Dock Holiday Description
Dock Holiday is a sleek and stylish 54.0 ft catamaran designed for unforgettable escapes. With 4 spacious queen cabins - each featuring a private en-suite head, - she comfortably hosts up to 8 guests, offering a boutique floating retreat with room to unwind. A professional 2-person crew ensures every detail is taken care of, from personalized service and tailored experiences, to crafting you delicious gourmet meals. Whether you´re lounging on deck, sailing turquoise seas, or dining under the stars, Dock Holiday brings the perfect mix of adventure and indulgence to your charter.
Cruising Area of Dock Holiday
Accommodations
Three Queen Cabins en suite with separate showers & one queen cabin with a wet head.
Specification
Water Sports
2 SUBLUE Sea Scooters
7x7 Bote - Floating Dock
2 Stand Up Paddle Boards
1 Sun Chill Raft
Scuba Diving 
Entertainment
1 Yoga Mat
Exercise Bands
Cuisine
Green Initiatives
Dock Holiday Crew Profile
Captain
Chef/Mate
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.
Dock Holiday Calendar
AvailableBookedHold (can be challenged)Unavailable| Jul 2026 | 1 | 2 | 3 | 4 | 5 | 6 | 7 | 8 | 9 | 10 | 11 | 12 | 13 | 14 | 15 | 16 | 17 | 18 | 19 | 20 | 21 | 22 | 23 | 24 | 25 | 26 | 27 | 28 | 29 | 30 | 31 |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Aug 2026 | 1 | 2 | 3 | 4 | 5 | 6 | 7 | 8 | 9 | 10 | 11 | 12 | 13 | 14 | 15 | 16 | 17 | 18 | 19 | 20 | 21 | 22 | 23 | 24 | 25 | 26 | 27 | 28 | 29 | 30 | 31 |
| Sep 2026 | 1 | 2 | 3 | 4 | 5 | 6 | 7 | 8 | 9 | 10 | 11 | 12 | 13 | 14 | 15 | 16 | 17 | 18 | 19 | 20 | 21 | 22 | 23 | 24 | 25 | 26 | 27 | 28 | 29 | 30 | |
| Oct 2026 | 1 | 2 | 3 | 4 | 5 | 6 | 7 | 8 | 9 | 10 | 11 | 12 | 13 | 14 | 15 | 16 | 17 | 18 | 19 | 20 | 21 | 22 | 23 | 24 | 25 | 26 | 27 | 28 | 29 | 30 | 31 |
| Nov 2026 | 1 | 2 | 3 | 4 | 5 | 6 | 7 | 8 | 9 | 10 | 11 | 12 | 13 | 14 | 15 | 16 | 17 | 18 | 19 | 20 | 21 | 22 | 23 | 24 | 25 | 26 | 27 | 28 | 29 | 30 | |
| Dec 2026 | 1 | 2 | 3 | 4 | 5 | 6 | 7 | 8 | 9 | 10 | 11 | 12 | 13 | 14 | 15 | 16 | 17 | 18 | 19 | 20 | 21 | 22 | 23 | 24 | 25 | 26 | 27 | 28 | 29 | 30 | 31 |
| Jan 2027 | 1 | 2 | 3 | 4 | 5 | 6 | 7 | 8 | 9 | 10 | 11 | 12 | 13 | 14 | 15 | 16 | 17 | 18 | 19 | 20 | 21 | 22 | 23 | 24 | 25 | 26 | 27 | 28 | 29 | 30 | 31 |
| Feb 2027 | 1 | 2 | 3 | 4 | 5 | 6 | 7 | 8 | 9 | 10 | 11 | 12 | 13 | 14 | 15 | 16 | 17 | 18 | 19 | 20 | 21 | 22 | 23 | 24 | 25 | 26 | 27 | 28 | |||
| Mar 2027 | 1 | 2 | 3 | 4 | 5 | 6 | 7 | 8 | 9 | 10 | 11 | 12 | 13 | 14 | 15 | 16 | 17 | 18 | 19 | 20 | 21 | 22 | 23 | 24 | 25 | 26 | 27 | 28 | 29 | 30 | 31 |
| Apr 2027 | 1 | 2 | 3 | 4 | 5 | 6 | 7 | 8 | 9 | 10 | 11 | 12 | 13 | 14 | 15 | 16 | 17 | 18 | 19 | 20 | 21 | 22 | 23 | 24 | 25 | 26 | 27 | 28 | 29 | 30 | |
| May 2027 | 1 | 2 | 3 | 4 | 5 | 6 | 7 | 8 | 9 | 10 | 11 | 12 | 13 | 14 | 15 | 16 | 17 | 18 | 19 | 20 | 21 | 22 | 23 | 24 | 25 | 26 | 27 | 28 | 29 | 30 | 31 |
| Jun 2027 | 1 | 2 | 3 | 4 | 5 | 6 | 7 | 8 | 9 | 10 | 11 | 12 | 13 | 14 | 15 | 16 | 17 | 18 | 19 | 20 | 21 | 22 | 23 | 24 | 25 | 26 | 27 | 28 | 29 | 30 | |
| Jul 2027 | 1 | 2 | 3 | 4 | 5 | 6 | 7 | 8 | 9 | 10 | 11 | 12 | 13 | 14 | 15 | 16 | 17 | 18 | 19 | 20 | 21 | 22 | 23 | 24 | 25 | 26 | 27 | 28 | 29 | 30 | 31 |
Dock Holiday Reservations & Port Locations
| Start Date | End Date | Details (Holds can be challenged) |
|---|---|---|
| Jul 06, 2026 | Jul 12, 2026 | Booked: Tortola, TBD to Tortola, TBD |
| Jul 21, 2026 | Jul 26, 2026 | Booked: Owner Use to Owner Use |
| Jul 27, 2026 | Jul 31, 2026 | Booked: St Thomas USVI to St Thomas USVI |
| Aug 01, 2026 | Nov 09, 2026 | Unavailable: St Thomas USVI to St Thomas USVI |
| Nov 21, 2026 | Nov 27, 2026 | Booked: Tortola, TBD to Tortola, TBD |
| Dec 28, 2026 | Jan 04, 2027 | Booked: Saint Thomas, USVI* to Saint Thomas, USVI* |
| Jan 13, 2027 | Jan 19, 2027 | Hold: Yacht Haven Grand to Yacht Haven Grand |
| Feb 17, 2027 | Feb 21, 2027 | Booked: Tortola, TBD to Tortola, TBD |
| Mar 03, 2027 | Mar 10, 2027 | Booked: Tortola, TBD to Tortola, TBD |
| Mar 17, 2027 | Mar 24, 2027 | Hold: St Thomas USVI to St Thomas USVI |
| Mar 26, 2027 | Apr 01, 2027 | Booked: Tortola, To be Decided - BVI to Tortola, To be Decided - BVI |
| May 02, 2027 | May 08, 2027 | Booked: St Thomas USVI to St Thomas USVI |
| May 30, 2027 | Jun 05, 2027 | Booked: Saint John, USVI* to Saint Thomas, USVI* |
Dock Holiday Rates / week
The prices shown are for the entire yacht for a week-long (7 nights) charter. Inquire for lowest rate.Low price: $25,000
High price: $31,000
| Season | 2 Pax | 3 Pax | 4 Pax | 5 Pax | 6 Pax | 7 Pax | 8 Pax |
|---|---|---|---|---|---|---|---|
| 2026 Summer | $26,500 | $27,000 | $27,500 | $28,000 | $28,500 | $29,500 | $30,000 |
| 2026/27 Winter | $27,500 | $28,000 | $28,500 | $29,000 | $29,500 | $30,500 | $31,000 |
| 2027 Summer | $27,500 | $28,000 | $28,500 | $29,000 | $29,500 | $30,500 | $31,000 |
Yacht terms: All Inclusive
An all-inclusive charter covers all provisioning and running expenses. This includes a captain and crew that is fully trained and committed to your safety and enjoyment of your trip. A chef will provide the kind of exceptional, personalized meal preparation that you would expect of a five-star restaurant. The listed rate may not include all local taxes, cruising permits, premium beverages and scuba activities. Inquire for more information.
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 @ $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
Dock Holiday Guest Reviews
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.
Kelly and Randy
Date of experience: May 2025
