10 of the Best Vacation Races for Your Bucket List

10 of the Best Vacation Races for Your Bucket List

There’s nothing quite like signing up for an athletic event knowing you have a ready-made vacation built into it. When you’re taking part in an event in a beautiful part of the world, pre-race relaxation is easy and post-race celebrations take care of themselves. And it’s even better when you have friends and family with you to enjoy the incredible destination, too! Sound like your type of trip? Here are some of the best vacation races on the planet that will satisfy your need to compete and your desire to explore.


10 Amazing Vacation Races to Put On Your Bucket List

Whether you’re a seasoned triathlete, casual runner, or biking buff, this list of awe-worthy races will give you plenty ideas for your next athletic endeavor — and vacation!


1. Rock ‘n’ Roll Las Vegas

Las Vegas doesn’t do anything small, and this event is no exception. You can choose from the marathon, half marathon, 10K, or 5K, so it’s suitable for all levels of runners. The “party within a race” involves fireworks, live music, dance parties, and cheer teams, giving you an enjoyable sensory overload as you run on the Las Vegas Strip. It’s perfect for distracting you from your tired legs!This race starts in the evening, and it’s the only time of the year when the Strip is closed for a private event, allowing this race to tap into the city’s energy in a unique way. And when it comes to post-race entertainment, you know you’ll be spoiled with choice in Sin City.

Date: November 10-11, 2018

Entry: $79.99 – $179.99

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2. Ironman 70.3 Cozumel

Set on the beautiful Mexican island of Cozumel, this half Ironman race is quite possibly one of the most idyllic on the circuit. The locals love welcoming athletes to their home for this event, which involves a 1.2-mile swim, 56-mile bike ride, and 13.1-mile run. The warm, turquoise waters are teeming with exotic marine life, ideal for pre-race swims and post-race snorkeling and diving. Prefer to stay on land? There are plenty of white sand beaches for basking in the sun.

The race itself feels like a giant Mexican fiesta, with enthusiastic crowds lining the streets, dancing, music, and live bands. As soon as you cross the finish line, it takes no effort at all to go into vacation mode.

Date: September 29, 2019

Entry: $150.00 – $350.00

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3. Cycle to the Sun, Maui

Perhaps one of Maui’s best kept secrets, this epic bike race is one you’ll never forget – and you’ll certainly earn your vacation doing it. Competitors of the Cycle to the Sun ride from the small town of Pai’ia on Maui’s North Shore up to the top of the Haleakala Volcano – that’s 36 miles and over 10,000 feet of climb! Each year this event attracts around 200 riders from around the globe who are eager to test themselves on this challenging climb.

When the racing is complete, a myriad of recreation opportunities await on this stunning Hawaiian island, including whale watching, hiking, snorkeling with turtles, helicopter tours, or simply lounging on a beautiful beach in a hammock.

Date: June 29, 2019 (Registration opens February 1)

Entry: $175 (for Hawaiian residents) – $300

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4. Nevis to St. Kitts Cross Channel Swim

Imagine swimming in some of the clearest waters of the Caribbean as you race across the open ocean. This 2.5 mile challenge starts from Oualie Beach on Nevis, goes across the “Narrows,” and ends at Cockleshell Beach on St. Kitts. Race among some of the best swimmers in the world as you compete for a top time, or opt for the assisted, non-prize category that allows use of fins, snorkles, flippers, and other items. You can also go in with a team and do the four-person relay, where each person swims one kilometer.

And if one swim isn’t enough for you, check out the seven-day St. Kitts and Nevis Swim Trek. This “swimming holiday” isn’t a competition, but instead swimmers get to explore different bays, beaches, shipwrecks, and more. Either way, the sandy beaches and picturesque islands make for a perfect vacation in the end!

Date: March 31, 2019

Entry: $75 – $115

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5. The Dipsea

The Dipsea is the oldest trail run race in America, and although the 7.4-mile course is well-known for its beauty, don’t be fooled – it packs a grueling punch. Winding from Mill Valley to Stinson Beach in Northern California, the stairs and steep trails across this rugged terrain make it a challenging course.

Entry is limited to 1,500 people, and the entry system is quite unique, consisting of several stages: The first 600 spots are awarded to those that finished in the top half of the previous year’s race. The next 500 spots are awarded on a “first come, first selected” basis to those who mail in their applications. If that doesn’t work out for you, you can bid for one of another 100 spots via silent auction. The final 300 spots are awarded through a lottery. If all else fails, you can try to persuade the race committee with a sob story (seriously—but you better be convincing), or being the highest bidder in an auction held the Friday before the event.

After the race, enjoy the quiet seaside town charm of Stinson Beach or head north to wine country for some well-earned indulgence.

Date: Second Sunday in June

Entry: Mail in your application, lottery, $90 fee, or compete in the previous year’s race.

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6. Blenheim Triathlon

Combine a visit to a UNESCO World Heritage site steeped in history and culture with an opportunity to take part in one of the UK’s most popular multisport events. Set on the grounds of Oxfordshire’s 18th century Blenheim Palace (the birthplace of Sir Winston Churchill), this race is perfect for beginners and seasoned triathletes alike since you can choose between three options: the Super Sprint (400m swim, 13.2 km bike, 2.9km run), the Sprint ( 750m swim, 19.8 km bike, 5.4km run), or the Sprint Team Relay, in which each person competes in one leg.

Participants never leave the grounds of the palace: they swim in the Grand Lake and bike and run around the landscaped gardens. Your cheering squad can enjoy the location too, just make sure they purchase spectator tickets. After this historic experience, Oxfordshire is the perfect gateway for exploring the UK. It’s just over an hour drive from London, and you’re also right next to Scotland and Ireland.

Date: June 1-2, 2019

Entry: £39 (with a £350 fundraiser commitment) – £114 (premium entry). Full price break down here.

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7. BolderBoulder 10K

With more than 50,000 participants and 100,000 spectators, the BolderBoulder is the second largest 10K running race in the US and the fifth largest road race in the world. Set in Boulder, Colorado at the foot of the Rocky Mountains and taking place on Memorial Day each year, this 10K destination running race is truly is open to all. You’ll find Olympians, weekend warriors, and grandparents with their little ones all lining up to enjoy the fun. The race finishes at the University of Colorado’s Folsom Field with a Memorial Day tribute, which is one of the largest in the US. After the race, stay a few days in Boulder to explore the many cafes, restaurants, boutiques, and attractions the city has to offer, or go off into the Rockies looking for mountainous adventure.

Date: May 27, 2019

Entry: $35 – $100

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8. Triple Bypass Ride

If you’re at peace in the mountains and prefer biking to running, then the Triple Bypass Ride might just be your ideal destination race. This epic bucket list ride takes you through three mountain passes during the course of 120 miles and 10,000 feet of climbing through Colorado’s Rockies. Afterwards, enjoy a few days R&R in one of the nearby mountain towns such as Vail, Breckenridge, Minturn, or Leadville, enjoying the mountain air, fine dining, and great craft breweries. If 120 miles is more than you’d like to bite off, try something shorter with the 30-mile Single Bypass ride or the 75-mile Double Bypass ride.

Date: July 2019 (Exact date, TBD. Registration opens the first week of January 2019.)

Entry: $185

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9. Walt Disney World Marathon Weekend

Perfect for those looking to treat the kids while also getting their own running fix, the Walt Disney World Marathon Weekend caters to all fitness levels. Options for this playful race includes short (100m to 200m) kid’s races, a 5K, 10K, half marathon, and marathon. Enjoy the magic of running through Disney World as you get cheered on by all the classic Disney characters! This is sure to be a vacation race and a weekend you and your children will remember forever.

Date: January 19-13, 2019

Entry: $20 (kids race) – $188 (marathon)

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10. Escape From Alcatraz Triathlon

San Francisco exudes style, sexiness, and boundless opportunities for entertainment, making it an obvious popular weekend getaway destination in the US. One of its most iconic tourist attractions – the former penitentiary on Alcatraz Island – also happens to be the starting point for one of the world’s most prestigious triathlons. Athletes swim 1.5 miles from Alcatraz to the San Francisco shoreline, bike 18 miles out to Golden Gate Park, and finish with an eight-mile trail run that includes the infamous 400+ step Sand Ladder. Competition for a place is almost as tough as the race itself, with thousands of people worldwide entering the lottery for one of the coveted 2,000 spots.

Date: June 9, 2019

Entry: $750

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