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   [Travel Destinations](/articles/travel-destinations)# Capt. Trip & His Personal Boating Adventures: Orange Beach, Alabama

 Aug 30, 2026

 

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  ### **Weekly BoatTEST Captain Showcase**

*Here at BoatTEST, we review thousands of hulls, technical architectures, and performance data points—but at the end of the day, boating is all about the pure passion for the water and the stories we build out there. That is exactly why we fell in love with Captain Trip Smith's channel, and why we just had to ask him to join our team.*



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#### 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.



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⚓

#### **Meet Captain Trip Smith**



**Capt. Trip Smith** holds a USCG 100-Ton license and brings more than two decades of hands-on experience navigating everything from center consoles and cruisers to his own C-Dory 22.

Trading in the typical 9-to-5 grind for a life on the water, Trip has built a passionate following as an adventure video creator. His background spans firefighting, outboard mechanics, boat rigging, and fiberglass restoration—making him just as skilled at fixing a hull architecture issue as he is at teaching his boys how to haul a line. We are thrilled to showcase his authentic storytelling, outdoor expertise, and family seafaring adventures here every week.



[ **Follow Trip Smith on YouTube** ](https://www.youtube.com/@TripSmith)