The most luggage I’ve flown with on my own was: 1 surfboard bag (Nacra 17 rudders), 1 mainsail roll (2 Nacra 17 mains together), 3 additional checked bags, and my carry on backpack. For reference, I’ve flown with bags like these without a problem:
American Airlines: Oneworld alliance
I can usually convince the staff at the baggage counter that I have Windsurfing Equipment which falls under the category of Sporting Equipment.
Fee of $150.
2 pieces of windsurfing equipment count as one bag. This means you can pack 2 oversize bags and only pay one fee. Each bag still receives its own bag tag. This is unique to only American Airlines.
Overweight charges apply for bags heavier than 70lbs. Airlines will not usually accept bags above 100lbs.
Bags must still be less than 126in (length + width + height).
Below is a direct quote from the American Airlines website (Jan 2020) outlining their policy of windsurfing equipment:
Allowance and requirements:
Any 2 of the following windsurf equipment will count as 1 checked item:
1 board
1 mast
a boom and sail
Cost
Delta Airlines: SkyTeam alliance
Delta is special in that sporting equipment can be counted in your standard baggage allowance. To date, I have only flown with Nacra 17 sails as Windsurfing Equipment on this airline and have not yet tried to pass a board bag in this category.
United Airlines: star alliance
This is my least favorite airline to fly with oversize sailing equipment. They enforce oversize and overweight fees which begin at a low threshold. Even when checking gear as Windsurfing Equipment or in another sporting equipment category the following fees apply:
Overweight charges apply for bags heavier than 50lbs. A second overweight charge applies for bags over 70lbs. Airlines will not usually accept bags above 100lbs.
Oversize charges apply for bags larger than 63in (length + width + height). Bags must still be less than 115in.
Sporting equipment bags may be charged an additional $150
For flying with Nacra 17 rudders and foils I have used the Dakine Club Wagon and the Surfboard Coffin bag. I have always passed my bags under the Windsurfing Equipment category, but others may be better suited for your gear.
If you have any questions about my experience flying with oversize sailing gear feel free to contact me at rparentsail@gmail.com.
International Airlines
Qantas: oneworld alliance
Partner with American Airlines with similar bag policies. Their excess baggage charge is typically greater than their overweight charge, so strategy here is to pack bags heavy (up to 70lbs), pay that fee, and avoid the extra bag charges. Check bag fees for your specific flight route to confirm.