ISLAND HOPPIN' 55

2026-2027 Season Crew
Kyle and Tilly have been running luxury charters for the last 4 years and bring a wealth of experience, energy and fun onboard. With over 60 charters around the Virgin Islands and time chartering in the Windward Isles, Scotland and even Tonga together, Kyle and Tilly know how to make your vacation truly unforgettable.

Kyle was brought up on the wild west coast of Scotland and spent every moment on the sea, whether that be teaching sailing at his local club, catching the ferry to school every day or kayaking round the coast line he calls home. After a summer spent teaching sailing in France he came back and met Tilly, they quickly realized they shared the same passion for adventure and the ocean and spent two years working and exploring the Highlands and Islands. After an especially cold and wet winter they jumped on a boat and sailed across the Atlantic towards the sunshine.

Tilly was always drawn to fresh food, finding joy in growing produce and creating dishes that champion local and seasonal flavours. Most of her professional life has been spent in the hospitality industry, both front and back of house, cooking in cafes, restaurants and for one summer a tent in the English countryside! After graduating university she moved to a remote Scottish island where she met Kyle. Although Tilly had plenty of experience driving power boats, sailing was a different story, and her first sailing trip was crossing the Atlantic ocean with Kyle in 2021. Completely hooked, they started chartering on a 50ft catamaran, before moving onto a larger vessel and then taking on a brand new 51ft lagoon which they delivered from Annapolis to the Virgin Islands together. After a break back home in Scotland they set out on another adventure, running vacations in the Pacific nation of Tonga on a catamaran and eco island retreat.

As a captain in the Virgin Islands, Scotland and Tonga, Kyle is known for his level headed attitude, commitment for creating the best vacation ever and his slight Scottish cheekiness! Charters with Kyle never have a dull moment whether that be non stop activities or finding the calmest bay with no other boats around to simply float and be. Tilly prides herself on making real connections with everyone that steps onboard through good food, special moments and her infectious laughter. Often found up early making homemade sourdough or sneaking in an early morning snorkel, she is our onboard marine biologist after all! Kyle and Tilly are delighted to now be chartering in the Virgin Islands where their career began and can't wait to welcome you aboard.

Captain Kyle Mealand Qualifications:

RYA Yachtmaster Offshore(Power/Sail)
PADI divemaster
AEC 1&2
STCW 95
Powerboat lvl 2
SRC VHF
RYA Dingy Instructor
Food Safety lvl 2
IOSH Managing safely


Chef Tilly Painter Jones Qualifications:
Ashburton Chef's Academy- Yacht Chef Course
PADI Divemaster
STCW Basic Safety Training
Food Safety & Hygiene level 2
RYA Day Skipper (power) commercial endorsement