Yacht offers rendezvous diving.
Rendezvous Dive Rates: Blue Water Diving
1 Tank Dive - $100
2 tank Dive - $130
Night Dive - $105
Discover Scuba - $140
Scuba On Board:
Yacht offers Rendezvous Diving only
Large Floating Mat- Lily Pad
Crew will take guests for free diving, lobster fishing, deep sea fishing, and hiking.
Kayaks 1 Pax:
Kayaks 2 Pax:
Water Skis Adult:
Yes, Aft Port
Water Skis Kids:
Fishing Gear Type:
Stephen moved to St Thomas 6 years ago from Hilton Head Island, SC where he operated a kayak excursion company. He really enjoyed seeing people interact with surrounding beauty and loved to facilitate their personal experiences with nature. Stephen also worked behind a few of the great restaurants and bars of Hilton Head and has put together quite an extensive list of cocktails and libations which he serves to guests on board. Stephen considers himself a mixologist and feels confident you will agree.
Once Stephen moved to St Thomas, he fully immersed himself in the culture and lifestyle of an islander. He quickly picked up free-diving and spearfishing and ran with it. Catching lobsters and shooting sustainable fish became a way of life, now these 100’s of hours spent underwater have translated to a wonderful way of providing wonderfully fresh seafood to his guests onboard. Stephen knows all the best spots for snorkeling, scuba, free diving, spearfishing (USVI only) and lobster snaring (USVI only). From jumping into the water with a mask and fins to seeing his guests take a bite of their fresh catch, its a pleasure to provide “Sea-to-Table”, both as a culinary and adventurous experience.
Stephen has his USCG Master Captain’s license/STCW and has logged over 7000 miles sailing many legs of the Atlantic and Caribbean Sea. From the top of the Chesapeake to to the southern shores of Trinidad and everywhere in between, Stephen has most likely sailed by.
The 2018-19 sailing season is Capt Stephens 3rd season cruising the US and British Virgin Islands. That being said, he has searched high and low for the most exquisite beaches, the perfect anchorages, all of the lobster holes, the busiest beach bars, and everything in between. He encourages people to visit the “must see’s” but also to get off the grid and experience the beauty and nature that the Virgins have.
Chef/Mate Caitie Rosko
"CERTIFICATE IN CULINARY ARTS" FROM ASHBURTON CHEFS ACADEMY IN THE UK.
Caitie has always had an inexplicable love for the ocean. Some of her favorite memories are bass fishing with her dad and hitting the open ocean on her grandfather’s boat. She never understood the meaning of this passion until she moved to the US Virgin Islands in 2013 after obtaining her B.S. in Biology from East Carolina University. That was just the beginning of her travel itch.
A year later she found herself living in South Africa, cage diving with great white sharks and free diving the reef systems off the Mozambique coastline. During this eye opening time, she realized that the ocean was where she was meant to be. She obtained her STCW 95 certification to work as crew aboard yachts and returned to the U.S. Virgin Islands. Then went on to join Stephen and three other crew assisting in the delivery of a catamaran from Tortola to Trinidad, stopping at over fifteen different islands along the way. After spending the next few years working for several different USVI charter companies, Caitie earned her USCG Masters License.
Working in the service industry since she was old enough to hold a job, Caitie has learned all about the importance of creating memorable experiences for guests. She believes it is always about the little things, the attention to detail, and that is what she and Stephen try to capture in every unique charter.
The cuisine is designed with adventure in mind. Sea-to-table is one of Caitie and Stephen’s specialties and they love to get their guests in on the action!
Caitie believes that there is nothing quite like reeling in a fish that they get to filet and prepare for guests just moments later. She delights in creating flavorful, delicious meals that are not only fresh and simple but healthy and beautiful.
Guests that are into photography will also enjoy the expertise of this dynamic crew. Not only do they love to create memorable experiences for their guests, they also enjoy using their drone, photography and video editing skills to creatively share their guest’s unique vacation moments.
They "Outsized" Our Expectations!
This was our second year on the catamaran with Captains Steve and Caitie. Last year we toured the BVI and it was by far the best vacation my family of four had ever experienced. This year, we stayed in the USVI and Steve and Caitie outdid themselves and our outsized expectations. Our anchorages were more beautiful than ever and the dishes Chef Caitie prepared have only become more exquisite. It’s an understatement to say the crew can make or break a trip but these two make the spacious boat feel like our own private island and even now that we feel close to them as friends, they remained ever professional and were once again magically present when we needed them and invisible when we were sharing special moments as a family. They intuit your needs before you know them yourself and tailor each trip to your activity level and interests. This year we did more diving and more isolated islands and bays. Next year, who knows? But I cannot wait to rebook and find out!
Our Time On Board Surpassed Every Expectation
Our week aboard was simply perfect—and we have you to thank for that. We discuss our trip almost daily.
Our time aboard surpassed every expectation. We wanted for nothing.
The accommodations were incredible—more comfortable than a five star hotel. We saw tons of cool spots, and never felt like we were on a schedule. There was always a new adventure ahead. For a week, our hectic reality slowed to a chill, which was good for the soul.
The way you two work together was like nothing we’ve ever seen.
Nothing was left undone, every detail accounted for. You two are the perfect team—working in sync like a fine tuned machine. Caitie, you are a master chef. The food was creative and delicious. Ya’ll captained Kailani like professionals—there was never a moment where we didn’t feel safe. Thank you for a wonderful trip!
We Cant Say Enough Wonderful Things About This Experience
We spent 6 days on our 10 day honeymoon aboard Kailani with Captains Stephen & Caitie. We can't say enough wonderful things about this experience, this boat, and most especially, these 2 people!
We decided to book a charter for the Virgin Islands for our honeymoon as we thought it would be an adventurous and perfect way to sail around the islands. After doing lots of research on the many available charters, we landed on Kailani and Stephen & Caitie simply because we liked the style of the boat with the hull master suite, and Stephen & Caitie's profiles seemed to be for 2 people that we would get along with and be able to rely on to provide an awesome experience.
Kailani itself is a beautiful boat - the setup is perfect for a couple, with the master suite, and there are several different lounging areas to spend time on if you want some privacy - which can be hard to come by on a boat. The bed in our master suite was incredibly comfortable, there is plenty of storage and closet space, and the bathroom was way bigger than what I was anticipating! But what really made the experience for us were Stephen & Caitie and their incredible service. From the beginning they were so helpful and welcoming. Stephen met us on our first day of our charter at Yacht Haven (which is a gorgeous marina) and brought us on board where Caitie was waiting to greet us with a cocktail and show us around.
As soon as we were ready, we took off on our week of sailing, in which we ultimately visited 8 islands and about 12 different gorgeous beaches. During our time spent on the boat, we got to know Stephen and Caitie, both personally about their backgrounds and life, and professionally about how they got into the industry and their love of sailing, charters and the islands. They taught us a lot about sailing, the charter lifestyle and answered any questions we had about anything. It was my first time doing true sailing, especially a multi-day trip sleeping on a boat, and was a bit nervous about seasickness and living on a boat for 6 days. Unfortunately, I did experience some sickness in our first 2 days, and Stephen and Caitie were absolutely amazing in making me feel comfortable and doing whatever they could to help.
Each morning they would check in with how I was feeling, and we'd make a plan for the day based on what I felt I could do, and how the weather conditions might affect me. They made every effort to do whatever they could to make me feel relaxed and comfortable, and I was so grateful for that.
We ran into some dangerously high winds for the last 2 days of our charter, and combined with how I was feeling, they made sure to get us back to St Thomas for safety, and still showed us an amazing time on our last day on St Thomas, despite not being able to be out on the boat. Safety and our comfort was always their number 1 & 2 priorities.
They both know the islands so well - every place we went, they knew the best spots to be and were sure to base our plan for the day on what we wanted to do. Stephen gave us tours of awesome unknown local spots to avoid tourists, and was also more than happy to take us to a beach or resort for the day to simply lounge and relax. Caitie's cooking each day was incredible - she makes wonderful breakfasts, lunches and dinners that were so delicious and satisfying, but also healthy! We left our trip feeling like we ate the most amazing meals, but that were healthy and fulfilling. The meals she can whip up in the tiny galley on a boat are so impressive!
And Stephen's cocktails were awesome - we compared his versions of popular island drinks with those on land at famous bars and restaurants, and Stephen's always had every one of them beat! Our favorite was definitely his BBC. They both were always making sure we had everything we needed, were comfortable, and that they were available to us, but also gave us privacy and time to ourselves.
We truly can't say enough good things about them and our time spent with them on Kailani. They made our honeymoon so enjoyable, especially despite how I was feeling, and truly showed us the trip of a lifetime.
Thank you Stephen & Caitie - we loved getting to know you both and spending time with you sailing on Kailani!
Sea To Table Deliciousness!
We traveled with our two boys, 11 and 13, and were expecting something fabulous and we were still blown away. We have NEVER had service at this level. We were pretty specific about our preferences and we were given all our creature comforts and more. The Kailani became home away from sweet home in less than a few hours and every time we turned around our needs were intuited and already fulfilled by the crew. We wanted some relaxation AND some adventure, some away from it all seclusion and some nightlife and they seamlessly gave us it all. Captains Caitie and Steve are both capable and at ease with those of us in the family who are more chatty and engaging and those of us who are less. They made the most amazing food we have ever tasted and we’ve been all over the world so we were impressed. We caught fresh lobster and fish and had sea to table deliciousness. Captain Steve was so good with our kids, teaching them all about sailing and the sea as my husband and I relaxed with the perfect cocktails. The service was impeccable and first class. They were somehow invisible yet available at all times. They also run a tight, clean vessel. It was easy to feel at ease when trash disappeared, beds were magically made, food and drinks appeared, and all your moorings are pre-booked and awaiting your arrival. It was magical to watch them set the sails and their passion for the ocean is evident at every stage of the journey. They knew all the secrets about where to moor, where to hike, where to eat off-boat (we took their recommendation for one meal offshore at the perfect place) and the list could go on forever. I can’t recommend this crew highly enough. They are stellar sailors and wonderful people. Our vacation was absolutely above and beyond fantastic.
Perfect In Every Way!
I suppose that most high end yacht charters in the Caribbean have a formidable level of luxury accommodations and amenities. The Kailani is no exception. The vessel is meticulously maintained and spotless in appearance. It has all the conveniences a guest could possibly wish for and then some. At no point on our week long cruise did I ever feel cramped or crowded. Every creature comfort is considered.
What sets the Kailani apart is the crew!
There are no words to sufficiently praise the Captains, Steve and Caitie. First and foremost you feel 100% safe in their capable hands (both are USCG Master Captains.) Whether you are a seasoned sailor or a newbie you will appreciate their knowledge of sailing. But that is only the beginning of the skills they posses that will enhance your days on the Kailani.
Caitie is a culinary wonder. Every meal was an event! From taste to presentation to ingredients it was all perfect. Add to this the considerable talents of Steve as a "mixologist" and you have the perfect balance between food and drink!
Their knowledge of the area, both above and below sea level, is immense. They know all the best local spots to cruise to for the perfect drink or gelato or souvenir. And they can put you in just the right spot for spectacular fishing, snorkeling, swimming or to watch the sunset. I was amazed by the adaptability they possessed to meet the expectations of the guests. At the end of the week I didn't feel like I missed out on anything.
Steve and Katie have the demeanor to put anyone at ease for a relaxing, worry free vacation. At no point during the week did I feel rushed or stressed thanks to the crew. They are simply extremely nice people who are very, very good at what they do.
After being back a few weeks and having had time to look back on the trip there is not a single thing we would change! Perfect in every way!
We're suffering from Kailani Withdrawals :)
We just finished a week charter on the beautifully luxurious new Kailani Catamaran. To say we are in “Kailani withdrawals” is an understatement. In actuality, a more accurate statement would be that we are in “Captain Stephen and Captain/Chef Caitie withdrawals”. Both vessel and crew are top notch; but, as we all know, people we surround ourselves with tend to affect our life experiences. My husband did extensive research before picking this boat and crew; and I am SO glad he did! Capt. Steve and Capt. Caitie are incredibly experienced, knowledgeable, skilled and genuine. They are each outstanding as individuals, yet also an extraordinary efficient team. They clearly love living life with zest, gusto and showing others the love of their surroundings. Their excitement, energy and joy cannot help but rub off on those around them. Because of this, our trip was more than just an experience of a lifetime, it was the reset button we didn’t know we needed. We not only enjoyed a trip we will never forget; but we also came away with some valuable life lessons. Lessons that we’ve known all along, but just needed a gentle reminder. My husband and I have traveled extensively, and yet THIS is a trip that will forever be referenced as a new high.
Every day was a new day of exploration. People chartering with this crew and vessel can do as much or as little as their heart’s desire. Some in our group wanted to relax, snorkel and do light activities. Others wanted to do things like reel in fish, learn to fillet them, learn about sailing, and even set the sails. Captain Steve and Captain Caitie were enthusiastically game for anything as long as we approached it with safety-first in mind. They found ways to make it all happen; adventures ashore and on the catamaran, snorkeling, chill-time, group time, private time. You dream it, it could happen. We all especially enjoyed Mixologist Steve’s extensive recipes of creative cocktails. Chef Caitie…Oh the meals! We requested a low-carb sea-to-table experience. We left the rest up to Chef Caitie to decide, and she constantly wowed us all. Each meal was light yet seeped in flavors and satisfying. After dining we were completely satiated but also were not in a food-coma and could still go snorkeling and move onto the next adventure offered. Captain Steve and Captain Caitie’s approach to each day was filled with the perfect balance of relaxation and exhilaration.
As our trip was approaching the end, our group talked about how we couldn’t wait to do this again. There are simply not enough adjectives out there to describe this experience. If you are on the fence at all, don’t wait 25 years like we did. DO IT NOW, and then again, as often as possible. I know we will. THANK YOU Steve and Caitie for being the type of people that left an imprint on our lives. Aside from all your proficiency, expertise and knowledge as sailors; we have great respect for you both as being the type of people this world needs more of. One day, we hope to have the honor of being your guests once again.
We can't wait to do it again.
Without trying to sound like I am exaggerating, there are not enough positive words in the world to describe how extraordinary our experience was. Our expectations were exceeded by a huge margin. It is difficult to find the words to express how outstanding this charter experience was.
The vessel being fairly new was obviously in great shape. Everything was in perfect working order. But it was also very apparent that the owner and crew were on top of upkeep, maintenance and cleaning of the boat. It was comfortable, clean, cool and had an ergonomically great layout.
However, what really made this charter stand out was no doubt the crew. Stephen and Caitie went way beyond 100% effort to make sure we were safe, comfortable, relaxed and taken care of. Their individual professionalism, personalities and approach were awesome. But when they worked together as a team, it just amplified all the positives even more. They made sure that for that week aboard Kailani, we were the most important people in the world and they showered us with the VIP treatment no question about it.
We requested a low carb/sea to table dining experience and boy did Caitie deliver. Her creations in the galley were right on target. Beautifully presented, tasty, healthy and light. It was obvious that she put much thought into meeting our requests and made every meal something to look forward to. Steve's cocktail mixologist experience also came in very handy as he presented us with various delicious cocktail combinations to enhance the mood and make our taste buds dance. There was not one drink or meal all week that was not delicious and satisfying.
Steve's and Caitie's desire to show us the first class BVI cruising experience was obvious. We basically asked them to determine our itinerary and stops to give us a nice balance of activities and they anticipated and executed that desire so effortlessly and beautifully. We were celebrating my wife's birthday on this trip and they made that special as well. My wife is all about getting in there and experiencing all she can so I asked Steve and Caitie to give my wife the full experience as much as possible. It was great to see my wife so involved and excited about this first time sailing charter for her. Steve and Caitie were right there to make sure it all happened. My wife snorkeled, fished, filleted the fish, worked the sails, swam, drove the dingy, collected shells, etc. But it was also fantastic how involved the crew made all of us feel and extended the same opportunities to all the guests aboard equally. Additionally, Steve's ability to teach, instruct and encourage us to try new things and experiences is definitely a strong point for him. He made it all easy, relaxed and fun.
Because of Steve's and Caitie's love for what they do, we also learned a lot. We learned about the islands, the ocean, the wildlife, the vegetation, the environment, the history and about the people. They had so much interesting information about the area that it was educational as well. And finally, we learned something about ourselves too. Seeing Steve and Caitie and their positive approach to everything in this beautiful part of the world made us pause and think to not sweat the small stuff and enjoy life more everyday. Something Steve said repeatedly when we were experiencing something new to us was " do it with confidence". That stuck with us and now is our favorite thing to say to each other. So I will wrap it up and say "WITH CONFIDENCE". Steve and Caitie are the best!!!!! Kailani is gorgeous!!!! And we can't wait to do it again!
It exceeded all expectations!
Our trip could not have gone any better. It exceeded all expectations, and they were high expectations! Steve and Caitie were unbelievable. There really aren't enough things we could say to express our gratitude. They were fun, thoughtful, and beyond accommodating. I would highly recommend them to anyone considering a charter. Additionally the Kailani was perfect. Beautifully maintained and amazingly comfortable. Couldn't have asked for more, honestly.
An Amazing Team!
Stephen and Caitie were absolutely wonderful. They make an amazing team. They have the magic of making you feel relaxed and have complete confidence in their sailing skills within only an hour or two of being on the boat. Even for 1st time sailors like myself!
They took care of every single detail to make sure our week was memorable, and memorable it is indeed. Everything from being able to adjust the daily itinerary depending on weather and winds to make sure we could maximize every moment with beautiful scenery, great sailing, amazing snorkeling and swimming, right down to every little attention they bring to everything. Caitie is an outstanding Chef! She concocted 5 Star delights at every single meal. Stephen is great on the grill (that bacon… Mmmmm!!!) and makes the yummiest drinks! They are also very patient and extremely good at teaching about sailing. The Guys had a blast learning how to put up the sails and actually sailing.
The fishing was great. Stephen was always ready and willing. It was a blast!
The boat is incredibly clean and tidy and the beds are very comfortable!
We honestly do not have one single negative thing to say about our week.
Over The Top Professional!
The most amazing girls trip I have ever been blessed to be a part of!!! We spent a week sailing around on a beautiful catamaran called "Kailani". As if that wasn't amazing enough, the two that captained the boat were over the top in handling the ship and taking care of every whim. They are the cutest couple and as sweet as sweet can be!! Today was a little humbling, now that I am home and had to fix my own breakfast without a mimosa! I would recommend this boat and crew to anyone anywhere! Steve and Caitie you two are over the top professional.
Recommend to Anyone and Everyone!
Stephen and Caitie are hands down the best at what they do. If you want the full, authentic VI experience, then book a trip with them. Both of them are so knowledgeable and talented, you'll be in the land of pure relaxation, with adventure mixed in if you wish. They will make you feel like a local as well as a VIP charter guest at the same time. We were fortunate enough to have fresh lobster caught that morning by Stephen, and the meals that Caitie prepared us completely blew us away, amazing! I will recommend this crew and this amazing boat to anyone and everyone, what an amazing experience and vacation we had.
Just Say Yes!
We had such a great week aboard Kailani with Stephen and Caitie. We couldn't be happier with the boat, the crew nor the destination! We haven't been off of her long and already our youngest is in tears because she misses everything and everybody! If you've ever wondered if a crewed yacht charter is for you.... just say YES!
Words Can't Describe How Awesome It Was!
We just spent an amazing week onboard Kailani for our honeymoon and words can't describe how awesome it was. Stephen and Caitie made the sail a 5 star event, from the food, to their great service - best vacation ever!!! if you are looking to sail the BVI's this is your crew and boat.
The crew are fabulous!
I want to thank you so much. Stephen and Caitie were awesome. My wife and I had the best time of our lives and that it was our honeymoon made it that much sweeter! The boat was beautiful and the food was amazing. The crew are fabulous. We wrote a nice review on Trip Advisor and can’t wait to come back.
An AMAZING team
I think I can confidently speak for all of us when I say we had an absolute BLAST. The boat was the perfect size for us. Not too big, not too small. But a huge pat of the success to our trip goes to the crew!!!!
They are an AMAZING team and by the end of the trip we felt like they were on vacation with us, like friends we had invited along! Steve is so chill and laid back, but knows when to get the job done, and he did many times! Bringing us frozen drinks on the beach via paddle board with even fresh nutmeg was a great touch! And the food that came out of that tiny floating kitchen was unbelievable! Her love for cooking was SO obvious and very much appreciated by us. You have a great crew there for sure!
We hope to make it back there again one day! ~The Laffler Group
Could Not Have Been More Perfect!
My husband and I have always dreamed of sailing a catamaran around the beautiful islands in the BVI, but we never dreamed it could have been as amazing as the trip we took with Captain Steve Cross.
The attention they took to understanding our desires for our trip was awesome. We love to snorkel and they made sure we went to outstanding snorkel spots. We prefer the more natural places away from the crowds and they delivered. They gave us great adventures like diving for lobster then preparing and cooking them on the grill.
The crew made all of us feel so comfortable. I appreciated their positive relaxed take on everything. It made you stop and be ever so thankful for your surroundings and life. Never have we seen stars so bright and plentiful.
We look forward to taking another adventure sailing, as well as many of our other friends who are anxious to go too. It could not have been more perfect!
The Crew Took This Trip to a Whole New Level!
This was our third time taking this trip - and this was by far the best. I did not think we could top our last two trips - but Steve took things to another level. The crew were both very professional but knew how to have a great time. We always look forward to eating at restaurants while we are down there but none of the restaurants lived up to what was made on the boat. There are many captains in the BVIs - but not many that know where to catch fresh lobster, conch and real in some fresh fish all in the same trip. I certainly would recommend this trip to friends .~The Hahn Family
Wonderful Christmas Vacation!
Captain Steve was an excellent host and truly made the entire experience wonderful. Our kids could not stop raving about how great it was, "best trip everrrrr!"
Relaxed and flexible sailing agenda
Captain Steve caught fresh lobster, conch and red snapper for dinner.
White sand beaches, great snorkeling, hiking and cliff jumping
Unbelievable quality family time.
~The Hartman Family