From Olympian-worthy ironman triathlons to the best Maine marathon coastal views, these five races are worthy enough to plan your vacation around.

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January–March, November

Swamp Buggy Races [Naples, FL]

While million-dollar homes and high-end retail are what Naples is known for, a bit of down home and dirty tradition can be seen at the Florida Sports Park just down the road. Started between hunters and fishermen as friendly competitions to see who could reach hunting ground first has now expanded into weekends full of high-powered engines rocketing through muddy waters. It’s a little local color without getting muddy yourself.

Where to Stay Edgewater Beach Hotel


Grandfondo Twilight Race [Delray Beach, FL]

Italian for “big ride,” this South Florida cycling tour  pairs camaraderie, coastal scenic views, and an atmosphere for both professional and recreational riders. It’s two days along the 100K loop through Palm Beach and Broward County, but ends with BMX stunt shows, beer gardens, and street disc jockeys.

Where to Stay Opal Grand Resort | Delray Sands Resort


Ironman Lake Placid [Lake Placid, NY]

Just as they did for the 1980 Olympics, athletes descend up on this small alpine village for a three-part race that proves it takes as much mental strength as stamina to complete the most epic of triathlons: a 2.4-mile swim, 112-mile bike leg, and a full marathon. With more than 2,500 athletes from 19 different countries, it’s like it’s a mini-tribute to the games.

Where to Stay Lake Placid Lodge


Mount Desert Island Marathon [Bar Harbor, ME]

Peak foliage season, trails along the coastline, and cool fall temperatures make up the most scenic distance run in the country. Paths dip into Acadia National Park, beside Maine’s famous ragged cliffs and headlands, and along postcard-worthy Hunters Beach Trail. It’s all downhill once you make it to Mile 25, the course’s highest point – and most breathtaking – section with views toward Southwest Harbor.

Where to Stay West Street Hotel | Harborside Hotel, Spa & Marina


Super Boat International [Key West, FL]

You can sail all over the world, but tackling the Keys in a vessel that could put a stock car to shame can only be done at the Super Boat International. The series has even drawn celebrity racers like Don Johnson, Kurt Russell, and Bruce Jenner to the waves. Think crystal-clear waters, high-power engines, and a full week of fan-friendly events like parades and parties.

Where to Stay The Laureate Key West | Sunset Key Cottages