The Great Loop Podcast

Chris and Deb are back after a month of cruising north aboard CDN, and this leg of their Great Loop adventure delivered everything from mechanical trouble to once-in-a-lifetime celebrations. The journey begins at Myrtle Beach Yacht Club, where a diver discovers a damaged propeller just days before departure. After replacing a massive starter battery, they finally head north along the Intracoastal...

Chris and Deb Winnenberg are back aboard SeaDAN with a huge Great Loop update from Hilton Head to Myrtle Beach. In this episode, they cover: Harbour Town and Shelter Cove Marina Golf at Hilton Head during the RBC Heritage Anchoring off the 18th hole at the tournament An unforgettable dolphin encounter Big Carolina tides Rough crossings near St. Helena Sound Charleston and the MegaDock Touring the...

Chris and Deb are back on the bridge with another Great Loop update—this time cruising from Amelia Island up into Brunswick, navigating rolly sounds, Coast Guard encounters, and even a close call in “Hell’s Gate,” before settling into the charm of Savannah and the iconic beauty of Hilton Head Island. From hidden gem restaurants and “Velcro marinas” to dolphin sightings, anchoring adventures, and a...

14 views Mar 23, 2026 Captain's Log Chris and Deb are back on the move, wrapping up their Florida chapter with a jam-packed stretch of family visits, boating challenges, and a few unforgettable stops along the way. From a magical trip to LEGOLAND with the grandkids (complete with pirate treasure hunts and 32 million LEGO bricks!) to cruising past manatees, dodging tight channels, and even spotting...

In this episode, Chris and Deb check in from a very cold and snowy Cincinnati after hopping off the boat for a quick Midwest pit stop (because apparently eight degrees sounded like a good idea). They recap the last couple of weeks aboard in Sanford, Florida , where life has been anything but boring. From learning to fly a brand-new drone over water (and surviving the backwards controls) to discove...

In this episode of the Great Loop podcast, we share a full update from Sanford, Florida, where we’ve taken a winter freshwater detour along the St. Johns River. We explore downtown Sanford, visit the Central Florida Zoo’s Asian Lantern Festival, tour Daytona International Speedway, scout fuel access by dinghy with close alligator encounters, and share favorite restaurants, golf courses, and marina...

In this episode, Chris and Deb check in from Florida with a story that perfectly captures the spirit of the Great Loop — part careful planning, part happy detour. They recap SeaDan’s time on the hard in Jacksonville, highlight standout boatyard work at Huckins, and share some favorite local discoveries, from golf courses and restaurants to an unexpected Jaguars game. Then the real adventure begins...

  Hosts: Chris & Deb Winnenberg Release Date: October 14, 2025 Description: Chris and Deb are back at the mic with stories that stretch from the banks of the Ohio River to the greens of TPC Sawgrass. In this episode, they revisit the riverside camp where their Great Loop dream first began 30 years ago — a sentimental stop that sparks memories of raising their kids on water-skis, campfires, and...

Chris and Deb are back with nearly 300 more miles under their keel! In this episode, they recap their journey from Fort Pierce to St. Augustine , with plenty of highlights along the way. Hear about surprise jewelry shopping and a great meal at 12A Buoy , a hot round of golf at the PGA Wanamaker Course , and an “oops” lesson in why you should always wash new boat fabrics. They also share their ding...

Join Chris and Deb as they embark on an unforgettable journey through sunny Florida! From the vibrant streets of Fort Lauderdale to the serene beauty of the keys, and the charming allure of Fort Pierce, their adventure is packed with exciting experiences and breathtaking views. Don't miss out on their stories of exploration, fun, and discovery. Hit subscribe and join the adventure!

EPISODE SUMMARY: This week, we say goodbye to the Keys and make our long-anticipated jump up the coast to Fort Lauderdale! But not before a little sandbar party, brewery-hopping, a surprise manatee visit, and some world-class ribs courtesy of “Brisket Bob.” Join us as we: ✔️ Hang at a 50-boat sandbar bash ✔️ Discover Florida Keys Brewing Co. and Square Grouper ✔️ Navigate a rental car fender bende...

This week on the Great Loop Podcast, Chris and Deb welcome special guests — Chris’s brother Todd and sister-in-law Tammy — for a full week of Keys fun, paddleboard spills, and waterfront memories aboard SeaDAN.

In this episode, Chris and Deb share their recent adventures in the Florida Keys, discussing their experiences exploring marinas, local attractions, and the unique lifestyle of living on a boat. They delve into the challenges and joys of traveling in the area, including their encounters with local culture, dining experiences, and outdoor activities like snorkeling and paddleboarding. The conversat...

After three sun-soaked weeks exploring the Florida Keys, Chris and the crew are back in Cincinnati—but not before making memories in Marathon and Islamorada. In this episode, we dive into the highs (and hilarious mishaps) of DIY scuba diving at Sombrero Reef, recount the best mini-golf course we've ever played, and share the story behind our accidental “Lost Buoy Dive Club.” We talk about the char...

In this conversation, Chris and Deb share their recent adventures in the Florida Keys, focusing on their experiences with dinghy exploration, wildlife encounters, diving, local dining, and boat maintenance. They discuss the beauty of Boot Key Harbor, the importance of wildlife conservation, and their plans for future family visits. The conversation highlights the joys and challenges of life on the...

In this conversation, Chris and Deb share their experiences at Marlin Bay Marina and their adventures in the Florida Keys. They discuss their travels, the unique aspects of Key West, and the challenges of living on a boat, including repairs and transportation. They also outline their future plans for exploring more of the Keys and potentially heading to the Bahamas.

In this episode, Chris and Deb share their exciting journey to Marathon in the Florida Keys, detailing their experiences with boat maintenance, navigating challenging waters, and their plans for exploration in the area. They discuss the importance of proper boat upkeep, the challenges faced during their trip, and the beauty of the Keys, all while sharing humorous anecdotes and insights from their...

In this conversation, Chris and Deb share their recent boating adventures, detailing their journey from Pine Island to Naples and Marco Island. They discuss the challenges and joys of cruising, including navigating under fixed bridges, enjoying local restaurants, and the importance of preparation when docking. They also recount a thrilling dinghy adventure and their plans for future travels to the...

In this episode, Chris and Deb share their recent adventures aboard SeaDan after returning from repairs. They discuss their journey through the canals, experiences with locks, and the beauty of Cayo Costa. The couple also recounts their visits to Cabbage Key and North Captiva, highlighting the local cuisine and unique experiences. They face challenges with fuel and navigation but enjoy the stunnin...