Posted on Sep 13, 2012


by Shawna Cropas

A windsurfing vacation with a group of single footloose and fancy free mates who all sail at the same level is a no brainer!  It requires minimal stress and with a load of fun tickets, (disposable income which shrinks the bigger your family gets) you’re pretty much guaranteed a good time. Fast forward into the future where singles mingle, turn into partners and multiply into families… Now try to organize a relaxing windsurfing holiday. NOT EASY! A vacation’s dynamics changes dramatically when you add the needs of a partner and/or children! Suddenly the logistics get more complicated as you juggle everyones personal needs.

Though it’s easy to find the worlds best windsurfing venues online it’s almost impossible to find something that declares the same about a family vacation. Where on earth is the perfect windsurfing destination that caters to the whole family or even just a non windsurfing partner as well as yourself, a dedicated windsurfer?

It was just the other day that Matt Pritchard and Shawna Cropas had this exact discussion, this precarious balance of what makes or breaks a family vacation! Both of them have been globe trotting around the four corners of the earth for most of their lives and now find themselves with young families with a whole new set of needs to consider well before boarding a plane to go on vacation.  Here are some things they consider before packing the bags:

1. A warm safe location for water sports and wind.

2. Accommodation on the beach where partners can watch each other sail to easily tag team and close to home for food and naps so the whole family is included. The water equivalent of ski in and ski out.

3. Food and provision shopping in easy walking distance or a very short drive.

4. Kids clubs and beginner area with lessons.

5. Different water conditions to suit an array of windsurfing levels.

6. Tons of activities to do outside of windsurfing.

7. Great shopping will always make the ladies happy.

8. Length of transfer from airport to accommodation

Anyone who has ever travelled with a family knows there is a painful amount of work involved before you even get to your destination and sink into holiday mode.  It can be positively ‘hair pulling’ packing kids, car seats and  toys as you drag your mountain of avalanching luggage to the check in. Just making it to the airport on time is a miracle only to find out the plane is delayed . The kids are beyond sleep deprived and ready to scream down the house . This is where exhausted parents start pacing the aisles to pacify their children as other weary travelers lay down their heads to rest at 2am. Getting there in one piece without contracting the latest bird flu is an act of faith in itself as your toddlers licks door handles and the bottom of their shoes while waiting to board!  Considering the potential travel hassles to any destination with a family you really want to make sure when you do arrive to your destination that everything is postcard perfect as promised in the brochure.

Throughout all our personal travel experience we consider Vassiliki, Greece and Cabarete, Dominican Republic to be great family windsurfing destinations. Maui, Hawaii though is, in our opinion the best location with the least amount of hassles and the most amount of relaxation possible. It’s a windy paradises for all level of sailors with a variety of other interest and activities to do close by. These destinations will also impress a non windsurfing partner who’d simply like to enjoy a gorgeous holiday in the sun.


Maui is not only the mecca of windsurfing, a tropical water sports playground and activity packed island, it’s also the most all time family friendly windsurfing holiday destination with year round conditions. Be prepared to simply ‘be’ on holiday and enjoy all that the Hawaiian islands offer you on a platter from windsurfing, surfing, SUP, snorkeling, whale watching, volcano hikes, bike riding or just enjoying the sun and beaches that most people will only dream about. The word “bored” is rarely heard in Hawaii.

1. Maui is the picture perfect postcard for warmth, sun, turquoise water, trade winds and a pretty safe hawaiian island culture.

2. There are plenty of rentals found all along the north shore which offer sailing right out the back door with views looking over the expanse of the north shore where whales breach and turtles lounge.  Here you can watch your partner sail, kids play on the beach in the safety of a private home where lunch is made and nap time doesn’t mean everyone needs to leave the beach. Hiring equipment from local shops can be picked up in just a five minute drive away and then left rigged on the lawn for the span of your vacation.

3. Food shopping is within a seven minute drive from your accommodation on the beach to the historic town of  Paia where you’ll find Mana Foods full of local and organic produce. Kahului is only a five minute drive where you can hit Costco for bulk shopping american style right next to Kmart for whatever extra kids needs you might require such as diapers, sunscreen or even masks and snorkels.

4. There are kids clubs going on at Kanaha a few minutes drive away but you can always hire an instructor to come to your door and teach the whole family. Most rental locations offer beginner gear and the light morning breezes are perfect for learning to sail.

5. Right out your Camp One or Sprecks door is flat water for beginner and intermediates with winds that picks up in the afternoon for flat water intermediate level sailors and breaking further out on the reefs are manageable waves for experts or windsurfers who’d like to be introduced to wavesailing.

6. Out of all the destinations, Maui has the most activities to do outside of windsurfing from zip lines up country, volcano treks, waterfall hikes and swimming pools, whale watching tours, visits to the aquarium, bike riding, sunset strolls all in the perfect climate… There’s an endless list of things to do and when you arrive on the island, we recommend checking out the local mag- “101 Things to do on Maui”.

7. Shopping on Maui is fun for foreigners and locals alike as there are lots of american outlet stores, fine boutiques with affordable fashion, tons of local art galleries and a variety of surf and windsurfing shops. For the ladies that like high end fashions, boutiques like Tamara Catz (Francisco Goya’s wife) with her original designs found only on Maui as well Le Tart bathing suits by Lisa Le Tart, Pete Cabrinha’s wife- again original local designs all found in Paia only a twenty minute walk along the beach from Sprecks. There are more original stores in the cowboy-esque town of Makawao. Wailea has all the Chanel, Guess, Betsy Jonston kind of stuff though Shawna recommend going to the Enchantress as it’s a funky boutique full of LA designers.

8.  An easy ten minute drive from the airport to any North Shore beach rental.


Vassiliki, Greece is so uniquely perfect for a family vacation that it ranks number one for the best family vacation, unfortunately it is not a year round venue. It is hands down the very best place to introduce windsurfing to absolutely anyone as it’s just an awesome holiday experience with or without windsurfing. Sprinkle old world Greek culture, mediterranean food and architecture over this holiday and you’ve got yourself a holiday feast.

Shawna was first introduced to windsurfing through Club Vass and it still remains one of her fondest windsurfing experiences to date. She arrived in Greece a non windsurfer and left with an insatiable appetite for windsurfing ever since . As a world traveller well before she stumbled across windsurfing, Shawna was just as stunned by the beauty, timeless culture and azure sea as she was thrilled to be introduced to a new sport.

1. Firstly you are surrounded by Greece’s old world ways, crystal clear waters, gorgeous sun, safe family friendly small village culture nestled in a crescent cove of the mediterranean sea where bone white stones frame the beaches. It’s a place where you’ll still see ladies dressed in black, riding donkeys side saddle herding goats as though they’ve just popped off a National Geographic’s page. The smell of sage fills the air and olive trees sway in the wind.

2. Accommodation can be found right on the beach looking over the windsurfing center with most rooms having a sea view. Another ski and ski out kind of location for windsurfing where the equipment is all rigged and waiting for so you could literally stop for a coffee at their restaurant, choose your equipment for the day and head out to sea all within a stumbling distance from your bed.

3. All local markets are in the village within walking distance from the the windsurfing center and accommodation. Mopeds are great ways to get around for quick supply runs. If you’re not feeling up for the walk you can always order from the restaurant on location while the kids play in the pool.

4. Vassiliki is a heaven for lessons, kids clubs, beginner lessons and advanced lesson all waiting for you outside your front door. The instructors are like windsurfing butlers waiting to satisfy your every windsurfing need. If you are a windsurfing addict and your partner has never windsurfed before, this is the place to take them.

5. Greece is a flat water venue with winds that are light in the morning for beginners and pick up in the afternoon to satisfy the needs of high wind sailors. Great for freestyle as well.

6. Vassilike is the best place to hire a moped and check out the island of Lefkas and all the quaint villages of the area, hire mountain bikes, indulge in local greek cuisine or just take a Sea Safari with the whole family to check out the surrounding coast lines. Club Vass’s night life is epic and legendary with hilarious BBQ parties, sketches and video nights. If you’re in the mood for fine dinning with your tables set next to the lapping sea of the mediterranean or you feel like dancing down the house at the Zeus bar head to the village for a night out.

7. Shopping in the local village is fun with plenty of fine greek pottery, art, jewelry, delis and fishing stores to view. Shawna spent most of her time in the deli’s trying out varieties of feta’s, olives and sun tried tomatoes… Usually you’re so windsurfed out by the end of the day you’re ready for a large meal and bed

8. Unfortunately the transfer from the airport to your lodging takes some time, about three hours, but they do such a good job of picking you up and taking care of everything that it makes it pretty painless.

Though there are tons of other absolutely fantastic windsurfing venues surrounding the mediterranean in places like Turkey, Spain and Greece, it’s the full package in Vassilike that makes it special. Everything you need is in a short walking distance from your room…. The ocean, the pool, the restaurant, the village, the windsurfing equipment.

Again there are many amazing windsurfing destinations to hit around the world but not all of them cater to a whole family with varying personal needs. This article is about destinations that cover all the needs for non windsurfers, beginners and improvers to experts in one single spot. Shawna and Matt feel these venues best cover all the needs of a family and/or a non windsurfing partner on a windsurfing vacation but that’s not to say there are not other places to sail which touch most the points on the list. For instance Egypt is a great place to sail and Shawna absolutely adores Egypt where the hotels, windsurfing centers, great instructors and restaurants are all on the beach- it did not make the top choice for kids and safety due to political unrest. Ireland would be another choice for Shawna and her family as they don’t mind a cooler or more isolated venue but it might not appeal to everyone. Cabarete is perfect for every level. Aruba and St. Martin are options that hit all the points on the list as well except these destinations are perhaps best suited for beginners and improvers as the winds tend to be on the light side with flat waters. These islands are perfect romantic holidays with easy conditions for everyone with plenty of other things to do.

Matt spends a lot of time at Punta San Carlos in Baja, Mexico but feels this is more of a solo session type of set up. If your significant other does not windsurf, it is not the best environment to be in- no shopping, no restaurants, no toilets! Not much of anything but insane down the line wave ripping….

Matt says, “No matter where you go just remember the saying, “Happy husband, happy wife, happy life….” You can also turn that around, “happy wife, happy husband, happy life.” It works both ways so get out there and have some fun!”