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With Weymouth and Portland scheduled to host 2012 Olympic sailing events the project reopened; the local authorities favouring a more environmentally friendly proposal than in the 1990s. On 5 April 2007, Dorset County Council granted planning permission for a modified proposal including a single carriageway running 7 kilometres (4 mi) north, and a 1000-space park-and-ride scheme, costing £84.5 million. Without major delays, work is expected to commence in 2008; it was agreed that the work be completed in three years, in time for the 2012 Olympic sailing events.

On the shores of Portland Harbour, 3 kilometres (2 mi) south of Wyke Regis, is Weymouth and Portland National Sailing Academy, where the sailing events of the 2012 Olympic and Paralympic Games will take place. The main reason that the resort was chosen to be an Olympic venue was because the National Sailing Academy had only recently been built, so no venue would have to be built. However, as part of the South West of England Regional Development Agency's plans to redevelop Osprey Quay, in which the academy is built, a new 600-berth marina and an extension with more on-site facilities will be built.[90] Weymouth and Portland are likely to be the first in the United Kingdom to finish building a venue for the Olympic Games, as construction started in October 2007 and will be finished at the end of 2008.

The waters of Weymouth and Portland were credited by the Royal Yachting Association as the best in Northern Europe for sailing. Local, national and international sailing events are regularly held in the bay; these include the J/24 World Championships in 2005, trials for the 2004 Athens Olympics, the ISAF World Championship 2006, the BUCS Fleet Racing Championships, and the RYA Youth National Championships. Weymouth Bay is a venue for other water-sports the reliable wind is favourable for wind- and kite-surfing. The sheltered waters in Portland Harbour and near Weymouth are used for angling, diving to shipwrecks, snorkelling, canoeing, jet skiing, water skiing, and swimming. The town also has a successful cricket club, who are currently in the Premier Division of the Dorset Saturday League.

The beach volleyball classic is held on Weymouth beach every July.Weymouth's wide and shallow sandy beach is used for swimming and sunbathing during the tourist season, and for beach sport events throughout the year, including beach motocross, the International handball championships and the beach volleyball classic. The international kite festival, held in May each year on Weymouth Beach, attracts around 40,000 spectators to the esplanade from around the world.

The local football club, Weymouth F.C. or 'the Terras', are outside the Football League but, in common with other non-league clubs, they became professional in 2005. The team enjoyed erratic success at their level; twice playing in the third round of the FA Cup, the highest club competition level. At the end of the 2005-06 season the team became champions of the Conference South (the sixth level of English football) meaning that they compete in the Conference National (the fifth level) for the first time since 1989. The Terras' ground is the Wessex Stadium; its record attendance is 6,500 against Nottingham Forest in the FA Cup 2005-2006 season.

The Wessex Stadium is out of town, but until 1987 the team played at a ground near the town centre, which is now an Asda supermarket. The club's move pre-dated the move to new out-of-town grounds by professional league clubs, and was the first football stadium opened in England in 32 years. Motorcycle speedway racing was staged at the stadium from 1954 until the redevelopment; Weymouth's team was revived in 2003, and 'the Wildcats' race at a track adjacent to the stadium. In 2005 a scheme was proposed to rebuild the Wessex Stadium to occupy a pitch-and-putt golf course, coincidentally with Asda building on the previous stadium site. Although the plans were to move by August 2007, the scheme was shelved before construction could begin.