From fall to early spring, the trade winds kick up across the Caribbean, making this the best time of year for kitesurfing. Finding lessons and a place to stay on the cheap is easy. Finding an inexpensive plane fare to get there isn’t. The key is to choose a destination that’s reachable by a direct flight from the US, and then troll fare-saving web sites like Kayak and Air Fare Watchdog for a decent deal. One other cost-saving tip: once you get to your sunny Caribbean beach of choice, every price is negotiable.
San Juan, Puerto Rico
Yes, the all the hotshot kitesurfers (and surfers) head to the beaches on the northwest part of the island, near Rincon. But San Juan offers the best kite surfing schools, mostly around a rocky outcropping called Punta las Marias, flanked by Ocean Park and Isla Verde beaches. Kitesurf PR offers lessons for $90 per hour and group clinics for $250 a day. An economy room at nearby Coqui del Mar guesthouse costs $69 per night peak during the peak season.
Kite Beach, Dominican Republic
The surf, steady winds, and shallow green waters of the Dominican Republic make it a hub of Caribbean kitesurfing. Cozy, reef-sheltered Kite Beach on the northern shore by the town of Cabarete is where you’ll find the best conditions, though you’ll have to brave the crowds and scene. It’s also where all the top schools are located. Group lessons at Kite Club Cabarete are $120, and rooms at Kite Beach Hotel start at $53 a night.
Long Beach, Barbados
No other island in the Caribbean gets better exposure to warm, steady winds and surf than Barbados. But at Long Beach and Silver Sands Beach on the south shore, the waves are tame, making it a prime playground for kitesurfers. Endless Kiteboarding Barbados runs two-hour group kitesurfing lessons for $120. The Sea U Guesthouse by the hip surfing village of Bathsheba on the east coast is a little bit of a drive, but the surfer vibe can’t be beaten. Studio apartments start at $119.