Good Times Key West

Good Times Key West runs its private charter operation from a dock at Mellow Cafe & Gastropub on North Roosevelt Boulevard, where guests meet the crew at a tiki hut before heading out for the day. Captain Justin, who owns and operates the business, has built the company around fully customizable private charters rather than a fixed public tour schedule, ranging from short two-hour outings to multi-day adventures for guests who want to see more of the Lower Keys than a single afternoon allows.

The range of trip types on offer is broad, covering fishing charters, snorkeling excursions, island hopping among the smaller keys near Key West, dolphin and wildlife watching, and standard sunset cruises, along with full-day trips out to Dry Tortugas National Park, a seventy mile boat trip to a remote coral atoll and nineteenth century fort that is one of the more ambitious day trips available from Key West. Multi-boat outings are also possible for larger groups that need more than one vessel.

Beyond the standard charter formats, the business has built out a set of more specialized offerings, including sea weddings performed aboard the boat, extended multi-day trips, dockside accommodation arrangements, expert guide services for groups that want more than just boat operation, and vessel delivery services. That range suggests an operation set up to say yes to a fairly wide variety of custom requests rather than steering every customer toward the same handful of packaged trips.

Operating multiple vessels with experienced captains allows Good Times Key West to run more than one type of charter simultaneously, an advantage for a business built around full customization rather than a single boat running one script all season. The Dry Tortugas option in particular sets it apart from many of the smaller inshore-focused charter operations around Key West, since reaching the park by private boat requires a larger, more capable vessel and a crew comfortable running open water well beyond sight of land, a logistical step up from a standard half-day reef or sandbar trip.

Because the operation runs multiple vessels rather than a single boat, larger groups or requests that combine several activity types, such as a morning of fishing followed by an afternoon at a sandbar, can generally be accommodated within one extended charter rather than requiring separate bookings. The Dry Tortugas option in particular is typically arranged as a full day trip given the distance involved, and guests are generally advised to bring sun protection and a change of clothes given the extended time on open water. Meeting at the tiki hut dock rather than a formal marina office gives the whole operation a fairly relaxed, low-key check-in process before heading out.