DOCKHOLIDAY
Overview
Accommodations
For Guest use: Four Queen Cabins en suite with dry heads. Crew occupy Starboard Aft Cabin.
Yacht specifications
Amenities & water toys
- Salon Stereo
- Board Games
- Sun Awning
- Bimini
- BBQ
- Deck Shower
- Hair Dryer
- Ice Maker
- Generator
- Inverter
- Smoking Allowed: On sugar scoops only
- Internet/WiFi: Onboard WIFI
- Dinghy: size: Yes, paxes: 8, engine: 25
- Floating Mats
- Stand-up Paddle Boards (2)
- Snorkel Gear
- Sea Scooters
- Boarding Ladder
- Beach Games
- Fishing Gear: type: Trolling and Casting, rods: 2
Crew information
Captain: Jason Mackay Crew: Lelani Bright 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/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. Chef/Mate: Lelani Bright Captain: Jason Mackay
Available destinations
Summer: Caribbean Virgin Islands (BVI), Caribbean Virgin Islands (US), Caribbean Virgin Islands (US/BVI)
Seasonal rates
Winter 2026 to 2027
$27,500
Additional Rate Details: 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. 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 @ $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
Inclusive
Summer 2027
$27,500
Additional Rate Details: 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. 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 @ $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
Inclusive
Additional Rate Details: 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. 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 @ $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 Additional Rate Details: 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. 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 @ $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
Caribbean Terms



