Plaintiff’s Rest is aptly captained by the one and only Phillip.  A true sailor, Phillip comes from a long line of avid boaters and spent a good number of his childhood days out on the water.  An ex-marine, world traveler and seasoned explorer, Phillip’s thirst for adventure and boat savvy are sure to take us to anywhere our hearts desire and bring us back in one piece.  For Phillip, sailing will be the fun part, but his true mission, should he choose to accept it, will be to keep me onboard, upright and sober, or conscious at least.  Good luck Phillip!

First MateAnnie


Phillip’s trusty first mate is yours truly, courageous and eager but, much to Phillip’s misfortune, painfully new at this whole sailing business.  But, we are both hopeful that despite the blond locks, I will take to it and (in time, of course) be able to find true north, grab the helm, hold our course and shout orders like a true salty, sailor.  You’re right, probably not in that order.  I’m sure I will try to master the shouting first, as that is clearly the most important.  At the very least, I’m an exceptional wine-pourer and joke-teller and I’m confident the other, more important skills will follow.  Either way, it’s going to be quite the adventure, my friends.



Join us, will you?

45 thoughts on “Crew

  • Have fun, Annie. If you go to Santoini, take a shot of ouzo and give an “Opa!” for me!

    • Told to me by a Greek at a working mans eatery in Athens about drinking ouzo…”drink slow, not…” pantomimed throwing a shot back, “do that and you’ll be bingo-bongo…” said while making small circles around his ear with his index finger. 🙂

  • Annie and Phillip, my wife Debbie and I sail our Ericson “Easy” in the same places you do so I’m sure we’ll run into you guys. We are at Island Cove and have logged a little over 1000 nautical miles a year since buying her in March three years ago. Loved reading your blog and can’t believe how your dinghy made it back on its own to FWB! crazy…
    Fair Winds

    • Hi Rick. So great to hear from you, and love that you’re enjoying the blog. “Easy” sure is beautiful. And, the footage – wow. Thanks for posting – really. Did you shoot that with a GoPro? I am dire need of one (or so I keep telling myself). My blog readers deserve it! Where all have you guys cruised around here? And, what are your favorite anchorages? Would love to meet up one time for a drink. Ahhh … the tale of the unsinkable dinghy. That was really a trip. She’s actually for sale now ( if you’re interested. Ha ha. Thanks again for writing and sharing. So glad to have you following along!

      – Annie

  • We go to Little Sabine (members of PBYC), Ft McRae, Redfish, Pirates Cove, the Wharf, Ingram Bayou. I’m heading to Key West on a delivery of a 38′ Leopard Cat in a week. Are you guys at Palafox?

    • Delivery to Key West, huh? Impressive. We’re at Baylen slips (right by Palafox). We’ll have to have you guys over for sundowners soon. Would love to ask you about some passages and anchorages down there. We’re really looking forward to it (both meeting you AND the trip to the Keys — but maybe the latter just a bit more ; ).

  • Annie, I like your attitude, real seaworthy. Sadly, despite all my efforts, my first mate is still too hands off when we need to work or sail our boat. It has descended to the point that, as an incentive, I bought her flowers (argh!) on our way home from the boat yesterday. I need a backup plan. Alcohol consumption has potential, but I don’t want her falling over board. Have any suggestions?

    • I agree. Flowers?!? Ugghh. I mean, what do you do with them? Give me a bottle of rum with a bow on it instead any day. If her heart’s not in it, Andy, it’s hard to say. As you know, sailing can be a lot of work. You’ve got to love it. What else does she like to do? Read, write, paint, take pictures, sunbathe? Next time you guys go for a sail, carve out some time just for her so she can do something she loves while on the hook. If that doesn’t work, I say go for the alcohol and just tie a line to her! Good luck, and thanks for following. Cheers!

    • I hope so. Thanks for connecting. Feel free to follow along and check out the Salt of a Sailor book. Hope to share some sea stories in person someday!

  • Annie, thanks for the videos and boat tours! Of all the sailing channels I subscribe to, I rely on your channel the most because you have regular updates and great content! Keep up the great work.

    By the way, Phillip is a “Former Marine”. Once a Marine, Always a Marine. Oh yeah, and we like to capitalize the “M”.

    Fair winds and following seas to you both, and please keep posting content. You guys are a lot of fun to watch.

    • Wow, thank you Scott for the thoughtful comment. I really appreciate the kind words. The blog and videos are definitely a labor of love but one that I am committed to, so it’s very nice to hear when a follower is truly finding value in the content. That is the reason I do it. Thank you Scott. I appreciate your support. (And the tip! Capitalize the M. Got it ; )

  • Just stumbled onto the blog…what an adventure. Looking forward to digging through the archives!

  • I really have to say – ANNIE IS ONE BONKERS GIRL!
    but just in the best way – keep up the good work annie, your videos make me laugh but also dripping some tears although i am a man. THANK YOU!

    • Hey hey, a new commenter! Hello there! Why thank you Henk. So glad to hear you’re laughing and crying your eyes out. I do give it the old college try and it’s always fun to hear when folks get a kick out of the content I create. If you haven’t read any of my books yet and would like to, I’m happy to share free eCopies. Just shoot me an email at Thanks for following along!

  • I follow you on Youtube a some time ago. I really enjoy your vids, and i wish many more adventure and passion on the next time!
    Cheers from Hungary

    • Thank you Balazs! I’m glad you’re enjoying “the show.” We definitely have a lot to share. I’m sharing the Atlantic-crossing adventure on the blog now, if you like to read as well, and I’m always happy to share free eCopies of my books if you would like. Thanks for the kind words. We’ve got many adventures in store!

  • Just finished reading your second book and loved it, and now found out you have a blog. Looks like great fun! I am so jealous, now I just have to convince my wife HAHA!!! But seriously, I think you’re progressing beautifully as a writer (love the STORIES they keep it from getting dry!). I just bought your novel, looking forward to reading that too. Count me as a fan!

    • Hey hey Pocopop! Welcome and thank you! I’m so glad you enjoyed the book and THANK YOU for leaving an Amazon review. Okay, not so much on the kite-boarding next time … Gotchya! Yes, there is a TON of content on the blog and vlog (if you like to watch YouTube videos). Thank you for buying a hard copy, although I wish you would have reached out to me first. Patrons get signed copies for free! Definitely check out all of the goodies I’m giving away there and give that a thunk as well. Until then, I hope you have a LOT of time on your hands as I have written and produced a LOT of stories. Kick back and binge on the HaveWindWillTravel goodness. Thanks for coming aboard!

  • Annie and Phillip,
    I really enjoy your videos…
    I know you guys are up in Pensacola Florida and I am down in Tampa. I hope you are weathering Hermine well… West Marine has a guide on hurricane tying. Are you going to enter the St. Pete to Havana race. I am listed as Crew looking for a boat. If you guys want to take an overnight to the Tampa Bay area let me know and we will host.

    • Hey Marc! Thanks for the kind note. Glad you’re enjoying the content. Thankfully we just got some really good news about Hermine and it looks like she’ll miss us, but our thoughts are with those in the Big Bend that she unfortunately has her eye on. Re: the St. Pete to Havana race, I didn’t know they were doing one. But, we are planning to make that trip sans the race. We’re going to sail to Cuba this winter on our Niagara! Very exciting. If we’re ever in Tampa, I’ll hit you up. Thanks again for following. I’m almost finished with the 2 hour movie from our recent Atlantic-crossing. It will be free to all Patrons if you think you’d like to watch that, get on board!

  • Hi Annie, I just watched your youtube clip where you mentioned “figuring out Vimeo for your movie release”. Check out I have used them to release content for VOD streaming and download. Very simple to use and great profit sharing deal. Blessings, JN

    • Hey Jon. Thank you for this. When I started exploring options earlier this week, the cost was ranging from $10-$60/month. Silly me, I just didn’t realize it would cost me so much to offer a rentable version, so any advice helps. I’ve heard you can rent on YouTube as well which I will explore as well as this VHX option now. Really appreciate the help! Thanks for watching and reaching out. Means a lot to me.

  • Hey Annie and Phillip,

    Are you guys thinking about coming down to St. Pete for the St. Petersburg Power & Sail Boat Show, Dec. 1 to 4..

    • Hey Marc! Unfortunately we are not as we will be swamped with final Cuba prep at the time. Buuuuttt … you’re going to be one of the first to know this … we will be coming to the Miami Boat Show in February! You going to be there?

  • So when are you going to Cuba??? It has been quite a few years since we did the Miami show and we loved staying for the Lats & Atts party… (Now Cruising Outpost). They will only throw the party in St. Pete this year. We may come down there for the seminars and we will look for what boats are there.

    • And another Shhhhh … I think I’ll be speaking at the Miami show. Very exciting! So no Cruiser’s Outpost party in Miami? Maybe we need to host one on Libra Saturday night ; )

  • And Ohhhh… BTW whoever is reading this blog just found out about your Cuba trip… SSSHhhhhh…

    • I know, right?! Shhhhhh … (As if I don’t blast everything all the time anyway). SailLibra is taking a group to Cuba over New Year’s Eve. Leaving Dec. 27th, returning Jan. 9th (if you can make the entire trip) or you can fly out of Key West on Jan. 2nd. Trip details here — My followers get a $250 discount. Want to go? : D

  • Annie,
    Came across one of your videos and decided to check out your website, in the short time I have looked it over I can say “great job!”
    My wife and I are refitting a 1973 Cal35 cruiser and we have a 1985 Macgregor 25 for local gunkholing.
    You folks are an inspiration! I have quite a few blue water miles but the wife is awaiting our first outings with the Cal, she got the bug on a 24 Grampian and 26 Columbia I had.
    Looking forward to going through all content and seeing new, perhaps sometime you could assist us with constructing a blog?
    Fair winds!

    • Hey there Hari! Happy to help anytime. I love writing and creating on our blog. It’s going to take you a while to get through it, but have fun! Enjoy it all. If you like to read, click on the “Free Stuff” icon on the right and enjoy a free eCopy of my first sailing book, Salt of a Sailor. We’re about to shove off to sail across the Gulf to the Miami Boat Show (follow on Facebook for our posts via the satellite tracker if you’d like) but then I’ll be back and can answer any questions or help get you set up. Hope to meet you guys in person someday. Glad you’re enjoying the content!

  • I loved the video’s of you sailing to Cuba ! The video’s are so much better than many other video’s I have watched. So: we want more video’s of your offshore cruising adventures ! Soooooo looking forward to that !

    • Hey Karel. Thanks so much. We are really proud of the offshore videos we put together too. It was fun sharing that experience, although I recently made the decision to stop making the YouTube videos and focus more on writing as the filming and production were really starting to interfere with our enjoyment and experience. When should you stop doing something? When it’s no longer fun, right? It was a tough decision but the right one. I wrote an article about it here: But, I did put together a complete two-hour movie from our Atlantic-crossing this past year if you haven’t seen that already, it’s a lot of fun. Enjoy >>

  • Just watched your cuban voyage , loved the voyage , especially the dolphins ,, Now do we sell our cuddy and speedboat and start sailing ? Yes you gave us a lot to think about over the winter ,,,

    • Hey Annie and Phillip,

      How are you guys and have not seen any videos in a while, as you know I am still down in Tampa and if you want to drop by I am a member of TSS in Apollo Beach. So we can workout an affordable place to stay.

      I understand how much work goes into video making and Annie you make it so much fun.

      So looking forward to hearing from you guys.



      Marc Holtzberg
      Sr. Engineering Technical Writer

      • Hi Marc! Thanks for reaching out. We’ve been very busy with the Atlantic-crossing. Another ocean voyage behind us, what a feat! I will definitely put together a video from that, but (you’re right) it may take a while. We have to focus on clients right now and paying work first to get caught back up. But, what an amazing life to live where we can take away from work for a voyage like that. We feel very lucky and blessed to have nice balance in our lives.

        But, I do have another Shipyard video coming out very soon. It’s about our propulsion system, replacing our cutless bearing and coupling and dealing with some rot in our engine stringers. B.O.A.T. … am I right? So be on the lookout for that.

        We appreciate you writing and checking in. We’ll be in Pensacola the next few months getting caught back up on work then we plan to sail our boat down to Grenada this coming season to keep her safe during hurricane season. If Tampa fits in those crosshairs, you are definitely high up on our list. Thanks again. Hope you had a great holiday! Happy 2019!

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