THE ADVENTURE COLLECTIVE® · Independent discovery and booking for outdoor travel
Set sail on The Lost Pearl for an unforgettable sunset cigar bar cruise around Hillsborough Bay. Enjoy scenic views, a lively pirate-themed atmosphere, and a complimentary cigar—perfect for a relaxed evening on the water.
Set sail on The Lost Pearl for an unforgettable sunset cigar bar cruise around Hillsborough Bay. Enjoy scenic views, a lively pirate-themed atmosphere, and a complimentary cigar—perfect for a relaxed evening on the water.
Book with The Lost Pearl
Verified experiences and guided adventures in the surrounding area.
Operated by The Lost Pearl · Tampa, Florida
Sailing through the shimmering waters of Hillsborough Bay, The Lost Pearl offers an experience that seamlessly blends relaxation with a touch of maritime charm. As you set out on the Sunset Cigar Bar Cruise, the boat’s deck becomes your vantage point for witnessing the vibrant colors of the setting sun reflecting off the bay’s gentle waves. This cruise provides a perfect escape for those looking to unwind while enjoying the unique ritual of savoring a fine cigar, with a complimentary J.C. Newman cigar included for each guest.
What makes this trip stand out is not just the scenic views, but the lively pirate-themed atmosphere, which adds a playful edge to your evening. Sip handcrafted cocktails from the full bar as the boat drifts past local landmarks and iconic shoreline sights, all set against a backdrop of sonic waves and a fiery sky. Hillsborough Bay itself boasts an interesting mix of urban coastline and protected natural areas, hosting a variety of bird species and marine life that occasionally make a splash near the boat.
The Lost Pearl’s cruise is ideal for both seasoned cigar aficionados and curious newcomers in search of a social yet serene outing. The relaxed vibe, combined with the stunning scenery and unique onboard amenities, makes this trip a stand-out activity in the Tampa Bay area. Whether celebrating a special occasion or simply enjoying a peaceful evening on the water, this cruise offers an enriching experience that perfectly captures the essence of leisure on Tampa’s waters.
Moderate.
6–8 hours.
Moderate fitness required; participants should be comfortable with outdoor activity.
Yes, reservations are recommended to secure your spot on this popular cruise.
While primarily aimed at adult guests, children over a certain age are welcome with adult supervision—please check with the operator for age restrictions.
The cruise provides a complimentary cigar, but you are welcome to bring your own if you prefer.
A selection of cocktails and beverages is available for purchase onboard.
The cruise typically lasts about 2 hours, from boarding to disembarkation.
Yes, the vessel is equipped with accessible seating options for guests with mobility needs.
Hillsborough Bay has been a vital part of Tampa's maritime history since the early 20th century, serving as a busy port and recreational hub.
The cruise supports local conservation efforts by promoting awareness of Hillsborough Bay's fragile ecosystem and wildlife.
The Lost Pearl is a themed pirate ship operating from Tampa, Florida, offering a lineup of interactive daytime and evening cruises on Hillsborough Bay and around downtown Tampa. The Lost Pearl provides a range of themed experiences designed for families, adults, and special occasions. Signature offerings include the Pirate Adventure Cruise — a 1.5-hour interactive voyage with treasure hunts and pirate games — and the Sunset Cigar Bar Cruise, which features a complimentary J.C. Newman cigar and a full bar for guests who prefer a relaxed, adults-only atmosphere. Seasonal and holiday events include A Pirate’s Christmas with festive games and floating ‘mail to Santa’ activities, the Holiday Lighted Boat Parade two-hour cruise to view illuminated vessels, and themed parties such as the Sunset & Full Moon Party and A Pirate’s Halloween. Many cruises offer complimentary beverages for adults or a free grog bar on special-event sailings. Family-focused events such as the Cannonball Countdown (a kid-friendly Noon Year’s Eve) and the Gasparilla Children’s Air Show and Fireworks Cruise provide lively, age-appropriate entertainment and prime viewing for aerial displays and fireworks. The Lost Pearl emphasizes immersive pirate-themed entertainment, accessible locations in downtown Tampa, and a mix of adult-oriented and family-friendly options to suit a wide range of guests.
Book with The Lost Pearl