Charter Kai
Charter Kai
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Week long all inclusive monohull sailing charters Caribbean wide. Based in St Thomas Nov - June 25th check out our destination and rates page on Charterkai.com
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Most Recent: Reviews ordered by most recent publish date in descending order.
Detailed Reviews: Reviews ordered by recency and descriptiveness of user-identified themes such as wait time, length of visit, general tips, and location information.
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5.0
20 reviews
Excellent
19
Very good
0
Average
0
Poor
0
Terrible
1
Angelina617
Boston, MA61 contributions
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.
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.
Written February 25, 2020
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
John DEVRIES
11 contributions
Jan 2021 • Solo
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!
Written February 14, 2021
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Michael S
1 contribution
Feb 2023 • Friends
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.
Written March 5, 2023
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Matt Finkes
Columbus, OH8 contributions
Jan 2021
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.
Written January 21, 2021
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Angie F
Mooresville, NC7 contributions
Jan 2024 • Family
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!!
Written March 30, 2024
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
John Faith
St. John2 contributions
Feb 2021
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!
Written February 14, 2021
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Claudia O
1 contribution
Jun 2024 • Couples
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!
Written July 9, 2024
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Conrad S
2 contributions
Apr 2024 • Family
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.
Written May 7, 2024
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Mark H
Ames, Iowa76 contributions
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.
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.
Written June 7, 2022
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
mengel5
Saint Louis, MO155 contributions
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.
Written December 31, 2019
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
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