If you’re a nautical enthusiast looking to fill your calendar for 2026, you’ll be pleased to learn there are plenty of exciting sailing regattas in the pipeline. Whether you want to participate in the competitions or enjoy them from the sidelines, we’ve compiled this list of the best sailing events in 2026.
What are the Top Sailing Events for 2026?
- Etchells World Championship
- Charleston Race Week
- Rolex Big Boat Series
- Helly Hensen Sailing World Regatta
- Nautique Southwest Regatta
- Head of the Charles Regatta
- USRowing RowFest National Championships
1. Etchells World Championship
Location: San Diego, CA
Dates: May 7-15, 2026
Why Add It To Your Sailing Calendar: Hosted by the prestigious San Diego Yacht Club, the Etchells World Championship is a 9-day competition that attracts sailors from around the world and offers plenty of opportunities for socialization.
Learn more about the Etchells World Championship.
2. Charleston Race Week
Location: Mount Pleasant, SC
Dates: April 16-19, 2026
Why Add It To Your Sailing Calendar: Held at Patriots Point, Charleston Race Week is a lively event near scenic Charleston that will celebrate its 30th anniversary in 2026.
Learn more about Charleston Race Week.
3. Rolex Big Boat Series
Location: San Francisco, CA
Dates: September 16-20, 2026
Why Add It To Your Sailing Calendar: Held at the iconic St. Francis Yacht Club, the 2026 Rolex Big Boat Series will combine with the ORC North American Championship, which is a leading offshore sailing competition in North America.
Learn more about the Rolex Big Boat Series.
4. Helly Hensen Sailing World Regatta
Location: Annapolis, MD
Dates: May 1-3, 2026
Why Add It To Your Sailing Calendar: The Helly Hensen Sailing World regatta takes place on breathtaking Chesapeake Bay and includes a variety of boat classes plus social events with BBQ, drinks, live music, and more.
Learn more about Helly Hensen Sailing World.
5. Nautique Southwest Regatta
Location: Lake Havasu, AZ
Dates: May 8-10, 2026
Why Add It To Your Sailing Calendar: If you own a Nautique boat (or appreciate these types of vessels), you can’t miss the Nautique Southwest regatta, which includes a poker run, exclusive getaways, and themed banquet dinners.
Learn more about the Nautique Southwest Regatta.
6. Head of the Charles Regatta
Location: Cambridge, MA
Dates: October 16-18, 2026
Why Add It To Your Sailing Calendar: The Head of the Charles regatta has been around since 1965 and features a challenging three-mile race upstream, along with a charity program that adds a philanthropic element to the event.
Learn more about the Head of the Charles Regatta.
7. USRowing RowFest National Championships
Location: Ann Arbor, MI
Dates: July 11-16, 2026
Why Add It To Your Sailing Calendar: Held by USRowing, the event features regatta racing, educational seminars, community events, and social gatherings.
Learn more about the USRowing RowFest National Championships.
2026 Sailing Events and Regattas Q&A
Q: How much does it cost to attend a sailing regatta?
A: Pricing for regattas varies greatly and depends on whether you plan to compete or spectate. In addition to potential travel expenses, you may have to pay entry fees, membership fees, or fees for food, drinks, and other extras. Of course, sailing events near me will be cheaper than those that require travel.
Q: How long do regattas last?
A: Most regattas are a few days, but some last a week or even longer.
Q: What types of races can I expect at a regatta?
A: Races vary by regatta. However, the most common ones include rowing, sailing, and watersport races.
