Barbados Sailing Week boasts some of the most consistently fantastic sailing conditions in the Caribbean. Big wind, big waves, big smiles all ‘round! We raced in Barbados for the first time in 2024 and walked away with a whole contingent of new friends (Barbados is possibly the friendliest island in the region!) as well as 2nd overall in the Coastal Series and 3rd in the Round Barbados Race. We returned in 2025 to a resounding 1st in the Calypso Cup (new course this year) and are already looking forward to what 2026 may bring!

BSW is a great event for those who are relatively new to racing or looking to expand their skill set into different roles. With three days of ‘round the cans’ racing in Carlisle Bay, a relaxing lay day to explore on shore, and a final day of racing the whole way round this beautiful island in open ocean conditions, this regatta has all the elements to be awesome.

2026 Schedule (subject to change as race organizers finalize details)

Thursday, January 15: Training day 1
Friday, January 16: Training day 2
Saturday, January 17: Racing day 1, Coastal Series
Sunday, January 18: Racing day 2, Coastal Series
Monday, January 19: Racing day 3, Coastal Series
Tuesday, January 20: Lay day!
Wednesday, January 21: Round Barbados Race, regatta closing ceremony & prizegiving

Pre-Requisites

• Prior sailing experience is required, and some racing experience is preferred. Contact us to discuss eligibility and where you will fit into the team.

• Reasonable level of physical strength and fitness. We strongly recommend preparing for the race by hitting the weights and/or resistance training for good core and upper body strength, as well as working on endurance through cardio training. This preparation helps protect you from injury, will give you more energy and strength throughout the race, makes you a more valuable team member and dramatically increases your likelihood of enjoying the race!

Questions? Just ask!

Cost
$2,400 CAD

OR $2,175 CAD Extra Early Bird Rate until August 30

OR book with Booking Package B: St.Maarten to Barbados Offshore Mileage Builder ($1,925) and Barbados Sailing Week ($2,400) together for just $3,325.

OR as part of the Ultimate Adventure Package: Booking Package B (described above) AND Rum to Spice Race from Barbados to Carriacou ($650) and Grenada Sailing Week ($2,400) all for just $5,225.

Maximum 10 crew + skipper & first mate.

Includes professional skipper, first mate, racing fees, fuel, moorage, yacht insurance and all other operating costs of the yacht, lunches and two team shirts (long-sleeve for sailing and short-sleeve for prize-giving). Participants are responsible for: food on shore and other discretionary spending, mandatory travel insurance, flights & on shore accommodation.

Logistical Note

Crew will join and leave the boat by dinghy each day in 2 groups, boarding from the beach nearby the Boatyard Beach Club, Chamberlain Bridge in the Careenage and/or Barbados Cruising Club in Carlisle Bay. The pickup location may vary depending on surf conditions or where crew accommodations are located, we endeavour to be as flexible as possible and so should all crew! Boarding and dismounting from the dinghy on the beaches can be wild and wet, depending on the surf. Be prepared with a good quality waterproof bag for your daily essentials.

No accommodation is available on board, but Sea to Sky can facilitate putting crew who register early in touch with each other for potentially sharing a crew house.

We recommend staying nearby to the Barbados Cruising Club as that is where the majority of the regatta shoreside events will be happening.

About life on board

As with all Sea to Sky racing, we will be as competitive as we can be together as a team, but safety will of course always come first by a long shot, followed by providing a positive learning environment where everyone can develop their skills and enjoy the experience. Expect to be pushed to achieve your best, to expand your skill set and truly challenge yourself, with ongoing support from our professional skipper.

We compete as a team and we prepare as a team, meaning everyone is expected to chip in with essential tasks before, during and after the race. This includes cooking, cleaning, provisioning, light maintenance tasks, rig and deck checks, etc. We also share sailing duties and do our best to rotate through positions on board when conditions allow for more experience building.

Read more about Panacea X and check our Caribbean FAQs for more information.