S/V Kailani meaning “Sea and Sky” is the epitome of pure beauty and comfort. The brilliant style of Fountaine Pajot’s Helia 44 makes for a perfect family vacation or trip with dear friends. Space opens up a multitude of lounging areas both indoors and outdoors. Reclined seating on the foredeck and built-in pillows on the trampoline create an exciting encounter with nature while sailing along. For the best panoramic views enjoy the sundeck just above the captain’s station where you can also take in the action of sailing or chat with the captain himself. This version includes a Queen Suite which expands over the entire starboard hull.

Catamaran Kailani Photo Gallery

Catamaran Kailani Crew: Captain Stephen Cross and Chef/ Mate Caitie Rosko

“We are a U.S. Flagged Charter Crew and we strongly believe in creating unique experiences while sailing throughout the U.S. and British Virgin Islands. Sea to the table is our specialty and our passion.”

Kailani Crew Captain Stephen CrossCaptain Stephen Cross

Stephen moved to St Thomas from Hilton Head Island, SC where he operated a kayak nature tour. He really enjoyed seeing people interact with the surrounding beauty and loved to facilitate their personal experiences with nature. Stephen also spent time working in the restaurant industry on Hilton Head, and he learned to become a very creative mixologist behind the bar! One of his specialties is a Coconut Mojito muddled from coconuts he fresh picks from palms on the beach for guests.

Once Stephen moved to St Thomas, he fully immersed himself in the culture and the lifestyle. He quickly picked up freediving and spearfishing, both as a way of enjoying his days off and spending time on the water and as a way of treating himself and his friends to delicious, fresh seafood. Stephen is an avid free diver and knows all the best lobster spots in the Virgin Islands. From jumping in the water with a snorkel and mask to seeing his guests taking the first bite of his catch, grilled to perfection, Stephen loves the whole process of “Sea-To-Table.”

Stephen has his USCG Master Captain License and an STCW 95 certification. He has logged over 1000 miles sailing in the Caribbean, visiting almost every island in the Windward chain. Stephen has experience navigating on both open ocean and near-shore bodies of water. He truly enjoys the life of a sailor. Onboard, guests can easily encourage Stephen to play his guitar or ukulele and sing some ancient Hawaiian songs about the sea or strum and hum some Jack Johnson tunes. He is a high energy captain and couldn’t be more excited about helping to make peoples’ dream vacations better than they ever could imagine.

This being Stephen’s second season as a captain aboard a term charter yacht, he knows ALL the secrets the US and British Virgin Islands have to offer and he has made a lot of friends along the way. It will not be uncommon to pull into a little beach bar and receive the local treatment when guests arrive with Captain Stephen!

Chef/Mate Caitie Rosko

Caitie has always had an inexplicable love for the ocean. Some of her favorite memories are bass fishing with her dad Kailani Crew Chef/Mate Caitie Roskoand 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.

Catamaran Kailani Sample Menu


Caitie’s  Sample  Sea Menu Gallery


Guest Testimonials Catamaran Kailani

Testimonial From The Sisters

Catamaran Kailani Iyachtclub Testimonials

Jeff Recommends Catamaran Kailani

Catamaran Kailani Iyachtclub Testimonials


Catamaran Kailani Testimonial From Blair

Catamaran Kailani Testimonial From Blair


Charter Calendar

Currently booked or requested dates:

Date Start Date End Status
Mar 23, 2019 Mar 29, 2019 Booked: Red Hook to Red Hook
Mar 30, 2019 Apr 06, 2019 Booked: Red Hook to Red Hook
Apr 07, 2019 Apr 08, 2019 Unavailable: St Thomas USVI to St Thomas USVI
Apr 14, 2019 Apr 20, 2019 Booked: Yacht Haven Grand to Yacht Haven Grand
Apr 25, 2019 May 02, 2019 Booked: Red Hook to Red Hook
May 03, 2019 May 09, 2019 Booked: Red Hook, St. Thomas, USVI* to Red Hook, St. Thomas, USVI*
May 11, 2019 May 18, 2019 Booked: St Thomas USVI to St Thomas USVI
Jun 01, 2019 Jun 08, 2019 Booked: Red Hook to Red Hook
Jun 10, 2019 Jun 17, 2019 Booked: Yacht Haven Grand to Yacht Haven Grand
Jun 22, 2019 Jun 29, 2019 Booked: Yacht Haven Grand to Yacht Haven Grand
Jul 10, 2019 Jul 17, 2019 Unavailable: Yacht Haven Grand to Yacht Haven Grand
Aug 17, 2019 Aug 24, 2019 Booked: Yacht Haven Grand to Yacht Haven Grand
Nov 16, 2019 Nov 23, 2019 Booked: Yacht Haven Grand to Yacht Haven Grand
Dec 29, 2019 Jan 05, 2020 Booked: Yacht Haven Grand to Yacht Haven Grand
Feb 07, 2020 Feb 16, 2020 Hold: Yacht Haven Grand to Yacht Haven Grand


BVI Crewed Yacht Chart

Best Rate
Passengers 2 3 4 5 6
Winter 2018
Per Person $5,800 $4,067 $3,225 $2,680
Totals $11,600 $12,200 $12,900 $13,400
Rates are All Inclusive


Yacht Specifications

Yacht Type
Yacht Name Kailani
Yacht Length 44ft
Year Built 2017
AC Yes
Cabins 2
Total Sleeps 5
Heads 2
Electric Heads 2
Showers 2
Pets No
Captain Only Yes
Internet Yes
Dingy Size 12
Dingy Engine
Generator Yes
Children OK Yes
Children Age Limits water safe
Gay OK Yes
Nude OK Yes (Inq)

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iYachtClub Perfect Caribbean Sailing Vacation BVI Yacht Charters, Bareboat & Fully Crewed All-inclusive
Average rating:  
 1 reviews
by James R on iYachtClub Perfect Caribbean Sailing Vacation BVI Yacht Charters, Bareboat & Fully Crewed All-inclusive
Miles and Rachel You Rock!!!

We spent a week cruising the U.S. and British Virgin Islands. The islands and water are beautiful. The trip was tremendous. But I believe a sailing trip around a pool would have been tremendous with these two.
Miles (the "merman" trust us you will see why) is a great captain. He had wonderful suggestions on activities and locations to visit. More importantly he navigated us to and from safely and with ease. He is a certified diver and lobster wrestler. We had lobster taco's, Miles wrestled that beast during breakfast and we had it for dinner. We can not say enough great things about Miles.
Rachel his first mate ("the most interesting woman in the world", you will see why) is a great first mate. She prepared three glorious meals a day. She made everything from scratch. The food was overwhelmingly delicious, she put great thought into its preparation and presentation. How she executed the meals on the boat I will never know. Every meal was 5 stars all the way. It is clear that she cares deeply about her guests and does everything to ensure they have a wonderful experience. You want fire dancing? She can make that happen. You want to see a mermaid? She can make that happen. You want to ride motorcycles? She can make that happen.
Rachel and Miles went above and beyond. I could write for hours and hours about how great they were. If you are looking for an average trip stay away from these two, if you want a good trip stay away from these two. If you want tremendous, I would not have anyone other than these two. There is a zero percent chance I would do another charter that did not include Rachel and Miles. Thank you guys so much for the whole experience.
Lindsey and James

iYacht C, Owner at iYachtClub, responded to this review
Responded 31 May 2018
WOW... what an amazing review. Thank you guys so much. We love Rachel (like one of my daughters) and Miles and I'm so happy you got to spend time with them