Islamorada food tour adds sunset boat cruise with waterfront dining stops

Craig Zabransky has taken Florida Keys Food Tours offshore in Islamorada, launching a three-hour evening excursion that folds waterfront dining, local history and a sunset cruise into one premium outing for up to six people.

The company lists the new experience as the Islamorada Sunset Boat Cruise Food Tour, priced from $1,400, with a route that starts at a harbor and docks at three additional local favorites for cuisine and cocktails. That puts the boat trip well above Florida Keys Food Tours’ other Islamorada offerings, including the original walking tour from $109, the locals’ happy hour tour from $99, the sunset happy hour tour from $129 and the golf cart food tours from $179.

The maiden voyage began at Wahoo’s Seafood Bar & Grill, which describes itself as a landmark waterfront restaurant sitting right above Whale Harbor Marina. Guests sampled wahoo bites, fried pickles and Key lime mustard aioli before boarding a luxury pontoon operated by Poppa Wahoo Collective and heading to Ocean View Pub, known locally as OV. The format gave diners a moving front-row seat to the water as well as the meal, a combination that Zabransky has built around the Upper Keys for nearly a decade.

The draw is not just the food. Zabransky also used the tour to narrate the layered history of the surrounding waters and islands, including Lignumvitae Key, Indian Key Historic State Park and Alligator Reef Lighthouse, while explaining the role mangroves play in the Keys’ ecosystem. Maggie Mistal, his wife and business partner, said the appeal was simple: people want to get on the water, and the boat version lets them do that while still visiting multiple restaurants.

That formula fits a tourism market where experience matters as much as a reservation. Monroe County says visitors spend about $3.5 billion a year in the Florida Keys, supporting more than 24,000 local jobs and generating nearly $400 million in tax revenue. The county’s 2024 visitor profile recorded 4,663,792 total trips and 18,862,818 visitor days, though visitor days fell 8.83% from 2023, a signal that operators are competing harder for high-value outings that feel distinctly Keys.

The route’s history stops deepen that pitch. Indian Key Historic State Park is an 11-acre island accessible only by boat, and Florida State Parks says it became the first county seat for Dade County in 1836 after Jacob Housman bought it in 1831 to build a wrecking empire. Lignumvitae Key Botanical State Park is also accessible only by boat or kayak; the state says William J. Matheson bought it in 1919, and the park is open Thursday through Monday from 8 a.m. to 4 p.m., with ranger-led tours Friday through Sunday at 10 a.m. and 2 p.m.

Alligator Reef adds another layer of local identity. Established in 1873, the light station sits about four miles offshore from Islamorada, and NOAA says the sanctuary preservation area is known for its diverse marine life, including a 1968 survey that documented 516 coral reef fish species. For Islamorada, the new boat tour turns that history, scenery and dining scene into one higher-priced evening built for visitors who want the Keys package in a single trip.