Sail Racing Academy

GAP Year / Sabbatical Sailing

Sail Racing Academy offers tailor-made GAP year programs to meet all appetites and open to all irrespective of where they live. From 1 month to 1 year; cruising to racing; the UK, Med or Caribbean; we have it all. Our experienced skippers are happy to work alongside you to help you gain experience and qualifications. We aim to find the perfect balance between practical hands-on experience, theory and fun.

You will be an active part of our team. During regattas, when not sailing, there is always a fully packed schedule of social events. This is a great time to have fun, as well as getting to know other sailors and developing your network.

Between regattas, there is always plenty to do with maintenance, repairs and cleaning. It’s a good time to learn about the mechanics of sailing. But you will also be able to see and enjoy the beauty of each location where the yacht anchors.

*SUBJECT TO CHANGE*
Some of the 2026 Caribbean Regatta dates have not been confirmed yet. The dates below are based on previous years and the CSA Caribbean Sailing Calendar. Please check this page frequently for updates.


28th Dec 2026 - 31st Dec 2026: Explore St Lucia
If you’ve just arrived in St Lucia here’s your opportunity to explore the island before we depart. Please note some of this time will be used for boat maintenance and training.

1st - 14th Jan 2026: Explore the Grenadines
Join us as we explore the Grenadines, visiting Union Island & Bequia as well as Tobago Quays and many other stops in between.

Please note some of this time will be used for boat maintenance and training.

15th - 22nd Jan 2026: Round Barbados Sailing Week
Spend some time exploring Barbados and then join us for Round Barbados Sailing Week; the first race of the season and a great opportunity to network and get to grips with round-the-cans racing.

22nd Jan 2026: Rum to Spice Race
This event was introduced in 2024 as a feeder race between Barbados and Grenada Sailing Weeks. From Barbados to Carriacou, Grenada, it should take under 24 hours to finish. We highly suggest anyone participating in Grenada Sailing Week to join this race and get some extra practice in.

23rd - 30th Jan 2026: Grenada Sailing Week
Grenada Sailing Week is a smaller regatta but one of our most experienced skippers describes it as their favourite. It involves some fun & fast round-the-cans and coastal racing. Starting from one of the most beautiful small islands in the Caribbean, Carriacou and finishes in Grenada, known as the Spice Isle!

31st - 16th Feb 2026: Island Hop Grenada to Antigua
A hugely popular part of our Caribbean season and a great chance to relax and visit some of the islands only accessible by boat and often forgotten. A wealth of hidden treasures.

Please note some of this time will be used for boat maintenance and training.


17th - 27th Feb 2026: Caribbean 600 (additional cost) / Explore Antigua / Undertake RYA Qualifications
There are a huge variety of options to suit every taste and budget this week. Join us for the Caribbean 600 for 4-5 days of amazing offshore racing, explore the island of Antigua, or attend our partner’s training sessions to secure RYA training. You won’t get bored during this week. Please note that the race is an optional extra and not included by default.

28th - 3rd Mar 2026: Sail Antigua to St Maarten
An opportunity to practice the sailing skills you’ve developed so far and take on more responsibility whilst our professional skipper acts as a safety net in case you require some additional support.

4th - 9th Mar 2026: St Maarten Heineken Regatta (additional cost)
This is another inshore round-the-cans & coastal race sailing event. Hugely popular in the regatta calendar. It’s as lively off the water as it is on the water racing, with it’s dedicated race village & live music. Please note that this is an optional extra and not included by default.

10th - 22nd Mar 2026: Cruise St Martin / St Barth
Ok, that’s far too much excitement, now is the perfect time to relax a little. This is a good week to explore St Martin, cruise around the island and recuperate in preparation for the next few regattas.

Please note some of this time will be used for boat maintenance and training.

23rd - 29th Mar 2026: BVI Spring Regatta
Experience the thrill of the BVI Spring Regatta with four days of competitive racing in the heart of the Caribbean. Sail through turquoise waters, soak up the stunning island views, and enjoy one of the most fun and vibrant party scenes on the regatta circuit. Perfect for sailors looking to race hard, make new friends, and celebrate in true Caribbean style.

After this regatta, you have the choice between the St Thomas International Regatta or Antigua Racing Cup. You have the option to join us here or instead take part in the Antigua Racing Cup. Due to the overlap in timing, our full fleet cannot attend both events, so at least one boat will remain in the Virgin Islands while another heads to Antigua, giving you the choice of where to race.

30th Mar - 6th Apr 2026: St Thomas International Regatta
Enjoy the laid-back charm of the St Thomas International Regatta, where three days of racing combine steady trade winds with a warm and welcoming island atmosphere. Set against the beautiful backdrop of the US Virgin Islands, this regatta offers competitive yet relaxed sailing that appeals to seasoned racers and newcomers alike. With its friendly vibe and family-oriented social scene, it is the perfect choice for sailors who want to enjoy the thrill of racing in a more easy-going Caribbean setting.

You have the option to join us here or instead take part in the Antigua Racing Cup. Due to the overlap in timing, our full fleet cannot attend both events, so at least one boat will remain in the Virgin Islands while another heads to Antigua, giving you the choice of where to race.

7th-12th Apr 2026: Antigua Racing Cup
Get ready for the Antigua Racing Cup, a high-energy event that blends world-class sailing with an unbeatable island atmosphere. Expect exhilarating races in steady trade winds, stunning coastal courses, and lively shoreside celebrations that showcase Antigua’s famous sailing culture.

You have the option to join us here or instead take part in the Antigua Racing Cup. Due to the overlap in timing, our full fleet cannot attend both events, so at least one boat will remain in the Virgin Islands while another heads to Antigua, giving you the choice of where to race.

13th - 20th Apr 2026: Cruise Antigua and Boat Prep
Sail around the beautiful island of Antigua and help with boat prep as we get ready for the final regatta of the Caribbean season. A perfect combination of island cruising, teamwork, and hands-on experience.

21st - 27th Apr 2026: Antigua Sailing Week
Antigua Sailing Week has become one of the biggest events in the international sailing calendar, and the final event we participate in before heading back across the Atlantic.

Before departure, we kindly ask everyone to help with a general cleaning and tidying of the boat.

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