The Northwest
The entire northwest of the island is teeming with superb surfing and diving beaches and is rich with good wave-sailing spots.
Shacks
World famous is Shacks, site of the PWA wave contests in the 90s, is located in the town of Isabela. Conditions range from inviting to threatening and can change daily. It’s windier here than anywhere on the north coast. If you only had one sail, it would be a 5.2. Kiteboarders would sail every day with a 9.5 to 11.5m. Although Shacks might get by as an intermediate spot when the waves are small, it’s definitely an experts-only break when the place goes off. The wave is hollow and pitches over a shallow and sharp coral reef. To the non-windsurfing members of the family, the reef offers incredible diving and snorkeling when calm. This is the only spot on the whole island where you can rent a place right on a wave-sailing beach overlooking the break. Imagine yourself waking up in a nice apartment at the cliff in Ho’okipa, well that’s basically what you get at Shacks (minus a few hundred sailors). If you’re not renting there, you’ll have a hell of a time finding a spot to park though.
Surfer's Beach
Just west of Shacks on the north side of the military base in Aguadilla, is an easy-access spot that goes off often, and it’s very sailable in northeast winds. The beach is easy to find once inside the base if you ask for directions. Its flat, rocky bottom is a lot more forgiving than Shacks, but the downwind shoreline is jagged rock and nasty. If you get caught on the inside and can’t get out, get ready for a painful walk of shame. This beach is popular with surfers. Show them the respect they deserve to guarantee a good time.
Jobos
Just east of Shacks is Jobos. This beach is good for less experienced sailors. The access is easy and the reef is gentle. The east part of the beach is a bathing area protected by a rock outcropping. Beware of the bathing area though. Once you're in shoulder height water there is a sketchy current that shoots offshore beside the rock. If you do get caught in the current don't fight it. Swim around past the break and swim in further downwind. Surfers take off just off the rock on waves that peel right. We sail more toward the middle of the bay. There are plenty of restaurants and bars on the sand hill overlooking the beach. Happy Belly’s is the best of the bunch. They serve a killer chicken quesadilla and have the coldest beer at a great price.
The Metro Area
Punta Las Marías
This is where the Velauno Store is located in the San Juan metro area. This must be the most under-rated windsurfing area in the Atlantic. The northwest has to be really going off to get the spoiled locals to drive out of town. A 4-mile-long barrier reef about a half-mile out provides some of the best wave sailing in Puerto Rico, with fantastic and uncrowded breaks everywhere. The most popular sail sizes for wavesailing are 5.3 to 5.8 and about a meter more for freeride blasting.
A good launch from which to explore the wave-sailing possibilities is the east corner of Park Boulevard Street, about 3 miles west of the airport. It offers beachfront street parking, a grassy rigging area and easy access to several of Punta's clean breaks.
Sunset
The leftmost break, Sunset, is hardly ever sailed because it’s so far downwind. It has a deep-water peeling right wave and holds a very big swell with ease.
Dominoes
Dominoes is popular only with the best sailors because it’s very shallow. When it goes off, it’s hollow and fast. This peak breaks both ways, just like Waimea, a break within easy reach directly in front of the launch at Ocean Park. Usually, most sailors stay near eastern-more reefs though.
Puntas
Puntas is the easternmost reef and the most popular. Be sure you understand how the reef breaks before you go out. The inside part of the take-off is dry reef, and local knowledge is critical. The protected area inside the reef provides great freeride cruising year-round. It’s awesome in the summer when the locals trade in their wave boards for slalom equipment to enjoy powered 6.0 to 6.8 free-riding. Sick freestyle riding is also very popular.
Caballos
The hard-core wave-sailors choose to cruise upwind about a mile to the Caballos, the best big wave break in the PR, located off the beach next to the San Juan Airport. This offshore wave will peel to the right up to double-mast high and end in a huge bowl that will swallow you alive if you don’t kick out early! Luckily, it has a channel that allows you to get out in all but the biggest waves even in light wind. This reef is a long (very long) swim back if you break down. Launch near the San Juan Plaza in Isla Verde neighborhood.
Metro Area Kiteboarding
The epicenter of Kiteboarding activity is in Isla Verde and Punta las Marías. Wide, sandy beaches with a steady sideshore breeze make them perfect for all levels. The cool thing about PR is that kiters and windsurfers actually get along pretty good so it's not unusual for both kiters and windsurfers to share the same beaches & breaks.
The South Coast
The south coast is fairly well known to local sailors but largely ignored by visiting windsurfers. With more than 100 miles of coastline, it’s a pity because the sailing can be very rewarding to those willing to explore a bit.
La Parguera
Located just east of our southwest corner, this gorgeous area features dozens of mangrove islands and sand cays spread over 5 miles of shallow, clear water. The winds are a steady 15 to 20 knots just about every day. The access difficulties will be a small price to pay to sail among the unspoiled, stunning charm of these islands. A floaty freeriding or course-racing board will make exploring easy. Your best bet it is to cruise into the town marina and rent a small open boat for the day. Pack a cooler, load the gear and head out to Cayo Enrique. At first, rigging in the shallows may seem like a hassle but after a few runs in smooth Parguera water you’ll know you hit the jackpot. Ask the locals to point you in the right direction to other launches, nightspots and places to stay. The flat water and steady tradewinds make this area really popular with Kiteboarders as well.
La Parguera's night secret is the bioluminescent bay. A very unique wonder that is known for glowing water during the night caused by millions of micro-organisms. It's definite must-see when there is no moon.
Guanica
Guanica offers a variety of conditions that will please both beginners and advanced sailors and kiters alike. Kayaking, snorkeling, biking, scuba, windsurfing and kiteboarding are only some of the multiple activities available in the area. Gilligan's Bay is a great spot with nice flat water and good steady wind. Lauching a kite can be sketch since there's no real beach available to set-up a kite. The beach at Gilligan's Island is awesome but it's not available to set-up kites. If you want to kite here you'll probably need to launch from a boat.
The best alternative for kiters at Gilligans is the Ballena Channel. The channel at Ballena is an awesome buttery flat water spot with a good beach to rig and launch from. You'll need a boat to get there. Don't worry, the ferry at San Jacinto Restaurant will take you there (or to Gilligan's Island) for $5 per person. Unfortunately there are mangrove trees downwind, so don't mess up or you'll land right into them. This is definitely not a beginner spot.
Finally, you have Ballena Ola about an hour walk east. It's known to be a very good wave spot when the occasional south swell hits. You can also access Ballena Ola by car to avoid the long walk from Ballena.
Santa Isabel
This little town is not famous for much but a bunch of San Juaneros visit Jauca, the muddy but windy bay, on a regular basis. It cranks here often and the short one-hour investment from San Juan pays off with almost Gorge-like conditions. The regular 18-25 knots winds blowing onshore with waves from 2 to 4 feet create some great bump and jump conditions and some of the best port-tack jumping in the island. This will keep drawing the regulars away from the blue waters of the north to the frothy chop of the south for some time to come.