Milano–San Remo Cycling Route — Cipressa & Poggio

Milan-San Remo is the longest one-day race in professional cycling, nearly 300 km, and one of the five Monuments. This route doesn't cover the full distance; it rides the finale, the part that decides the outcome. The approach from Menton is excellent in its own right, but the race proper begins at San Lorenzo al Mare, where the road turns inland toward the Cipressa.

The first stretch is flat coastal riding. You cross into Italy after a few kilometres, roll through Ventimiglia and Bordighera, and at Ospedaletti pick up the Pista Ciclabile del Parco Costiero della Riviera dei Fiori, a smooth, traffic-free path built on the old Genoa-Ventimiglia railway, running 24 km right along the sea. The best part is the tunnels: cool and shaded, providing natural air-conditioning in the coastal heat. One of them, the Capo Nero tunnel, is decorated with phrases celebrating Milan-San Remo's most famous moments. The race itself doesn't go through it, but riding it is a highlight of its own.

At San Lorenzo al Mare the railway path ends and the Monument's finale begins. The road turns inland to the Cipressa: 5.6 km at 4.1%, winding up through olive groves with the Mediterranean opening up behind you. It was added to the race in 1982, and for decades it rarely decided anything. Then in 2025, Tadej Pogačar tore the race apart here, the first truly decisive Cipressa attack since Gabriele Colombo in 1996. One thing that surprised me riding it: the gradient is gentle enough that you carry real speed, so the tight hairpins turn into a game of brake-and-accelerate, sprinting out of each corner to hold your pace. Watching it on television, I'd never noticed that rhythm. Ride it hard and that momentum is the challenge; take it steady and it's a smooth climb with a view.

A technical descent and a few flat kilometres bring you to the Poggio di San Remo, more famous, and older: added in 1960 to break up the sprint finishes. It's short, only 3.6 km at 4.1%, with the same tight hairpins, ramps to 12% near the top, and the same sea views all the way up. This is where the race is most often won: Vincenzo Nibali in 2018, or Mathieu van der Poel's solo attack in 2023. The descent drops fast and technical straight into San Remo, then it's a flat 31 km back west to Menton. A note on the names you'll hear on these climbs: Eddy Merckx holds the record with seven Milan-San Remo wins, but he raced the Poggio, not the Cipressa. It didn't exist until six years after his last victory. Pogačar finally won the race himself in 2026.