Watch Sailing & Boating Adventures Around the World – Page 27 of 43
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 625-648 of 1014 results
How to race a sailboat – Lady K Sailing – Episode 101
Support Lady K - Or Join Lady K as we PHRF race in the Great Lakes
Is Lockdown OVER?! Sailboat Life in St. Croix | SailAway 114 | Sailing Around The World
As the Lockdown begins to ease, the restaurants in the USVI begin to open...and we eat our way through St. Croix! Lol...not really, but it kinda felt that way. The novelty of eating in a restaurant with no mask was simply too much to resist! Somehow we found time for sunsets, touring historical C...
EPISODE F’N 100!!!! – Lady K Sailing – GO SMALL, GO SIMPLE, GO NOW!!!
Support Lady K - Or
Catch Clean & Cook Lobster & Crab the Belizean Way – Ep 120 Sailing Luckyfish
This week, Zaya aka Island Girl Catch Clean Cook Lobster & Crab Belizean Way. Belize delivers the best snorkeling we've had. Relax to a bonus extended version by becoming a Luckyfish supporter on Patreon. Just $2 a month from you makes all the difference. Become a Patreon here: New Lucky...
A WHALE Three Feet From Our Hull! – Sailing To St. Croix | SailAway 113 | Sailing Around The World
A WHALE Passes Our Hull! We SAIL to ST. CROIX and Hop The USVI SAFARI!! We have a lot going on this week! First, we take our first "Safari" ride in St. Thomas, the self-made transportation system, island wide for only $2! This spawns a road trip involving much needed supplies and roadsi...
Buddy Sailing with a CLASSIC CATAMARAN – Ep 119 Sailing Luckyfish
Sailing Belize again at last after 60 days in self-isolation and another 2 weeks on the hardstand. Liked this? Check out our latest LIVE video shot yesterday "Search for a hurricane hole" at We meet Jeff, Theresa, Deon and Vaughn from Daytripper Charter Catamarans ( and visit Scipio Cay....
Boat Projects – Covid-19 Lockdown – Grand Cayman – Hallberg-Rassy 54 Cloudy Bay Mar-May’20. S20 Ep18
Following a quick island tour, we completed several boat projects and boat maintenance while on Covid-19 lockdown in Grand Cayman. Installing solar panels, making dinghy covers, sunshades and more. Having arrived to Grand Cayman from Jamaica just hours before the border closed, we settled into bein...
Dinghy Adrift While Snorkeling! – And Other Sailboat Life Tidbits | SailAway 112 | US Virgin Islands
Dinghy ADRIFT! USVI Cruising and BOOZY Ice Cream! This week we check back into our video timeline after a brief "real time" departure to cover the passing of Gonzalo. Back in St. Thomas, USVI, we do some spearfishing only to resurface to a missing dinghy! Later we make an epic hike for ...
SailAway Special Episode – Gonzalo Passes Grenada – Prepping Our Sailboat In Quarantine
Prepping Our Sailboat for GONZALO While In Quarantine In GRENADA! Today we bring you a special episode as a follow up to Episode 111 as we prep our boat for the coming of Hurricane/Tropical Storm Gonzalo. After a mad scramble to seek safe harbor, we show you our steps to ready ourselves for the po...
Toilet Truths – Episode 99 – Lady K Sailing
Support Lady K - Or A run down on the pros and cons of the natures head composting toilet after two years
Damaged Plywood Boat SOAKS for 60 DAYS – Ep 118 Sailing Luckyfish
Damaged plywood boat soaks for 60 days. We get permission to move the vessel and haul-out to see how much water we soaked up in 60 days since the grounding. See the grounding here: Luckyfish needs your support! $2 a month from you makes all the difference. Become a PATREON: New Luckyfish Merch a...
Screw it – Let’s have an adventure – Episode 98 – Lady K Sailing
Support Lady K - Or
Sailing Jamaica to Cayman – Lively Sailing – Hallberg-Rassy 54 Cloudy Bay – Mar 2020. Season20 Ep17
2 days of lively off-wind sailing from Jamaica to Grand Cayman. With Covid-19 starting to cause concern, we departed Jamaica and headed for the medical security of Grand Cayman, which we hoped to explore before any restrictions were applied. We left Montego Bay on a fast beam reach, aiming to arri...
Quarantined On A Sailboat With A Hurricane Coming! – Gonzalo Approaches Grenada | SailAway 111
Quarantine in GRENADA with HURRICANE GONZALO Coming Our Way! FAST FORWARD to, well, almost now! This week we're skipping ahead a bit in light of very recent developments. As we sit in quarantine in Grenada due to Covid 19 and the closed borders and unable to check into the country, Hurricane...
Going CUCKOO in Self-Isolation – Ep 117 Sailing Luckyfish
This week we're going cuckoo in self-isolation. 60 days compressed in 27 mins. Enjoyed this? Watch more here Luckyfish needs your support! $2 a month from you makes all the difference. Become a PATREON: New Luckyfish Merch and the latest syndicate update. Check out the brand new Luckyfish s...
SailAway LIVE from GRENADA! WE MADE IT!
Join us for a LIVE stream (7:00pm EST) where we'll discuss our passage from the USVI to Grenada (we literally just arrived today) and answer any questios you may have. Enjoy!! And be sure to SUBSCRIBE for WEEKLY CONTENT EVERY FRIDAY! Cheers!! Thanks for watching SailAway, the travel documen...
Sailing Jamaica – Sailing Montego Bay – Hallberg-Rassy 54 Cloudy Bay – Mar’20. Season20 Episode16
Always wanted to visit "Mo-Bay" area and the famous Montego Bay Yacht Club. From Ocho Rios we motor-sailed to Montego Bay, our last stop in Jamaica. Anchored off the quiet Montego Bay Yacht Club, where we sheltered from a strong NE weather front for 3 days before exploring the local area...
What’s It Like Living on a Sailboat With a Family? | Virgin Islands Cruising | SailAway 110
REAL LIFE of a CRUISING FAMILY! Sailing from MAGEN"S BAY to MAHO and hiking the ANNABERG PLANTATION RUINS! This week we start off by celebrating Mother's Day in true Loren style...we sail and fish!! She get's her catch which Eric fries up for the family, then the following day we h...
Sailing Jamaica – Family Reflections in Ocho Rios – Hallberg Rassy 54 Cloudy Bay – Mar’20. S20 Ep15
From our anchorage in Oracabessa we sailed the short distance west to Ocho Rios, a major tourist center in Jamaica. Ocho Rios is the place where Glen’s parents had their happiest holiday, back in 1967. By record of his Mum’s diary, we visited their hotel and all the places they enjoyed during their ...
Let’s talk about dinghies! – Episode 97 – Lady K Sailing
Support Lady K - Or
ONE YEAR! We’ve Lived and Sailed On This Sailboat | SailAway 109 | Sailing Around The World
ONE YEAR of Life Aboard a LIVEABOARD SAILBOAT! The GHOST TOWN of CHARLOTTE AMALIE! And SAILING to Magen's Bay! In this week's episode we celebrate ONE YEAR of living and cruising aboard Cecilia! This happens to coincide with some businesses finally opening back up in the USVI, so we se...
3 Things We Made to Survive 2 Months L0CKD0WN – Ep 115 Sailing Luckyfish
In 3 things we Made to survive 2 months lockdown on Luckyfish we show you how small things can make a big difference when you are confined on a boat for weeks on end. Luckyfish needs your support! $2 a month from you makes all the difference. Become a PATREON: New Luckyfish Merch and the latest s...
World Cruising Sailboat – Episode 96 – Lady K Sailing
Support Lady K - Or Take a tour of a world cruising Hughes 38 - Fatty Goodlander had one! Lady K has a big sister - wait till you hear the story!