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The bridge as an official height of 18 meters in C-Map and of 20.5 in the Imray pilot. Other sources say 20 at HW and 23 m at LW. Boats with a 20.8m mast have cleared it (see external link below).
The Guadiana is tidal and the current can run quite fast; sail with the tide and go under the bridge near low water which will give more clearance.
There are no electronic charts and no channel marking buoys north of the bridge. The depths can be more than 20m in places, sometimes right near the shore. Safest water is on the side of the steepest bank. There is a shoal well out to the middle of the river in the first bend just above the bridge on the east side. Tributaries often have a gravel bank on their south sides. The biggest is the one at Alcoutim, just north of the pontoons, which will actually dry to nearly the middle of the river at LWS. South of Pomarão is a sandbank on the west side, then a rocky patch on the east side, where navigating gets tricky. Even trickier it gets near Mertola, but we know boats of 2.1m draught have gone there (and we know boats of lesser draught getting badly stuck).
Anchoring can be done just about anywhere. The holding is fairly good in muddy sand but there are many gravel patches. Experience will show where the current runs strongest and where the most debris gets caught in the anchor chain. “Caña”, long pieces of reed, can be quite a hazard. Large rafts of them can wrap themselves around anchor chains and cause boats to drag. Beside caña there are (semi)submerged logs and the occasional dead sheep to bump against the boat or get in anchors or chains. As the river is tidal, the four times a day change of direction may cause anchors to break free and mooring lines to get tangled. There is no swell once around the first corner, but wind against tide can build up a chop and make anchoring uncomfortable. Getting ashore by dinghy is not easy when there is no public pontoon available especially not with an inflatable dinghy.