Jokes 'n' Smokes Caribbean Cigar Cruise 2027

Event Overview

Jokes 'n' Smokes Caribbean Cigar Cruise 2027 is a seven-night destination event combining premium cigars, stand-up comedy, Caribbean travel, themed entertainment, and community experiences. The cruise brings cigar enthusiasts together aboard Crown Princess for private activities, sponsor experiences, social gatherings, and visits to several Caribbean destinations.

Cruise Route & Setting

The 2027 cruise is scheduled to sail round-trip from San Juan, Puerto Rico, aboard Crown Princess. The itinerary includes stops in St. Thomas, St. Kitts, Dominica, Grenada, and Barbados, followed by a full day at sea before returning to San Juan.

Event Experience

Jokes 'n' Smokes is designed as a cigar lifestyle vacation rather than a traditional trade show or business conference. Guests can enjoy a relaxed environment centered on cigars, entertainment, travel, and connections with other members of the premium cigar community.

Advertised experiences include:

• Private cigar-smoking events and organized smoke sessions.

• Stand-up comedy performances and live entertainment.

• Themed parties, cocktail receptions, game nights, and social gatherings.

• Poker activities, cigar competitions, and the popular Longest Ash contest.

• Sponsor activations featuring premium cigar manufacturers and industry partners.

• Optional pre-cruise and post-cruise parties, excursions, and merchandise packages.

Tickets & Cruise Pricing

Cruise packages are sold by cabin category, with published prices starting from approximately $1,567 per person for an interior cabin. Oceanview, balcony, and mini-suite options are available at higher prices. A deposit is required to secure a reservation, and optional parties, excursions, merchandise, beverage packages, gratuities, and other cruise expenses may require additional payment.

Featured Cigar Partners

Cigar brands promoted in connection with Jokes 'n' Smokes include La Flor Dominicana, J.C. Newman Cigar Co., Rocky Patel Premium Cigars, and Ferio Tego. The final list of participating brands, comedians, hosts, excursions, and scheduled activities for 2027 may be updated as the event approaches.

Travel Planning

Guests should plan to arrive in San Juan before the ship's departure on March 14, 2027. Travelers attending the optional pre-cruise party should arrive no later than March 13. A valid passport and any required visas or entry documents should be confirmed based on the traveler's nationality and the cruise line's current requirements.

Important Booking Information

The event organizer advises that deposits and subsequent payments may be non-refundable. Guests should review the complete booking terms, cancellation conditions, cruise inclusions, smoking policies, and travel insurance options directly with the organizer before making a payment.