Watch Sailing & Boating Adventures Around the World

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 1-24 of 237 results
ST. MARTIN SAILING – GRAND CASE, BUSCO RUM, REAL REGGAE, A PARADE AND SIMPSON BAY
Sailing PILAR - Blue Dot Voyages

ST. MARTIN SAILING – GRAND CASE, BUSCO RUM, REAL REGGAE, A PARADE AND SIMPSON BAY

Our St. Martin Sailing adventure visiting Grand Case for the night life, Busco rum for day drinking, listening to REAL Reggae, a night parade and Simpson Bay Bridge. TIMELINE: 0:00 Introduction to St. Martin 0:24 Grand Case 1:06 Busco Rhum 3:00 REAL Reggae and nightlife 4:00 Night Parade 4:46 Simp...
Sailing to the BRITISH VIRGIN ISLANDS | Sailing Sunday | Ep.209
Sailing Sunday

Sailing to the BRITISH VIRGIN ISLANDS | Sailing Sunday | Ep.209

Join us this week on passage sailing from St Maarten to the BVI's. We exit through the famous Simpson Bay Bridge in St Maarten and set sail for an overnight passage to explore an amazing peice of Caribbean Paradise, The Brittish Virgin Islands! SAILING SUNDAY WEBSITE: SAILING SUNDAY SHOP: ...
Sailing to Paradise: Hauling our Boat for Maintenance in St. Maarten
Holly and Ray

Sailing to Paradise: Hauling our Boat for Maintenance in St. Maarten

This week we left the USVI in light winds and calm seas. We motored through the night and arrived in St. Maarten before sunrise. We anchored for a day while we rested up, then hauled out at Bobby’s Megayard for our Lagoon 42’s 5 year insurance survey and some routine maintenance. We got a fresh bott...
Sailing with a broken knee 🦵
Sailing Lady Africa

Sailing with a broken knee 🦵

EP 221: Sailing with a broken knee 🦵 Since we we're in St Maarten which is considered the more built up island of the Caribbean, we opted to go to the doctor to see if we could get Ricky's "what we though was a torn meniscus" sorted. We booked an appointment for surgery which en...
Sailing to St Maarten | Private Jet Island ✈
Sailing Lady Africa

Sailing to St Maarten | Private Jet Island ✈

EP 219: Sailing to St Maarten | Private Jet Island ✈ We checked out of Antigua and made our way to St Maarten. This time we actually managed to sail and not motor the whole way which was so nice and we caught our selves some fish for dinner. It's been a minute since we could do both of those t...
New Catamaran Owners Trust “the Professionals”… – Ep 81
Sailing Jibsea

New Catamaran Owners Trust “the Professionals”… – Ep 81

We help new sailors and Lagoon 440 owners tow their catamaran from the Dutch Caribbean island of St. Maarten to the French island of Saint Martin. Their catamaran has no auxiliary power, meaning it has no engines. We go through shallow spots, dodge ship wrecks and use small inflatable dinghies to t...
We had to see this for ourselves – Ep 79
Sailing Jibsea

We had to see this for ourselves – Ep 79

Thanks to Skillshare for sponsoring this episode. The first 1,000 people to use the link or our code sailingjibsea will get a 1 month free trial of Skillshare: It's another boat life birthday this week in Caribbean Dutch island of Sint Maarten. We visit the famous and popular Maho Beach in P...
Ep 119 Break’in Stuff, Plus Some Fun Mogul Skiing
Sailing Talisman

Ep 119 Break’in Stuff, Plus Some Fun Mogul Skiing

This is a continuation of our boat maintenance and disaster prevention series. But it starts with some great footage we took skiing moguls and trees at Winter Park Resort Ski Area at our home location of Winter Park, Colorado. Once that's done, we move to a flaw I found that will need work comi...
ep61 – Sailing St. Maarten – Sailing St. Martin – Hallberg-Rassy 54 Cloudy Bay – Jan-Feb 2019
Sail Cloudy Bay

ep61 – Sailing St. Maarten – Sailing St. Martin – Hallberg-Rassy 54 Cloudy Bay – Jan-Feb 2019

Sailing to the joint Dutch-French island of St. Maarten (St. Martin) where we stayed for 1 month, doing maintenance, attending a multihull regatta, exploring and trying kite-foiling. After our short stay in St. Barts, s/v Cloudy Bay (Hallberg-Rassy 54) set sail to St. Maarten. First anchoring in Sim...
Why we travel to the Caribbean Islands | Boating Journey
Boating Journey

Why we travel to the Caribbean Islands | Boating Journey

In episode 98, we share why we travel to the Caribbean Islands every year. While it is much easier to get to Hawaii or Mexico from Seattle, we simply love the Caribbean vibe. Boating Journey began on our honeymoon in 2003 in Antigua when we fell in love with the Caribbean Sea while sailing. Take a...
SSL ASMR Boat Life ~ Sailing to St Martin!
Captain Rick Moore

SSL ASMR Boat Life ~ Sailing to St Martin!

This footage was filmed in May of 2018 when it was just my son Brenden and myself onboard.. this was our last sail through the Eastern Caribbean as we were documenting all the hurricane recovery progress at all the islands that were destroyed by Hurricanes IRMA and MARIA. Along the way amidst all t...
Sailing fail! We ran aground – TWICE in St. Maarten – Sailing Seatramp
Sailing Seatramp

Sailing fail! We ran aground – TWICE in St. Maarten – Sailing Seatramp

SY Seatramp rans aground in St. Maarten... This video was a preview for our beloved Patrons in April and should have been part of our 100 episode. As you all know, we got robbed in July and all material is gone. We will start soon with new videos. During our stay on St. Maarten we tried to use to...
Sailing upwind back to St Maarten – EP 99 Sailing Seatramp
Sailing Seatramp

Sailing upwind back to St Maarten – EP 99 Sailing Seatramp

We try to find a supermarket on the BVIs, before we make our way to St. Maarten. Unfortunately this trip is no fun, upwind sailing for 24 hours. On the way we catch a Barracuda, Mario has slight doubts to eat it . A trip to the other side of the island completes this episode before we get visitor...
Our Plans for the Future & Meeting a Legend [EP 55] | Sailing Millennial Falcon
Sailing Millennial Falcon

Our Plans for the Future & Meeting a Legend [EP 55] | Sailing Millennial Falcon

When the strong winds stop in Marigot Bay, St Martin, the neighbourhood comes out to play in the beautiful blue water! We take a break from the boat work and enjoy a good swim and dive. After discussing and deciding on our future plans however, we know we need to get back to work... We meet the sa...
Star Flyer Caribbean Cruise Review – How was it? | Boating Journey
Boating Journey

Star Flyer Caribbean Cruise Review – How was it? | Boating Journey

In episode 33, we review our Star Flyer cruise through the Caribbean Islands. The Star Flyer, is part of the Star Clipper Cruise Ship line. On this cruise, we cruised the Leeward Islands from Sint Maarten, down to St. Barths and back. Follow our blog at www.boatingjourney.com. Please like and subs...
Caribbean Cruise on the Star Flyer from Sint Maarten |  Boating Journey
Boating Journey

Caribbean Cruise on the Star Flyer from Sint Maarten | Boating Journey

In episode 30, we set sail on the Star Flyer for our Caribbean cruise through the Leeward Islands. In part 1 we visit Sint Maarten, Nevis and Dominica. This was a fantastic cruise through the Caribbean islands and Sint Maarten is a great island to visit. We stayed on Dutch side just a mile from th...
SSL 316 ~ We get our NEW HIGHFIELD DINGHY and YAHAMA ENGINE in St Martin!!
Captain Rick Moore

SSL 316 ~ We get our NEW HIGHFIELD DINGHY and YAHAMA ENGINE in St Martin!!

This is the episode we've all been waiting for... what happened to PACMAN?!? Yes, our old centre console dinghy is sold, and we finally take possession of a new lighter, stronger dinghy made by Highfield Boats that has a double aluminum hull and a new Yamaha 25hp 4-stroke motor... this baby fl...
SSL 314 ~ Shattered Dreams in ST MARTIN
Captain Rick Moore

SSL 314 ~ Shattered Dreams in ST MARTIN

New SSL Video Collections just released on Vimeo! For more real-time updates, follow us on Instagram at: Support SSL Videos at: Want info about our drones? Contact our friend Frank at: New SSL Gear available at:
Dude! Wheres My Dinghy!?!  Dinghy stolen right off the back of my boat while I was sleeping inside!
Another Adventure

Dude! Wheres My Dinghy!?! Dinghy stolen right off the back of my boat while I was sleeping inside!

First "Show Me Your Dinghy" because lights save lives! Please check out the link to the most durable, affordable, and non-consumable dinghy light available anywhere. I designed, manufactured and made these lights available after a very unfortunate accident. Email [email protected]...
Island hopping from St Maarten to Saba – Episode 5
Sailing Parlay Revival

Island hopping from St Maarten to Saba – Episode 5

In this episode we get all our repairs done after a disaster of a sail to St Maarten, we then bounce over to Fourshue island and St Barths to get some waves, then end up in Saba where we scale some mountains and explore the underwater world. To support us on Patreon and get a chance to come sailing...
SSL 283 ~ St Martin – First glimpse since HURRICANE IRMA
Captain Rick Moore

SSL 283 ~ St Martin – First glimpse since HURRICANE IRMA

First glimpses of our trip to St Martin (SXM) to survey the recovery efforts and progress since Hurricane IRMA devastated the islands in September of 2017. This is just a sample of the footage and interviews we have collected during our travels the past few weeks to give you a near real-time glimps...
SSL 269 ~ What happens in Grenada, STAYS in Grenada!
Captain Rick Moore

SSL 269 ~ What happens in Grenada, STAYS in Grenada!

This episode edited by Shascha Z! Hope you guys enjoy, this is the 2nd of 3 weddings we did with Bill and Lori for their Valentine's wedding in Paradise aboard 'Sophisticated Lady'... Next episode you'll also meet some very special guests arriving that you may remember from past...
SSL 205 ~ Devastation of HURRICANE IRMA in St Martin & British Virgin Islands
Captain Rick Moore

SSL 205 ~ Devastation of HURRICANE IRMA in St Martin & British Virgin Islands

HURRICANE IRMA is definitely taking her toll and destroying everything in her path. This update features some of the first aerials and images I was able to find on social media of the affected areas, including Tortola in the British Virgin Islands (BVI), and many areas of St Martin shot just after ...
LAGOON CATAMARAN SOLO SAILING- S1:E37
Sailing Doodles

LAGOON CATAMARAN SOLO SAILING- S1:E37

Bobby Solo sails the new Catamaran from St. Martin to San Juan Puerto Rico and Megan does some Pina-Colada research to find out who made the first one, The Caribe Hilton or Barrachina. Check out our new website! We need your help to keep making videos Become a Patron! Donate Via Paypal to he...
WeBoating
Logo
Shopping cart