When formed, it consisted of the Borough of Boston and the wards of Burgh le Marsh, Friskney, Frithville, Ingoldmells, St Clement's, Scarbrough, Seacroft, Sibsey, Wainfleet, and Winthorpe in the District of East Lindsey.

[11] The constituency then consisted of the Borough of Boston, and the District of East Lindsey wards of Burgh le Marsh, Croft, Frithville, Ingoldmells, St Clement's, Scarbrough, Seacroft, Sibsey, Stickney, Wainfleet and Friskney, and Winthorpe.

The market town of Boston is an important administrative centre for rural Lincolnshire, and its modernised port, which brings thousands of tonnes of steel, timber and paper into the constituency, a key employer.

The resort of Skegness has recovered from a damaging dip in trade caused by pit closures in the East Midlands during the 1980s, and following regeneration through millions of pounds in EU grants, is now one of Britain's most popular resorts, particularly among the elderly during the winter months.Boston, Lincolnshire, is a historic town,[18] famous for the tower of St Botolph's Church, known by locals as the "Stump".

[21] The constituency also has a lower employment rate and a higher level of people on unemployment benefits than the averages for the region and the country.

[21] According to the 2011 UK Census, Boston was "home to a higher proportion of Eastern European immigrants than anywhere else in England and Wales".

[23] People born in other EU countries, most of whom came from Eastern Europe after the 2004 enlargement of the European Union, made up 13% of the town's population.

[25][26] The academics Robert Waller and Byron Criddle attributed his victory to the Referendum Party's decision not to stand, which they did because of Body's Eurosceptic views.

[27][28] Body's successor, the Conservative Mark Simmonds, won an even smaller majority of 1.3% over Labour in the 2001 general election (515 votes).

[33][34] UKIP also performed strongly in several local council elections in Boston on the same day, winning more than 20% of the vote in some wards.

[50] UKIP performed strongly in and near the town of Boston, which was historically a safe Conservative area; this was seen as a surprise and was attributed to voters being concerned about immigration and feeling ignored by politicians.

[54] On 11 August 2014, Simmonds resigned as a minister and announced that he would step down as the Member of Parliament for Boston and Skegness at the 2015 general election.

[55] Explaining his decision, he said that his salary and expenses of over £100,000 were not enough to maintain a home in London, which he said caused "intolerable" pressure in his family life.

[55] After Simmonds announced that he would not stand at the 2015 general election, the local Conservatives decided to select their candidate using the open primary system.

[57] Interviews were used to narrow down the number of applicants to four, with the winner then being chosen at a public meeting that all voters in the constituency could attend and vote in.

[59] Warman, who was 33 at the time of the primary, argued that UKIP's support in the area was partly due to "a real disconnect between voters and politicians"; his wife's family lived in the constituency.

[68] However, an internal poll conducted by UKIP (not released to the public) close to the election found a Conservative lead of seven points.

[72] Warman's maiden speech discussed the positive and negative effects of immigration on Boston and Skegness, saying that the pressures on public services "allowed divisive, single-issue political campaigns to flourish".

[75][c] On 29 April 2017, Paul Nuttall, the leader of UKIP at the time, announced that he was standing in Boston and Skegness, noting that the constituency had the highest Leave vote in the country.

[81] Liberal Democrats and Labour also planned to contest the seat, with the Green Party intending to if they could find the funds for a deposit.

[86] Based on estimates produced by Professor Chris Hanretty of Royal Holloway, University of London, Boston and Skegness had the third-highest vote share for the Brexit Party in the 2019 European Parliament election.

According to Hanretty, 56.4% of votes cast in the constituency were for the new anti-EU party, which was led by Farage, behind only Castle Point and Clacton.

[87] The seat was discussed in 2019 as a potential target for the Brexit Party in the next general election, due to the high level of support for leaving the European Union in the constituency.

[90] However, the Brexit Party support decreased over time,[91][92] and in the run-up to the 2019 general election, which took place in December, some analysts thought that the large Conservative majority made victory there unlikely.

[98] Leading up to the 2024 United Kingdom general election, analysts considered this constituency of interest for Reform UK due to its high Euroscepticism.