The 10 Best Regatta Parties in the US

Every sailor knows the truth: the race decides who gets the trophy, but the party decides whether you come back next year. You can grind upwind for three days in a dying breeze, blow out a spinnaker and finish dead last, and still call it a great regatta if the rum is cold and the band is loud when you tie up.

So we went looking for the best post-race parties in American sailing. We weighed the size of the fleet, the mix of boats, the setting, and above all what happens once the sails come down: the food, the drinks, the music and the stories. Some of these are black-tie affairs on a hotel porch. Others involve rafting up six boats deep and singing Journey until the island runs out of ice.

Here they are, counting down to the best party on the water.

10. Columbus Day Regatta, Miami, Florida

When: Columbus Day weekend each October (about October 9–10, 2027)
Where: Biscayne Bay, off Coconut Grove
Fleet: Hundreds of sailboats

The Columbus Day Regatta earns its spot with a big asterisk. The yacht club race itself is a fairly genteel affair, sailed on Saturday and Sunday mornings on Biscayne Bay. The party everyone talks about is the unofficial one: a sprawling raft-up off Elliott Key that has been called one of the biggest floating parties in the world.

There’s no stage, no caterer and no headliner. The entertainment is thousands of boaters, sound systems and a very long Saturday. It is loud, boozy and not for families. It has also turned deadly after dark, so the smart move is to arrive early, anchor well and stay put once the sun goes down.

9. Marblehead Race Week, Marblehead, Massachusetts

When: Late July (July 23–26 in 2026)
Where: Marblehead Harbor, with the host club rotating among the town’s yacht clubs
Fleet: More than 200 boats expected in 2026
Classes: Led by the International One Design (IOD), plus a wide range of one-design and handicap classes

Marblehead calls itself the yachting capital of America, and Race Week is when the town proves it. More than 200 boats crowd one of New England’s most beautiful harbors, with the classic IODs as the centerpiece.

The parties are proper New England yacht club affairs held at the host club after racing. Organizers don’t publish much about the social schedule, so this one ranks on reputation and setting. It’s less wild than some on this list, but few places beat a summer evening on Marblehead Harbor with 200 boats on their moorings.

8. Harvest Moon Regatta, Galveston to Port Aransas, Texas

When: October, timed to the full moon (October 9–11 in 2025)
Where: About 150 miles offshore in the Gulf, from Galveston to Port Aransas
Fleet: About 200 boats in recent years; organizers claim more than 250 at its peak
Classes: Handicap (PHRF) only, from family cruisers to J/120s and Hobie 33s

Hosted by Lakewood Yacht Club since 1987, the Harvest Moon Regatta started with 17 boats and grew into one of the largest offshore races in the country. Part of the appeal is the overnight sail under a full moon, which turns a lot of cruising couples into first-time offshore racers.

The other part is Port Aransas. After a night at sea, crews roll into the finish and straight into a shoreside celebration in a beach town built for exactly this. It’s Texas-sized, casual and easy to love.

7. Put-in-Bay Bay Week, South Bass Island, Ohio

When: Late July into early August (July 29–August 2 in 2026)
Where: Put-in-Bay Yacht Club, Lake Erie
Fleet: More than 100 boats
Classes: PHRF, cruising, non-spinnaker (JAM) and a centerboard course for dinghies, with feeder races from Cleveland, Sandusky, Toledo and Detroit

The Inter-Lake Yachting Association has been holding Bay Week on this little Lake Erie island for more than a century, and it may be the rowdiest party on our list. Big boats raft up six deep at the public docks, crews sleep aboard, and the fleet has ranged from windsurfers and Hobie Cats to old IOR boats and Tartan 10s.

Ashore, there’s an opening ceremony with food under a tent, sponsored kegs on the docks, and a packed Frosty’s bar when racing runs late. Sailing World reported that Journey songs echo across the whole island all week. If you don’t know the words to “Don’t Stop Believin’,” you will by Sunday.

I’ve taken my boat and friends boats to this island many times. It’s a really good time when there is no regatta party going on. Add a bunch of drunken sailors to the mix and things can only get better.

6. Bacardi Cup, Miami, Florida

When: March 7–13, 2027 (the 100th edition)
Where: Biscayne Bay, based at Coral Reef Yacht Club and Shake-A-Leg Miami in Coconut Grove
Fleet: About 194 boats from 25 nations in 2026
Classes: Star (80 boats) sails the Cup itself; J/70, Melges 24, VX One, Snipe and Viper 640 sail the Bacardi Invitational

When your title sponsor is a rum company, the party takes care of itself. A Bacardi bar opens under the palm trees after racing every day, and Shake-A-Leg Miami hosts hospitality every night of the Invitational. The social calendar usually runs from a welcome cocktail party through a mid-week party to a prize-giving dinner, with food, drinks and live music.

The Bacardi Cup is also one of the most international events in the country, with teams from 25 nations mixing with local sailors in Coconut Grove. Next March marks the 100th edition, so expect Bacardi to go all out.

5. Transpac, Los Angeles to Honolulu, Hawaii

When: Starts July 6, 8 and 10, 2027; finishes in Honolulu about a week later
Where: 2,225 miles of open Pacific, from Point Fermin to Diamond Head
Fleet: 53 boats in 2025
Classes: Rated divisions from cruisers to maxis, multihulls, and a new Open division for foiling monohulls in 2027

The Transpac party has the best welcome in sailing. Every boat, whether it arrives at noon or 3 a.m., is met at the dock with fresh flower leis and Mai Tais, followed by food and cocktails with the crew.

Then comes a full week of parties across Hawaii Yacht Club, Waikiki Yacht Club and Kaneohe Yacht Club. Highlights include the ‘Okole Maluna party, a Cheeseburger in Paradise party, a Hawaiian BBQ of kalbi ribs, mac salad and guava cake, and a closing party at Kaneohe. It has the best food on this list. It ranks fifth only because you have to sail across an ocean to get there.

4. Block Island Race Week, Block Island, Rhode Island

When: June 21–25, 2027 (it runs every other year)
Where: Champlin’s Resort and Marina, Great Salt Pond
Fleet: 163 boats in 17 classes and about 1,400 sailors in 2025
Classes: ORC, PHRF, one-design, and a Coastal division for non-spinnaker, double-handed and multihull boats

Storm Trysail Club bills Block Island Race Week as “the last true race week on the East Coast,” and it lives up to the name. Five days of racing, a fleet packed into the Great Salt Pond, and the famous Round the Island Race make it a bucket-list event for New England sailors.

The shoreside scene centers on Champlin’s, with sponsored race days from Mount Gay Rum and Regatta Craft Mixers. One skipper summed up his plans for 2025 as “mudslides, hospitality, and great racing,” and that’s about right. A whole week on a small island with 1,400 sailors means the party never really stops.

3. Charleston Race Week, Mount Pleasant, South Carolina

When: Mid-April (April 16–19 in 2026)
Where: Patriots Point, on Charleston Harbor
Fleet: 153 boats in 2026; the record is 287 in 2010
Classes: 14 classes, led by J/70 (30 boats) and Melges 24 (24), plus J/22, J/24, J/88, J/105, Melges 32, VX One, ORC sportboats, PHRF and offshore pursuit racing

How many regattas let you party aboard an aircraft carrier? Since 2023, Charleston Race Week’s nightly post-race party has been held aboard the USS Yorktown, a World War II carrier museum docked at Patriots Point, with the whole ship open to sailors.

The bar is stocked by Mount Gay Rum, Westbrook Brewing and Regatta Craft Mixers, and the backdrop is a Lowcountry sunset over Charleston Harbor. Add top-level one-design racing and a downtown full of great restaurants, and it’s no surprise one skipper called the parties and nightlife “the absolute best.”

2. Chicago Yacht Club Race to Mackinac, Chicago to Mackinac Island, Michigan

When: Mid-July (July 10–11, 2026, the 117th race)
Where: 290 nautical miles from Navy Pier in Chicago up Lake Michigan to Mackinac Island
Fleet: About 252 boats in 2026: 44 Cruising and 208 Racing
Classes: About 20 sections, from turbo sleds to J/120s, Beneteau 40.7s and Tartan 10s

I have done the Chicago Mac race a couple of times as well. It has better scenery

The Chicago Mac is the oldest annual freshwater distance race in the world, and it throws the best party in American sailing. It starts with the Warning Gun Party at Chicago Yacht Club, where blue blazers and ties are required.

You finish the Chicago to Mac race downwind under kites, crossing under the bridge and then the finish line at the island. The scenery is good for both the start and finish.

Once the fleet reaches the island, the celebration moves to the front porch of the Grand Hotel, overlooking the finish line. The Porch Party serves smoked salmon, caviar and champagne, and the ladies wear Derby hats. Down the hill, the Pink Pony fills up with sunburned crews. The week wraps with the Sailors Celebration on the great lawn of Mission Point Resort, where flags go to the top boats in every section.

No cars, horse-drawn carriages, a Victorian island, 250 boats and a porch full of champagne. Nothing else on the water comes close.

1. Bayview Mackinac Race, Port Huron to Mackinac Island, Michigan

When: Mid-July (started July 18, 2026)
Where: Lake Huron, on a 204-mile Shore Course or a 259-mile Cove Island Course
Fleet: 203 boats entered and about 1,600 sailors in 2026
Classes: Racing, cruiser-racer, cruising and double-handed divisions, from Catalina 320s to a 104-footer

I’ve joined in the action on this one several times. Both the night before and the island are a good time. It might lack the scenery of downtown Chicago, it makes up for it in local atmosphere.

The Bayview Mac throws two parties for the price of one. Before the start, Port Huron hosts Boat Night, which Great Lakes Scuttlebutt compared to Mardi Gras, with crowds lining the St. Clair River and live bands playing. The beads are there too. Port Huron Boat Night occurrs at the end of “Blue Water Festival” that runs from Wednesday through Saturday so it isn’t strictly just a sailing party.

The real fun starts on Mackinac Island, where up to 2,000 crew, family and friends pack the downtown bars. The Port Huron to Mackinac Race typically ends in a beat to the island where you can smell the horse crap for the last couple of hours. That’s how you finish 2 days of racing non-stop. The party just has to great to make up for that. Party central is the Pink Pony at the Chippewa Hotel, right on the water, with drinks from sponsors like Tito’s Vodka and Bell’s Brewery. Crews in matching team shirts swap stories about holes in the wind until Tuesday’s awards party, where the last boat home gets the “pickle boat” flag. On a light wind year, the last place boat has been known to finish during the party while everyone is watching.

Which one should you sail?

If you want class, go to the Chicago Mac. If you want chaos, go to Port Huron Boat Night or Put-in-Bay. If you want the best food, it’s worth the ocean crossing to Honolulu. Whatever you pick, enter early, pack a team shirt, and save some energy for after the finish.

Tell us in the comments: which regatta party did we miss?