City brief Caribbean cruise The fare includes the dining room. Specialty, drinks, and the dock kiosk are the trap. Loading the printable brief… VacationMath orientation — not live rates When to go Early May, early September, and late October–early November — after spring break, before holiday sailings. Top money-saving tips Run the drink-package break-even before you tap yes. À-la-carte wins if you are not a five-drink day.Interior or obstructed oceanview on Lean. You bought the itinerary and the deck, not the porthole.Main dining room every night on Lean. One specialty night only if leftover covers it.One independent port walk plus one ship excursion — not three dock tours.Automatic gratuities are a line (age 2+). They are not optional math and they are not buried in the fare.Shoulder weeks (early May, early September) cut the cabin and the air to Florida ports.Kids soda is often the only package that wins on a short sailing. The latte habit is not a package.Room-service fees add up — backup, not breakfast. The buffet is already in the fare. Build a hard-budget plan