Cabins are selling fast — 2026 sold out completely.
Embark on the Ultimate Cigar Lover’s Adventure
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The people on this cruise aren’t passengers. They’re your people.
Aficionados who know the difference between a good draw and a great one. Who show up dressed for Sundresses & Brims. Who laugh loud at the Sticks & Giggles Comedy Show and then stay up comparing blends under open Caribbean skies.
Seven uninterrupted days aboard the Crown Princess. World-class cigars from our premier sponsors. Exclusive J&S events — comedy shows, game nights, cigar smoke-outs, themed parties, and port excursions you can’t book anywhere else – San Juan, St Thomas, St Kitts, Dominica, Grenada, and Barbados.
Like a perfectly aged stick — this experience only reveals itself to those who light it up.
2026 sold out. 2027 will be no different.
Before you set foot on the Crown Princess, we’re already celebrating.
Join us the night before sailing — Saturday, March 13, 2027 — for the Jokes ‘n’ Smokes Pre-Cruise Cigar Party. Great music, premium cigars, craft cocktails, and the moment you realize these are your people.
*Pre-Cruise Cigar Party is an additional fee. Venue details TBA.
The moment that horn sounds, the clock stops and the fun starts.
Seven days of cigar smoke-outs under open skies, game nights that go late, comedy shows that go hard, cocktail parties, the Longest Ash competition, Sip Puff & Paint, poker nights, and memories that don’t need a filter.
There is always something happening on a Jokes ‘n’ Smokes cruise. Always.
You didn’t come to blend in.
Our signature “Sundresses & Brims” themed party is where the leaf community dresses up, shows out, and shows off. Ladies bring their most elegant sundresses. Gentlemen bring their most debonair hat — and a complete outfit (yes, that’s the rule). Music, laughter, and the kind of energy you only get when everyone in the room came to be there.
— Bill SanFelice, Guest
— Dean Elmore, Guest
— Thurland Adams, Guest
Be first to get exclusive discounts, event updates, and insider access for the Jokes ‘n’ Smokes 2027 Caribbean Cigar Cruise aboard the Crown Princess — March 14–21, 2027.
