The next few months in the Caribbean bring some of the most anticipated regattas of the season, events that blend sport, community, culture, and the unmistakable rhythm of island sailing.
For travelers planning a charter, these regattas offer more than racing. They shape the energy of entire islands. Harbors feel livelier, coastal bars fill with crews swapping stories, and anchorages take on that extra spark that only a race week can create. From the deck of your yacht, every day becomes part of the event.
Below, we highlight three standout regattas happening soon, each with its own character, history, and charm.
1. La Course de l’Alliance (St. Maarten • St. Barth • Anguilla)
December 11–14, 2025
A true tri-island classic, La Course de l’Alliance brings together sailors from St. Maarten, St. Barth, and Anguilla for four days of coastal racing. Now in its 22nd edition, it remains one of the most relaxed yet spirited regattas in the northeastern Caribbean.
This year introduces something new: a Rally Class, ideal for cruising and charter yachts looking to participate in a more flexible format. It runs alongside the Round the Rocks Regatta, adding even more energy to the fleet.
2025 Schedule
- Dec 11 – Registration & Skippers Briefing
- Dec 12 – Simpson Bay (St. Maarten) ➝ Gustavia (St. Barth)
- Dec 13 – Gustavia ➝ Road Bay (Anguilla)
- Dec 14 – Road Bay ➝ Simpson Bay
Why it stands out
Three islands, three cultures, one welcoming sailing community. A perfect event for guests who enjoy movement, coastal scenery, and days shaped by the rhythm of the sea.
2. Budget Marine Jol Byerley Hightide Series (Antigua)
December 13–21, 2025
Hosted by Antigua Yacht Club
Entering its 25th edition, the Hightide Series remains one of Antigua’s most loved seasonal regattas. Spread across warm-up races, a midweek event, and a full weekend finale, this series captures the pure spirit of Caribbean racing.
Classes Expected
- Division A & B
- Classic yachts
- Sportsboats
- RS Elite
- Additional classes as entries allow
2025 Racing Schedule
- Dec 13 – Warm-up (up to 3 races)
- Dec 17 – Midweek race
- Dec 20–21 – Hightide Series (up to 7 races total)
Racing takes place just outside English Harbour and Falmouth Harbour, two of the most iconic anchorages in the Caribbean.
Why it stands out
The atmosphere around Nelson’s Dockyard and Falmouth during this week is unmatched. Crews gather at sunset, yachts line the docks, and every restaurant and quay feels alive.
3. DinghyCoach Clinic (Lanzarote, Canary Islands)
December 19–23, 2025
Although not in the Caribbean, this event is relevant for families and sailors connected to the MCC community, especially junior sailors or young athletes preparing for the next training cycle.
This five-day clinic offers coaching, charterboats, and hands-on training in Lanzarote, mixing warm weather with top-tier instruction.
Schedule
- Dec 19–23 – Coaching sessions
- Dec 23 – Departure
Pricing
- €700 clinic fee
- €450 charterboat rental
Participants bring sails, sheets, lines, and essential hardware, while accommodation is independent (discounts available at THB Tropical Island Hotel).
Why it stands out
A strong option for young sailors or families mixing travel with skill-building before heading into the Caribbean season.
Thinking of Chartering During a Regatta?
Regatta weeks bring a special kind of energy to the islands. Some guests prefer to follow the fleet from anchorage to anchorage, while others enjoy the view from a quiet bay and join the celebrations when races end.
At My Caribbean Charters, we help guests choose the right yacht and sailing week so the experience feels effortless from start to finish.
If you’d like to plan a charter around one of these events, or simply want to sail during an especially vibrant time of year, we’re here to guide you.
📩 bookings@mycaribbeancharters.com
🌐 www.mycaribbeancharters.com
With warm island wishes,
Andrea González
Founder, My Caribbean Charters
Yacht Charter Broker | Caribbean Travel Specialist