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 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

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.

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.

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 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.

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.

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 tips. From boat projects to drone plans, this episode captures why Sanford is one of our favorite unexpected Great Loop stops.

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 as they follow a weather window inland and head down the St. Johns River — a side trip that quickly becomes one of their favorite stretches of the entire Loop.

Along the way, they anchor in remote jungle-like coves, spot manatees and their first alligator, cross Lake George on glassy water, and finally settle into Sanford, a historic river town that feels instantly like home. They talk marinas, river life, e-bike explorations, breweries, wildlife, and why letting the Loop wander often leads to the best memories.

A relaxed, story-driven update filled with practical insights, favorite stops, and a reminder that sometimes the best moments come from listening to the weather and following curiosity.

 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 late-night laughter.

From there, the journey winds south to stormy St. Augustine and its unexpected treasures — a classic car museum full of chrome nostalgia, a speakeasy hidden in a historic ice plant, and a five-star meal that made them laugh as much as it dazzled.

The adventure continues north to Jacksonville Beach and Palm Cove Marina, where a chance encounter leads to golf clubs custom-built by a 50-year pro — and a surprise bar conversation with a former Lynyrd Skynyrd pianist who once opened for the Rolling Stones.

Then it’s on to the bucket-list moment every golfer dreams of: playing the 17th-hole island green at TPC Sawgrass. Spoiler alert — neither Chris nor Deb make the green, but they walk away with a story that’s pure SeaDAN magic.

Now back home in Cincinnati for the fall, they reflect on family, golf, and the joy of slowing down while C-DAN gets a little TLC at Huckins Boatyard. Looking ahead, they share plans to explore the St. Johns River — one of the few rivers in North America that flows south to north — before heading up the East Coast in 2026.

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 dinghy adventure to the Navy SEAL Museum and Little Jim’s, the thrill of watching a rocket launch in Titusville, and a full day exploring the Kennedy Space Center.

The trip continues north with wildlife encounters and beach strolls in New Smyrna, a quick but delicious stop in Palm Coast, and finally, days of historic charm in St. Augustine—complete with trolley tours, Castillo de San Marcos, and prepping for a bucket-list tee time at TPC Sawgrass.

It’s equal parts travelogue, boating lessons, and “did you see that?!” moments—classic Great Loop adventure storytelling.

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!