Watch Sailing & Boating Adventures Around the World tagged “Sailboat caribbean” – Page 13 of 15

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SailAway 66 | 3rd Contract in 3 Weeks! Our Sailboat Search Concludes | Sailing Around The World
SailAway World Sailing

SailAway 66 | 3rd Contract in 3 Weeks! Our Sailboat Search Concludes | Sailing Around The World

We found THE BOAT!! In Contract for 3 BOATS in less than 3 WEEKS!! Well, it's been an interesting ride, especially in the last month or so, but we ACTUALLY, FINALLY, found our liveaboard sailboat...FOR REAL! Lol. But the road wasn't without a last coup...
SailAway 65 | Our Sailboat Contract FELL APART | Sailing Around the World
SailAway World Sailing

SailAway 65 | Our Sailboat Contract FELL APART | Sailing Around the World

IN CONTRACT for a LIVEABOARD SAILBOAT, CONTRACT FALLS APART, NEW BOAT, SECOND CONTRACT!! Yes, it was an eventful time between last week's episode and this week's! Due to numerous issues with financing, some because of our self-employment and some because...
SailAway 64 | We Made an Offer on a Liveaboard Sailboat! | Sailing Around the World
SailAway World Sailing

SailAway 64 | We Made an Offer on a Liveaboard Sailboat! | Sailing Around the World

THREE MORE BOATS TO TOUR!! And we FINALLY MAKE AN OFFER ON ONE!! Yes, this week we make a trek up "North" to check out 3 more liveaboard sailboats - all Hunters - a Hunter 460, Hunter Helsen 470, and a Hunter 466. AND after all our searching and weighin...
SailAway 63 |  Miami Boat Show Sailboat Tours!! | Sailboat Living Sailing Vlog
SailAway World Sailing

SailAway 63 | Miami Boat Show Sailboat Tours!! | Sailboat Living Sailing Vlog

BENETEAU, JEANNEAU, DUFOUR, HYLAS, OUTREMER and MORE!! We take one last break from our liveaboard sailboat search to go to the Miami International Boat Show and soak up the latest, greatest and shiniest of the new sailboats on the market! No we can't aff...
SailAway 62 | Buying a LIVEABOARD SAILBOAT! The Final Research Boats | Sailboat Living Sailing Vlog
SailAway World Sailing

SailAway 62 | Buying a LIVEABOARD SAILBOAT! The Final Research Boats | Sailboat Living Sailing Vlog

MORE LIVEABOARD SAILBOATS! We CLOSE IN on our QUARRY! This week concludes the "research" portion of our search for a liveaboard sailboat to sail around the world! We've looked at a ton of boats to try and narrow down what might work for us. After this ...
SailAway | New Boat Update May 2019  |Sailboat Living Sailing Vlog
SailAway World Sailing

SailAway | New Boat Update May 2019 |Sailboat Living Sailing Vlog

We Moved on to our new (to us) boat and subsequently didn't put out a video this week (so much moving and cleaning). This is our apology and update with whats going on. Be sure to SUBSCRIBE for WEEKLY CONTENT! Cheers!! Thanks for watching SailAway, the...
SailAway 61 | The Key West LIE No One Wants You to Know! | Sailboat Living Sailing Vlog
SailAway World Sailing

SailAway 61 | The Key West LIE No One Wants You to Know! | Sailboat Living Sailing Vlog

SOUTHERNMOST POINT!? The KEY WEST LIE NO ONE WANTS YOU TO KNOW! ;-) And MORE Key West Hijinks. This week we conclude our little land voyage to beautiful Key West with more beautiful sunsets, even tastier drinks, and TONS of live music. We also expose th...
SailAway 60 | Between Sailboats – Road Trip to Key West | Sailboat Living Sailing Vlog
SailAway World Sailing

SailAway 60 | Between Sailboats – Road Trip to Key West | Sailboat Living Sailing Vlog

LAND SAIL TO KEY WEST!! Having no sailboat can't hold us down!! This week on SailAway, we take a little break from our search for a new liveaboard sailboat to take a little raodtrip to Key West. It just so happened to be our 5th wedding anniversary. So...
SailAway 59 | We’re Buying a Liveaboard Sailboat! – Sailboat Tours 2 | Sailboat Living Sailing Vlog
SailAway World Sailing

SailAway 59 | We’re Buying a Liveaboard Sailboat! – Sailboat Tours 2 | Sailboat Living Sailing Vlog

BOATS BOATS AND MORE BOATS!! The Liveaboard Sailboat Tours continue! Will one of these be our new roaming aqua home? You're gonna find out real soon because, in real time...we're only 2 weeks from closing!!! Enjoy!! And be sure to SUBSCRIBE for WEEKLY...
SailAway 58 | Buying a Liveaboard Sailboat – Sailboat Tours Part 1 | Sailboat Living Sailing Vlog
SailAway World Sailing

SailAway 58 | Buying a Liveaboard Sailboat – Sailboat Tours Part 1 | Sailboat Living Sailing Vlog

WE'RE BUYING A LIVEABOARD SAILBOAT!! We fill you in on WHAT we're looking for and TOUR THE FIRST THREE BOATS!! Yes, the new SailAway era has officially begun. Well, technically it began close to a year ago, because we've been going on liveaboard sailboa...
SailAway 57 | WE SOLD OUR SAILBOAT!! The Final Layla Episode | Sailboat Living Sailing Vlog
SailAway World Sailing

SailAway 57 | WE SOLD OUR SAILBOAT!! The Final Layla Episode | Sailboat Living Sailing Vlog

Well this is it!! Layla is OFFICIALLY SOLD!! And this is her VERY LAST EPISODE!! Yeah, we know...take a moment. Well, the survey went great, the sea trial was a hit and the deal has officially been finalized. Layla is no longer our boat. Okay...hol...
SailAway 56 | Selling our Sailboat – Survey and Final Sail | Sailboat Living Sailing Vlog
SailAway World Sailing

SailAway 56 | Selling our Sailboat – Survey and Final Sail | Sailboat Living Sailing Vlog

The SURVEY and SEA TRIAL of LAYLA! Plus our FINAL SUNSET SAIL!! Yes, it's another bittersweet episode as we finalize selling our sailboat by conducting the official survey and sea trial. It's been a long period of hoop jumping to get to this point and b...
SailAway 55 | WE’RE SELLING OUR SAILBOAT! Goodbye to Layla – Pt . 1 | Sailboat Living Sailing Vlog
SailAway World Sailing

SailAway 55 | WE’RE SELLING OUR SAILBOAT! Goodbye to Layla – Pt . 1 | Sailboat Living Sailing Vlog

WE'RE SELLING OUR SAILBOAT! But it's a NEW BEGINNING as we start our search for a BIGGER LIVEABOARD SAILBOAT!! Yes, you read that right, it's a bittersweet episode this week as we explain our happenings and plans. Not only was Layla listed for sale last...
SailAway 54 | Angry Storms on the Intracoastal Waterway | Sailboat Living Sailing Vlog
SailAway World Sailing

SailAway 54 | Angry Storms on the Intracoastal Waterway | Sailboat Living Sailing Vlog

Inventive Dock Departure, CRAZY STORMS on the ICW, and general day in the life sailing!! After a fun weekend with Beau and Brandy of Sailing Saoirse and a sailing regatta that got cancelled by some pretty violent weather, we left Ft. Pierce to head south ...
SailAway 53 | Sailboat Racing with Sailing Saoirse! (almost) | Sailboat Living Sailing Vlog
SailAway World Sailing

SailAway 53 | Sailboat Racing with Sailing Saoirse! (almost) | Sailboat Living Sailing Vlog

THE FEARLESS CREW AWAKES! The DOG EATS like a KING! THEY PLOW the waves FEARLESSLY to the RACE START...and get their a%#es kicked by the channel! That about says it all! We had sailed Layla up to Fort Pierce to take part in the Ft. Pierce Yacht Club'...
SailAway 52 | Back to Florida and ICW Cruising | Sailboat Living Sailing Vlog
SailAway World Sailing

SailAway 52 | Back to Florida and ICW Cruising | Sailboat Living Sailing Vlog

More Northern Antics, BACK TO FLORIDA, and ICW CRUISING for another voyage!!! This week we finally get back from our Ohio hiatus and discover a sea of green algae surrounding Layla! Only one thing to do, and that's to get her out in some crystal clear wa...
SailAway 49 | Partying at Put-In-Bay – The Key West of Lake Erie | Sailboat Living Sailing Vlog
SailAway World Sailing

SailAway 49 | Partying at Put-In-Bay – The Key West of Lake Erie | Sailboat Living Sailing Vlog

Sailboat Racing, Sunset Horn Blasting, and Partying on the Strip in Put-In Bay!! This week we continue our Put In Bay series up on Lake Erie. After some challenging racing in fluky winds, we bring the J-24 Orange Whip back in in the pouring rain. But th...
SailAway 48 | The Key West of Lake Erie – Put In Bay – PART ONE | Sailboat Living Sailing Vlog
SailAway World Sailing

SailAway 48 | The Key West of Lake Erie – Put In Bay – PART ONE | Sailboat Living Sailing Vlog

The Great Watery North, The KEY WEST of LAKE ERIE, and a Boat Delivery to start off the weekend! This week we head even further north to the Lake Erie Island of Put-In-Bay, Ohio. Many people don't know about this crazy party/vacation/sailing spot just a ...
SailAway 47 | A Homecoming and a Full Moon Sail | Sailboat Living Sailing Vlog
SailAway World Sailing

SailAway 47 | A Homecoming and a Full Moon Sail | Sailboat Living Sailing Vlog

A Return HOME, a FULL MOON SAIL, and LATE NIGHT SHENANIGANS! Even wanderers make it home once in a while and this week we show you a little slice of ours. That being our HOME home of Ohio and the lake we both learned to sail on, met on, AND got engaged o...
SailAway 45 | Something’s Floating! Is it VALUABLE?! Is it HUMAN?! | Sailboat Living Sailing Vlog
SailAway World Sailing

SailAway 45 | Something’s Floating! Is it VALUABLE?! Is it HUMAN?! | Sailboat Living Sailing Vlog

Leaving the BAHAMAS, Mysterious Floating Object, and entering the ST. LUCIE INLET!! We survive a ROUGH night at anchor and our surly moods the following morning to enjoy a beautiful transit back across the Gulf Stream in the Atlantic Ocean toward the Fl...
SailAway 44 | Birthday BLOOD on the High Seas!! | Sailboat Living Sailing Vlog
SailAway World Sailing

SailAway 44 | Birthday BLOOD on the High Seas!! | Sailboat Living Sailing Vlog

More THUNDERSTORMS, the Birthday Boy tries to SEVER HIS OWN TOE, and we MOTOR SAIL on FUMES towards WEST END!! Very shortly after waking up to heavy rain and wind, hauling anchor, and sailing towards West End, Grand Bahama, Eric takes a little slip and ...
SailAway 43 | Dodging Thunderstorms and Swimming Naked! | Sailboat Living Sailing Vlog
SailAway World Sailing

SailAway 43 | Dodging Thunderstorms and Swimming Naked! | Sailboat Living Sailing Vlog

Thunderstorm Laundry, Strolling New Plymouth, SWIMMING NAKED, and Anchoring at NIGHT in a LIGHTNING STORM!! It's a full episode this week as we learn when NOT to hang out our laundry to dry - right before a thunderstorm with 30 knot winds! ;-) Not much w...
SaiAway 42 | The OTHER Swimming Pigs of the Bahamas | Sailboat Living Sailing Vlog
SailAway World Sailing

SaiAway 42 | The OTHER Swimming Pigs of the Bahamas | Sailboat Living Sailing Vlog

SWIMMING BAHAMIAN PIGS (NOT in the Exumas), Dark and Stormy Dark and Stormies, and 4th of JULY in the BAHAMAS!! This week we visit No Name Cay in the Abacos, home of the OTHER and lesser known swimming pigs of the Bahamas. Just as cute, just wet, just as...
SailAway 41 | BIGGEST Cheeseburger Party IN THE WORLD!! | Sailboat Living Sailing Vlog
SailAway World Sailing

SailAway 41 | BIGGEST Cheeseburger Party IN THE WORLD!! | Sailboat Living Sailing Vlog

SAILING to SUN, SAND, FREE cheeseburgers, and FREE booze! ALL BY BOAT!! This week the Crew of SV Layla find themselves at the biggest Cheeseburger in Paradise Party this side of Margaritaville. Never having been before and with only the knowledge that ...
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