SKIFF Rally—a Five-Day Boat Camping Expedition Navigating the Waters of Orange Beach, Alabama, and Pensacola, Florida.
In this 42-minute adventure log, popular YouTube adventurer Trip Smith hosts the 2023 SKIFF Rally—a five-day boat camping expedition navigating the waters of Orange Beach, Alabama, and Pensacola, Florida.
Accompanied by a small group of fellow boaters, Smith sets off on a multi-stop journey combining open-water cruising, shallow-water anchoring, and historical exploration. The group kicks off their journey by crossing Pensacola Pass to visit Fort Pickens, showcasing proper bow-and-stern anchoring techniques to secure small pocket cruisers and skiffs against inlet waves. After exploring the Civil War-era fort and surrounding tunnels, the crew cruises toward Fort McRee and Big Lagoon, taking advantage of pristine weather and turquoise waters.
Throughout the five-day trip, the expedition stops at local waterfront landmarks, including a beach dock-and-dine visit to Pirates Cove for their famous burgers and an afternoon at the iconic Flora-Bama. Along the way, Smith provides practical boat-camping insight—sharing customized DIY sleeping setups, anchor management strategies for tight coves, and advice on adapting to overnight wind changes while anchored in locations like Cotton Bayou.
Despite minor mechanical setbacks that force one boat to retire early, the remaining fleet completes the loop, illustrating the utility and freedom of small, efficient pocket cruisers. Rich with aerial drone footage, underwater snorkeling shots, and camaraderie on VHF Channel 69, the video serves as an inspiring blueprint for small-boat coastal cruising along the Gulf Coast.