
KAI is a beautifully restored 72-foot Wellington sloop offering a unique and comfortable monohull sailing experience. She features a modernized classic design equipped with green energy solutions including solar panels and wind generators.
Everything you need to know about KAI — from build year to onboard specifications.









6 guests in 3 guest cabins.


Justin was born in Connecticut and raised by seafaring grandparents. He received his master's license at age sixteen and has over 11 years of experience in the charter business, specializing in rebuilding classic boats.

Born in Colorado, Lecil has a background in theater and sculpture. She joined the team on Kai in 2024, combining her passions for sailing and gourmet cooking.





Starlink Unlimited, Cocktails of choice

Overnight Generator Use $10/hr after 8pm. A/C fee $10/hr. BVI Flat Fee $25,000 includes customs/immigration. Relocation fee for trips out of USVI $1,000 - $2,000.
"Our 6 days sailing on the KAI were magical! The KAl is a BEAUTIFULLY restored boat and provided a unique, comfortable monohull sailing experience."
"If you are looking to sit back and relax and enjoy all that The BVI has to offer then look no further than Charter Kai. It was a once in a lifetime experience."
"Awesome experience every time. This was our 4 year and trip with Justin on Kai. Every year is a vacation of a lifetime."
"I'm not a sailor, but have always wanted to take my family on this trip of a lifetime. If you have romantic notions about sailing, wooden boats, exploring islands and waking up to amazing meals... this is the way to do it. Huge thanks to Justin and Maddie for accommodating all the very varied experiences my wife and three teenagers were looking for. For those of you thinking of chartering - don't overlook the huge upside of the Captain who everyone knows."
"We have chartered Kai since 2021 and never regretted one trip. Justin is an amazing captain and takes you to the best, non tourist filled spots. We have traveled to the US Virgin Islands, Spanish Virgin Islands, Puerto Rico, The Grenadines and Connecticut on Kai. She's a beautiful boat and you will feel at home. The food is top notch! Book Kai today!!"
"This was our 4 year and trip with Justin on Kai. Every year is a vacation of a lifetime. Maddie is an excellent chef and Sam is our favorite boat dog ever!"
"Charter Kai does it right. Captain Justin is one of the most knowledgeable and well respected captains in the industry. Chef Maddie is a top level chef and absolutely everything was "on point". Couldn't ask for a better experience."
"My wife recently celebrated her 70th birthday and because she and my daughter both love snorkeling and sailing, they decided to charter the yacht Kai for a week of sailing the US Virgin Islands. Although I wasn’t at first sure that this kind of vacation was really my thing, I subsequently decided to go along with them, and was very glad I did. My wife rates this (see her review, below) as one of the two best vacations she has ever taken in her entire life; while I am not prepared to go quite that far, I would certainly describe it as a five-star experience, and would not hesitate to recommend it to others. Chartering a yacht is, in a number of respects, a lot different than taking a cruise. For one thing, the ship is smaller (the Kai is 70 feet long) and this allows you to get to places a cruise ship cannot. (As one example, our captain Justin took us to a secluded reef for snorkeling.) I definitely feel that I got a much more in-depth look at the Virgin Islands than I could ever have gotten on a cruise ship. (Justin devised an itinerary that matched our interests, communicated in a pre-cruise questionnaire.) Also, unlike on a cruise ship, you don’t have to contend with hundreds (maybe even thousands) of other passengers; there are no lines for excursions, dining, etc., and you have a real sense of peace that simply cannot be matched on a cruise ship. And, of course, there are very few cruise ships that give you the experience of actually sailing in the open ocean. On the other hand, yachts are somewhat harder to get around on. Walking on deck requires you to step over and duck under all manner of lines, sheets, knobs, pulleys and whatnot. And I (age 72, creaky and not in the best of shape) found getting on and off the yacht to be nerve-wracking; it entailed walking up and down a vertical ladder flush against the ship, getting from the ladder onto a wooden platform, and then getting from the platform to the water (or dinghy, as the case may be). However, my wife a"
"Chartering a yacht is the best way to get to good snorkeling sites, avoid crowds, and have a truly relaxing vacation while seeing a lot. It is also a dream come true for those who love sailing. Our one-week charter of Kai sailing around the US Virgin Islands was one of my best two vacations in more than 50 years of extensive travel both domestic and international. Caveat: Chartering may be less than ideal for people who have mobility issues or prefer a cruise ship environment. Itinerary: Day 1: We boarded Kai at noon and were welcomed by Captain Justin, First Mate/Chef Maddie, Sam the sweet dog who lives aboard Kai. After settling in we motored over to Brewer’s Bay with lunch on deck en route. The snorkeling here was mostly good but not great- reasonable variety of fish but fairly far below you since the water was deep, but there was good water clarity. I was thrilled to see a stingray and Justin pointed out several turtles swimming on the surface. After snorkeling, we had an amazing dinner (scallops or beef skewer on a half pineapple filled with rice). Day 2: We sailed to Christmas Cove between Great James Island and Fish Cay. We beat and tacked into the east wind all the way, which was fun for the sailors. The site was gorgeous (probably my favorite for scenery). Fish were very good and around Fish Cay the water was not too deep so you are closer to the fish; the water was also crystal clear. I again saw a stingray, this time swimming by closer to the surface. We also snorkeled in the afternoon, after using the paddleboards like kayaks (sitting on them and paddling) since it was choppy. In the evening, Justin turned on the lights, which attracted several stingrays that we snorkeled with. Day 3: We motored along the coast of St. John to Maho Bay Beach where we snorkeled with many turtles in shallow water off the beach, and another member of the party saw a stingray. Maho is the one site we visited where you are pretty much guaranteed turtles. There is also goo"
"Just finished a great trip with Charter Kai from St John to St Croix. Captain Justin Smith is a extremely knowledgeable sailor and Kai was laid out perfectly for our group of four. Sarah the first mate is a excellent cook. The food was incredible. I will definitely be taking more trips on Charter Kai. Five stars all the way around!"
"Absolutely awesome! Everything about this trip had us planning our next one before we even left the boat. The food, views, experience were all once in a lifetime. Justin and Sarah were great hosts and guides. I would highly recommend them to anyone looking for this kind of experience."
"Regina and I had the trip if a life time. Sara and Justin were great. The food was amazing and they made sure we always stayed in calm waters every night. The way they really were prepared for all of our special requests including making us great desserts such as Key Lime pie and creme brulee was fantastic. They even mastered my perfect Manhattan and made Regina and I delicious Arancini as an app! When we wanted to eat outside they made us a table out of the SUP that was perfect! They are a lot of fun with no drama and we're always accommodating to our requests! 5 Stars!"
"1. Was the crew friendly and accommodating? Yes! They had everything we needed, including anticipating things we didn't know we needed. They both are very professional, which we appreciated. I felt both well taken care of and also in the hands of a competent crew should anything go wrong (which it didn't ... hugely successful trip!) 2. Was the yacht comfortable and clean? Yes, the best part was beanbags on the forward deck for lounging ... But also great was the spacious dining area below deck and the berths were more spacious than anticipated for the size. 3. Was the yacht well ventilated? AC was on and offered if needed, we could open hatches if not raining (obviously), fans available. 4. Was the food good and well presented? FANTASTIC. Sarah created the most delicious meals and we were only disappointed when we went out to eat, because it wasn't as good as Kai! Seriously delicious food, restaurant quality, nice presentation, attention to detail... Even snacks! 5. Did you like the area you sailed? LOVED the area. We couldn't have planned a better route ourselves. Our captain knew many quiet anchorages that felt like no one else was there, but also knows the hot spots. Our trip was a mix of places that first time BVI tourists should go, and many lesser known spots that are so special. We felt like the captain tailored the trip to our taste after getting to know us, and it was a perfect itinerary for our group."
"Without a doubt, the highlight of our recent VI trip was our special time aboard KAI. She is a big, beautiful and very comfortable boat. Our family of five found ample space to hang all together playing games in the saloon or to find some alone time out on the deck. The boat had gorgeous woodwork throughout, holly and teak etc. Cabins were great size and had very cozy beds, interior tastefully decorated. We couldn't have picked more gracious hosts. Justin is clearly an attentive and very experienced captain. We were lucky enough to be able to enjoy some great wind and travel under sail which was a thrill for all. Sarah breezed back and forth as first mate and chef (no easy task) always with a ready smile. She prepared beautifully presented meals which were delicious and customized for our family - including a couple picky eaters. Her desserts were amazing! Our 12-yo daughter exclaimed one dinner of sirloin steak, cheesy mashed potatoes and bacon wrapped fresh green beans was the best meal she ever had and has already asked me to replicate 😲! As local guides they had tons of knowledge of the flora and fauna of the islands and knew some great spots off the beaten path which were interesting and provided spectacular views. Our kids loved trying tamarind and cactus fruit along the way. Justin and Sarah both had great senses of humor and instinctively knew how to spend just the right amount of time alongside us. We highly recommend sailing aboard KAI for your next family adventure. It is one ours will never forget."
"There are so many things that can make or break a luxurious trip like sailing on your private yacht in the pristine waters of the Virgin Islands. The crew is the most important part for your safety, sailing skills, knowledge of the area and desire to be great hosts. I can honestly say Captain Smith (Justin) and First Mate, Sarah over-delivered on everyone on of these areas. Justin is such an experienced sailor and knows the Virgin Islands so well regardless of the wind we had or where we wanted to go we always felt in great hands. The boat was steady, ALWAYS clean, and in amazing condition. The boat itself is beautiful and as owner/operator Justin takes incredible pride in every square inch of the yacht. I enjoyed speaking with Justin and hearing about all his experience sailing around the world on more than 30 different boats, many he rebuilt and later sold. Last but not surely not least great drinks and awesome food were Sarah’s specialty. After every afternoon swim we were greeted with cocktails of our choice, appetizers or whatever else we needed to make our stay on the boat amazing. Justin and Sarah were incredible hosts and always made us feel welcome with even the craziest request like a few special meals for the picky eater in our family. Always served with a smile. I cannot wait to take another trip on Kai with Justin and Sarah."
"1. Was the crew friendly and accommodating? Extremely - We enjoyed our time with Justin and Alyse. 2. Was the yacht comfortable and clean? Yes - everything was very nice! 3. Was the yacht well ventilated? When the HVAC was running - yes! 4. Was the food good and well presented? Yes indeed; the food and presentation exceeded our expectations. Alyse is an amazing chef! 5. Did you like the area you sailed? Yes, very much. Both Justin and Alyse were quite knowledgeable about the islands and offered details, big and small, that added to our overall experience. 6. Additional comments on your charter? We had a fabulous charter aboard Kai. Justin & Alyse were very in tune to our "style" of relaxing and having fun - both on and off of the boat. They were accommodating and very interested in ensuring that we enjoyed every moment of our vacation."
"This was easily the best trip I’ve ever been on. Justin and Sarah were amazing and so much fun to be around. Kai was beautiful inside and out, literally nicer than my own apartment! Sleeping on the boat was my favorite, it was so comfortable and I got the best nights sleep. They were so accommodating and took us all over the USVI and BVI. Justin was a great captain and kindly answered all of my 10 million questions. Sarah was so sweet and made the best food and drinks, making it a trip of a lifetime. They were both so honest and knowledgeable, pointing out historical sights and wildlife, taking us to amazing beaches, and great restaurants! I would never want to experience the Virgin Islands any other way again! I definitely would recommend booking a trip with them, you wouldn’t be disappointed! I will definitely be back!"
"My family and I had the pleasure of experiencing the wonder of the US and British Virgin Islands in March, 2019. Justin and Sarah were wonderful guides, sailors and partners on the journey. The Kai is a wonderful sloop which Justin expertly navigated through the crystal clear waters of the Caribbean. We were able to go to places that most tourists will never see, including pristine out-of-the way bays and coves. Sarah prepared delicious meals for us everyday and kept our thirst well quenched at all times! If you want to experience true sailing and see the most of the USVI and BVI, please consider taking a charter cruise on Kai. Thank you Justin and Sarah for the unforgettable adventure!"
"1. Was the crew friendly and accommodating? Extremely 2. Was the yacht comfortable and clean? Yes 3. Was the yacht well ventilated? Yes 4. Was the food good and well presented? Yes. A nice variety of well-prepared delicious food with excellent presentations. 5. Did you like the area you sailed? Captain Justin designed the route for optimal sailing time, which was a priority of ours. 6. Additional comments on your charter? Captain Justin Smith and First Mate Sarah Ford were welcoming, informative, cheerful, helpful, and accommodating. We felt very safe and secure in their able hands. We feel fortunate to have sailed with Justin and Sarah on beautiful KAI, having enjoyed many interesting conversations and unforgettable sailing experiences. A great team, a great boat, a great trip!"

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