I love summer. I love the warm water and long days and predictable winds (at least here in the Gorge where I live). And as much as I also love the cool, crisp autumn days for hiking and biking, and the inevitable winter snow for skiing and snowboarding, if the truth be known I'd rather have summer all year around.
In fact, I've spent many of the past several winters searching around the globe for the perfect spot to while away those dark winter days in a place more conducive to sun tans and perfect sailing.
Although I've visited perhaps twenty potential spots (leaving another two hundred for future winters), the top contenders for almost guaranteed warmth and wind go to the following five. This list also takes into account that you might want to vacation for three months or you might just have a week.
The Overall Fun Quotient includes nightlife, other things to do, friendliness of the locals, good food, ease of travel, etc. Overall Sailing Quotient includes wind consistency and dependability, water temperature, equipment availability and condition, and variety of sailing conditions available. Overall Dollar Rating includes cost of meals, accommodations, car and equipment rental, but not the cost to get there since this may vary greatly depending on where you live.
In alphabetical order, here they are.
ARUBA
Yes, I know, Aruba is hardly a secret to the windsurfing world, but that's because it is really that good. The winds are hot and steady and for East Coast intermediate sailors, it's probably one of the best wintertime spots in the world.
PROS: Aruba is fairly easy and fast to get to for East Coast residents. The water is very warm and when it doesn't blow t snorkeling and scuba diving is great. But you're there to sail and the hot Caribbean wind in Aruba is about as reliable as it gets. It generally ranges between 4.0 and 6.0, with excellent 5.0 conditions being the norm.
Aruba is the perfect place for waterstarting intermediates to work on their jibes since the water is almost dead flat. There are also several spots for beginners to learn to waterstart and several places to rent equipment and get lessons.
There are a variety of accommodations from budget hotels and windsurfing packages from several operators to luxury beachside cabanas. The beaches are long and white and clean and the locals are very friendly and helpful. Rental cars are readily available but if you're staying in a beachside hotel you might not need one.
The package deals offered by several tour operators make windsurfing in Aruba a really painless vacation if you have limited time (5-10 days) since they include everything.
CONS: As easy to get to as Aruba is from the east coast, from anywhere else it requires substantially more time, patience, and money. And Aruba is not all that cheap once you arrive. If you're taking your own gear you might be hit with as much as $300 in excess baggage fees if you're coming from somewhere like Seattle.
The wind blows pretty much straight off shore so if you happen to break down you might find yourself drifting to Venezuela. And unfortunately, because of several new high rise hotels right on the beach, you have to sail quite a ways out to find good wind not disturbed by the wind shadow of these huge structures.
Aruba is truly a desert island and the sun is insidious. Even well tanned sailors need plenty of SP 20 while real whities will want SP 1000+. I try to drink several gallons of water each day and wear a large hat just to survive.
Really good sailors might get a bit bored with the flat water sailing after a few days. While there is the potential for wave sailing on the north shore, the coast is rocky and not many people sail there.
The nightlife is sparse and much more geared to the well-healed traveling nightclub and gambling set than to vagabond boardheads. Even during the day there is not a whole lot to do besides a few normal tourist activities like drive around the island, shop, or swim.
Overall Fun Quotient: 7
Overall Sailing Quotient: 9
Overall Dollar Rating: 7

BAJA
Baja has long been the 'spot of choice' for bargain hunting West Coast boardheads. Since the paving of the Baja highway, it is a fairly painless road trip and there are lots of places to hide out and sail all by yourself.
PROS: You can drive or fly to southern Baja where much of the winter sailing happens, depending on your time frame and budget. If you drive you can bring all your toys but either way, Baja is probably one of the cheapest, most accessible windsurfing destinations I can think of.
Speaking of toys, there are lots of other things to do in Baja besides sail. There is great surfing, mountain and dirt bike riding, fishing, golf, snorkeling, or, for the less active, shopping or exploring.
The weather is usually hot, dry, and windy December through February. The wind usually comes up in the late morning, lasting until late afternoon, with sail sizes from 4.0 to 5.5 being the norm. There are a few more popular areas (such as Los Barrilles) if you want to sail around people but if solitude is your inclination there are literally hundreds of little spots and endless beaches from which to launch where you'll be all alone.
For superb wave sailing or for those not wanting to make the long trek all the way to Cabo San Lucas, there are a dozen excellent spots on the northwest coast of Baja. Some, like Punta San Carlos and Punta Abreojos are well known and within reasonable one day driving distance from the U.S. The camping is primitive - to say the least - but the experience is unique.
Like Aruba, there are several options for all-inclusive windsurfing vacation packages which make a short (5-10 day) sailing holiday both fun and easy. Most of these windsurfing 'resorts' are located on the southeast coast of Baja and all offer packages complete with meals, hotel, equipment, and instruction. If you don't require all the amenities you can usually just rent equipment or get a meal.
CONS: Baja is generally not for the luxury resort oriented sailor (although there are many luxury hotels near Cabo San Lucas). The climate is very hot and dry but the water can get quite cold, especially on the Pacific side.
If you plan to drive and camp your way down, plan on bringing two of everything you might possibly need including car parts and sailing gear. While the chances of having problems might be small, small problems can become major ones in Mexico. Unless you are near the windsurfing resorts in the Los Barrilles area, there is no gear to rent, buy, borrow, or get repaired.
The beauty of Baja - the lack of civilization - might be a drawback for some people. And when you do find civilization, the traditional Mexican attitude of manana will drive the average investment banker crazy. There is not much nightlife by resort standards and, like just about anywhere these days, you'll want to keep an eye on anything not locked up tight.
Overall Fun Quotient: 7
Overall Sailing Quotient: 7
Overall Dollar Rating: 9
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