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The inner harbour at Weymouth was refurbished in two phases, in 1994-1996 and in 2002, to include a new marina with hundreds of berths for pleasure boats, cruisers and sailing boats.Local boats offer fishing and diving trips, pleasure cruises along the Jurassic Coast, and thrill-rides to the Isle of Portland.

Brewers Quay museum and shopping centre on the harboursideThe main shopping centre in the area is in Melcombe Regis, consisting of two pedestrianised streets (St. Thomas's and St. Mary's Street), shops along the esplanade, and a new precinct stretching from St. Thomas's Street to the harbourside, built in the 1990s. There are shops and restaurants in the pedestrianised Hope Square and Brewers Quay, which are linked to the town centre by town bridge and a small passenger ferry service across the harbour. In 2005 the town centre had 292 shops and 37,500 square metres (404,000 sq ft) of floorspace, and there was 0.4 square kilometres (100 acres) of industrial estate in the area. Weymouth, Portland and Chickerell have been a Fairtrade Zone for three years.Fashion company New Look has its national head office in Weymouth, and until 2005 the company's regional distribution centre was based at the same site.[68] Plans were approved in 2007 to develop the New Look site to include new headquarters, retail warehouses and industrial units, a hotel, fire station, and a medical centre with ambulance station.

Weymouth railway station is the terminus of the route from London Waterloo and the route from Westbury and Bristol. Its size was appropriate for the rail traffic that came in and out of Weymouth on summer Saturdays, however it was oversized as trains became less popular, and was demolished in 1986. A smaller station took up part of the site, and the rest was given to commercial development. Parts of the South West Main Line west of Poole have been reduced from dual to single track; as part of preparations for the 2012 Olympic Games, local councils have lobbied the Department for Transport to relay the track and increase services to London and Bristol, and to introduce new direct services to Exeter. Services to London Waterloo began running every 30 minutes from December 2007, but services through Bristol to Cardiff were reduced.

An unusual feature of the railways in Weymouth was that until 1987 trains ran through the streets along the Weymouth Harbour Tramway to the Quay station at the eastern end of the harbour, to travel to mainland Europe by sea. Due to declining business, goods traffic ceased in 1972, but passenger services continued until 1987, when these services ceased from lack of use. The Quay Station houses the Condor Ferries Terminal; Condor Ferries' main UK port is Weymouth, and the HSC Condor Express runs from the harbour to the French port of St Malo, and the Channel Islands of Guernsey and Jersey.

Local bus services are run by First Hampshire & Dorset, which bought the local Southern National company. Services run from Weymouth to the Isle of Portland, Dorchester, Bournemouth, Wool, Beaminster, Axminster, other villages and the town's holiday parks. Weymouth is connected to towns and villages along the Jurassic Coast by the Jurassic Coast Bus service, which runs along the route of 142 kilometres (88 mi) from Exeter to Poole, through Sidford, Beer, Seaton, Lyme Regis, Charmouth, Bridport, Abbotsbury, Weymouth, Wool, and Wareham. This service is convenient for walkers who can ride the bus to or from a walk along the coast.