Booking lodging for a group
A larger suite or connecting rooms works better for a group than several separate standard rooms scattered across a resort — call the hotel directly rather than booking online only, since larger resorts often have group or party-specific booking desks that can do more than the standard website flow.
Book the big-ticket items early
A specific show, a table at a popular club, or a group dinner reservation at a well-known restaurant can sell out or fill up well in advance of a weekend, especially around holidays — lock in anything non-negotiable to the trip before you arrive rather than assuming you can walk in.
Pace a multi-day trip
Groups that try to pack every night with a big, expensive event tend to burn out by day two — mixing at least one lower-key night (a casual dinner, a quieter bar) with the bigger planned nights out generally makes for a better whole trip than back-to-back peak nights.
Splitting costs as a group
Agree on a shared payment approach for group items (a table, a group dinner bill) before the trip rather than sorting it out in the moment — a simple shared expense app removes a genuinely common source of trip friction.