Watch Sailing & Boating Adventures Around the World tagged “Virgin Islands Sailing” – Page 2 of 2

Explore sailing, boating, and water sports through our curated video archive. From epic sea voyages to serene diving escapes, discover unforgettable adventures from top YouTube creators. Start your journey. Dream big. Sail far.

Showing 25-35 of 35 results
SailAway 14 | Finding Layla’s Home – Puerto Rico Marina Tours | Sailboat Living Sailing Vlog
SailAway World Sailing

SailAway 14 | Finding Layla’s Home – Puerto Rico Marina Tours | Sailboat Living Sailing Vlog

Every Marina on Puerto Rico's East Coast!! In this week's episode of sailboat living with SailAway, we hop on that sailboat in the sky on an adventure to Puerto Rico! Our goal? To do a massive recon of the Eastern Coast to choose a home for ourselves and...
SailAway 13 | Gulf Streamin’ in a Sailboat | Sailboat Living Sailing Vlog
SailAway World Sailing

SailAway 13 | Gulf Streamin’ in a Sailboat | Sailboat Living Sailing Vlog

Haulin' A$! on the GULF STREAM for TWO DAYS! SailAway Ep. 13 - This week in our sailing vlog we complete our Florida shakedown trip in high fashion. A downwind sled ride of a sail on the Gulf Stream for 2 days out on the Atlantic as we roll our way back ...
SailAway 12 | Beach Baby and Sailboat Bums | Sailboat Living Sailing Vlog
SailAway World Sailing

SailAway 12 | Beach Baby and Sailboat Bums | Sailboat Living Sailing Vlog

Bikini Beach Bummin' in Daytona! SailAway Ep. 12 - This week in our sailing vlog we learn to accept the folly of plans and enjoy the present as we sail into two different and really cool marinas in the Daytona Beach Florida area, both with different vibes...
SailAway 11 | Sailboat Slacking in St. Augustine | Sailboat Living Sailing Vlog
SailAway World Sailing

SailAway 11 | Sailboat Slacking in St. Augustine | Sailboat Living Sailing Vlog

Aggressive peacocks, the Fountain of Youth, and a CREEPY stuffed animal house!! Sailboat living with SailAway #11. This week we duck out of the unrelenting wind on the Intracoastal Waterway and check the sailboat into not only one, but two marinas in St....
SailAway 10 | Sailboat DENIED, Stymied By The Sea | Sailboat Living Sailing Vlog
SailAway World Sailing

SailAway 10 | Sailboat DENIED, Stymied By The Sea | Sailboat Living Sailing Vlog

The ICW bridge that WOULD NOT LET US PASS!! Sailboat living with SailAway #10. After making some modifications and upgrading the boat for sailing the Bahamas we head south to Florida via the Atlantic and ICW with a Bahamas adventure as our goal. But i...
SailAway 9 | Messing About on a Sailboat, Wave One | Sailboat Living Sailing Vlog
SailAway World Sailing

SailAway 9 | Messing About on a Sailboat, Wave One | Sailboat Living Sailing Vlog

ALL NEW LINES from EBAY, Boomkicker, Custom Adjustable Backstay and more!! In this week's episode of sailboat living with SailAway we switch it up a little bit. Learn all about the improvements and sailboat maintenance we did in the first 15 days of ownin...
SailAway 8 | Sailboat Aground In Charleston | Sailboat Living Sailing Vlog
SailAway World Sailing

SailAway 8 | Sailboat Aground In Charleston | Sailboat Living Sailing Vlog

We RUN AGROUND, drink all our booze, and swim with DOLPHINS!! SailAway Ep. 8 Travel Vlog - So we made it 600 miles living on a sailboat from Atlantic City to Charleston after one day of owning the boat...but sometimes it's all about enjoying your own "ba...
SailAway | Official Trailer | Sailboat Living Sailing Vlog
SailAway World Sailing

SailAway | Official Trailer | Sailboat Living Sailing Vlog

Cruising couple, 2-year-old, and trusty dog cruise the world on a 35' sailboat, Layla!! Ahoy, there from SailAway and welcome to our travel vlog! After only ONE DAY of owning our 35' sailboat, we sailed her 600 miles from New Jersey to South Carolina! W...
SailAway 3 | Lazy Day Sailing in the Dismal Swamp | Sailboat Living Sailing Vlog
SailAway World Sailing

SailAway 3 | Lazy Day Sailing in the Dismal Swamp | Sailboat Living Sailing Vlog

GETTING PRIMAL and hitting stuff in the Dismal Swamp!! Sailboat Living with SailAway Ep. 3 Travel Vlog - Our new sailboat delivery continues as we bump logs in the Great Dismal Swamp in the Intracoastal Waterway, sail big winds in the Pamlico Sound, and t...
SailAway 2 | 30 Hours Sailing On The Atlantic | Sailboat Living Sailing Vlog
SailAway World Sailing

SailAway 2 | 30 Hours Sailing On The Atlantic | Sailboat Living Sailing Vlog

CRAZY WAVES, 30 hours on the ocean, and bioluminescent algae!! Sailboat Living with SailAway Ep. 2 Travel Vlog - On Day 2 of ownership and after a single day of upgrades and preparations to the sailboat, we begin our long sail down the east coast back to...
SailAway 1 | New Sailboat, New Adventures…Sailing 600 Miles | Sailboat Living Sailing Vlog
SailAway World Sailing

SailAway 1 | New Sailboat, New Adventures…Sailing 600 Miles | Sailboat Living Sailing Vlog

We buy a SAILBOAT and leave the NEXT DAY on a 600 mile voyage!! Sailboat living with SailAway Ep. 1 Travel Vlog - Join us aboard SV Layla as we learn about living on a sailboat. We travel from our home in Charleston SC to Atlantic City, New Jersey to pi...
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