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The destruction of the town at the hands of Prince Llewelyn, in
1260, provided a graphic demonstration to the Earls of Pembroke
that the defences of Tenby were inadequate for the important role
they wished to play in the colonisation of the south of the county.
It was decided to increase and extend the scope of the existing
flimsy defences of the town so that the entire settlement would
be enclosed behind an impregnable ring of walls, towers and gateways.
Within these structures the cliff-top castle would form yet another
defensive bulwark. At the same time a new street pattern would be
imposed on parts of the new town.
Construction of the new walls began under William de Valence, who
became lord of Pembroke around 1264. In 1328 Edward III granted
Tenby the right to levy dues on merchandise entering the town for
the next seven years. This order had two purposes: to help with
the construction and maintenance of wall and defences - murage;
and of quay - quayage.
The funds raised led to the construction of extra towers in the
curtain wall and the outer Barbican tower for the West gate - the
present Five Arches.
 In 1457 Jasper Tudor's Letters Patent made the Mayor and burgesses
of the town fully responsible for the upkeep of the walls and the
defence of the town. This led directly to the lower sections of
the walls being increased to six feet in thickness, to the walls
being considerably heightened, and in many places a parapet walk
added.
Outside
the landward walls, in what is now South Parade, and St Florence
Parade, a dry ditch nearly thirty feet wide was dug for extra protection.
In 1588, with the Spanish Armada threatening, the section of wall
to the south of the West Gate was rebuilt and strengthened Two large
gates led through the walls to the medieval town beyond. The North
gate was the largest of these and stood on the site of the present
Royal Lion Hotel. It controlled access to the Carmarthen Road. The
arch and walls over this entrance had been removed by 1706-7. A
later council order, dated 19th June, 1781, stated that 'that part
of the gateway' by projecting into the street is a great nuisance
and ought to be removed. 'It is hereby unanimously agreed that the
said gateway be taken down'. The old West Gate was the present Five
Arches
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Tenby town
walls