Congrats on the first step...many more to go! Enjoy the journey with you....glad to see Bobby is ok! Man what a scare!

Its great to see someone actually give a damn about Bobby!!! Major credibility for that and for starting your trip, and buying what seems like a really nice boat. Fair winds.

You have done a great job on your boat. You should be proud for what you have accomplished. Nice to see Bobby come up again to join you on your maiden voyage. Can’t wait to see more of your sailing adventure as you head south to warmer waters. 🇨🇦👍

Nice to see Bobby there with you. Stay safe. Have fun.

Happy to see Bobby is good, and that you are ready to sail, Good luck in you travels

All the best !! You are fortunate to have a good friend like Bobby.

Nice shakedown cruise. Nice to see Bobby with you and okay after his crisis.

Its awesome that Bobby came up to help out and I hope naughty Dogs is back up soon

Good for you Taylor! Bobby is a good friend to help on your first sail. Happy you found your boat and are heading to warmer climates.

Congratulations Taylor, and I’m proud of your bravery. 👍🏾❤️

Taylor congrats on the new boat. I saw where you put in a mechanical pressure switch for the oil pressure. Good idea! Hopefully Bobby can help you find the electrical pressure switch and make that repair so that you have indication in the cockpit. Our prayers also go out to Bobby.

Lets be thankful Bobby is alright 👍 and you stay safe

Congrats on the boat! Looking forward to following you both on your adventure! Also, nice edit/shots at 4:00.

Wow Taylor, you made it all real life with Bobby's issues. Real tears and concern for your friend. Love your vlog, stay safe, God speed, enjoy your life on the waters, most importantly come home to us . Enjoy your adventures!! You are a beautiful young lady! Your mom and dad are so very proud! 💕

Sea Gypsy! Looks like a great boat! Nice upgrade. Fair winds! Bobby will recover.

Loving your vlogs Taylor. Glad Bobbies there for you.The timing of his boat taking a crap seems to be a blessing for you. You two work well together.

I am watching your video with a huge smile. I am so happy for you and your dreams come true. Be safe and follow your heart.

LOVE LOVE LOVE this...OMG, this is a big accomplishment. Buying the boat, setting it up and having the guts to leave the dock and just GO. That is really impressive. I really liked the part of you doing boat jobs, oil changes, services, etc...WOW WOW WOW, that is impressive and really shows your skills. YOU ARE AMAZING, really. Congrats.

Major respect for Bobby because of his skills and even more that he was cool enough to help you here.

So bitter sweet, really bummed for Bobby, and so happy for your new adventure! Glad you had a first rate, first mate! 😆

Looking good, Taylor! Great that you're standing by Bobby in his hour of need!

Way to go Taylor! So proud of you and happy to see your first sail on the Sea Gypsy! You will get your sea legs again!

Congrats Taylor, glad you brought Bob along. That first trip is nerve wracking. Takes me about a year to trust a boat. Make sure you bring several impellers, diesel fuel filters (racors) lots of belts. Looking forward to 2021....

So happy to see you & Bobby working together again!!🙌🙌 Good luck. Safe travels

Such a great. Video and you have charted a course for the rest of your life we are all so proud

Wild horses couldn't tame Taylor when she gets the bit in her mouth...in this case the purchase and commissioning of her new sailboat so she can beat the winter and head south. Taylor you did an amazing job of getting everything done in record time to be on your way although you look like you could do with a week on the beach sleeping throughout the day. I admired how you stayed in touch with Bobby when his boat conked out. That's terrible news for him because he has worked so hard on keeping his boat shipshape and what does he do as soon as he is docked, he flies north to help you on your maiden voyage. Now that's a friendship worth a million bars of gold. It doesn't get any better and speaks well about the relationship the two of you developed while sailing on Naughty Dogs. Hopefully, Bobby's patreon's will step up with a Christmas bonus and help him get his boat sorted out. Go Taylor Go! You are living your dream life. All the best.

Awesome job on the first sail. I am glad to see you have Bobby with you and that you are not alone for this. I am also glad Bobby is safe and ok. You two make a great Vlogging couple and should really stick together

Congratulations on the first miles under the keel, also for your First 100, thousand subs. Bobby I's sad too hear about your boat troubles, that really sucks. At least it didn't happen in some small island where services are not available. So good of you to help out Taylor on her first outing. CHEERS AND FAIR WINDS Steve h.

I love seeing a young person stepping out of your comfort zone. Keep at it Taylor . Love that Bobby was able to come down and help. The sailing will be good for the soul. See ya next time.

Cool music on this one. I think that buddy boating is a great idea to get you south from Anapolis. It’s always more fun and safer with some friends.

Love the maiden voyage!!! Great to see Bobby with you as always in Sailing Doodles.

Great feeling on maiden voyage. Especially when you alone on a boat. I had a pleasure to experience that 20 year ago. This feeling stay with you for rest of your life. Congratulations!

Leaving the dock for the first time is exhilarating On your own boat too That feeling never gets old Enjoy

Well done Taylor! I would be just as nervous casting off and probably more than you looked docking the boat for the first time! Well done to Bobby for getting his boat safe. Hope the sea sickness passed!

Good luck Taylor. Bobby is a first-class friend. I’m glad to see you two still work together.

Well done Taylor, big congrats to you and your nerves. As you sailed out, I was smiling my face off for your joy. You looked sooo happy. Looking forward to all your adventures with great expectations. And well done to Bobby, for helping you out. Funny role reversal, now your the skipper, and Bobby is your crew!! All the to you. 😍☺

Very excited for you Taylor! Glad Bobby is ok and able to join you on your maiden voyage. 🌈🙏✌️

Happy fo you Taylor. Bobby keep it up. I am sure that in few months you will be back on another boat !!!

Good to see you and Bobby together. He seems like he is a true friend and an all around good guy. Best of luck in your new adventure.

delighted for you to be underway with your own boat and a very happy 2021 - stay safe

Many new adventures await you. Thank you for sharing them! Love watching you and Sailing Doodles.

Super great job Taylor! You are, without a doubt, the most genuine! You are not afraid to show your emotions, happy sad or scared, and your skills will only get better. Keep Bobby close and take care of him until Nauti Dogs is back in the sea lanes, don't let him go to the dark side! I have to go the patreon to support you two. Keep smiling and keep a weather eye on the horizon. Fair winds from the Great Lakes.

Perfect DUO Taylor & Bobby!!

Nice to see you on your own boat and now reversing roles with Bobby. We now have Captain Taylor. I hope Bobby will continue to tag along. You both make a great team with awesome energy. Good sailing!

Glad to see Bobby is alright, you left us a bad cliff hanger last episode. Even better to see he is helping out with the departure.

Thank you for sharing your life......may your journey be safe......

Hey Tailer your narration is spot on!!! good to see Bobby safe and sound

Great job, looks like you were in good hands & company with Bobby. Awesome accomplishment no doubt, hope you got your sea legs back!

Nice to see your first sail...glad to see Bobby lending you a hand in the light of what happened to his boat

Proud for you Taylor! Enjoying your channel.

What a really nice video...great shots and music!

Rock On Taylor you are your Own Champion nothing can stop you . Maverick is watching over you both always

Go ahead girl! Good Luck! All planet is your playground!

I'm happy you're with Bobby, I'm sure the two of you can tackle any tantrums the boat or the environment will throw your way :-)

Boddy and you are my favorite taylor you know you have a true friend when bobby is gooing through what he is but still comes to help you im so sorry to here about bobbys boat i have been off work since july had back surgey and my neck fused so i have wacthed ALOT of you guy and you have been a big part of taking my mind off the pain!im going to try and crape up a few buck for bobby and you sail safe and take care of bobby he seemed sad on his last video

Great job getting underway. Blessing on you for your concern for Bobby and great job to him for being by your side on this first outing.

Congratulations Taylor so excited for you glad to see Bobby around

You are a really good friend

Congrats on leaving the dock!

Everything in this video is awesome, particularly those sunset shots of NYC. Amazing!

Couldn't be happier for you Taylor. I hope you have many great sails in your future. Please talk Bobby into fixing his boat back up. By the way , I think you both have some serious Chemistry going on. Just saying.

Your on your way girl! So glad Bobby could join you!

Taylor I sent a link for my daughter to subscribe and ring the bell. She needs someone like you in her life who’s independent, smart, lovely and a risk taker. Bless you and bless your parents. ❤️😎

Be careful out there. I’m glad Bobby will be there to help a little

You’re captain of your own vessel and your life, well done you. I’m betting your Dad is very proud of you.

Super awesome to see you out on your own boat! And with Bobby onboard no less. And don’t worry about him, he’ll bounce back and get an even better boat than before.

You must remember material things can be replaced, just be safe we love you because you can't be replaced.

Glad Bobby is okay, so sweet of him to help out. 👍🏻

Kudos to the Coast guard and all they do!

Glad to see Bobby helping

So glad Bobby is Ok! congratulations on your maiden voyage!!!!

Great maiden voyage! Congratulations Taylor! Fair seas and following tides!

Congrats Taylor. Bobby, it sucks that you lost your boat. Truly sucks. But you can roll with the best looking captain and she’s got a boat. Lol.

the videoography is exceptional. i love how sailing doodles sailing life has influenced many people. outdoor living! thanx! :)

Congratulations on your first sailing as Captain Taylor of the Sea Gypsy. It is always great to have Bobby on your first sailing. Sorry to hear about Bobby's boat. May the wind be always at your back. Ahead forward.

I understand why neither of you did because I am sure it was emotional considering what he had been through, but I would have loved to have seen when you met him when he got there. You two are so great together.

Taylor I appreciate how much you look out for Bobby and how that friendship is as solid as a rock. Your frienship with Bobby is truly a beautiful thing to see these days and Happy New Years to you along with Bobby. God Bless and stay safe .

Great content Taylor. Good to see you letting yourself out there and being human :-) You got this and things will get easier as time goes on. Looking forward to your continued adventures! What an awesome bunch of friends you have. Bobby is the best!

P.S: CONGRATS FOR OVER 100K SUBS IN LESS THAN 1 YEAR. CHEERS.

So happy for you Taylor, you are a force to be reckoned with! You are a good friend to Bobby as well, as he is to you. You may not have been able to be with him on the night his boat was almost lost, but you rescued him nevertheless. He's a stand up guy to come north after all that, to sail on `Gypsies maiden voyage... you could do a lot worse for a first mate... best of luck to you both!

Sea Gypsy looks awesome. I'm so proud of you and wish you happy and safe travels. ⛵

I am happy to see you with your own boat. You and Bobby have good energy. I subscribed for this season on your channel.

Looking great, Taylor. You captured the emotions of being on your new home well, as well as the fear for your friend, Bobby. Well done!

Súper cool and awesome Taylor. Good wind and good sea! Bravo Zulú!

WOW TAYLOR!!!.........I'm so happy for you!!!.........You're such a beautiful human!!!.........Thanks for sharing!!!

Congrats Taylor on your new ride and adventure. Hope all goes well in your travels. God speed!

Congratulations!! Glad to see you are on your way. I believe in you!!! You can do this!! Now, enjoy yourself.

Thanks for being by Bobby's side ,its gonna be a while before his boat is seaworthy and I'm sure your support is appreciated!

Congratulations on the boat..I’m very proud of you and you can see in Bobby’s face he’s also very proud and happy for you. Good job to both of you. You guys have a very special relationship and chemistry. And it shows. Fair winds and following seas. When you pass by Kingsbay Ga. you might see a US submarine. I’m an old Submarine sailor myself. Anchors aweigh!

Congrats on the first twenty. Many more to come I’m sure. Good luck and fair winds. 👍

I loved this video SO much! I just feel your joy and excitement and I am so totally proud of you!! This was a great maiden sail, just perfect and one of so many. I also love you for your heart for my boy. I don't know what he would have done without you, so blessed to have such a dependable friend. All the best as you start your own adventure. And SO excited to see you in your upcoming sail with your mom!!

congrats Taylor !!! what a great accomplishment, enjoy your new boat it looks great. I Feel bad for Bobby here's hoping all turns out well for him.

So happy for you, fellow Canadian. Glad to see Bobby come help even though he had his catastrophe. Tell him I'm still a sub, of you both, and wish him success in getting back under way.

You’re lovely 😊. Glad to see Bobbie is ok and on form 😁

Always take your time to navigate, especially if there is bad weather at your planned destination.

I loved this vid! And Bobby sure knows how to lovingly talk to you! Lol. Good seeing u both together again. You both look so comfortable when you’re together! Love it!

You and Bobby are a good team!

You two are awesome.

Great video ! Congratulations. It's nice to see people who are genuinely happy amongst so much negativity and thanks for the shots of our iconic treasures too :)

I appreciate your hard work hope you will reached to 1M subscribers soonnnn..... ❤️❤️... Boby is very helping person... great ❤️