Skip to main content
Adventure Collective Logo
Adventure ExperiencesLocal ExpertsLocationsAbout
Menu

The Adventure Collective

The Adventure Collective Discover, plan, and share your outdoor adventures with our global community of explorers.

Add as a preferred

source on Google

Explore Adventures

  • All Adventures
  • Boat Charters
  • Water Activities
  • Fishing
  • Land Adventures
  • Motorized Land
  • Winter Sports

Explore Adventures

  • Aerial Adventures
  • Wildlife & Nature
  • Camping & Overnight
  • Climbing & Mountaineering

Find Local Experts

  • Browse Local Experts
  • Become a Featured Expert

Company

  • About Us
  • Editorial Policy
  • Advertising
  • Add Your Business
  • Contact Us
  • The Adventure Network

Legal & Privacy

  • Privacy Policy
  • General Terms and Conditions
  • Cookies and Marketing Preferences
  • Legal Notice
  • Information according to the Digital Services Act
  • Do not Sell or Share my Personal Information
  • Sitemap

Adventure Town Guides

View All Adventure Towns

© 2026 The Adventure Collective. All rights reserved.

Editorial Policy
Skip to main content
Adventure Collective Logo
Adventure ExperiencesLocal ExpertsLocationsAbout
Menu

The Adventure Collective

The Adventure Collective Discover, plan, and share your outdoor adventures with our global community of explorers.

Add as a preferred

source on Google

Explore Adventures

  • All Adventures
  • Boat Charters
  • Water Activities
  • Fishing
  • Land Adventures
  • Motorized Land
  • Winter Sports

Explore Adventures

  • Aerial Adventures
  • Wildlife & Nature
  • Camping & Overnight
  • Climbing & Mountaineering

Find Local Experts

  • Browse Local Experts
  • Become a Featured Expert

Company

  • About Us
  • Editorial Policy
  • Advertising
  • Add Your Business
  • Contact Us
  • The Adventure Network

Legal & Privacy

  • Privacy Policy
  • General Terms and Conditions
  • Cookies and Marketing Preferences
  • Legal Notice
  • Information according to the Digital Services Act
  • Do not Sell or Share my Personal Information
  • Sitemap

Adventure Town Guides

View All Adventure Towns

© 2026 The Adventure Collective. All rights reserved.

Editorial Policy
Water-activities: The Lost Pearl Sunset Cigar Bar Cruise in Hillsborough Bay

Water-activities: The Lost Pearl Sunset Cigar Bar Cruise in Hillsborough Bay

  1. Home
  2. Local Experts
  3. The Lost Pearl
  4. Water-activities: The Lost Pearl Sunset Cigar Bar Cruise in Hillsborough Bay

Adventure Brief

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.

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.

Hang tight — photos are loading

This usually takes just a second.

Trip Details from the Operator

Keep the Adventure Going

More ways to explore the area's outdoor wonders

Frequently Asked Questions

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.

Local Insights

Wildlife

  • dolphins
  • ospreys

History

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.

Conservation

The cruise supports local conservation efforts by promoting awareness of Hillsborough Bay's fragile ecosystem and wildlife.

Related Adventures & Guides

  • See other trips from The Lost Pearl
  • Explore more Tampa adventures
  • Browse more water activities experiences
  • Read our Tampa travel guide

Operated By

The Lost Pearl

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.

About The Lost Pearl

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.

Festive pirate ship illuminated beside floating Christmas tree in harbor
Family pirate-themed kids' party on outdoor ship deck in Tampa Bay

Home Port

Tampa, FL

Departures from downtown Tampa

Typical Duration

1.5 hrs

Most cruises last one-and-a-half hours

Family-Friendly

Yes

Events for kids and adults

Tours Offered

11 experiences

Year-round themed sailings

CTA Section Background Image

Reserve a Lost Pearl Cruise in Tampa Today

Secure tickets for themed pirate adventures, sunset sailings, and holiday parties on the Lost Pearl — book online for the best dates and departure times.

Adventure Tips

Arrive early to secure your spot

Arriving 15-30 minutes before departure ensures a good seat and the best sunset views.

info

Bring layers for changing weather

Evenings on the water can be cooler; dress in layers and consider bringing a light jacket.

warning

Sip responsibly and enjoy the atmosphere

Moderation enhances your experience—relax and soak in the views without rushing.

info

Capture the sunset from the bow

The front of the boat offers unobstructed views for stunning photos during golden hour.

essential

Recommended Gear

Light jacket or sweater

Evenings can be cool; dress in layers for comfort.

spring|fall|winter

Essential

Sunscreen

Protect your skin during the daytime before the cruise.

summer|spring

Essential

Camera or smartphone

Capture the dramatic sunsets and scenic views.

Essential

Reusable water bottle

Stay hydrated during your cruise adventure.

Essential