The Isle of Wight packs an extraordinary variety of coastline into a modest 147 square miles. You can walk chalk cliffs in the morning, sheltered woodland after lunch, and finish beside a harbour full of yachts. The island's paths are generally well signposted, the gradients are rarely punishing, and there is almost always a pub within reasonable stumbling distance of the trail. Here are five routes that show off the best of it.

Tennyson Down and the Needles

Start at Freshwater Bay and climb steadily towards the Tennyson Monument, a granite cross marking the spot where the poet laureate walked daily. The ascent is gentle enough to manage in conversation, and within twenty minutes you are on open downland with the Solent glittering on one side and the English Channel on the other.

From the monument, the path continues west along a broad chalk ridge to the Needles Old Battery. The final stretch offers the classic view: three jagged stacks of chalk rising from the sea, with the lighthouse standing sentinel beyond. On a clear day you can pick out Hurst Castle on the mainland.

• Distance: roughly 4.5 miles one way
• Terrain: chalk downland, exposed to wind
• Refreshments: the Needles Old Battery tea room, or the High Down Inn back towards Freshwater
• Getting back: the number 7 bus runs between Alum Bay and Freshwater Bay in season

Yarmouth to Freshwater Bay Along the Coast

If Tennyson Down feels too crowded on a summer weekend, this western stretch offers similar drama with fewer boots on the path. Begin at Yarmouth, a small town with a proper working harbour and a castle built by Henry VIII, then follow the coast path south past Fort Victoria Country Park.

The route threads through scrubby clifftop vegetation before dropping into a series of quiet coves. Compton Bay is the highlight, a long sweep of sand popular with surfers and fossil hunters. Keep an eye on the tide: at low water you can walk the beach rather than the clifftop, but the cliffs are soft and prone to slipping, so stay well back from the base.

• Distance: about 7 miles one way
• Terrain: mixed clifftop and beach, some steep steps
• Refreshments: the cafe at Compton Bay, or the Sun Inn at Hulverstone if you detour inland

Ventnor to Steephill Cove and the Undercliff

The Undercliff is the island's best-kept secret: a sheltered shelf of land beneath the cliffs between Ventnor and Niton, warmed by its own microclimate. Palms and subtropical plants grow here, and the walking is easier than the dramatic terrain suggests.

From Ventnor Esplanade, follow the path east through the Botanic Garden and on to Steephill Cove, a tiny fishing hamlet accessible only on foot. There are a handful of cottages, a couple of seasonal cafes, and a beach of smooth pebbles. It is the sort of place that makes you check the property prices on the noticeboard.

Continue towards St Lawrence and Niton for a longer day, or turn back along the upper path through woodland for a shadier return. The Spyglass Inn at Ventnor is a reliable spot for a late lunch with a sea view.

Bembridge and Culver Down

For an easier half-day, head to the island's eastern tip. Park at Bembridge and walk out along the harbour wall, then follow the coast path up to Culver Down. The climb is short and the reward is a wide panorama taking in Sandown Bay, the white cliffs of Culver, and the fort at Bembridge.

The path here forms part of the longer Bembridge Trail, and the going is mostly firm underfoot. Families with younger children will find this stretch manageable, with plenty of benches and a couple of ice cream vans in season. The Crab and Lobster at Bembridge is a good spot to finish.

Practical Notes for Walking the Island

The Isle of Wight's coastal path is waymarked with the familiar acorn symbol, but a paper map is still worth carrying. Signal is patchy in the Undercliff and along the western cliffs.

• Best time to go: May, June and September offer the best balance of weather and quiet paths
• Footwear: proper walking shoes rather than trainers; chalk and clay get slippery after rain
• Tides: check tide tables before any beach section, particularly around Compton and Brook
• Transport: the island's buses carry walkers and accept dogs; services are frequent in summer but thin out in winter
• Pubs: most coastal villages have at least one, and many serve food until 9pm

Walking the Isle of Wight coast is one of the great pleasures of southern England. The scale is manageable, the scenery is varied, and the island's gentle pace means you can finish a day's walking with sand in your boots and a pint in your hand before the sun goes down.