9 Reasons Everyone Should Sail With A Dog

During the long wait to buy our new sailboat, I’ve had plenty of time to say to myself, “MY DOG. AM I CRAZY TO WANT TO LIVE ON A SMALL BOAT WITH A BIG DOG?”

Yes, yes I am crazy.

But I’ve also thought of a few reasons everyone should sail with a dog.

Honey the golden retriever wades in the marsh at Janes Island State Park.

Well for one thing the places I want to go are too far to walk. You want me to swim to Bimini?

Sail With A Dog? Heck Yeah!

By the time I’m finished with my list, America’s Cup captains will be visiting shelters, looking for the perfect sailing dog.


1. A sailor has to know which direction the wind is blowing, right? With light golden hairs flying off Honey at all times, it’s obvious. Just look to see where the fur is blowing.

2. One of the toughest problems on a tiny boat is getting rid of trash. In fact, I should probably trade Honey in for an eat-anything Labrador.

Or get a goat.

3. Boat insurance companies are kinda fussy about hurricanes. They won’t allow insured boats to travel south through hurricane alley until after October.

I don’t know about you. But if the only thing between me and freezing cold water is a thin wall of fiberglass, I want a dog to cuddle.

Honey the golden retriever chews a stick.

There will be sticks on the boat, right?

4. A dog fits much better in a boat cabin than a pet elephant.

Just saying.

5. If a $100 winch handle goes flying out of the cockpit, I want a water dog standing by with an insane desire to retrieve stuff.

6. Because having to dinghy the dog to shore twice a day for potty and exercise breaks will keep us from becoming lazy lushes like so many other cruising sailors.

(Sorry, but I do worry that I don’t drink enough to be a cruising sailor. The ability to hold liquor is more valued in some sailing circles than the skill of approaching a dock in opposing wind between two mega yachts without nicking gel coat.)

7. In a hurry, when all cleats are taken, I want the ability to stick a line under a dog butt and know it will stay put.

8. In a buggy anchorage, I’d like to think every mosquito isn’t feasting only on me.

Sorry Honey. But I can’t afford to be the only one feeding the little bloodsuckers.

Honey's bear is in a bucket.

Don’t think hiding in a bucket will save you from mosquitoes, Bear.

9. And the best reason anyone could have for sailing with a dog?

When everyone else thinks you’re crazy for selling your house and living in a tiny vessel with almost no money, it’s nice to have someone by your side who is up for absolutely anything and never makes fun of your choices.

Honey and Pam on beach

Awww, shucks.


Sailboat Update

For everyone who waiting for cute pictures of Honey on tropical beaches, this has been a long process.

We’re currently waiting for the owners of our boat to make repairs so we can take over and move aboard.

Y’know, having water come aboard through the hole where the rudder attachment passes through the boat is not a good thing. We should probably have that fixed before we go anywhere.

Hopefully we’ll moving aboard in a couple more weeks.

And if you want to virtually join our adventure, don’t miss out. You have only one more day to win your dog his or her very own Kurgo Surf ‘n Turf life jacket. 

After all, every adventure starts somewhere.

Your Turn: Crazy to live on a small boat with a large dog? Or really crazy to live on a small boat with a dog? Or would you do it too if you had a chance?


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  1. Those are all valid reasons, but I’ll stick to the RV. I’m so excited for you guys, it’s all finally coming together!

  2. I could never be a crime fighting FBI agent, or a medical examiner doing autopsies, or a fearless private eye, but I love reading about them on lazy summer days and long winter nights. I will add fearless sailors with a large dog to my Walter Mitty fantasies.

  3. We’re so glad everything is coming together for you. Just because I wouldn’t do what you’re doing, despite the fact I love sailing, doesn’t mean you should be any less enthusiastic about your dream coming true. Who cares what I, and other doubters may think? Live your dream.

  4. I would never say crazy….brave, adventurous, but no, not crazy. Besides, you can stop and get on dry land pretty much whenever you feel the need. You are not crossing the Atlantic….or are you? That might be crazy 😉

    I never thought about boat insurance restricting your movements in hurricane season….so you will be staying in the MD waters until November?

    • Mike Webster says:

      From the Husband:

      Since there’s so much we have yet to learn about sailing, I’ve suggested to my wife that we might not leave the Chesapeake Bay until 2017. (That could still take us out of MD waters since the bay’s southern end is in VA.)

      But given Pam’s eagerness to see and feel the warm blue waters of the Caribbean, I can’t afford to be too dogmatic about this. Otherwise, I might wake up one morning to find that she’s hitchhiked to Bimini.

  5. I can relate – do what you love with whom you love, regardless of the fur and the tail…

  6. So how far south can you go during hurricane season? Never knew about that but I’m not a sailor (get too seasick). I am sorry about your elephant not being able to go but I live in the south and still cuddle my warm pups. Hope you have the best time Pam!

    • Hi Becky,

      During hurricane season, most sailors either stay north of the Carolinas or south toward Grenada, Panama, or Venezuela. That keeps you out of the worst of the hurricane zone.

      Of course, this is weather we’re talking about. So nothing is ever certain. :)

  7. I am sooooo jealous… You are totally living our retirement dream! <3
    I love sailing and miss racing. I definitely love the idea of selling everything for a boat with a dog on it. Maybe you can sail up to the oregon coast sometime and we could meet you and take you out for lunch! We'd love to see your boat, meet Honey, and of course have a toast to your fun adventures!

    • Mike Webster says:

      From the Husband:

      Oregon, here we come! A few thousand miles south to Panama, turn right; through the canal, turn right again. . . but, boy, do I like lunch!

      (Of course, you could suggest that we stop being so wimpy, and take the hard way around Cape Horn instead. But then I would have to insist on dinner.)

  8. Had to read because I’ve sailed with a dog before. And I have a feeling I commented about it before. It was a scary experience for me! Small sailboat, 75 pound 11 year old girl, windy day, Shetland Sheepdog = flipped boat lol. You must be very excited though! I’m sure there are tons of adventures waiting for you and Honey.

  9. I bet your getting those funny feelings in your tummy…nervous excitement and fear combined. Reality is about to become real! We hope it all works out as you all want it to.

  10. Those are some great plus points for having a dog.

    P.S. I can’t get any sense out of my biped at present – she’s still laughing because she doesn’t think Honey is big!

  11. Sailing with a dog sounds like an amazing adventure. We can’t wait to hear your tales, but we’re pretty happy right where we are.

  12. During our RV trial overnight I admit I was appreciative of Zoe’s attraction to most of the mosquitoes (I justify this selfish thought by doubting the biters could made through the fur to her blood supply.)

    Congrats on the boat! You’ll be in it in no time. Maybe we’ll happen to drive by a harbor where you’re anchored one day so we can offer to take you’ll to dry land for the dogs to romp.

  13. The best reason of all is the unconditional love and acceptance!!