SpringMarch - May
The Caldey Island ferry restarts for the season around Easter, and the town is calmer than it gets by midsummer.
Spring is when Tenby's boat trips come back. The Caldey Island ferry typically resumes around Easter after its winter break, and the crossing runs on a fuller schedule from April, so this is the first real window to make the trip out to the monastery without a summer queue at the harbour steps. The three beaches are at their emptiest, the walk out to Waterwynch Bay along the coast path is manageable without crowds, and North Beach car park still has space most mornings. Confirm the ferry's current sailing days directly before travelling, since the schedule tightens around the shoulder-season dates and does not run on Sundays.
SummerJune - August
Peak season and the busiest weekend of the year: Ironman Wales in September aside, July and August fill the town from breakfast onward.
June to August is Tenby at full stretch. The three beaches get properly busy, the North Beach car park fills early, and restaurant tables are genuinely hard to get without booking between six and half eight in the evening through July and August. It is also the best window for the harbour boat trips: the Caldey Island ferry and the seal safari and wildlife boats run their fullest schedules, and Castle Beach's low-tide crossing to St Catherine's Island is worth timing carefully against the tide table rather than the crowd. The Long Course Weekend multisport festival lands in late June or early July and fills the town's accommodation, so book well ahead if a summer visit lines up with it.
AutumnSeptember - November
Ironman Wales in September closes roads and fills every bed in town; Tenby Arts Festival runs the same month with a gentler crowd.
September is Tenby's biggest month, for two very different reasons. Ironman Wales, run since 2011 and widely rated one of the toughest courses on the circuit, starts and finishes in the town and brings road closures, a very early alarm if you are staying centrally, and a fully booked town for the whole weekend; if that is not the draw, avoid mid-September or book a year out like the athletes do. Tenby Arts Festival runs across town venues the same month with music, poetry and drama and a much calmer crowd. Once both events clear, late September and October are genuinely good: mild sea temperatures, thinner crowds, and Lamb-House-style museum and heritage openings still running full hours before the winter cutback.
WinterDecember - February
The Boxing Day Swim off North Beach has run since 1970 and is the one date the off-season town properly fills for.
Winter empties Tenby out, in a good way if a quiet walled town on a stormy headland appeals. The Caldey Island ferry stops for the season, several harbour-facing restaurants cut back their opening days, and the museum and Tudor Merchant's House move to reduced winter hours or close for the season, so check before building a visit around them. The exception is Boxing Day, when the town's charity sea swim off North Beach, running since 1970, draws a large crowd of swimmers and spectators into the cold for a genuinely local tradition rather than a tourist event. A fire-lit pub afterwards, the Coach and Horses or the Baytree, is the reward for anyone who did not go in the water.