Captain Jason Mackay
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 Ginger Perez
Ginger Michelle Perez grew up in California where she graduated from the Santa Monica College Film Program and continued her undergrad at the University of California Irvine (UCI). During her time at UCI, she learned to sail FJ's by joining the UCI sailing team and quickly worked her way up to skipper. Her culinary experience began after High School when she was hired as the cook on a ranch in the Eastern Sierra Mountains where she cooked for cowboys, guests and outfitted for trips that lasted up to a week in the backcountry where she had to pack in her the provisions on a mule train. Since then she has worked both front of house and back of house for many restaurants thus her service experience ranges from bar tending at high volume ski bars to cooking on superyachts. When she's not at sea, she enjoys country line dancing, salsa dancing, making short films, reading, skiing, running, and playing guitar.
Rates
| Season Name |
Season Year |
Pax 2 |
Pax 3 |
Pax 4 |
Pax 5 |
Pax 6 |
Pax 7 |
Pax 8 |
| Winter |
2025 |
$24,500 |
$25,000 |
$25,500 |
$26,000 |
$26,500 |
$27,500 |
$28,000 |
Price Details
Additional Rate Details:
USVI Embarkation/Disembarkation: Dock Holiday is happy to offer to and from USVI for an additional $2000.
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.
HALF-BOARD: Includes: 7 breakfasts, 4 lunches & 3 dinners. Requires 3 lunches & 4 dinners ashore at client expense. $150 discount per person.
CHRISTMAS/NEW YEARS: 7 night minimum
CHRISTMAS: 1-8 guests @ $32,000 - charter must end on 12/27 or earlier
NEW YEARS: 1-8 guests @ $33,000 - charter may not start prior to 12/28
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. Kelly and Randy Date of experience: May 2025