Charter Kai
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week long charters in BVI and New England, day sails, sunset sails, honey moon trips and more.
St. Thomas, U.S. Virgin Islands

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Charter Kai
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(2 reviews)
(2 reviews)
(2 reviews)
Detailed Reviews: Reviews order informed by descriptiveness of user-identified themes such as cleanliness, atmosphere, general tips and location information.
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4.5
15 reviews
Excellent
14
Very good
0
Average
0
Poor
0
Terrible
1

Angelina617
Boston, MA60 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.
Written February 25, 2020
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.

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.

Matt Finkes
Columbus, OH1 contribution
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.

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.

markh111
Ames, Iowa68 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.
Written June 7, 2022
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.

mengel5
Saint Louis, MO164 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.

Hayleigh1856
Temecula, CA5 contributions
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!
Written May 15, 2019
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.

VicsQuickTripPicks
1 contribution
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!
Written April 16, 2019
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.

Deb ~Tampa, Florida
6 contributions
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!
Written March 20, 2019
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.

Charles Boyle
1 contribution
Dec 2018 • Friends
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!
Written January 24, 2019
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.

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Charter Kai (St. Thomas) - All You Need to Know BEFORE You Go