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Dominica Didn’t Let Us Leave Easily… E400
Wildly Intrepid Sailing

Dominica Didn’t Let Us Leave Easily… E400

Our time in Dominica comes to a pretty rough ending! We grab a mooring in Roseau and head ashore to explore downtown, only to realize we’ve LOST our cellphone as we head back home. 😩 Not exactly how we planned to spend our last days on one of our favorite Caribbean islands! Back at the boat, thing...
We Found the WILDEST Island in the Caribbean
Finding Our Isla Sailing

We Found the WILDEST Island in the Caribbean

We thought we knew what Caribbean adventure looked like… then we got to Dominica. This island completely blew us away. We chased waterfalls through the rainforest, swam beneath one of them, explored the famous Indian River, stepped into a filming location from Pirates of the Caribbean, and somehow ...
Sailing Panama…We Found a Secret Jungle River 🇵🇦 Ep-237
Leading the Escapade

Sailing Panama…We Found a Secret Jungle River 🇵🇦 Ep-237

Sailing in Bocas del Toro, Panama is starting to feel a little too comfortable… so naturally, we find ourselves leaving the boat to explore what’s hiding beyond the islands. 🌴⛵️ This week aboard Escapade takes us from Starfish Beach into the canals and jungle of Bocas del Toro, with light-wind sail...
WORTH NO SLEEP? Dominica’s hidden gem E399
Wildly Intrepid Sailing

WORTH NO SLEEP? Dominica’s hidden gem E399

Sometimes the best cruising stops are the ones you never planned! ⛵🌴 We sail out of Portsmouth, Dominica, hoping to make a quick hop around the coast and drop anchor just around the corner. But our anchoring plans don’t exactly go as expected… That little failure leads us to Coulibistrie, an unexp...
Eastern Caribbean Was NOT What We Expected
Finding Our Isla Sailing

Eastern Caribbean Was NOT What We Expected

This was NOT the Caribbean we expected. Sailing south through the Eastern Caribbean brought us to Guadeloupe—and what we found completely surprised us. After leaving St. Kitts and Nevis and making a quick stop in Montserrat, we sailed Isla into Deshaies, Guadeloupe, ready to get off the boat and e...
We Got LOST in the Pirates of the Caribbean Indian River! E398
Wildly Intrepid Sailing

We Got LOST in the Pirates of the Caribbean Indian River! E398

We set out to explore Dominica’s famous Indian River… but somehow managed to lose the trail! What followed turned into one of those adventures that makes Dominica so incredible. We wandered through thick jungle, crossed the river and found ourselves surrounded by huge twisted roots that looked str...
Living the Dream in Bocas del Toro 🌴 Sailing, Tropical Paradise & Starfish
Leading the Escapade

Living the Dream in Bocas del Toro 🌴 Sailing, Tropical Paradise & Starfish

After days of nonstop rain, we finally get some sunshine and make the most of it! 🌴☀️ In this episode, we start with a few cosmetic boat jobs we’ve been putting off while waiting for the weather to improve. Then we set sail through Bocas del Toro, Panama, heading to Dolphin Bay Yacht Club to check ...
ROUGH Sail to Dominica But it’s WORTH IT E397
Wildly Intrepid Sailing

ROUGH Sail to Dominica But it’s WORTH IT E397

We say goodbye to Guadeloupe and set sail for Dominica, but it definitely isn't the smooth Caribbean sail we were hoping for! The day starts with a bad feeling in my gut before we head out into a rough, lumpy sea for the crossing to Dominica. 🌧️⛵ It isn't our most comfortable passage, but...
WE’RE BACK AT SEA! 🌴 San Blas, Boat Repairs & Insurance Update! Ep-235
Leading the Escapade

WE’RE BACK AT SEA! 🌴 San Blas, Boat Repairs & Insurance Update! Ep-235

Sailing the San Blas Islands, Panama after months of sailboat repairs, boatyard damage and an ongoing insurance claim! ⛵️🌴 After months stuck in the boatyard, Escapade is finally back on the water and we’re sailing again! In this episode, we take you along for our first week back aboard Escapade as...
Hidden Hot Springs & Sailing life of a family in Guadeloupe E396
Wildly Intrepid Sailing

Hidden Hot Springs & Sailing life of a family in Guadeloupe E396

Sailing Guadeloupe with the family ⛵ Another beautiful stretch of Caribbean cruising! We start out anchored in Malendure, where it’s time to tackle one of the less glamorous parts of boat life — the grocery run! With the boat stocked up, we jump into the clear Caribbean water for another incredible...
We Almost Quit Sailing
Finding Our Isla Sailing

We Almost Quit Sailing

What was supposed to be a manageable overnight sail from the USVIs to St. Martin turned into one of the hardest passages we’ve experienced as a sailing family. The forecast said one thing. The ocean gave us something completely different. We found ourselves beating directly into the wind and waves...
Our 4-Year-Old Started DIVING in the Caribbean! E395
Wildly Intrepid Sailing

Our 4-Year-Old Started DIVING in the Caribbean! E395

Our 4-year-old Coral is taking her underwater adventures to a whole new level! 🤿🌊 We explore the incredible Réserve Cousteau in Guadeloupe, where the water is crystal clear, the reef is full of life, and Coral starts diving below the surface all on her own. Watching her confidence grow underwater a...
PLANS CHANGE. THINGS GO WRONG
The Cruising Kiwis

PLANS CHANGE. THINGS GO WRONG

PLANS CHANGE. THINGS GO WRONG Sometimes you put a hole in your boat, races don't go your way, and whole course of life changes.This isn't an episode about a disaster; it's about how a family responds when things doesn't go to plan. This week we continue our Caribbean sailing ad...
Sailing Our Damaged Catamaran to Trinidad
The Cruising Kiwis

Sailing Our Damaged Catamaran to Trinidad

Sailing Our Damaged Catamaran to Trinidad We're sailing our damaged catamaran south through the Caribbean, island hoping from Guadeloupe towards Trinidad, where we plan to haul out and repair the hull after our recent grounding. With hurricane season underway, Trinidad is our destination for r...
“Pour Yourself a Glass of Wine…”  7 to 33 Knots E394
Wildly Intrepid Sailing

“Pour Yourself a Glass of Wine…” 7 to 33 Knots E394

One last adventure at Grande Anse, one of the most beautiful beaches we’ve found in Guadeloupe before making the short hop to Deshaies. There we enjoy some delicious local treats and cool off with a swim in the river. Then it’s time to keep sailing south along the coast of Guadeloupe. The condition...
The Greatest Gift My Parents Gave Us Wasn’t a Thing
Finding Our Isla Sailing

The Greatest Gift My Parents Gave Us Wasn’t a Thing

Sometimes the greatest gifts aren't things—they're the lessons and memories that stay with you forever. ❤️ This week aboard Isla, Nana and Gogo join our family to celebrate my 40th birthday, and what started as a family visit became one of our favorite weeks of boat life. We waste no tim...
We Found Guadeloupe’s Most Beautiful Beach! | Grand Anse by Sailboat E393
Wildly Intrepid Sailing

We Found Guadeloupe’s Most Beautiful Beach! | Grand Anse by Sailboat E393

Anse Leroux, Guadeloupe is perfect, with crystal-clear water, a close by beach and fantastic snorkeling just a short ride from the boat. From there, we take a long dinghy ride to the colorful village of Deshaies, where we wander the charming streets and discover an amazing local bakery serving deli...
Been to the BVI? Sail these islands next!
Sail Stillwater

Been to the BVI? Sail these islands next!

If you have sailed the British Virgin Islands and are looking for a new challenge or just new scenery, look into sailing Antigua or the Abacos Bahamas. In this video, we're comparing Antigua and The Abacos in the Bahamas as two of the best alternatives to a BVI sailing charter. Whether you�...
Goodbye Saba… A 3-Day Caribbean Sailing Adventure to Guadeloupe E392
Wildly Intrepid Sailing

Goodbye Saba… A 3-Day Caribbean Sailing Adventure to Guadeloupe E392

Leaving Saba was one of the hardest departures yet. It quickly became one of our favorite islands in the Caribbean, but the weather had other plans. With stronger winds on the way, it was time to keep heading south. Our original plan was to spend a few days exploring St. Kitts and Nevis, but the an...
SSL776 ~ First Overnight Test after Refit.. How did She perform?
Captain Rick Moore

SSL776 ~ First Overnight Test after Refit.. How did She perform?

After almost a year on the hard, Sophisticated Lady is back where she belongs — offshore, under full sail, heading somewhere extraordinary. We pulled anchor from the stunning Rosario Islands of Colombia at dawn and pointed the bow toward one of the most legendary sailing destinations on the planet:...
Our FINAL Day on Saba | The Caribbean’s Most Incredible Island? E391
Wildly Intrepid Sailing

Our FINAL Day on Saba | The Caribbean’s Most Incredible Island? E391

Saba completely stole our hearts, and saying goodbye wasn't easy. 🌋❤️ Before setting sail, we squeezed every last adventure out of what has become our favorite island in the Caribbean. Our final day starts with one last spectacular hike from The Bottom to Windwardside via the beautiful Crispee...
Sailing to Saba: The Caribbean’s Hidden Jurassic Island E390
Wildly Intrepid Sailing

Sailing to Saba: The Caribbean’s Hidden Jurassic Island E390

Saba completely blew us away. 🤯 After waiting for the perfect weather window, we finally sailed to one of the least-visited islands in the Caribbean—and it instantly became one of our favorites. Towering straight out of the sea, Saba looks more like something from Jurassic World than the Caribbean...
We Hiked a Volcano with a 2 & 4 Year Old! | Mount Scenery, Saba E389
Wildly Intrepid Sailing

We Hiked a Volcano with a 2 & 4 Year Old! | Mount Scenery, Saba E389

After finally finding the perfect weather window, we arrive in spectacular Saba and check in by sailboat to one of the most unique islands in the Caribbean. Our adventure begins with a ride along the legendary "Road That Couldn't Be Built"—an engineering marvel carved into impossibly...
ANSE DE COLUMBIER IN ST. BARTS – A MUST SEE SAILING ANCHORAGE.
Sailing PILAR - Blue Dot Voyages

ANSE DE COLUMBIER IN ST. BARTS – A MUST SEE SAILING ANCHORAGE.

Discover the serene beauty of Anse De Columbier, a perfect spot for your next boating mooring ball pickup. This marine park offers peaceful waters, scenic hiking trails, and picturesque beaches for sailors of all levels. Subscribe for more sailing destination guides and cruising tips. LINKS: SUB...
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