After a month in Colombia—soaking in the historic charm of Cartagena and cooling off in the lush mountains of Minca—we finally had the boat dialed in and were ready to move on. We sailed out to the Rosario Islands off the coast, the perfect spot to wait for the right weather window before making our passage to Panama. With strong currents against us, we needed a rare day of light winds and calm seas so we could motor our way through the 125 nautical miles to Puerto Obaldía, right on Panama’s southern border. Once checked in, we set our sights on exploring the remote Atlantic coast as we make our way toward the legendary San Blas Islands.

In this episode of Sailing Big Lost, we head inland for a change of scenery—trading the Caribbean coast for the lush mountains of Minca, Colombia. Nestled in the Sierra Nevada range, Minca is a charming mountain town known for its cool climate, cloud forests, and cascading rivers. We’re joined on this adventure by our cruising buddies from S/V La Vida Shred and S/V Palarran. You may remember La Vida Shred from our time together back in Allen’s Cay, Bahamas—but this time, we’re swapping turquoise water for misty mountain trails! Join us as we make the five-hour drive to our Airbnb in the hills, explore the La Victoria Coffee Farm, and take a veryrefreshing dip in the cold mountain rivers of Colombia. From teeter-totters in town to breathtaking views in the cloud forest, this episode is all about slowing down, connecting with friends, and soaking in the natural beauty of the Sierra Nevada.

After three days at sea in light winds, dodging debris from the Magdalena River, we finally make landfall in Cartagena, Colombia! 🇨🇴 It was a surreal feeling arriving in port after days offshore — calm seas, warm breezes, and the colorful skyline of Cartagena rising on the horizon. Once tied up and settled in with our friends, we set out to explore this incredible city in the most fun way possible… on electric scooters! 🛴 The Walled City of Cartagena is a vibrant maze of narrow streets, lively plazas, and historic architecture bursting with color and energy. We cruised past street vendors, sampled delicious local food, and soaked up the bustling atmosphere that makes Cartagena one of the most unforgettable cities we’ve visited yet.

After three incredible weeks in Bonaire, it’s time to say goodbye to this beautiful island—famous for its crystal-clear waters and vibrant underwater life. We also have an emotional farewell as Grams heads home to Idaho after two unforgettable weeks making memories with her grandchildren. Before we leave, we squeeze in one last snorkel and say goodbye to friends before setting sail for Cartagena, Colombia! With a 400 nm downwind passage ahead, we’re excited (and a little nervous) to fly our Gennaker for the first time—especially after ripping two sails on previous crossings. Along the way, we catch some fish, enjoy dolphin and whale sightings, and soak in the open ocean magic. Join us for this memorable Caribbean passage as we sail from Bonaire to Colombia and prepare to explore the colorful city of Cartagena! 🌊⚓

Life in Bonaire has been nothing short of incredible! From swimming, snorkeling, and scuba diving with our boat buddies and Conor’s mom, to spotting vibrant coral and an incredible octopus encounter — the underwater world here never ceases to amaze us. But as every cruiser knows, boat life isn’t always smooth sailing. Between the crystal-clear dives, we tackle more boat projects, discover yet another raw water pump leak, and even rip another sail. It’s all part of the adventure as we live, learn, and explore this beautiful island by sea. If you love sailing, diving, and seeing what real life aboard a cruising catamaran looks like, join us for another unforgettable week in paradise. 🌴⚓🐙

Our time in Bonaire has been action-packed! We rented a car for three days and were determined to explore everything this island has to offer. From the salt flats to the donkey sanctuary, Washington-Slagbaai National Park, and searching for flamingos — the adventures didn’t stop there. We also found some incredible snorkeling and diving spots, and even had the once-in-a-lifetime chance to swim alongside wild dolphins. But the best part of all? Conor’s mom (Grams!) joined us for the adventure, making this week extra special. It’s been busy, exhausting, and unforgettable — join us as we share the highlights of our whirlwind Bonaire experience!

We set sail from Grenada to Bonaire on our Vision 444 catamaran for the final leg of our passage west. The trip begins as smooth downwind sailing—perfect conditions, fresh mahi on the grill, dolphins dancing at the bow, and plenty of laughs with our buddy boat. But of course, no sail is complete without a little drama… and ours happens in the middle of the night when our Code 65 suddenly comes loose. The entire crew scrambles on deck to get things under control before the situation spirals out of hand. With teamwork and quick action, we recover and continue on to Bonaire—where crystal-clear waters, epic diving, and an 8th birthday celebration with friends make the reward worth every challenge.

After a month of boat work and marina life in Grenada, it’s finally time to say goodbye to friends and set sail west toward Bonaire! This passage is extra special because it’s our first downwind sail on our Vision 444 catamaran, and we’re eager to see how she performs. With the weather on our side, we hope to fly our Code 65 and enjoy smooth sailing across the Caribbean Sea. While we’ll be keeping a cautious distance sailing past Venezuela, we’re excited for the adventure ahead and grateful to be crossing with our friends on Pink Flamingo. Join us as we leave Grenada behind, chase the trades, and sail toward the crystal-clear waters of Bonaire!

This week we share some of the ups and downs of life aboard while waiting for a weather window to sail west. One of the greatest gifts of boat life has been meeting incredible cruising families and watching our kids form lasting friendships—learning to stay connected across distances and rekindling bonds when we meet again. Grenada has been both rewarding and challenging, but it’s given us experiences we’ll always be grateful for. I also tackled a new project—finishing our bow shade—which we’ll test out soon (with fingers crossed that it fits!). As always, thanks for following along on our journey. Some weeks are more adventurous than others, but we’ll continue to share honest reflections of what it’s really like living the boat life.

Not every week is turquoise water and perfect anchorages. This week in Grenada, heavy rain, canceled plans, and marina life kept us tied to the dock — and gave us a real dose of the cruising lifestyle. Between endless boat chores, a soggy anniversary outing, sewing a DIY bow shade, and watching our kids navigate marina friendships, we did our best to find the silver linings. From tackling stubborn grime on the hull to finally upgrading our cockpit cushions, we kept busy even when adventures got rained out. Cruising isn’t always waterfalls and sunshine — sometimes it’s maintenance, rainstorms, and the ups and downs of living in close quarters with other sailors. But that’s boat life… and it’s all part of the journey.

After some much-needed time on the hard at Clarke’s Court Marina in Grenada, SV Big Lost is finally splashed back into the water! 🚤🌊 We tackled a few essential boat projects, including servicing our Gori Prop with the help of our good friend and fellow Vision owner, Michael. With the work complete, we’re excited to be floating again and ready for the next chapter of our Caribbean sailing adventure.

After months of island-hopping through the Caribbean, we make our final sail south to Grenada—our home for hurricane season and the place where we’ll tackle some much-needed boat work and cruising projects. We’re excited to reconnect with friends we’ve met along the way and finally slow down to relax and enjoy life in Grenada, the Spice Island. On the way south, we pass stunning Caribbean islands, dramatic volcanoes, and even get a surprise visit from a playful pod of dolphins. This journey marks the end of one chapter and the beginning of another as we prepare for an exciting season of sailing, exploring, and living aboard.

Over the past week, we sailed down the eastern coast of Martinique – a charming French island in the Eastern Caribbean. We explored the colorful towns of Fort-de-France, Petite Anse d’Arlet, and Saint Anne… and ate more baguettes than we care to admit! The highlight of the week? Hiking Mount Pelée – an active volcano – with dear boat friends who have become like family since we set sail from Saint Martin. From breathtaking summit views to the beauty of Martinique’s towns and clear waters, join us as we sail, hike, dive, and soak up every moment on our slow journey toward Grenada.

What started as a smooth sail from Îles des Saintes to Martinique quickly turned into one of our wildest passages yet. As we sailed south through the Eastern Caribbean, we were surrounded by massive mats of sargassum, battled unpredictable gusts near Dominica, and watched fearless kiteboarders tear across the waves off Scotts Head. But things really got interesting after leaving Îles des Saintes—when our old dinghy completely submerged in open water and literally sank beneath the waves. We explored the historic Fort Napoléon, swam and checked our prop underwater (again!), and finally arrived in Saint Pierre, Martinique under a double rainbow—just in time for a traditional yole boat race and a visit to the Zoo de Martinique, nestled among the ruins of a 17th-century estate destroyed by Mount Pelée’s eruption in 1902. It’s moments like these—chaotic, beautiful, and unforgettable—that remind us why we live this sailing life.

What started as a simple passage from Saint Kitts to Guadeloupe quickly turned into one of our more stressful sails. With winds stronger and angles tighter than forecasted, we made the mistake of flying our Code 55—and paid the price. A loud snap, a torn sail, and a lot of lessons learned. After the chaos at sea, we finally arrived in Deshaies, Guadeloupe—a peaceful anchorage that was just what we needed. From wandering through the lush botanical gardens to indulging in amazing French cuisine, Guadeloupe reminded us why we love this lifestyle, even when it gets a little rough.

After an unforgettable time in Sint Maarten—celebrating Bastille Day, ziplining through the lush hills of Loterie Farm, and soaking up the cruiser-friendly vibes of the lagoon—it’s finally time to hoist the sails again. In this episode, we say goodbye to the comforts and conveniences of Simpson Bay and point our bow south toward Saint Kitts as we continue our journey to Grenada for hurricane season. Along the way, we reflect on our time in Sint Maarten, test out our brand-new GoDu dinghy, and embrace the bittersweet feeling that comes with every island departure.

Yes, we’re still in Sint Maarten… and honestly, we’re not mad about it! We’ve been anchored in Simpson Bay for over a week now, and this island is quickly winning us over. Sint Maarten is truly a cruiser’s paradise—getting around by dinghy is easy and efficient, with everything you need just a short ride away. From well-stocked marine stores and helpful technicians to endless provisioning options, this is the kind of place that makes boat life a little easier. And when the work is done? There’s no shortage of stunning beaches to explore and amazing food to enjoy. While we wait for our new dinghy to arrive, we’re soaking up island life and spending time with our boat buddies. Not a bad place to be stuck for a while!

We set sail from the British Virgin Islands, taking on one of the most challenging points of sail: east into the trades. As we make our way to Sint Maarten, we reflect on the many passages that have brought us to this point—and why it always seems like we’re heading against the grain. With our sights set on Grenada, reaching Sint Maarteen marks a major milestone and, hopefully, the end of the hardest legs of our journey. After weeks of grinding miles and navigating wind, waves, and doubt, we’re finally able to exhale. The easting is behind us. Now it’s time to enjoy the vibrant island life, soak in the culture, and—fingers crossed—find some new friends for our kids to play with. Come along as we regroup, recharge, and prepare for what’s next on this sailing adventure aboard Big Lost.

After picking up long-awaited spare parts in the US Virgin Islands, we leave Honeymoon Bay behind and set sail for the British Virgin Islands—our next stop on the journey south to Grenada for hurricane season. Our first destination: Norman Island, where we blow off some steam at the infamous floating bar, Willy T. The next day, we make our way to Virgin Gorda’s Saint Thomas Bay, waiting for a good weather window to cross to Saint Martin. While in Virgin Gorda, we return to The Baths and reflect on just how far we’ve come. Nearly one year ago, our boat life journey began right here in the BVI—and now, almost 5,000 nautical miles later, we’re back aboard a new boat, full of memories, lessons, and excitement for what’s ahead.

After our 7-day passage to the USVI, we find ourselves in island time — waiting on delayed packages before we can continue our journey south to Saint Martin for hurricane season. While we wait, it’s a week of boat projects and island adventures! We spend time troubleshooting a radar that won’t activate, fixing broken hatches, sorting out some rigging issues, and questioning if we’re really getting the best performance from our overdrive props. But it’s not all work! We also make time to relax and enjoy the beauty of the US Virgin Islands — exploring the National Park on St. John, snorkeling in crystal-clear water, and checking out Cruz Bay.

After 7 days and 2 hours at sea, we finally made landfall in Saint Thomas! This was our longest passage yet — and our first without extra hands on deck — so we’re incredibly proud to have safely navigated 1,051 nautical miles as a family. Along the way, we battled rough seas and squalls, replaced a failed exhaust fan and raw water pump, and managed our sails and watch shifts through it all. This marks a major milestone on our journey south as we make our way to Grenada for hurricane season. There’s still a long way to go, but it feels good to have the biggest leg behind us.

After months of chaos—selling a boat, buying a new one, and surviving endless shipyard setbacks—we’re finally on the move. But we’re late. Hurricane season officially began on June 1st, and we’re already behind schedule. Rather than take the traditional Thorny Path through the Caribbean, we’ve chosen the route less traveled—heading east into the Atlantic from The Bahamas in hopes of bypassing the slow and brutal slog to windward. Our goal: reach the Virgin Islands fast and make our way to Grenada or the ABCs before the storms roll in.

This week hit hard. After being told the marina would cover the damage they caused during our haul out—damaging our sail drive and prop—we got a call no boat owner wants: the general manager overruled the previous decision. Now, we're left with the full bill. Another crushing blow in what’s felt like a never-ending uphill battle to get our new home ready to sail. While waiting for our new prop to arrive, we kept grinding away on other boat projects, trying to stay focused and productive. But it’s tough when all we want is to start living aboard, set sail, and head south before hurricane season really ramps up.

After months of dreaming, planning, and searching… we finally bought a boat! 🥳 This episode is packed with all the wild and wonderful moments that led up to closing on our new Vision 444 catamaran — our floating home for the next chapter of our sailing adventures. We kicked things off with a thrilling airboat ride through the Everglades 🐊, then dove into the intense process of boat surveys, rigging inspections, and test sail. From the highs to the hiccups (spoiler: we got sideswiped by another boater 😳), this was a week to remember. We officially closed escrow and took the keys (figuratively) to our beautiful new catamaran. Our first sail didn’t go quite as planned thanks to rough seas, but the day was saved by an unexpected submarine sighting that left us speechless. 🚢👀 Now the real fun begins — getting her ready to head south ahead of hurricane season. We can't wait to share the journey with you!

From the snowy mountains of Idaho to the turquoise waters of the Caribbean, Conor’s life has always been about chasing adventure. Dirt bikes, skiing, waterskiing, hunting, and sailing — his childhood was packed with energy, freedom, and a growing love for the outdoors. In this video, Conor shares how he turned a life of grit, hard work, and wild dreams into a reality aboard Sailing Big Lost. Discover how a construction worker with a love for motorcycles and boats set his course for the open sea — and never looked back. Adventure is out there — and Conor’s proof it’s worth chasing.

Meet the Crew – Kelly | Sailing Big Lost Where do you even start when telling your life story? In this episode, Kelly shares her raw, real, and inspiring journey—from Seattle roots and horse show dreams to high-powered real estate and a full pivot to life at sea. This isn’t just a story about sailing—it's about reinvention, resilience, and following your gut when life asks for more. As the heart of Sailing Big Lost, Kelly opens up about growing up the responsible oldest sibling, chasing Olympic dreams in the equestrian world, weathering family upheaval, and ultimately finding her way back to joy and purpose. After building a successful career, starting a family, and hitting burnout during the COVID real estate boom, Kelly and her husband Conor made a bold decision: to trade the house and hustle for a catamaran and connection. If you’ve ever wondered what it takes to completely change your life, this episode will hit home.