The Great Loop Podcast

About The Great Loop Podcast

Originally from Cincinnati, Ohio, this married couple is embarking on their next great adventure. They’ve always been boat people and were excited when they had the opportunity to purchase their dream boat. They are now traveling around the great loop at their own pace and enjoying every minute. They plan to create a podcast interviewing different captains they meet along the route, giving tips to future loopers, and sharing their stories with those interested in a similar route. The Great Loop is a recognized waterway that follows major rivers, oceans, and currents. More importantly, it represents a journey and a great American adventure, similar to the Appalachian or Pacific Crest Hiking trails. Likewise, becoming a “Looper” is a membership into an exclusive community. Loopers will experience challenges and successes along the route, meet new friends, and visit local cultures. The opportunities are endless, and it’s an unpredictable adventure that will generate limitless stories.

Publisher

SEADan

Category

society & culture

Language

en

Explicit

No

First episode

28 Mar 2025

Latest episode

29 Jun 2026

Latest episodes

19 episodes in the feed.

1. 

   29 Jun 2026

   Captain's Log 19 |Cruising the ICW from Myrtle Beach to Norfolk | June 27th 2026

   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 Waterway, stopping in Southport, Wrightsville Beach, Mile Hammock Bay, Beaufort, River Dunes, Belhaven, Coinjock, and Portsmouth. Along the way, they encounter soft groundings, strong currents, gusty anchorages, a live military firing range, a dock line wrapped around a propeller, a record-breaking marlin tournament, a violent storm with nearly 70-mile-per-hour winds, and a rough crossing of the Albemarle Sound. The trip ends on an unforgettable high note when they arrive at Tidewater Yacht Marina just in time for Sail250 Virginia. From the top of CDN, they watch an international parade of tall ships and enjoy two nights of spectacular fireworks over the Norfolk waterfront. Now safely in the Chesapeake, Chris and Deb face their next big Great Loop decision: continue pushing north toward the Great Lakes or slow down and spend the summer exploring the Chesapeake Bay. Featured destinations: Southport, Wrightsville Beach, Mile Hammock Bay, Beaufort, Oriental, Belhaven, Coinjock, Portsmouth, and Norfolk. Episode topics: Great Loop cruising, Intracoastal Waterway travel, ICW anchorages, Albemarle Sound crossing, boat maintenance, docking in strong winds, severe weather aboard a boat, Sail250 Virginia, Norfolk tall ships, and Chesapeake Bay cruising

2. 

   28 May 2026

   Captain's Log 18 | From Hilton Head to Myrtle Beach Aboard SeaDAN | 5/27/2026

   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 USS Yorktown at Patriots Point Beautiful anchorages on the South Santee and Waccamaw Rivers Cruising through the Rock Pile Myrtle Beach adventures with family Broadway at the Beach and PopStroke Plus, Chris and Deb share what’s next as SeaDAN continues north toward Norfolk and the Chesapeake Bay.

3. 

   8 Apr 2026

   Captain's Log 17 | Crossing Hell's Gate | 4/7/2026

   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 bucket-list golf tournament experience, this leg of the journey is packed with stories, laughs, and a few lessons learned along the way.

4. 

   25 Mar 2026

   Captain's Log 16 | Wrapping Up Florida on the Great Loop | 3/23/2026

   14 views Mar 23, 2026 Captain's Log (https://www.youtube.com/playlist?list=PLseR2KfBqx_-20iibkAMqVR7pN7oNewBF) 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 gators by drone — this leg of the Great Loop had a little bit of everything. They share the realities of life on the water too — from pricey marina fuel and lost fishing rods to upgrading their onboard washer/dryer and navigating tricky tides along the Intracoastal. Plus, hear about their time at TPC Sawgrass, favorite waterfront restaurants, and what’s next as they head toward Savannah and Hilton Head. If you love boating, travel, or just good stories from the water — this one’s for you.

5. 

   17 Feb 2026

   Captain's Log 15 | Frozen Lines & Florida Sunshine – Life Aboard in Sanford

   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 discovering hidden gems like the Old Jailhouse restaurant and local breweries, they’ve been soaking up everything this charming river town has to offer. Highlights from this episode include: Their first overnight anchorage at Butcher’s Bend — complete with alligators, manatees, glassy water, and incredible star-filled skies Exploring Winter Park and finding what might be one of the best steaks ever Testing out alternative transportation options like bikes, rental cars, and the SunRail A competitive (of course) Topgolf outing More fun at their favorite German spot, Hollerbach’s And a true boater lesson learned the hard way: always tie down the dinghy cover when 40+ mph winds are in the forecast They also share what it’s like when a polar vortex makes its way to Central Florida — frozen hoses, icy dock lines, and a near $900 dinghy cover replacement that thankfully turned into a muddy but salvageable recovery mission. Looking ahead, family visits, a cruise up the St. Johns River, and dreams of anchoring off Harbour Town during tournament week are all on the horizon as they prepare to push north on the Great Loop. It’s everyday loop life — part adventure, part problem-solving, part golf, and always a good story. As always, thanks for tuning in and following along on the journey.

6. 

   20 Jan 2026

   Captain's Log 14 | Freshwater, Brick Streets, and Gator Crossings | 1/20/2026

   The hosts share their experiences detouring along the St Johns River in Sanford, Florida, highlighting favorite restaurants, attractions, and close encounters with alligators.

7. 

   29 Dec 2025

   Captains Log 13 | From the Hard to the Heart of Florida | 12/18/2025

   Chris and Deb recount their Great Loop adventure through Florida, detailing boat repairs, river explorations, wildlife encounters, and the charm of Sanford, revealing how unplanned detours create lasting memories.

8. 

   14 Oct 2025

   Captains Log 12 | Back on the River: From St. Augustine to Sawgrass | 10/14/2025

   Hosts Chris Winnenberg and Deb Winnenberg share stories from their river journey, reminiscing about family memories and navigating stormy seas from the Ohio River to St. Augustine.

9. 

   22 Aug 2025

   Captain's Log 11 | From Fort Pierce to St. Augustine: Dolphins, Dinghies & a Whole Lotta “Did-You-See-That?!” | 8/22/2025

   Chris and Deb share their journey from Fort Pierce to St. Augustine, detailing dolphin sightings, dinghy adventures, and lessons learned on the water.

10. 

    4 Aug 2025

    Captain's Log 10 | Heading North | 8/4/2024

    Chris and Deb recount their travels through Florida, highlighting experiences in Fort Lauderdale, the Keys, and Fort Pierce, as they head north.

11. 

    18 Jul 2025

    Captain's Log 9 | Sandbars, Storm Fronts, and Birthday Birdies | 5/9/2025

    The hosts recount their adventures leaving the Keys, including sandbar parties and brewery visits, as they head up the coast towards Fort Lauderdale.

12. 

    11 Jul 2025

    Captain's Log 8 | Retirement | 7/11/2025

    Siblings Todd and Tammy join Chris and Deb on SeaDAN, creating waterfront memories and paddleboard spills during a fun-filled week in the Keys; this is an interview episode.

13. 

    23 Jun 2025

    Captain's Log 7| Why We're Skipping Miami | 6-20-2025

    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 conversation highlights the beauty and excitement of life in the Keys, along with practical insights for f...

14. 

    23 May 2025

    Captains Log 6 | Pirates and Crab Pots | 5/23/2025

    Chris and the crew recount their Florida Keys adventures, including DIY scuba diving mishaps and encounters with sea turtles, after exploring Marathon and Islamorada.

15. 

    12 May 2025

    Captain's Log 5 | Diving, Repairs, and Exploring Marathon Key | 5/9/2025

    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 water, along with practical insights into boat insurance and maintenance.

16. 

    2 May 2025

    Captains Log 4 | Key West Adventurers | May 2th 2025

    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.

17. 

    18 Apr 2025

    Captains Log 3 | Marco to Marathon | 4/18/2025

    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 adventure.

18. 

    11 Apr 2025

    Captains Log 2 | From Pine Island to Naples | 4/11/2025

    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 Florida Keys, emphasizing the beauty of the locations and the camaraderie experienced along the ...

19. 

    28 Mar 2025

    Captain's Log 1 | Back in the Water | 3/28/2025

    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 stunning scenery and marine life along the way. The episode concludes with plans for future stops and ac...

Reach and audience

Public platform figures. Ratings count people who left a rating, not total listeners.

Apple Podcasts (US)

5.0 / 5

3 ratings