New Crew & Season - S6:01
Welcome new crewmember Aly! IG @harborHotness
we also get a brand new dinghy from Highfield. It really is a beast!
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  • Dale Fearnley
    Dale Fearnley

    Be wonderful if you could connect it to your charging system to keep that battery topped off and ready for use.

  • GetErDone

    nothing like a new toy to make a guy smile.

  • james sutton
    james sutton

    Bobby , goggle permatrim for the outboard ....well worth it .

  • Proper Pythons
    Proper Pythons

    That dinghy costs more than some sailboats!! NOOOOOT a big deal. :)

  • Ian Gibson
    Ian Gibson

    the USS nonce daddy takes me downstairs

  • Menta Rilang
    Menta Rilang

    How too i order keeps bud

  • Jet Taca
    Jet Taca

    Racing sailor, Yep😅 Cheers to harbour hotness😂

  • road glider
    road glider


  • The Punisher
    The Punisher

    Where do you get such companions

  • K Brickell
    K Brickell

    That is an inflatable boat or tender and dinghy has 1 sail

  • Dawn Marlin’s Sugar Shack
    Dawn Marlin’s Sugar Shack

    Quit playing with your dinghy!

  • Mercury Rising
    Mercury Rising

    Okay, can someone please explain to me what I am watching? Are these people swingers?

  • Lolindir Surion
    Lolindir Surion

    Taylor lead me here. Nice channel, so a new sub :)

  • Richard Taylor
    Richard Taylor

    Ha Ha! Bobby is excited about his new dinghy? The rest of us are excited about Aly, what a BABE! And Megan returning too? This season is going to be unmissable!

  • Bryon Ensminger
    Bryon Ensminger

    I would bet you could wake board behind that little dingy

  • Bryon Ensminger
    Bryon Ensminger

    Dont sweat the break in period if your gonna break it do it when it's still under warranty 🚤🤣🤣🤣😂

  • okeanos467

    After having Highfield 310 dinghy for bit over a year i wouldn't buy another. doesn't age so well as Caribe. handles were stripped in few months. velcro "holding" paddles was not holding since very beginning. it's powder coated. but paint starting to flake. and it's kinda expensive too. so for my next we're going to test cheaper, bigger, roll up pvc dinghy cover it with chaps and see how it goes in the tropics.

  • DavesWorld

    Wow! Aly is one of the hottest women ever and seems like a real pro about sailing.

  • Ontario Andrews
    Ontario Andrews

    No disrespect to Aly, but .....starting off slowly and then building momentum .....Taylor, Taylor, Taylor, TAylor, TAylor, TAYLOR, TAYLOR, TAYLOR .......!!!!!!!!!! :)

  • Me Now
    Me Now

    She does "racing" around the world? Well, that is pretty vague.

  • Handsome Dan Bodamer
    Handsome Dan Bodamer

    About time, Now that’s what I call “crew”, smart, beautiful, expert sailor and did I say smart, the best of both worlds.

  • Horton Farms
    Horton Farms

    I'm from Annapolis. Brings back great memories. Have fun and stay safe.

  • Villo Devillain
    Villo Devillain

    You cheeky bastard 😂 i guess I will do the same having different woman sailing around american/world with ..

  • Philip Wilson
    Philip Wilson

    Another thought on the dingy winch.. I told you about what Rick Moore SSL did for his davit winch. Then I realize I have on my wildcat sport side by side a wren winch that would be perfect for your use. The cost was $350. It’s a 3000 pound pull with dineama rope. It’s very small and you can get a wireless remote for it.. check it out it will save you a ton of work..

  • Jessica Crawford
    Jessica Crawford

    I'm going to take a guess that the majority of his followers are men so he needs to make sure there is "eye candy"...

  • luvanotafighta

    I wonder what Bobby’s crew adverts are like..... Hot babe wanted for sailing and Vlog appearances, must have a good rack and be willing to pose in a bikini or skimpy outfit for click bait thumbnails?

  • David Hageage
    David Hageage

    Is there an alternator, or do u have to charge the battery. A small solar would rock

  • David Hageage
    David Hageage

    Where have I seen Ally from, another sailing show? She looks familiar. Anyways, nice picks for crew, thank you, you rock buddy

  • Mfanawemkosi Fakudze
    Mfanawemkosi Fakudze

    Welcome aboard Aly. Maybe you can teach Bobby a few sailing tricks from the racing world. People may forget that when he started Sailing Doodles he was a newbie. He's done well but I am sure there is still room teach an old dog new tricks.

  • Navigating El
    Navigating El

    Bobby does the best gear rundowns online. Should be his SELLING POINT. Does he get free sailing merch from companies and all that?

  • Mark Girven
    Mark Girven

    With all your experience in boats I am amazed that you haven’t got a kill chord attached whilst driving the highfield.

  • قناة خالد بن سفران الغامدي
    قناة خالد بن سفران الغامدي

    Beware, this type of boat needs a seat belt, because it has high speeds and you may hit a wave that makes you fly off the boat. 😁🌹

    • Mark Girven
      Mark Girven

      Kill chord

  • David Hardesty
    David Hardesty

    She races and knows what trim tabs are for. Oh yeah! You won the crew lotto for this cruise.

  • Mark Crawford
    Mark Crawford

    Bobby! Please wear a real mask- a neck gaiter doesn't protect you or others well enough!

  • 1william B
    1william B

    Well much was it dude

  • WR ZL1
    WR ZL1

    Aluminum definitely has its pros but it has two very bad cons 1 if it’s a riveted hull it will leak eventually 2 salt water rapidly corrodes aluminum so don’t ever beach that dingy OR anode that hull ( salt water prep it).

  • Michael DeNicola
    Michael DeNicola

    Good luck with the new toy I can tell you they are worth the money. lI love mine. and Congratulations on a new crew member. Thanks for sharing and safe sailing

  • DJ

    I've lived within an hour from Annapolis all my life and I've never been able to explore what it has to offer. I'd love to learn sailing and do this. Bobby is living the dream. And I'm looking forward to getting to know Aly in future adventures on this channel.

  • wuthering1234

    Dinghy for sale, properly broken in.

  • Chingy not dead
    Chingy not dead

    how did i get here. bad luck for man to need a dingee - medical mirical - couldn't watch

  • Slcm02

    Bobby you are the best. A hot blonde chewing gum and sails. Get her into the uniform of the day. Thong bikini I hope. Be safe

  • Island Life Of BQ
    Island Life Of BQ

    Where do these women come from? Why do they bunk with this Gerbil looking dude? Lol. How does this work? Do these women just want more Instagram followers??

  • Steph Liveright
    Steph Liveright

    Tell your guests to TAKE OFF THE MASKS. No one watching this is going to catch anything through the internet... Mask hysteria has gone nuts in this country.

  • Snarkapotamus

    The boy has a type -- doesn't he...

  • daveamtwo

    Question. When you put a add out for new BOAT HO'S, is one of the Requirements >> Must have BIG FLOATAION DEVICE"S ??????

  • irgski

    I can tell that girl likes to go fast!

  • Keith Conville
    Keith Conville

    I know it doesn't make for good video, but watching you drive the dinghys around with no kill switch attached or at least a hydrostatic low profile life preserver on makes me nervous for you guys, especially when you stand up. The odds of mishap may be slim, but it only takes one running those speeds to end badly for you or the crew. I know I'm being that guy, but I enjoy the channel too much to see it end with something that could have been prevented.

  • Lucky Travel Team
    Lucky Travel Team

    hahaha great video

  • laxmannate07

    Is this a weird sex cult thing?

  • Ashton Pierre
    Ashton Pierre

    Nice Dingy! I’d like to buy a shirt with your logo on the back and a pocket on the front left side if you got em!

  • Chad

    "Crew member", huh? Thats what they are calling them these days?

  • Jon Morrison
    Jon Morrison


  • Rob Banks
    Rob Banks

    your dingy is nicer than your sailing boat.

  • Robert Maheu
    Robert Maheu

    and the porn starts later?

  • Chris Maxwell
    Chris Maxwell

    Have you slept with her yet?

  • Sudz

    New? or... Megan! Wooo!

  • Fred Kaminski
    Fred Kaminski

    Looks like the dingy is a little small.

  • S Mash
    S Mash

    New Meat

  • Bert Kelly
    Bert Kelly

    They say to break it in like you stole it, : )

  • Jason H
    Jason H

    Wow. Great content. Sounds like Taylor is your meal ticket.

    • Harpoon_Bakery

      Taylor is gone

  • Rick Bourne
    Rick Bourne

    how many hph did it go?

  • joel stevens
    joel stevens

    Looks looks like the new dinghy is doing it's level best to flinghy your ass out of it!!!

    • Mark Girven
      Mark Girven

      That’s why he should be wearing a kill chord, to kill the engine if he gets thrown out.

  • blinddogroofer

    The Music at 7:01. Catchy, I probably missed it in the credits someplace. Who/what is it?

  • Jimmie USAF-POL
    Jimmie USAF-POL

    These comments/questions are totally rhetorical..."yes, you too"!lol Does no one else realize this is an online entertainment business, that thrives from funds directly related to content, and Bobby understands this very, very well? :o) And, these are real people, who have families that possibly read through the comments, it is not always fun and games, and none of these beautiful and intelligent ladies have ever come to the boat screaming and kicking? Work hard/smart, play hard/smart...learn it, live it, and love it! :o) Taylor has such a sweet heart...and her own channel now...check it out! Tears are raindrops from our emotional clouds, when our clouds are to full to hold back overwhelming emotion! :o)

    • Jimmie USAF-POL
      Jimmie USAF-POL

      Amnata Pundit , very interesting view point, and I'd say sure point the con out if there is one, though I don't believe there is a con going on and the ladies know exactly what is going on, before they ever get on "this" boat. My comment was to those who assume Bobby and ALL the ladies automatically hook up...which I don't think always happens, since it is and always has been 100% up to females for that to happen, unless a pig dog decides to try/take something not veritably being offered. I re-watched the video since I was here, and have to agree with many, Aly is very attractive and will/should be entertaining to watch this season. :o)

    • Amnata Pundit
      Amnata Pundit

      Jimmy USAF Pol, youre right, but do you believe that those who can see the con have no right to point it out? Absence of kicking and screaming is not absence of con..

  • Dr. Hook
    Dr. Hook

    Bobby changes women more often then he changes his socks.

    • Harpoon_Bakery

      Austin Powers - man of mystery

  • Patrick

    How long will it take until only 1 stateroom being used?

  • Pistol Pete
    Pistol Pete

    So how long will this lady stay, before she dumps you.

    • fastdude2002

      Pistol Pee I doubt he worries about her dumping him, he is always getting a fresh face to sail with.

  • Les Bentley
    Les Bentley

    Nice dingy Mr Bobby. I followed Miss Harborhotness for a while and was surprised and happy she's the new deck hand. She's a legit sailor.

  • Anthony T.
    Anthony T.

    So after seeing only two videos, its pretty easy to gather that an average looking dude gets a sail and uses it to lure in chicks to smash under the guise of "traveling" the world. Welp, cant hate the player..

  • Amphictyon1

    Amazing how one ugly guy goes through so many hot, beautiful women. No accounting for stupidity, I suppose; the blonde jokes must be true!

  • Skip Rope
    Skip Rope

    Hugh Heff is da man. Way to go Bobby! Your new shipmate is named Dingy? Now that is funny. So do tell us. Where do you hold these castings for the shipmates? In the starboard quarters or on top deck? Regardless you provide much entertainment and education on sailing. For that I thank you. Good Ruck man be safe. Same to your new shipmate!

  • Luc Armyfool
    Luc Armyfool

    These white sunglasses, soooo gay !!!

  • Light Mechanic
    Light Mechanic

    I own a Highfield. Got a whale tail on the motor. Boat is a bit squirrely without it. Fixes stability and excessive bow rise. Hi Allie!

  • Mera bharat Mahan
    Mera bharat Mahan

    no new women crew

  • James Tanner
    James Tanner

    Looks like he is going to ride that dinghy hard.

  • Dartmoor Dave
    Dartmoor Dave

    At least with the new tender, Bobby, you could tow the yacht to a mooring in calm seas.

  • Jim Bendtsen
    Jim Bendtsen

    You got a haircut and shaved the beard. Looks better.

  • my surly trucker
    my surly trucker

    Thats a really nice dinghy, when am in the market thats the type I will get for sure .

  • Lisa Fike
    Lisa Fike

    What's with the fuckin masks?

  • Lucky C
    Lucky C


  • Stephen Hunt
    Stephen Hunt

    Wondering can you trade in the old dingy? Nice ride! 👍

  • Tony Kurzendoerfer
    Tony Kurzendoerfer

    Wow, she said, needs trim tabs! I'm impressed already! That has to be why Bobby invited her to travel with him. She is so knowledgeable!

  • hadd13

    Screw the Dingy show the Hottie

  • Archimedes

    Bobby, you are a man of taste. Your new guest is a beauty!

  • Robert Lee
    Robert Lee

    That motor is sooooo heavy. That’s not a dinghy. It’s a damned speed boat! You’ll never drive it as fast as it can go because the bottom isn’t designed for it. I think you’ll regret it.

  • Dominic

    Grow your beard back so you don't look so damn creepy

  • johny z
    johny z

    and today, bobby shows us his upgrades!

  • Timothy a
    Timothy a

    I cant believe you videoed her chewing gum. Not becoming.

  • david kettell
    david kettell

    yummy i can see a lot of bikini makers checking out your channel now.

  • Anthony Siegel
    Anthony Siegel

    Wow dude, sailing and hot women,champagne.. what a live..

  • Vicki White
    Vicki White

    Ali is not only gorgeous, she speaks "sailboat!!"

  • Solocanoe

    Huh. She's not my cup of tea build wise...I like lean, but hey, I'll check back next year.

  • Greg

    Something tells me that boat will be rocking quite a bit this sailing season.

  • Bernard Huther
    Bernard Huther

    You new help woumen

  • killerrush77

    so, some random girl sales around the world with you, on your boat? is this not strange? or just me.

    • Harpoon_Bakery

      I don't think they are that random. Carefully chosen more like it. I mean, you have to live with them on board a vessel.

  • Robbie Surfer
    Robbie Surfer

    I like Highfield so much but the smaller ones are so unbalanced, why drive set up so far at the back, I’ve had ribs from 4m to 655 and it’s pretty obvious where you need to drive them from, no idea why it was set up so badly

  • Nate M
    Nate M

    I freakin love the smug face as you ride away in the beast of a dinghy lol

  • Michael Dougherty
    Michael Dougherty

    Looking forward to another season, Bobby. Great to see you got a haircut and got rid of the beard. Now, about those sunglasses...

  • Lando Leaves Land
    Lando Leaves Land

    Man I NEED a highfield. Great vid Bobby

  • Leo D
    Leo D

    Another beauty crew member.