Clearwater & St. Petersburg, Florida
Dock and Dine Charters
Arrive at lunch by boat instead of by car. Captain Keith ties up at the restaurant dock and your group walks straight in — no parking, no traffic, and nobody has to stay sober to drive home.
Dock and dine means pulling up to a waterfront restaurant by boat and walking straight in from the dock. Six restaurants across Clearwater and St. Petersburg, every one of which Captain Keith has personally docked at.
Available on the 4-hour Half-Day Island Escape ($575 flat, up to 6 guests) or longer — not on the 2.5-hour charters. There is no extra charge for the stop. You pay only for your own food and drinks.
And because Captain Keith is your licensed captain for the whole day, every adult in the group can have a drink at lunch.
Why it needs the four hours
Docking, ordering, eating, settling up, and getting back underway realistically takes an hour and a half. On a 2.5-hour charter that leaves under an hour of actual water time, which is not the day anyone books.
There is a second reason. Restaurant dock space is first come, first served almost everywhere — no operator can reserve you a slip. Boca Ciega Waterfront Bar & Grill has nine, which is generous, and they can still all be taken on a Saturday. With four hours there is room to wait a few minutes or move to a different stop. With two and a half there is not.
A typical dock and dine day: a run out with sightseeing and dolphins along the way, a sandbar or island stop, lunch at the dock, then a relaxed cruise back. The meal is part of the day rather than the whole of it.
Nobody has to be the designated driver
This is the part guests mention afterward more than the food.
Drive to a waterfront restaurant and somebody in your group is not drinking. Arrive by charter and nobody has to make that arrangement — Captain Keith is your licensed captain for the entire day, and he is the one taking you home. Every adult aboard can have a drink at lunch and another on the way back if they want one.
It also removes the parking problem entirely, which anyone who has tried to find a space at Caddy’s on a Saturday will appreciate.
Where Captain Keith has docked
Every restaurant here is one he has tied up at personally. No guesswork on the approach.
Island Way Grill
Clearwater Beach island
Also one of our Clearwater pickup points, which makes it the simplest dock and dine on the list. Upscale coastal seafood, a sushi bar, and a good raw bar, right on the Intracoastal.
Because we already dock here, the logistics are effortless — no extra run, no unfamiliar approach.
20 Island Way, Clearwater, FL 33767
Caddy’s on the Beach
Indian Shores
Beach bar with sand under your feet and a Gulf view. Casual, loud in the good way, and popular with groups who want the stop to feel like part of the boat day rather than a break from it.
Parking here on a weekend is genuinely difficult. Arriving by water skips all of it.
14995 Gulf Blvd, Indian Shores, FL 33708
Boca Ciega Waterfront Bar & Grill
St. Petersburg · Boca Ciega Bay
Nine slips, first come first served, on Boca Ciega Bay just off John’s Pass and about five minutes from Madeira Beach. Waterfront dining with an upstairs deck over the water and live music daily.
Worth knowing if you have been before: this was Doc Ford’s Rum Bar & Grille Jungle Terrace until August 2026. Same owner, same dock, same view — new name and a new menu built around the waterfront setting.
The approach runs through the calm water inside Boca Ciega Bay, past mangrove shoreline and some of the more striking waterfront homes in Pinellas County. It is an easy, comfortable run even on a breezy day.
8790 Bay Pines Blvd, St. Petersburg, FL 33709
The Shore Restaurant
Longboat Key
The longest run on the list and the one that needs a full four hours with little else planned. Worth it for groups who want the journey to be the point rather than the destination.
801 Broadway St, Longboat Key, FL 34228
Wahoo’s Bayside Pub and Grill
Madeira Beach
Casual bayside pub with a relaxed dock and a straightforward menu. A good stop for groups who want something unfussy without leaving the water for long.
12924 Village Blvd, Madeira Beach, FL 33708
Doc Ford’s Rum Bar & Grille
St. Pete Pier
On the St. Pete Pier, with the downtown skyline behind it. The approach across Tampa Bay is half the appeal — you come at the Pier from the water, which is a completely different arrival than walking out along it.
How to plan it
- Book the 4-hour Half-Day Island Escape — dock and dine is not available on the shorter charters
- Mention it when you book so Captain Keith can plan the route and timing around it
- Call the restaurant for a reservation once your charter is confirmed, and tell them you are arriving by boat
- Expect first come, first served on the dock — no restaurant on this list holds slips in advance
- Bring a card — you pay the restaurant directly. There is no charge from us for the stop
- Or skip it entirely — bring your own food and drinks instead. We provide the cooler and ice. Non-glass containers only
Tessa’s one request. Whatever comes off the boat at lunch comes back onto it afterward — napkins, straws, plastic cups, and especially anything that can blow off a dock.
A plastic bag on the water looks exactly like a jellyfish to a sea turtle. She has opinions about this, and she is right.
You can also end a charter at a restaurant dock rather than returning to the departure point, then make your own way home afterward. Popular for bachelorette parties, birthdays, and anniversaries where the celebration carries on after the boat. Mention it when you book so the timing and the meeting point work out.
Which charter to book
All flat rates for the whole boat, up to 6 guests.
Half-Day Island Escape — $575
4 hours · up to 6 guests · required for dock and dine
The only charter that includes a restaurant stop. Sightseeing, dolphins, a sandbar or island, lunch at the dock, and a relaxed run back.
Gulf Escape — $395
2.5 hours · up to 6 guests
No restaurant stop. Sightseeing, dolphins, and a nearby sandbar — the full mix, closer in. Bring your own food and drinks instead.
Sunset Escape — $425
2.5 hours · up to 6 guests
No restaurant stop. Timed to the evening sunset, you pick the backdrop, champagne flutes at sundown.
Plan the rest of the day
Island hopping
Four hours reaches the barrier islands with real time at each. Pairs naturally with a lunch stop.
See island hopping →Sandbar charters
Shallow, calm water you can stand in — a natural first stop before lunch.
See sandbar charters →Sightseeing tours
The Don CeSar, the bridges, and the waterfront homes along Boca Ciega Bay on the way through.
See sightseeing charters →Special occasions
Bachelorette parties, birthdays, and anniversaries — where the drop-off option gets used most.
See occasion charters →Common questions
What is dock and dine?
Arriving at a waterfront restaurant by boat instead of by car. Captain Keith navigates to a restaurant with its own dock, ties up, and your group walks straight in. No parking, no traffic, no circling for a space on a Saturday.
Which Pinellas County restaurants can a private charter boat dock at?
Captain Keith has personally docked at Island Way Grill in Clearwater, Wahoo's Bayside Pub and Grill in Madeira Beach, Caddy's on Indian Shores, Doc Ford's Rum Bar and Grille at the St. Petersburg Pier, Boca Ciega Waterfront Bar & Grill on Boca Ciega Bay, and The Shore Restaurant on Longboat Key. These are verified from firsthand experience, not pulled from a directory.
Do I need a longer charter for a dock and dine stop?
Yes. Dock and dine is available on the 4-hour Half-Day Island Escape ($575) or longer, and not on the 2.5-hour charters. Docking, ordering, eating, settling up, and getting back underway realistically takes an hour and a half. On a 2.5-hour charter that leaves under an hour of actual water time, which is not the day anyone books.
Can we drink at the restaurant since we came by boat?
Yes, and it is one of the better reasons to do this. Because Captain Keith is your licensed captain for the entire charter, every adult in your group can have a drink at lunch. Nobody has to stay sober to drive the boat home, and nobody has to stay sober to drive the car.
How much does a dock and dine charter cost?
The 4-hour Half-Day Island Escape is $575 flat for up to 6 guests. The restaurant stop is included at no extra charge — you pay only for your own food and drinks. The 2.5-hour Gulf Escape at $395 and the Sunset Escape at $425 do not include restaurant stops.
Can Captain Keith drop us off at a restaurant at the end of the charter?
Yes. The drop-off option ends your charter at a waterfront restaurant dock — your group steps off, sits down, and makes their own way back afterward. Popular for bachelorette parties, birthdays, and anniversary charters where the celebration continues after the boat.
Do we need a reservation?
We recommend one, especially at weekends and in peak season. Call the restaurant directly once your charter is confirmed and tell them you are arriving by boat. Mention the plan when you book with us so Captain Keith can time the run around it.
What if the restaurant dock is full?
It happens, particularly at weekends. Dock space is first come, first served almost everywhere — Boca Ciega Waterfront Bar & Grill has nine slips, for instance, and none can be held in advance. This is another reason dock and dine needs the four hours: there is room to wait a few minutes or move to a different stop. On a short charter there is not.
What happened to Doc Ford's Jungle Terrace?
It was rebranded. The restaurant at 8790 Bay Pines Boulevard served its last guests as Doc Ford's Jungle Terrace on August 2, 2026, closed for a week, and reopened on August 10 as Boca Ciega Waterfront Bar & Grill. Same owner — HM Restaurant Group, which also runs the Doc Ford's locations at the St. Pete Pier, Sanibel, and Fort Myers Beach. Same dock, same water, new name.
Can we dock and dine from either departure point?
Yes, though the options differ. From Clearwater the natural stops are Island Way Grill, Wahoo's, and Caddy's. From Maximo Park in St. Petersburg it is Doc Ford's at the St. Pete Pier and Boca Ciega Waterfront Bar & Grill. Longboat Key is a longer run from either and needs a full four hours with little else planned.
Do we still get time on the water?
Yes — that is what the four hours buys. A typical dock and dine day is a run out with sightseeing and dolphins, a sandbar or island stop, lunch at the dock, and a relaxed cruise back. The meal is part of the day rather than the whole of it.
Can we bring our own food instead?
Absolutely, and plenty of groups do. We provide a cooler and ice, and you are welcome to bring your own food and drinks in non-glass containers. Dock and dine is an option, not an expectation.
Is dock and dine good with kids?
Very. Every restaurant on our list is casual and family friendly, and being able to get off the boat, sit at a table, use a proper restroom, and eat something hot resets everyone mid-charter. Minimum age aboard is 5, per U.S. Coast Guard life vest requirements.
How do I arrange a dock and dine charter?
Mention it when you book, or call or text 727-355-3717. Captain Keith will help you choose the right restaurant based on your departure point, your charter length, and what your group wants from the day.
Ready to plan your dock and dine charter?
Book the 4-hour Half-Day Island Escape and tell us which restaurant appeals. Captain Keith plans the route and the timing around it, and there is no extra charge for the stop.
Half-Day Island Escape
$575
4 hours · dock and dine available
Gulf Escape
$395
2.5 hours · no restaurant stop
Sunset Escape
$425
2.5 hours · champagne included