Island Way Grill sits on the Intracoastal Waterway north of the Clearwater Causeway, near the Clearwater Marine Aquarium — and it's also one of Wayward Key Tours' charter pickup points. Captain Keith knows this dock extremely well. The restaurant offers reliable boat access, a beautiful waterfront setting, excellent fresh seafood, and a relaxed atmosphere that fits naturally into a charter day at any pace.

A morning charter that departs from Island Way Grill, heads north for dolphins and a sandbar, and returns for a waterfront lunch is one of the most complete Clearwater charter experiences available anywhere in Pinellas County. Guests who start their day here often end it here too — stepping off the boat and straight into lunch with the Intracoastal right beside them.

Wahoo's Bayside Pub and Grill has been a Redington Shores institution for over 23 years — fresh seafood, local favorites, live music, and beautiful bayside views. It's quintessential Florida Gulf Coast dining: casual, colorful, genuinely local, and exactly the kind of place that feels right after a morning on the water. A dock and dine stop here breaks up a longer charter naturally and gives guests a taste of a local waterfront spot that most tourists never find on their own.

Caddy's in Indian Shores is a classic Gulf Coast bar and grill with plenty of docking and a laid-back beach atmosphere — perfect for a mid-charter stop for drinks and food without anything feeling overly formal. It's the kind of Florida waterfront spot that regulars love and visitors immediately feel comfortable in. A natural fit for a casual group charter where the vibe matters as much as the food.

Arriving at the St. Petersburg Pier by boat is one of those experiences that stops people mid-sentence. The approach across Tampa Bay toward the Pier's striking angular architecture rising out of the water is genuinely unlike anything else on the Gulf Coast skyline — and it sets the tone for everything that follows.

Captain Keith has docked at Doc Ford's Rum Bar and Grille at the Pier, and it ranks among the most visually spectacular dock and dine stops in the entire Tampa Bay area. The ahi tuna in particular is exceptional, and the waterfront dining experience with Tampa Bay spread out around you is hard to match anywhere in the region. This stop works naturally for charters departing from Maximo Park in St. Petersburg — the bay crossing to the Pier and back bookends a beautiful day with something genuinely special at the midpoint.

For charters willing to travel further south, The Shore on Longboat Key is the most upscale dock and dine option Captain Keith has taken guests to — a beautiful waterfront setting, excellent food, and a more refined atmosphere than the casual Gulf Coast stops further north. This works particularly well for anniversary or special occasion charters where the restaurant stop is meant to be part of the celebration, not just a casual break.

The combination of a private charter and a properly special waterfront lunch at The Shore makes for an extraordinarily memorable full-day experience — less like a boat tour and more like a completely curated Gulf Coast day. It's a longer trip from either departure point, so plan for the 4-hour Full-Day Charter if you're considering this one.