But I would decide spontaneously and look at forecasts then book a flight.
Also check Cartagena, Colombia, since it might have good winds and it a beautiful city, you lady would like it. Direct flights from Miami available.
I'm considering visiting Colombia in July, is that good time for wind around Cartagena ? how safe is it to travel in rental car to kite beaches
In wouldn't worry about safety. I never did, always felt safe.
July is not good for wind in Cartagena. You have to go all the way east to the Cabo for wind. But July is great for winds in San Andres Island! Most beautiful spot I have seen so far...great flat water! Belongs to Colombia bits sits 800km off the coast to the North from Colombia. Direct flights from Canada, Bogota, Cartagena.
I've had some great sessions at Bahia Honda. You have to pay a few bucks to get in to the State Park, but it's worth it. After you enter, you're at the eastern end of the "old" beach. The "new" beach is further (north)east and is better for kiting.
Local Beach: Naish Beach - Kanaha - Maui, HI USA Teach Beach - Kanaha - Maui, HI USA
Favorite Beaches: _ Crandon - Key Biscayne, FL Sherman Island - Antioch, CA Crissy Field - San Francisco, CA Kanaha - Maui, HI Anne's Beach - Islamorada, FL Curry Hammocks - Marathon, FL Kite Beach - Cabarete, Dominican Republic Tableview - Cape Town, South Africa Main Beach - Langebaan, South Africa Mui Ne Bay - Ham Tien, Vietnam
If you choose Aruba, look at Surinam Airways. THey only hit me for $300 round trip from Miami, offer two pieces of luggage included plus carry on, and did not charge extra for my kiteboard.
Be aware they only cover $500 for lost luggage though and they do NOT sell Excess Value coverage. I took my kite in a backpack as my carry on and used a credit card that offered $3,000 lost luggage insurance as secondary insurance.