This would completely depend on time and place. The era referred to as the "Golden Age of Piracy" sometimes covers the entire century from about 1630 all the way to 1730 and spanning most oceans in the world. In the early part of this period, the buccaneers as they were called often skirted a fine line between piracy and legitimate privateering during times of war but they were generally tolerated by their respective governments. There were many notorious port towns in the Caribbean during this time such as Port Royal and Tortuga that became known as pirate havens, where not only were buccaneers tolerated by the local governors but often the buccaneers had almost free reign to do as they wished in these towns, even killing governors when they didn't cooperate. I've written a post about this here. Buccaneers would have almost always preferred to sleep ashore in inns or brothels whenever they got a chance in this period.

Later in this period toward the latter half of the 17th century, European governments began to both make greater peace with each other and expand their standing professional navies which made privateers increasingly more of a nuisance than a net benefit given their tendency to continue preying on "enemy" ships even when there was no war currently being waged. After 1670 when England signed the Treaty of Madrid with Spain, the town of Port Royal in Jamaica no longer became the safe haven for buccaneers and pirates it once had. The buccaneer leader Henry Morgan was arrested when he returned to Port Royal after raiding Panama in 1671 (although he was later knighted and made the new governor of Jamaica due to political maneuvering). To be sure, buccaneers still visited there but they had to be much more careful. Gone were the days when the Dutch buccaneer Rock Braziliano could openly rampage through the streets of Port Royal, flaunting all authority, and mutilating random passers by with his cutlass. For example, when the Scottish buccaneer James Browne landed in Jamaica in 1677 and tried to sell off an illegally captured Dutch cargo of slaves he was arrested for piracy by governor John Vaughan, tried and hung, although his crew was pardoned. Examples like him served as an example to other buccaneers that they had to be more wary about going ashore and flaunting their crimes, although many still got away with it. Browne's real mistake was that he tried to openly sell a huge amount of contraband (150 slaves) in Jamaica. If he had just wanted to stay at an inn without showcasing his crimes or even discretely sell a lesser amount of contraband I think he easily would have been able to do that and many buccaneers did.

During the 1680s, the French followed the example of England and cracked down on piracy in their Caribbean colonies and especially pirate havens like Tortuga. By the 1690s, the situation was increasingly unfriendly to pirates although in some circumstances they were still able to flagrantly get away with it and be accepted with open arms into port side towns spend their stolen wealth. I've written a post here that gets into how the governor of New York was in league with pirates like Thomas Tew in the early 1690s and Tew was welcomed back when he returned from his voyages and his men were allowed to carouse in the city. By the mid-1690s, that was cracked down on and pirates were pushed further to the margins. The international manhunt for members of the notorious pirate Henry Avery's crew in the late 1690s and the public trial and hanging of the privateer-turned-pirate William Kidd and members of his crew in 1701 after returning to New England served as a powerful example to other pirates to keep a low profile. By this point pirates would have to be very careful about visiting any major town or city lest their crimes be discovered just like any other type of criminal, though it probably wasn't very hard for most if they were smart about it (i.e. they would be unwise to go around spending lots of money they couldn't account for).

In 1702 the Spanish War of Succession broke out between Britain against France and Spain and many would-be pirates were once again commissioned as privateers. This made many of them not technically pirates for over a decade and allowed them to flourish in their old haunts in the Caribbean, especially a new town called Nassau on the island of New Providence in the Bahamas which functioned in a similar way as Port Royal and Tortuga once had. During this period, privateers could pretty much go into any town and stay at an inn without any trouble as long as they could show they could pass themselves off as legitimate privateers. However, this came to an end in 1713 when Britain made peace in the Spanish War of Succession and most of the British privateers had their commissions to attack French and Spanish ships revoked. When many of these privateers refused to stop attacking ships, the British government cracked down on them and in response they began for the first time attacking British ships with no regard to nationality.

The era from about 1713-1726 became the last major wave of piracy in the 18th century before it was suppressed. During the first five or so years after the end of the Spanish War of Succession, the many privateers-turned-pirate made their principle base on Nassau in the Bahamas which, again, functioned like Port Royal and Tortuga had in the 17th century. Pirates could go ashore there to carouse and spend their loot. Elsewhere in any major town they would have to be more cautious than ever to avoid suspicion of piracy for which they could be arrested and hung. Most of the time they would try to avoid any large towns. They were outlaws living on the fringes of society with their only true refuges being criminal enclaves like Nassau. In 1717 the British government offered a pardon to all pirates who surrendered themselves in an attempt to crack down on piracy, and finally invaded Nassau itself in 1718 to root out the remaining pirates and they succeeded in doing so. After July 1718, pirates had no real place at all that they could count on to offer them a safe haven from government authority. Some like Edward Thache (Blackbeard) sailed to the American colonies around South Carolina where he tried to negotiate a pardon for himself but was killed in November of that year after reverting to piracy to again. In the brief period that Thache was granted a royal pardon from piracy in June 1718, he briefly settled in Charles Town, South Carolina with members of his crew, married and bought property. Earlier while blockading Charles Town in May, an incident occurred in which Thache sent a prisoner ashore (accompanied by a couple of pirates to ferry him in the rowboat) in order to demand medicine chests from the town. Although the pirates were given medicine chests by the frightened townspeople, the pirates sent to collect it did not return to Thache's ship for several days because they decided to go off drinking in the town with friends of theirs. Probably one reason they were able to do this is that they were protected by the pirate flotilla blockading and threatening the town but I think it also shows how random pirates could often slip through the cracks in towns if they wanted to. It's not like they had a badge on them constantly identifying them as a pirate (they did not wear skull and crossbones insignia). As I said, Thache was killed in November 1718 and that put an end to him and many of his crew.

As an example of how pirates could sometimes pass themselves off as non-pirates in this period, the pirate Howell Davis repeatedly managed to pass himself off as a legitimate privateer or merchant to Portuguese and English officials off the west coast of Africa in 1719 where he and his crew were many times invited to stay ashore before he was finally discovered and killed in an ambush, as I discuss in this post.

By the 1720s, the remaining pirates were increasingly persecuted and on the run like never before and it really wouldn't have been smart to go ashore in any large town without being extremely careful. The successful pirates like Bartholomew Roberts and Edward Low stayed far away from large towns and were basically forced to live on their ships all the time or stop on uninhabited island or coastlines to make repairs and divide up their plunder. That might sound lonely but the pirates of this brief final period weren't planning to live their entire lives as pirates. Most of them just wanted to get rich quick by taking some good prizes and then abandon piracy to covertly retire somewhere. Some in fact succeeded in this either by accepting the royal pardon issued in 1717 and valid until 1718, and others by simply slipping away and being smart. The famous pirate Henry Avery may have in fact done this with a huge amount of stolen plunder in 1696 since he was never heard from again after sailing for Ireland. Other times, pirates would stop in non-Eurpopean towns and villages to get some pleasure on shore and often exploit the inhabitants. The largest example of this was the former pirate John Plantain's kingdom he created in Madagascar in the 1720s after deciding to stay behind after a pirating voyage which I discuss in detail in this post.