Watch Sailing & Boating Adventures Around the World
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We Found The Most AMAZING Spot On This TINY Island – S4EP6
In this episode we officially check into a new country! We explore the Grenadines with our buddy boat @SailingSunday and have a ton of fun on the water. We then have some BIG NEWS as Kiki and I let ya'll in the loop about our recent engagement. After discovering this cool sailor friendly resort...
24 Hours of Raw, Unfiltered BOAT LIFE – S4EP5
In this episode we take you along for what 24 hours of REAL boat life looks like - and reality check... it's not always sunshine, cocktails and bikinis! There are also times where nothing seems to go right. Living on a boat means constant repairs and often things break at the WORST times. But w...
NEW CREW! Best Friends Reunited – S4EP4
In this episode we welcome a very special new crew member onboard!! Some of you might recognize her from our old Somerset Sailing videos, or past videos on my channel. Everyone welcome Cass! I'm so excited to be reunited with one of my best friends and get to spend some quality time together on...
Back to the Sea She Goes! – S4EP3
In this episode we return to Spice Island Marine ( ) in Grenada to get Gypsy Moon ship shape and ready for another season of cruising! We check a ton of things off our long to do list including a NEW BIMINI and installing our new Precision Sails Mainsail ( ). We make some new boatyard buddies, Ry...
All Good Things Must Come To An END… S3EP18
TRAVEL WITH ME: In this episode we stop in the magical island of Dominica on our way south to Grenada. We finally make it to Grenada safe and sound just in time for our haul out date. We pack up the boat and prepare it for hurricane season on the hard at Spice Island Marine before saying our goodb...
BROKEN RUDDER! A Sailors Nightmare – S3EP17
In this episode we experience every sailors worst nightmare - a broken rudder! We have to haul out last minute and take you through the process of repairing it as quickly as we can. Thanks for watching! If you enjoyed this video be sure to like/leave a comment. Also don't forget to SUBSCRIBE! ...
DESERTED ISLAND in Puerto Rico – S3EP16
Check out highfieldnorthamerica.com if you are in search of a dinghy, they have a wide variety to choose from! In this episode we explore one of Puerto Rico's most mysterious deserted islands, Isla Caja De Muertos (aka Coffin Island). We share some of the tales of it's past as we hike up ...
The MOST Beautiful Beach in Dominican Republic – S3EP15
In this episode we gather our whole buddy boating gang and hit the road! Feeling wild and free we roam around the island on our dirt bikes and eventually make it to the most beautiful beach in Dominican Republic called Playa Rincon. Then we depart Dominican Republic and sail to Puerto Rico, a crossi...
Waterfalls, Ziplines & Motorcycles – Dominican Republic 🇩🇴 – S3EP14
This episode is packed full of adventure! We have a bit of a sketchy incident upon our late night arrival and woke up the most rolly anchorage ever. We move into Luperon and set out on a grand adventure for Aj and Nelly's last few days. We rent motorcycles and ride over to a well known spot in ...
Our Longest Passage Yet! Sailing to Dominican Republic – S3EP13
In this episode we set sail from Turks and Caicos to Dominican Republic, our longest passage on Gypsy Moon yet! Although we had to change course to a different destination we had a great sail an arrived in DR around 2:00am. If you enjoy my videos please like and/or comment! Also don’t forget to SU...
Sail to a VERY Remote Island – S3EP11
Thanks to Kamikoto for sponsoring this video! Get $50 off on any purchase with code TAYLOR. Got to and help support the channel In this episode we have a great sail to our last stop in the Bahamas - a very remote island called Mayaguana. It was my brother and his girlfriends first overnight sail ...
Young Cruisers Float & 10 BOAT RAFT UP! – S3EP7
For 16 FREE meals with HelloFresh across 7 boxes AND 3 FREE gifts use code TAYLORSTRAVELS16 at In this episode we have a MASSIVE 10 boat raft up for FLOATCHELLA 2022 organized by the Young Cruisers Association Then we have a bumpy sail over to Staniel Cay to continue the fun with kiteboarding an...
Bound for the Exumas – S3EP6
Get 4 months for free on a 2 year plan here: with code TAYLOR. It’s risk free with Nord’s 30 day money-back guarantee! In this episode I share a typical day of cruising in the beautiful blue waters of the Bahamas. We bring the boat into Spanish Wells to get fuel, water and do a grocery run befor...
Finding Love at Sea – S3EP5
Thanks to Established Titles for sponsoring this video! Get 10% off on any purchase with code TAYLOR . Go to and help support the channel! In this episode I share what we've been up to in Hope Town, Bahamas before leaving and heading to Royal Island where we hunker down and wait out strong wi...
Setting Sail to the BAHAMAS 🇧🇸 – S3EP4
Check out EcoFlow Power Stations: #EcoFlow #EcoFlowDELTAMax #Powerstation In this episode I finally leave the dock in Stuart, Florida and set sail once again!!! With Kiki as my first mate we travel down the ICW to Palm Beach before making the crossing over to the Bahamas. Thanks for watching, gi...
Leaving My Monohull For A CATAMARAN?!?! – S3EP3
In this episode I take a short break from working on my boat to join Tara and friends on a charter in Key West with Restless Native Charters. It was a wonderful break from the reality of the to do list still ahead of me. But after some fun I return back to work and get a ton of projects completed. ...
Refitting My 38ft Sailboat – S3EP2
Click my link to try AG1 by Athletic Greens - Get 1 Year supply of Vitamin D3K2 & 5 FREE travel packs: Time to check some things off the to do list! In this episode I get some help from Ryan and Kiki to get some big jobs done. We install my new solar arch, radar and anemometer. Thanks for wat...
Back on My Boat!!! New Engine Install – S3EP1
Welcome to a NEW SEASON of Taylor's Travels! In this episode I give my campervan Ruby some upgrades and make her more like a home again as I begin this next chapter. I drive from Canada down to Florida to be a part of the install of my new Beta Marine 50 hp engine and to attend the Annapolis bo...
Sailing to Mexico with SV Delos -S2EP24
In this episode we enjoy the last of our time in the Dry Tortugas aboard @svdelos before setting off on a 2 day sailing mission to find the perfect tacos in MEXICO! Thanks for watching! If you enjoyed the video please give it a thumbs up and don't forget to subscribe to make sure you don'...
Teaming up with the LEGENDARY Sailing Family SV DELOS – S2EP22
In this episode Sea Gypsy gets towed to her resting place where the work of replacing the engine will be done. As this chapter of my adventure comes to a close another begins to unfold. Luckily my path aligned with some legends within the Youtube sailing community - @svdelos I hop aboard as crew in...
You Know What BOAT Stands For… – S2EP21
Video Sponsored by Rosetta Stone In this video I wrap up my whole journey since buying the boat. The good times and the issues that lead to the not so good times. I explain why I had to make the hard decision of re-powering. Which has set me back a lot but also allowed me the opportunity to embark...
Sailing Alone on the ICW – S2EP20
In this episode I leave Melbourne, FL and finally get sailing on the nearly 40 mile passage down the ICW to Fort Pierce. I share some of the disadvantages to travelling within the protection of the ICW vs being on the open ocean. Once I arrive and drop the hook I get to relax and enjoy the beautiful...
Here I Go Again On My Own – S2EP19
Now that my Mom has gone back to Canada, in this episode I am back to being solo. The atmosphere is much different on the boat without her and I definitely miss her. I make the decision to leave Titusville and continue moving south down the ICW! (Filmed February 2021) Thanks for watching! Don’t ...