Skateboarding Holidays: The Best Cities For An Awesome Skateboarding Trip

More skateboarders are going on skateboarding trips as shredding on a new skatepark or street structure allows them to connect with local cultures and meet likeminded people. Travelling to new environments is an essential part of the sport, and it's why many individual skaters and skate crews are hitting the road in search of the most iconic places to shred or pop an ollie. Some cities have gained a reputation for being a skateboarder's paradise as they feature a plethora of street spots, skate parks, ledges, bowls, and plaza-style street set-ups. If you're lucky enough, you may even chance upon a hidden spot, such as the DIY skate park in Calgary under the Crowchild and Bow Trail overpasses.

If you're just getting into the sport or have never travelled before, the thought of skateboarding in an unfamiliar destination might seem a bit unnerving, especially if you're travelling solo. Pro skateboarder Evan Smith says that the key to having an enjoyable trip is to just go out there and experience the culture. “Obviously be respectful, see the sites, skate-rat the plazas, make sure to reach out to locals and introduce yourself,” he advises. Indeed, the best way to experience a place is to skateboard it, so grab your deck, book a ticket, and consider these cities for an awesome skateboarding trip.

Calgary’s Cowboy Park located at the western edge of the city has a huge skate park.

Los Angeles, California

For a fun and successful skateboarding holiday, you need to pick a destination, then create a skateboarding travel itinerary to make the most of your trip. If you plan to carry your skateboard around during your travels, bring a smaller model since it will make navigating crowded spots like airports and malls a lot easier. You'll also want to be prepared for emergencies and bring tools in case of wear and tear. Don't forget to bring bearings, as well as an extra set of wheels like some Spitfire skateboard wheels so you can adapt your deck to different skating surfaces and environments.

One of the best places for your first skateboarding trip is Los Angeles, considered as the birthplace of skateboarding and home to modern icons like Tony Hawk and Eric Koston. Be sure to go to must-session spots like the Venice Skatepark where you can do cool tricks in the graffiti-lined bowls, or go to Stoner Plaza to test your skills on the ledges and rails. Advanced skateboarders should also check out the iconic Hollywood High 16, a 16-stair handrail spot that's a staple in LA skateboarding. Challenge yourself to land a kickflip front blunt, or just hang around and watch skateboarders, BMXers, and even snowboarders as they show off their best tricks.

Need lots of space to nail some cool tricks or shoot an amazing skateboarding video? Head to the Santa Clarita Skatepark, which is under an hour’s drive away from downtown LA. This place has two cloverbowls, as well as obstacles like a 10-foot square bowl, a half pipe, and lots of ramps, ledges, and stairs that vary in size and difficulty. The park is open 365 days a year and is free for all users, but be sure to abide by the safety rules and wear your helmet, elbow pads, and knee pads while skateboarding.

Tokyo, Japan

Want to explore a shredding destination with a cool, underground vibe? Then think about going on a skateboarding trip in Tokyo, Japan. Compared to some Western skateboarding scenes which can get a little rowdy at times, the vibe here is completely chill and respectful. However, many skateboarders find that they're able to hone their skills in this city since they have to learn to navigate the narrow sidewalks and the rush hour crowds. While you're there, check out the Miyashita Park, a rooftop skatepark atop a shopping mall in Shibuya. Note that the park isn't entirely free, and you'll be charged 1,000 JPY or about $6.45 USD to skateboard here for a few hours. Helmet use is required, so make sure to bring one. Left your gear in your hotel? Don't fret. They offer helmets for rent, and the rental is usually free of charge.

You'll also want to do a session at Murasaki Park Tokyo, also known as Amazing Square. This is Japan's ultimate skate park, and it features an indoor and outdoor park with an impressive array of street and transition obstacles, as well as a 14-foot halfpipe. Entry fee on weekdays is 864 JPY or about $5.55 USD, while it costs 1,080 JPY or $6.93 on weekends and holidays. If you're in Japan, note that it's illegal to skateboard on busy roads and most public areas, so stick to local skateparks or find secluded spots that are far from residential areas. For guidance, consider joining local skateboarding groups on Facebook or YouTube so you can have a safer experience.

Barcelona, Spain

Dreaming about going on a skateboarding adventure in Europe? Then book a trip to Barcelona and enjoy the rich history, beautiful architecture, and some of the most unique skateboarding parks in the world. Its smooth roads, legendary spots, plazas, and skateparks make the city a haven for skateboarders. Also, unlike other places, the locals are generally accepting of the skateboarding culture so you can find people practicing their tricks just right in front of places of interest, like the Barcelona Museum of Contemporary Art. Anyone is allowed to skateboard on the streets, and there are weekly community events like the Friday Night Skate where everyone is invited to participate and have fun.

Once you arrive, check out the skateparks first, starting with the Marbella Skatepark, located near the beach in Poblenou. This massive park has a mix of obstacles like banks, quarter pipes, and ledges, spread over 6,600 square metres of even concrete. It's the perfect place if you love to enjoy stunning beach views while taking a breather between sessions. Best of all, Marbella is a free public park, and it's open daily for street or pool/bowl skating.

For a beginner-friendly spot, check out the Parc de la Trinitat which is situated in the Nou Barris district. This park offers a lowkey, quieter vibe, perfect for newbies of all ages, and it has a skatepark with rails, ramps, banks for both advanced and beginner skaters. Afterwards, have a picnic on the park grounds, or go for a walk and see the beautiful sculptures gracing the park.

La Paz, Bolivia

For an underrated destination with a vibrant skateboarding scene, look no further than La Paz, Bolivia. This South American city is home to Pura Pura, which has the distinction of being the highest skatepark in the world. This DIY park is located about 3,600 metres above sea level, created by over 100 volunteers from 15 countries who came together to build this magical space. The park features ramps, quarter pipes, and other obstacles for a fun yet challenging session, and it’s free for everyone.

Need to build speed and confidence on your flow tricks? Head on over to the Zona Sur Park, which is one of La Paz's most popular skate parks. Skateboarders usually come to this place to perfect their tricks as the park has bowls, rails, and ramps where skaters can improve their skills. As with other places, don't forget to wear your protective gear while shredding to stay safe at all times.

There are skateboarding meccas all over the world that are just waiting to be explored. Plan a skateboarding trip to do sessions in iconic spots, and let your wheels take you to your next adventure.