Watch Sailing & Boating Adventures Around the World tagged “Calico skies sailing” – Page 5 of 9

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 97-120 of 207 results
YOLO Baby! Chasing our Dream b/c We’re Not Getting Any Younger (Calico Skies Sailing, Ep. 135)
Calico Skies Sailing

YOLO Baby! Chasing our Dream b/c We’re Not Getting Any Younger (Calico Skies Sailing, Ep. 135)

Our last days cruising in the amazing San Blas Islands will prove to be THE best yet! Two months behind us in this pristine cruising ground has meant beautiful anchorages with good holding and protection, white sand and turquoise water for days and palm tr...
Mom PLEASE Don’t Watch This 😂..The Multiple Ways Hanging with Plukky almost got me killed (Ep. 134)
Calico Skies Sailing

Mom PLEASE Don’t Watch This 😂..The Multiple Ways Hanging with Plukky almost got me killed (Ep. 134)

Why don't I want my Mom to skip this one? It starts out innocently enough with a bonfire in the new spot we sailed to last time - A gorgeous beach in the beautiful San Blas Islands, Panama. We're here with friends on Delos and Plucky of Sailing into Freedo...
Is Every Sailing YT Channel in the San Blas? Racing Delos & Plucky! (Calico Skies Sailing, Ep. 133)
Calico Skies Sailing

Is Every Sailing YT Channel in the San Blas? Racing Delos & Plucky! (Calico Skies Sailing, Ep. 133)

We’re sailing to a new island here in San Blas, Panama to check out a new spot with our buddy boat s/v Delos - Our ‘routine’ while cruising here. We recently added friends Andy & Charli to the mix (friends since the TTYC days) and today we’re a...
Are we lonely in this life? (Calico Skies Sailing 132)
Calico Skies Sailing

Are we lonely in this life? (Calico Skies Sailing 132)

A question we are often asked is if we are lonely living and traveling full-time on a sailboat? Is it difficult to be without family and a grounded community?? In our experience the sailing community has been one of the biggest draws to this lifestyle, as ...
What you’ll never see on vacation!! Guna Yala Revolución Celebration(Calico Skies Sailing 131)
Calico Skies Sailing

What you’ll never see on vacation!! Guna Yala Revolución Celebration(Calico Skies Sailing 131)

Isla Tigre, a San Blas island with a population of fifteen hundred is celebrating Independence Day and they are happy to have us participate . We spend a day at the festival which begins with a reenactment of the revolution that secured for the Guna people...
Sailors Beware: This Place is Chock FULL of Coral Reefs (Calico Skies Sailing Ep. 129)
Calico Skies Sailing

Sailors Beware: This Place is Chock FULL of Coral Reefs (Calico Skies Sailing Ep. 129)

Though our current spot in San Blas is pretty sweet - We get regular deliveries from veggie boats, where we load up on fresh fruits & veg, booze and chicken at great prices - it's time to check out the infamous 'Hot Tub', an anchorage just 7 miles from...
You Won’t Believe What It Costs to Sail Here!!!! (Calico Skies Sailing Ep. 128)
Calico Skies Sailing

You Won’t Believe What It Costs to Sail Here!!!! (Calico Skies Sailing Ep. 128)

The cost to cruise the paradise that is San Blas is less than we’d imagined. Our new spot, a beautiful island with deep water all the way up to the shore, has that untouched feeling. But when a veggie boat selling Budweiser comes by we begin to understan...
The Best Cruising Ground, Remote…. But Not Too Remote (Calico Skies Sailing Ep. 127)
Calico Skies Sailing

The Best Cruising Ground, Remote…. But Not Too Remote (Calico Skies Sailing Ep. 127)

We decide to move spots and explore a new island in the San Blas chain but when Bill goes to pick up the anchor the windless won’t power up. With no obvious reason for the malfunction and a buddy boat, s/v Delos whose already departed Bill decides to pul...
Remote living on the cheap: Together in paradise and on the hook (Calico Skies Sailing Ep. 126)
Calico Skies Sailing

Remote living on the cheap: Together in paradise and on the hook (Calico Skies Sailing Ep. 126)

The first cluster of beautiful islands we explore in San Blas are featured on the cover of our guide book - And they are just as stunning as the picture. We check out the beach on the closest island and hang out with friends of s/v Delos. Nugget is especia...
Passage ANXIETIES! First Offshore Passage in Six Months!  (Calico Skies Sailing Ep 124)
Calico Skies Sailing

Passage ANXIETIES! First Offshore Passage in Six Months! (Calico Skies Sailing Ep 124)

We leave Bocas del Toro and sail offshore 220 miles to the San Blas islands. We’re headed east and the normally strong easterly winds have left a choppy sea state for us. And, thanks to the current we’re pointed even more upwind than expected. This mea...
Off Grid Living! Can we Fit 3 Months of Supplies on our 36ft Sailboat?!(Calico Skies Sailing Ep 123)
Calico Skies Sailing

Off Grid Living! Can we Fit 3 Months of Supplies on our 36ft Sailboat?!(Calico Skies Sailing Ep 123)

Preparing to cruise off the grid for three months begins with a massive stock up of provisions. After taking an inventory we head into to hot Bocas Town via panga boat. Every store carries different items and are spaced out so it’s many hours of strategi...
First Time Moving our Boat in Six Months, What Could Possibly Go Wrong…😂 (Calico Skies, Ep 121)
Calico Skies Sailing

First Time Moving our Boat in Six Months, What Could Possibly Go Wrong…😂 (Calico Skies, Ep 121)

We’re super excited to 1) have my little sister aboard with us and 2) officially leave the dock and move Calico Skies for the first time in MONTHS!! After picking Molly up in Bocas town we waste no time casting the lines and heading for an anchorage near...
YouTube versus Reality! Sailboat Life….High High’s, Low Low’s (Calico Skies Sailing Ep 120)
Calico Skies Sailing

YouTube versus Reality! Sailboat Life….High High’s, Low Low’s (Calico Skies Sailing Ep 120)

This weeks video is sponsored Kamikoto Knives, use the code CalicoSkiesSailing for for $50 off the purchase of any knife! https://kamikoto.com/Calicoskiessailing Calico Skies is docked in the insanely beautiful Red Frog marina on Bastimentos Island, Boca...
Chasing Waterfalls in Boquete; First Mates Days off! (Calico Skies Sailing Ep 119)
Calico Skies Sailing

Chasing Waterfalls in Boquete; First Mates Days off! (Calico Skies Sailing Ep 119)

Grace wanted to visit the mountain highlands of Boquete, Panama since she first saw the immense peaks of Volcan Baru on the horizon and in this episode the first mate finally get’s her wish! The trip begins first with closing the sea cocks to make sure C...
The Sailing Hillbillies are Back! How did our boat survive 4 months of tropical storage!?  Ep. 117
Calico Skies Sailing

The Sailing Hillbillies are Back! How did our boat survive 4 months of tropical storage!? Ep. 117

We return to our boat after leaving her in humid Panama for rainy season and are faced with lot's of dirt and a variety of mold in every shade of the rainbow both on deck and down below. We start by scrubbing the deck and cockpit clean and then turn to the...
What DO Salty Sailors get up to while on Shore Leave? (Calico Skies Sailing, Ep. 115)
Calico Skies Sailing

What DO Salty Sailors get up to while on Shore Leave? (Calico Skies Sailing, Ep. 115)

What's it like for cruising sailors who have been onboard full-time for the past five years to temporarily "swallow the hook" ? In this episode we will show you! This is a departure from our normal sailing content documenting what we got up to during our f...
How to Store a Boat for the Long Term?!  (Calico Skies Sailing, Ep. 114)
Calico Skies Sailing

How to Store a Boat for the Long Term?! (Calico Skies Sailing, Ep. 114)

We had a good run, this was is our first time leaving Calico Skies in five years of cruising 😂. We decide to go home to visit family and friends in the States while it is rainy season in Panama. Getting the boat ready for long-term storage in the tropic...
Back to Life on Anchor, Exploring Starfish Beach, Bocas Del Toro (Calico Skies Sailing, Ep 110)
Calico Skies Sailing

Back to Life on Anchor, Exploring Starfish Beach, Bocas Del Toro (Calico Skies Sailing, Ep 110)

It's amazing to be in Panama after a 1,000 mile sail from Mexico. This is our first time in Central America and we love the "off" the beaten path vibe as well as all the amazing wild-life in this jungle environment. The first order of business is to move...
Sailing During Covid: Low Fuel.. Can we Divert?! (Calico Skies Sailing Ep.107)
Calico Skies Sailing

Sailing During Covid: Low Fuel.. Can we Divert?! (Calico Skies Sailing Ep.107)

We knew the route from Mexico to Panama would require a lot of motoring and that there was always a possibility we would have to divert course to get more fuel. Traveling during COVID makes these passage decisions even more difficult. Our route to Panama h...
Would You Jump in 13,000 ft of Water 100 miles Offshore? (Calico Skies Sailing Ep.106)
Calico Skies Sailing

Would You Jump in 13,000 ft of Water 100 miles Offshore? (Calico Skies Sailing Ep.106)

We need a break in the trade winds to make easterly progress from Mexico to Panama. On the second day or our passage we find ourselves in pond like conditions about a hundred miles offshore. The crew decides this would be a good time to jump into the 13,00...
Saying Goodbye 🥲- 1,000 Mile Offshore Passage Apart (Calico Skies Sailing Ep.105)
Calico Skies Sailing

Saying Goodbye 🥲- 1,000 Mile Offshore Passage Apart (Calico Skies Sailing Ep.105)

The time has come for us to say goodbye... After sailing nearly 30,000 miles together, Grace has decided to not sail this passage and will meet Calico Skies in Panama giving new crew the opportunity to log some offshore miles. After saying goodbye the boys...
Will We Escape Hurricane Season?! (Calico Skies Sailing Ep.104)
Calico Skies Sailing

Will We Escape Hurricane Season?! (Calico Skies Sailing Ep.104)

With two tropical cyclones spinning up within a week it's time for us get moving out of the hurricane zone. The only problem is that we have put ourselves a bit into a corner here in Mexico. We need to fight our way a few hundred miles east against persist...
We Made it! Back to Cruising Life, aka Fixing All the Sh*t we Broke 😂 (Calico Skies Sailing Ep.102)
Calico Skies Sailing

We Made it! Back to Cruising Life, aka Fixing All the Sh*t we Broke 😂 (Calico Skies Sailing Ep.102)

Well, we made it to Mexico! And that mean's we're officially back to Cruising Life and done with Passage Life, at least until the next time. There are a few priorities upon arriving and the specifics change depending on where we are, but one thing that nev...
What Fighting 25 Knots in the Gulf Stream on a 36 ft Boat Feels Like (Calico Skies Sailing Ep.101)
Calico Skies Sailing

What Fighting 25 Knots in the Gulf Stream on a 36 ft Boat Feels Like (Calico Skies Sailing Ep.101)

The last part of our passage to Mexico was a perfect demonstration of what fighting 25 knots in the Gulf Stream on a 36 foot sail boat feels like . . . Choppy seas form when wind goes against current but sometimes it's just a battle out there and there's n...
Epic water experiences, one click away.

Something AWESOME is coming!
Be the FIRST to know⛵

Sign up for exclusive updates and be the first to hear when we go live!
Get sneak peeks, exciting announcement, and special content straight to your inbox!

We don’t spam! Read our privacy policy for more info.


WeBoating
Logo
Shopping cart