents and my husband and I had an amazing time on our sunset sail! Tony was extremely helpful and had tons of island knowledge and fun facts/history to share with us that we all loved! The view was incredible and the relaxing nature of the sail was just what we wanted! I highly recommend Captain Tony and Waikiki Sailing Tours!!!

Captain Tony is one of the most fascinating people I've ever met! His knowledge of Hawaii and other countries in general is incredible. My wife and I did a sunset cruise with Captain Tony on our honeymoon, and we continually think back to how this was one of our favorite experiences of our trip! We couldn't recommend this enough!

Great sail w/ experienced competent captain Tony, an accomplished all around waterman. I'd highly recommend if you're looking for a sunset sail w/ a small group.

If you hate crowds, then this experience is for you. Only a max of 6 people at a time which made the experience exactly what we wanted. Captain Tony was very knowledgeable about Hawai’i and we enjoyed our time on his boat! 10/10 recommend!

Highlight-fun Captain Family trip beautiful sunset, Captain Tony provides a great service on this small group intimate cruise for a good price, share lots of Hawaii history helpful information about future trips around the island .we also booked a turtle early morning snorkeling before everyone we swim and saw so many turtles and dolphins made our vacation and my 10 year old daughter very happy I would highly recommend his tours

This was a fantastic experience. Captain Tony was friendly and knowledgeable, and he sent us detailed meet-up instructions the day before. My 11 year old said it was one of the best experiences of his life. We were able to see several whales and dolphins during the sail, as well as a beautiful sunset. This is great for a small-group setting and the perfect way for us to wrap up our time on Oahu.

As one of our last nights on Waikiki we decided to enjoy a stunning sunset by sail boat. Our captain Tony, provided an expert sailing experience, was very friendly, provided local tips and we even saw a whale! It was great experiencing this as a small party of four versus with 75 drunk people on a catamaran!

Captain Tony went above and beyond, great conversation and smooth sailing for our experience. Beautiful sunset, amazing photos and memories for a lifetime

We are experienced sailors and have enjoyed Waikiki for years. Capitan Tony’s sunset cruise added a unique, relaxing perspective filled with beautiful views of Diamond Head, Waikiki, and the nearby mountains,

Captain Tony was great company! It was us and another couple. We were able to sit at the stern of the ship and it felt like our own private yacht. We spotted 10-15 whales and many other animals during our cruise. Lovely conversation and company. Would book with Cap Tony again!

Captain Tony is the best. We are sailors and Captain Tony really knows how to manage his sailboat and the waters. He is extremely talented and knowledgeable about the islands and waters.