Born in South Africa and raised in Louisiana, Captain Jason Mackay has always been drawn to the water and the sense of freedom it brings. With an adventurous spirit and a deep respect for nature, Jason has built a life around exploration, community, and the sea. From spearfishing along the coasts of Mexico to navigating the crystal waters of the Caribbean, Jason’s journey has been defined by his passion for the ocean and the connections it inspires. Over the years, he has hosted more than 65 charters and welcomed over 600 guests aboard, earning a reputation for his calm leadership, professionalism, and genuine care for those in his charge. Now entering his fourth season in the Virgin Islands, Jason takes the helm of Dock Holiday as her captain—bringing together his love for the sea, his hands-on experience, and his dedication to creating unforgettable adventures under sail. Whether charting a course through hidden coves or sharing stories at anchor, Jason ensures every guest experiences the magic of life on the water.
Chef/Mate Lelani Bright
I specialise in creating beautiful, nourishing meals and adapting to dietary preferences, while ensuring that the entire guest experience feels effortless and luxurious. My passion for wellness and global cuisine influences every dish I prepare, and I approach service with a hospitality heart, anticipating needs, creating moments of joy, and going the extra mile to ensure guests are always in their “wow” moment.
As a chef, I bring not only skill, but soul. I love introducing guests to Caribbean culture and history, sharing stories, and creating the kind of environment that lingers in memory long after the charter ends. I believe food is an extension of love and celebration, and dancing through life with grace — even under pressure — is the essence of great service and positive reviews.
Meet the Crew
Lelani Bright
Chef/Mate
Nationality: South African/American
Languages: English
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Jason Mackay
Captain
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Yacht Menu
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Culinary Experience
Chef Lelani's Caribbean Yacht Menu
Wake-Up Goodness
Tropical Papaya Sunrise BowlFresh papaya star, vanilla yogurt, seasonal tropical fruits, and house granola. Served with artisan toast, crispy baco...
Sample Menus
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Guest Reviews
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Absolutely the Best Experience!
This trip was terrific, there literally is not one negative thing I could say.
The boat was just like our boat before and was great. The BVI was different than the USVI but it was terrific. The sailing was superb. We sailed to Anegada where we rented a truck and our Captain drove us around the island, taking up to snorkeling spots, and various beaches. We had dinner at Sid’s, it was fabulous. We saw the flamingos!!
Let’s talk about our crew.
Captain Jason and Chef Juan - WOW!!!!
These two work together like a well oiled machine. They compliment each other well. When Captain Jason said we received an upgrade when Chef Juan came on board he was not kidding. The food was fantastic and we all brought back at least 10 pounds each. Captain Jason took us to unique places and we always had optimum yacht placement.
If you have any first time charter groups, Captain Jason is the person and this is the boat to send them on. Captain Jason and Chef Juan were both very chill, calm, and always smiling. If they asked once, they asked 100 times if there was anything we wanted or anything they could get us. They never sat down and had dinner with us or interjected into our conversations unless asked and then only for the parts that pertained to them. They truly realized this was our vacation and they were there to take care of us and let us be worry free.
Provisions were more than we needed and no one ever wanted for a thing.
Just absolutely the best experience and 100% will do a trip with Captain Jason again at some point.
Trip of a lifetime with a crew of a lifetime!
When we arrived at Manuel Reef Marina, Jason and Jason were waiting with warm and inviting smiles as they helped with luggage and we embarked onto Dock Holiday. Jason and Jason made it clear from the beginning..." What can we do to help? What questions do you have that we can answer? We are here for you!"
Jason "squared" had such an in-depth knowledge of everywhere we went; Norman Island, Virgin Gorda, Anegada, etc. Starting with Veuve Clicquot and charcuterie one could not imagine the incredible meals that Jason (2) worked round the clock preparing! Scrambled eggs and bacon to perfection; Mahi Bowls, Pork Chops with butternut squash and almond cake to name a few.
The Bali54 was so incredibly functional and well laid out. The automatic wall enclosure converting to a/c or open air at the flip of a switch! Just one of the wonderful features aboard Dock Holiday!
My husband and I along with our daughter and very dear friends are beyond grateful to have had the privilege of Captain Jason Mead and Chef Jason Mackay for our crew May 3rd to May 10th, 2025. Like most we have hundreds of combined photos, I have an entire book documenting every day, every island, every meal and every priceless memory.
I will refrain from the treasured details. Simply put booking your own charter on Dock Holiday is the only way to experience your trip of a lifetime with a crew of a lifetime.
USVI Embarkation/Disembarkation: Dock Holiday is happy to offer to and from USVI
MINIMUM NIGHTS: 5, Inquire for less
For 6 night charters, divide weekly rate by 7 nights X 6 nights. For 5 nights or less, divide weekly rate by 6 nights X number of nights.
SLEEP ABOARD: Sleep aboard the night before charter dates. Available for half the calculated daily rate. Includes boarding after 4pm, welcome cocktail and canapes plus a light breakfast the next morning. Dinner is to be taken ashore at client expense.
CHRISTMAS/NEW YEARS: 7 night minimum
CHRISTMAS: 1-8 guests @ $36,000 - charter must end on 12/27 or earlier
NEW YEARS: 1-8 guests @ $38,000 - charter may not start prior to 12/28
USVI Embarkation/Disembarkation: Dock Holiday is happy to offer to and from USVI
MINIMUM NIGHTS: 5, Inquire for less
For 6 night charters, divide weekly rate by 7 nights X 6 nights. For 5 nights or less, divide weekly rate by 6 nights X number of nights.
SLEEP ABOARD: Sleep aboard the night before charter dates. Available for half the calculated daily rate. Includes boarding after 4pm, welcome cocktail and canapes plus a light breakfast the next morning. Dinner is to be taken ashore at client expense.
CHRISTMAS/NEW YEARS: 7 night minimum
CHRISTMAS: 1-8 guests @ $36,000 - charter must end on 12/27 or earlier
NEW YEARS: 1-8 guests @ $38,000 - charter may not start prior to 12/28
USVI Embarkation/Disembarkation: Dock Holiday is happy to offer to and from USVI
MINIMUM NIGHTS: 5, Inquire for less
For 6 night charters, divide weekly rate by 7 nights X 6 nights. For 5 nights or less, divide weekly rate by 6 nights X number of nights.
SLEEP ABOARD: Sleep aboard the night before charter dates. Available for half the calculated daily rate. Includes boarding after 4pm, welcome cocktail and canapes plus a light breakfast the next morning. Dinner is to be taken ashore at client expense.
CHRISTMAS/NEW YEARS: 7 night minimum
CHRISTMAS: 1-8 guests @ $36,000 - charter must end on 12/27 or earlier
NEW YEARS: 1-8 guests @ $38,000 - charter may not start prior to 12/28
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