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?? ...

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 ...

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 ...

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 ...

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 ...

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 ...

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 ...

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 ...

SV CUBA Fun Sailing Adventures ⛵💙 We have perfect wind sailing down the Italian coast of Sicily, the Mediterranean cost is whizzing past. SV CUBA is healing, ...

This weeks video is sponsored Kamikoto Knives, use the code CalicoSkiesSailing for for $50 off the purchase of any knife! ...

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 ...

SAILING SOUTH! Our Longest OFFSHORE PASSAGE Yet (On Our Own) | Harbors Unknown Ep. 51 This week we’re embarking on our longest #offshorepassage EVER on our ...

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 ...

We had a fantastic week sailing around the Greek islands with five other YouTube sailing channels. I hope you find this video as exciting as we found the trip. ...

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 ...

Today I am pulling back the curtain on our YouTube earnings and showing you exactly how much we make by posting our sailing adventures on YouTube. If you ...

Freediving Greece: Underwater caves and hidden sea lakes in the Aegean If you enjoy the content and want to support us further then there are some suggestions ...

What do cruiser's do with all of their time? Quite a lot as this episode demonstrates 😉. It starts out with pizza night aboard Delos. We make the dough (from ...

Ever wondered what it would be like to live in the Keys? How about living in a place like the Dry Tortugas, a paradise only accessible by boat and sea plane, ...

In this episode we prepare for a big storm coming with 30 knots expected wind predicted to blow for four straight days. We move anchor spots and then Bill gets ...

In this episode we continue the installation of our marine air conditioner. We get right down to it, drilling a sea water exit hole in the hull. Typically this ...

EP 179: Don't Fear When Ricky is Near.. We're settling down nicely in the anchorage (Prickly Bay) We weren't to pleased with the holiding of where we ...

Two days ago I thought I was losing my boat and everything I owned with it. One day ago I was kitesurfing around a tropical island with sharks chasing me. ...

EP 178: Our boat is EMOTIONAL We get ready to move over to our new anchorage spot (Prickly Bay) Our plan is to try every anchorage out in Grenada as we have ...