KAI

Amy: Charter Kai Provides Trip of a Lifetime! Feb 2026

Our 6 days sailing on the KAI were magical! The KAl is a BEAUTIFULLY restored boat and provided a unique, comfortable monohull sailing experience.
Captain Justin, Chef Lecil and "mate" Sam are kind, caring people and absolutely perfect hosts! Justin has 10+ years experience doing charters in the USVI and his knowledge and insight enhanced every minute of our vacation! Chef Lecil was an absolute gem! Our meals were gourmet-level treats! I will never understand how she did that in such a small space! Although the KAI can accommodate 6 people/3 couples, we loved our experience with just the two of us.

Claudia: Couples Charter June 2024

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. My husband and I booked our trip a year out for our 10 year anniversary. Let me just say it was a once in a lifetime experience. We sailed to six different islands in 8 days. Ate the most delicious meals by Chef Maddie and my sailing husband learned so much more about sailing from Captain Justin. By the end of the week we were sad to say goodbye to them, deckhand Sam too. Through a questionnaire and preference sheet we were able to let them know exactly what kind of trip we wanted down to what our favorite foods are. (We aren’t picky, but I suggest telling Chef Maddie exactly what you like and don’t like, she is there to make every meal the best, so let her know) Some relaxing, some adventure, and to be able to take in as much of the beauty of the islands as possible. They delivered tenfold! Not only was it the best adventure we’ve been on as a couple, but we left with two new friends. Booking a charter with Charter Kai will be the best thing you’ll ever do!

Conrad: Amazing Experience on One of the Few Monohulls in the USVI

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.

Angie: Best way to see the islands!

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!!

Matt: Awesome experience every time.

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!

Michael: Fantastic Captain and crew! Great experience!

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.

Mark: Fantastic Vacation

May 2022
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 and daughter had no difficulty with the ladder at all, so this is likely an issue that will not affect most people.

Another potential drawback to a yacht concerns the crew. Since it’s just you and them on the yacht, if you are unlucky enough to get a bad crew you can easily have your vacation ruined. This is, I want to emphasize, most definitely not an issue with the Kai. The captain Justin and first mate/chef Maddie are superb at their jobs. They are highly competent folks who are about as friendly and accommodating, without being intrusive, as you can possibly ask for. (Another “crew member” who should be mentioned here is second mate Sam, who is a dog that has lived on Kai just about all her life. She is friendly and adorable, and all three of us loved playing with her.)

Dining is not the same on a chartered yacht either. On a cruise ship you have multi-course meals with multiple choices for each course. That, of course, is just not possible when you have one chef working in a small galley. However, Maddie did an exceptional job preparing meals. She sent us a pre-cruise survey asking our food preferences; we presented her with something of a challenge because our tastes are somewhat incompatible: my wife and daughter love seafood, but I hate it. I fully expected that there would be some meals where I ate just a salad or nothing at all, but Maddie came through excellently: even on nights when she prepared seafood for the ladies, she usually managed to make the same dish for me but with meat instead. For example, one evening she prepared a skewer of scallops, served on a pineapple half with rice; I got a skewer of steak instead. The food was also delicious: if you charter this boat, be sure to request that Maddie make her key lime pie.

Leslie: Dream Vacation

May 2022
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 good snorkeling with fish and coral at the edges, and the beach is lovely.
Day 4: We motored to through the channel between the British Virgin Islands and St. John, staying well on the US side since BVI still do not allow US boats to enter. We continued on around the eastern edge of St. John to Coral Bay. and anchored off a private beach next to Hansen's Beach. I snorkeled upon arrival (to the beach and back) and saw a lovely stingray in moderately deep but crystal clear water, as well as several nice fish and good coral. After lunch everyone except Justin snorkeled from Kai to the beach. Maddie spotted some turtles and pointed them out to me; I had a good snorkel with one turtle.
Justin met us with Sam on the beach (Sam loves to chase a ball on the beach) and we all went back to Kai in the dinghy.
Day 5: We had a nice sail to St. Croix. The wind was from the eastsoutheast so we had one long tack that was not quite a beat. The wind started strong but dropped a bit, which slowed us down, but we sailed the whole way to St. Croix. We then motored a short distance to nameless reef that our family now calls Justin’s reef. The fish and coral here were spectacular and the water crystal clear and shallow along the reef, making for excellent snorkeling.
Day 6: We motored into Chritianstad in the morning and went ashore by dinghy to explore Christanstad. Although our main interests were snorkeling, sailing, and natural scenery, we enjoyed walking around the town and seeing the fort. After lunch Justin took us in the dinghy to Protestant Cay, otherwise known as the cay with the hotel. The underwater environment is not as good as some others but I had amazing luck here. I snorkeled with two turtles in the grassy area in front of the beach at moderate depth. I then snorkeled parallel to shore to the point but saw only few fish and no good coral. I then heard that a ray had been spotted in deeper water so I snorkeled out and looked around but saw nothing. As I was snorkeling my way back through shallow water over grass close to the beach, all of a sudden I saw a ray in the grass and sand ahead! He saw me and was not pleased so he swam away but since it was only two feet deep I was closer to him than the other rays.

Sailing: The sailing was great. Kai is a sloop, which means she really sails (including heeling and spray), unlike a catamaran. It was great fun to experience open ocean sailing; previously I have only sailed in bays and lakes and smaller boats.

Scenery: The scenery was beautiful. The turquoise water and sunrises/sunset were highlights.

Food: No review of Kai would be complete without commenting on the amazing meals Chef Maddie served us. We had three wonderful cooked meals and an afternoon snack every day. Both the taste and presentation were amazing and she accommodated our group of incompatible eaters exceptionally well. How she does it in the tiny galley I will never know.

John: Sailing Trip

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!

Matt: Awesome Experience

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.

John: Awesome!

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!

Name: Lisa
Yacht: KAI
Charter Dates: 02/24/2020 11:00 am to 03/01/2020 11:00 am
Area Cruised: Virgin Islands
Overall Rating: 5/5

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.

Angelina: Highlight of our VI trip!

Feb 2020
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.

Fantastic Week Aboard Kai Dec 2019
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.

Name: Chris
Yacht: KAI with Justin Smith
Charter Dates: 2019-11-15 12:00 to 2019-11-22 12:00
Area Cruised: Virgin Islands
Overall Rating: 5/5

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.

May 2019 • Friends
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!

Mar 2019 • Couples
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!

Name: Victor
Yacht: KAI KAI with Justin Smith and Sarah Ford
Charter Dates: 2019-03-20 12:00 to 2019-03-27 12:00
Area Cruised: Virgin Islands
Overall Rating: 5
5 being the highest 0 being the lowest
We hope your charter lived up to your expectations. We would love to know some of your impressions about your yachting vacation. Please answer the following questions and add any comments you may have.

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!

Deb: AMAZING TIME ON KAI

Feb 2019 • Friends
Wow what a great time we had staying on Kai in the USVI. The boat is absolutely beautiful and the crew was the BEST! Justin and Sarah went out of their way to ensure our trip was PERFECT. Can't wait to sail with them again next year!

Pepper: Jan 2019 • Solo
Had a great four day trip from Fajardo to USVI with two over nights to Culebra and culebita , Justin a great sailor ,no motoring. IN my 40 years of sailing this was my best trip.Ate fresh fish everyday. Sarah a great cook and person.

Taylor: Amazing experience!

Sep 2018 • Couples
Four of us decided to book a night on the charter yacht Kai during a weekend visit to block island. It was beyond excellent! Justin and Sarah were spectacular hosts, welcoming us into their home and making sure we were comfortable. The boat was gorgeous (and sparkling clean), and after a fun evening, we had a great night sleep! We woke up to delicious hot coffee, with a few different options for breakfast (eggs, bagels, apples etc). I would love to book another trip aboard the Kai in the future.. wish we could have stayed longer!

We were blessed to spend our 28 year wedding anniversary on a Kai for weekend sail. Unlike many charter companies, Justin and Sarah customized a trip just for us. We left Niantic CT and sailed to Sag Habor,NY on day one and on day two we sailed to Montauk. We were moored in beautiful locations and Justin was always available to drop us off and pick us up from the dock. Although the boat is older, it feels far more solid than any other we have been on. Everything was extremely clean and comfortable. An unexpected delight was the special foods prepared by Sarah. She made it a point to get to know us ahead of time and to stock the galley with everything we liked from meals to snacks to cocktails. She is an incredible chef preparing the freshest fish ceviche, shrimp cakes and from the farm greens with fresh tuna and grilled chicken. Breakfast was made to order. Justin who was raised on boats is a master sailor. We never felt unsafe with him. He is brilliant when it comes to all things boats and sailing. Aside from that, both Sarah and Justin are warm and welcoming and we couldn't have thought of a better way to celebrate our anniversary. We look forward to joining them in St John and around the BVI- also a place they know intimately.

I was fortunate enough to sail with the crew of Kia from Marathon Florida to Georgetown Bahamas. To call it the trip of a lifetime would be an understatement. It was truly a life changing adventure. I am a sailor myself and am always weary about sailing on another captain's boat, but Justin is an exception to the rule. He has more experience on the water then most sailors twice his age and he is always willing to pass his knowledge to others. Hanging out with Justin and Sarah on all the islands along the way, hiking, fishing, swimming, and sometimes just chilling, will be memories that I will cherish forever. Thank you both from the bottom of my heart. Fair winds my friends

The captain and first mate are super professional, welcoming, laid back and open minded people, they know best spots for snorkeling, fishing or best Mohitos. It was a great pleasure spending a week on the beautiful and very comfy boat having delicious meals and great conversations with Justin and Sarah. Thanks a lot for this unforgettable experience and see you on my next holidays with Kai!

Charles: Awesome boat, wonderful captain and crew, and perfect trip.

I was lucky enough to get to sail on Kai, with Justin and Sarah on a trip from NC to The Virgin Islands. We had a wonderful 10 day passage offshore and 4 more perfect days Island hopping. Caught fish every day, including one yellowfin tuna! Sashimi for days....

Kai is a strong, fast, beautiful and exciting boat to sail. Justin is as good a captain as you could hope to find. Sarah is a magician in the galley, and very competent crew! Not to mention they are both fun and interesting to spend time with.

The sailing was spectacular. Justin let us help when we wanted and experience offshore sailing at its best, while always keeping a watchful eye that I didn’t crash the boat.

The accommodations are extremely functional, comfortable, and beautiful as well.

If your looking to sail offshore and hone your skills, or island hop in the Virgin islands and beyond, or just spend a few quite restful days at anchor in a beautiful location, I can’t recommend this boat and it’s crew strongly enough.

Can’t wait to do it again. Thanks Justin and Sarah. Love you guys! We will be back!