In Search of the Best Sailing Hat Ever

, In Search of the Best Sailing Hat Ever
, In Search of the Best Sailing Hat Ever
Actually, my crew here is searching for an offshore spring. They already have the good hats!

My love affair with straw hats began one summer in the 70’s when I found the first best sailing hat ever. We were cruising the Bahamas on my parents’ 30 foot Pearson sloop, “Albatross.”

My First Hat Purchase

One of our first stops was Nassau, and I had already planned what to do with my $.50 a week allowance money that I had saved. I had been planning for months to buy a big straw hat. I was about ten years old.

, In Search of the Best Sailing Hat Ever
That’s not me – that’s Dave – with the second best hat ever!

A huge hat was not something tourists liked to wear in the islands. This was in the 70s, when everyone else was eagerly seeking that Coppertone tan. Visitors wanted to be tanned and glowing from the sun. But not me.

My parents laughed, but I held firm, wearing my huge hat everywhere. I spent the summer under the Bimini, under the dodger, and under my enormous straw hat. On a dinghy ride away from the protection of the canvas overhead, I had my own umbrella-sized portable shade. After three months in the Bahamas, I returned to the states looking like I had spent the summer in Maine.

, In Search of the Best Sailing Hat Ever
Visor, straw hat, canvas hat all represented on board “Stimulus.”

Lily-White Skin!

I’d also read “Gone With the Wind,” so there was that influence too. People asked if I had been ill all summer! Now I realize now I was the healthiest vacationer of all.

The funny thing is, after about a month of me dragging this enormous hat around, my parents realized what a “cool” hat I had found. We swung back by Nassau, and they found their own straw hats.

, In Search of the Best Sailing Hat Ever
Our early Bahamian straw market hats looked like this, but with a shorter crown and a wider brim. The construction was completed on site.

Annual Trips to the Nassau Straw Market

And thus began a lifetime of really great Bahamian straw hats. We annually sought out the perfect hat in the straw market in Nassau and braided head bands from cordage.

The brim hat to be rather wide, but not so wide that it was a sail in the wind. The crown rise angle had to exact – not stovepipe, not funnel-shaped. The hat could not be too tall, and definitely no embellishments were acceptable. Also, there could not be too much height in the crown.

We wore these hats for years and years; we wore them out! It was a big event to return to the Nassau straw market and seek out a replacement every five or ten years.

, In Search of the Best Sailing Hat Ever

Next Phase: Canvas Surfer Hats

Always looking to stay out of the sun, I then went through a phase of wearing canvas surfer hats while I was first teaching at the sailing school.

I needed to stay out of the sun, but I also needed a hat with a smaller brim to navigate around shrouds, and not pick up so much wind and blow off my head. Working on smaller daysailors, my Bahamian hat brims were just a couple inches too wide.

To the local surf shop I went, and the next several years, I sported a couple canvas hats. One was khaki, one was light blue, and I rather liked the surfer emblem. I felt pretty darn salty!

These canvas hats also held up well in the rain. They became sun bleached fairly quickly, and combined with perspiration and my ever– present sunscreen; they broke in quickly.

After about 10 years of wearing these “surfer hats,” our company introduced a new line of breathable khaki ball caps, and I wore those for the next 10 years.

Then Came Tennis Visors

After that, in order to look a bit more trendy, I realized that with absolutely no hair showing, I could be mistaken for a boy. About that time, we all started wearing visors, with the added benefit of my hair getting nicely blonde.

, In Search of the Best Sailing Hat Ever

When I was a youngster in those days of cruising the Bahamas every summer, I was so fair, my hair was almost white. One time, a Bahamian lady latched onto me and did not want to let go, because she wanted to touch my nearly white hair!

, In Search of the Best Sailing Hat Ever
Stream2Sea reef-safe sunscreen also comes in a tinted variety. Mineral-based is best for you.

Yes! I Wear Sunscreen Too!

Even while wearing a hat, I always wear sunscreen on the boat. The sunlight reflects up from the water – just like it does from the snow when you are skiing. So, being under cover of a hat and canvas shade is good, but not enough to protect you from the sun’s rays.

Stream2Sea has reef-safe sunscreen, so that’s the best choice to have on the boat where whatever touches the boat washes off into the water. You can read all about the effects and concerns with toxic sunscreens here, at Stream2Sea. I’ll leave the link again and a discount code for you at the end.

A diving friend of mine gave me this tube of sunscreen, after yanking a tube of sunscreen unsafe for reefs out of my hands before a dive at Blue Heron Bridge in Jupiter, Florida. I have to thank her a dozen times.

Due to her giving me that first tube, I have since become a brand ambassador for Stream2Sea because I believe in their brand’s goals for the environment. That’s how much I believe in their mission and product.

No Geezer Hats, Please!

My father works as a sailing captain as well. He captains a traditional sailing vessel, in Maine in the summers. He’s fairly conscious of the way a hat looks, and anything that looks like a “geezer hat” is shunned.

About six months ago in my sailing class, a student named Dave came along what the absolute best hat EVER. It combined all the coolness of a straw hat, the rigidity of my surfer canvas hats, and the shape was absolutely flattering, perfect, and nowhere near geezer status.

, In Search of the Best Sailing Hat Ever
Sailing school student Dave, with the best hat EVER.
Plus a UPF (ultraviolet protection factor) shirt.

Dave lost this hat during class. It blew off his head during sailing maneuvers in the Tolomato River. It was blowing and drifting toward shallow water where we could not follow to rescue it. His wife Debbie said she would re-order one as soon as they got home; that’s how much he loves the hat. It would arrive in two days, and that’s how I learned they are offered on Amazon. (link below) Hooray!

And that was really great news because Father’s Day was approaching. For a really great Fathers Day gift, I needed useful gifts for the men in my life. I did not have time to sail to the Bahamas. So, I ordered one for my dad and one for my boyfriend and received them in a couple days. My dad promptly removed the embellishment, of course!

, In Search of the Best Sailing Hat Ever

This week, I noticed an Instagram photo of Jimmy Buffet wearing the exact same hat. I guess he must have seen how awesome Dave looked in his! I notice he didn’t remove the advertising logo.

, In Search of the Best Sailing Hat Ever

I will tell you, I did have to exchange both hats I initially ordered – they run a bit large. When you see the hat, you will be surprised at the quality and construction. They rival hats four and five times as expensive from terribly famous makers.

Here’s a link to the average men’s hats I ordered: Volcom Men’s Quarter Straw Hat in Small/Medium  Or, here’s the same hat, but the first ones that were far too large. It’s called: Quiksilver Men’s Pierside Straw Hat in Large/XL.

The hats are exactly, exactly the same even though they sport two different surfer brand logos. For some reason, some varieties come in some sizes, others in others, but they truly are all exactly the same except for the size and having a different patch sewn onto them.

Since Father’s Day, I’ve become an Amazon Affiliate – that means when you click on my links, the price to you is the same, but I might receive a very small percentage of the sale. This helps me afford to keep bringing you this fun content. I paid – and still pay – full price for anything I order from Amazon.

American Academy of Dermatology Association Comments on FDA Proposed Sunscreen Rule

February 21, 2019, the AADA released a statement including the statistic that skin cancer is the most common cancer in the United States. Yowza.

“Unprotected exposure to the sun’s ultraviolet rays is a major risk factor for skin cancer. The AADA recommends a comprehensive sun protection plan that includes seeking shade; wearing protective clothing, including a lightweight, long-sleeved shirt, pants, a wide-brimmed hat and sunglasses; and generously applying a broad-spectrum, water-resistant sunscreen with an SPF of 30 or higher to exposed skin,” they wrote.

Their commitment to human-safe sunscreen is clear; “Because sunscreen is an important tool in the fight against skin cancer, the AADA supports any and all regulations to ensure that the public has access to safe and effective sunscreens. We are encouraged that the U.S. Food & Drug Administration is taking this action on the Sunscreen Innovation Act, and we look forward to working with the FDA as it develops and finalizes the proposed rule.”

Stream2Sea Reef- and Human-Safe Sunscreen

Here’s the link to that eco-friendly Stream2Sea sunscreen. It comes in spf 20 and 30, and I can’t say enough about the company, their commitment to reducing our damage to coral reefs, and the quality of their products.

Stream2Sea Sunscreen is the link, and please use my discount code “KimW” at checkout to save yourself 10%. Using my link does not increase your price. You actually get a discount, and I receive a small portion of the sale. This allows me to buy more sunscreen for myself and my sailing crew! Thank you for your support! I really appreciate it!

What to read next: Learn why your cheap gear really costs you more in the long run: Vanderkitten Cycling Kits – Cost Per Wear – Review

Thanks for reading, and if you have any great hat stories – leave your comments below! I’d love to hear from you!


  • Kimberly May 14, 2020 at 8:22 pm

    Well… every photo actually is on a 36′ Hunter sailboat… Yes, you need something a lot stiffer for wearing on a motorboat with all that apparent wind. Thus, best “sailing” hat ever… Rated up to 8 knots! : )

  • logisch_dede May 7, 2020 at 6:01 am

    talking about sailboats and showing only motor boats in the first half of the article?
    motor boats have a pretty different need for hats: much of winds, up to some 30 mph.
    by the way – your favourite has failed the wind test – perfectly! 😉

Leave a Comment

WP2Social Auto Publish Powered By :
Application-Confirmation 1.0 Verify-File 013e980104dec2d39acba78865f09e1e316adccd