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Route guide

Routes and destinations

Areas our boats often visit from Tampa, the usual stops in each and suggested trip lengths. This is general geography; the actual route depends on that day's wind and sea.
  1. Two-masted wooden schooner on open blue waterSample image

    01 · Hourly or full day

    Hillsborough Bay and downtown

    The shortest route: out of the marina and along the downtown waterfront and the upper bay.

    Popular stops: Downtown waterfront, Davis Islands, Hillsborough Bay, Old Tampa Bay

    The upper bay is sheltered compared with the open Gulf, which makes it the usual choice for hourly trips and sunset cruises.

  2. Wooded point and a small sandy cove, from aboveSample image

    02 · Full day

    Mouth of Tampa Bay

    Islands and beaches where Tampa Bay meets the Gulf, a common goal for full-day trips.

    Popular stops: Egmont Key, Fort De Soto area, Shell Key

    It takes a while to get there from downtown, so plan a full day. Some islands are protected areas with their own landing rules; the captain will tell you before you go ashore.

  3. Light blue shoreline lined with rocksSample image

    03 · Full day or 1 - 2 nights

    Anna Maria Island and the south shore

    Beaches and passes along the southern side of the bay entrance.

    Popular stops: Anna Maria Island, Longboat Pass, Sarasota Bay

    Conditions near the passes can change quickly with wind and tide; this area is easier to enjoy on a full day or an overnight plan.

  4. Sailboats anchored in a calm cove below a pine-covered pointSample image

    04 · Full day or weekend

    Clearwater and the Pinellas beaches

    Gulf-side beaches and islands north of the bay, often visited on longer day trips and weekend charters.

    Popular stops: Clearwater Beach, Caladesi Island, Honeymoon Island

    A one-way charter between Tampa and the Clearwater area can be arranged; ask ahead about the boat and available dates.

  5. White sand beach and turquoise water with a sailboat offshore, from aboveSample image

    05 · 3 - 7 nights

    Multi-night Gulf Coast routes

    Longer routes south along the Gulf Coast, anchoring off barrier islands and coastal towns.

    Popular stops: Sarasota, Venice, Boca Grande, Charlotte Harbor

    These areas are far from Tampa; plan a multi-day charter or a one-way trip.

Good to know when picking a route

When do trips run?
Trips run year-round on the Gulf Coast. Spring and fall tend to bring milder temperatures; summer is hot, with frequent afternoon thunderstorms.
How does weather change the route?
In summer, thunderstorms often build in the afternoon, and winter cold fronts can bring strong wind. The captain picks sheltered spots and timing, so the same route is not run in the same order every day.
How long do you stay at each stop?
A swim or lunch stop usually lasts one to two hours. The length depends on the number of stops and your return time.
Can we go ashore?
Some spots have a beach you can walk onto, others are for swimming only. Whether landing is allowed depends on local rules, especially in parks and wildlife areas; the captain will tell you ahead of time.
Message us to plan a routeSee the boats

This page is for general information only and is not navigation, weather or safety advice. Channel access, restricted areas and anchoring rules can change; the captain checks current conditions every day.