Premium Sailboat Charters & Regatta Transport

Logistics shouldn't distract you from winning. At Simmons Boatworks, we take the stress out of regatta travel with our premium sailboat charters and professional transport services. Whether you are flying in for a national championship or simply want to avoid the wear and tear of towing a trailer across the country, our regatta support ensures you step into the boat park completely focused on racing.

World-Class Regatta Charters:
Compete at the highest level without the logistical nightmare of cross-country travel. We offer meticulously maintained, race-ready charters for the most competitive fleets. Reserve a world-class Winner Optimist, a premium ILCA, or one of our high-performance Simmons Boatworks C420s for your next major event. Every charter is prepped and delivered directly to the regatta venue, ensuring you have top-tier, reliable equipment waiting for you when you arrive.
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Transport/Truck Boats:
If you already own a Winner Opti or a Simmons C420, let us do the driving. Our specialized transport service provides secure, white-glove transit for your personal boat to all events listed on our schedule. We handle the loading, secure highway transit, and careful unloading, treating your boat with the exact same care and precision we apply to our own fleet.
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Save your energy for the racecourse, not the highway. Browse our upcoming event schedule above to reserve your regatta charter or secure a spot on our transport trailer today.