Boca Grande Boat

Looking for the best way to maximize your trip to Boca Grande? Then you have to get out on the water! While Boca Grande offers so many things to do from golf cart rides, beaches, lighthouse climbs, shopping and restaurants – a Boca Grande boat tour should be at the top of your list! With so many things to see by water, will highlight a few of the best things to see by Boca Grande boat with Captain Roger Chapin and Lady Grey Charters.

Cayo Costa

Cayo Costa is an island just to the south of Boca Grande. Only accessible by boat, Cayo Costa is a State Park that allows visitors pristine beaches, world class shelling and plenty of room to have the beach to yourself. Lady Grey Charters will incorporate a Cayo Costa stop into your charter or set up for for the day with beach chairs, umbrellas, paddle boards and more. Captain Roger will even grill your own “Cheeseburger in Paradise”.

Lunch or Dinner? – Cabbage Key or Tarpon Lodge

Why visit an island if you are aren’t going to do some “island hopping” of your own? There are several great places to stop in for breakfast, lunch or dinner on nearby islands from Boca Grande. By far, the most popular is Cabbage Key known for their burgers, fresh fish and the “cabbage creeper”, a tasty rum drink. A little “local knowledge” goes a long way when it comes to visiting this popular watering hole.

“No matter where you go to dine by water, it’s important to know the weather, time of year and potential crowds,” says Captain Roger Chapin with Lady Grey Charters. “If it’s a super busy weekend, I might recommend lunch on the boat instead of lunch at a restaurant or I might suggest an earlier dinner to make sure clients don’t miss an amazing sunset in the Boca Grande Pass. The key is to maximize your custom charter.”

Tarpon Lodge on Pine Island is another wonderful dining opportunity by boat. Open for lunch and dinner, this restaurant is a bit more “upscale”, but still with a laid back attitude. The food is incredible. Their fresh catch of the day, amazing salads, cuban sandwich, or special compilation dish will rival any “big city” offerings!

“A no-frills escape, Tarpon Lodge was built in 1926 on a sweep of green lawn with magnificent views out to sea…sunny restaurant dishes up creative surprises.”

Fodor’s Travel

Boca Grande Boat to Useppa & Collier Inn

If you want to “step back in time”, then a visit to the Collier Inn on Useppa is in order. Initially inhabited by the Calusa Indians thousands of years ago, today the island remains a natural wonder designated on the National Register of Historic Places and boasting a beautiful botanical trail.

The Collier Inn serves lunch and dinner. You can dine inside or outside on the patio overlooking Pine Island Sound under the huge Banyan Tree. Useppa is only accessible by boat and you must also be a “member” or guest of the Useppa Island Club for dining, touring and pool privileges.

Boca Grande Boat to Matlacha

Matlacha is a small, artsy town on Pine Island. A boat ride from Boca Grande to Matlacha takes about 30 minutes. Once there, you can enjoy great restaurants, shopping and unique art galleries. Lunch recommendations include Blue Dog Bar & Grill, Bert’s Bar and Grill and the Olde Fish House Marina. Take in some shopping with a must visit to Leoma Lovegrove Gallery & Gardens as well as ice cream at Great Licks! Getting to Matlacha by boat requires local knowledge of the waters and depth as well as docking opportunities.

North Captiva – Barnacles Restaurant

Just south of Cayo Costa, you will find North Captiva. North Captiva is only accessible by boat (ok, there is a grass airstrip too), and boasts some fun restaurants. The primary restaurant is Barnacles. A large dock greets boaters to a small restaurant with plenty of outdoor seating under the large thatch roof hut. Cold drinks, great lunch baskets and a cool vibe are all on the menu!


Boca Grande is known for its year-round world class fishing. Depending on when you visit, you have a better chance at catching your desired species. However, overall fishing is great year-round! Tarpon, redfish, snook, grouper, snapper, trout and more are just a few of the fish to target around the waters of Boca Grande and Gulf of Mexico. There are dozens of qualified fishing guides in the area to choose. The Boca Grande Fishing Guides Association and Gasparilla Outfitters can offer a guide for any trip.

Lady Grey Charters specializes in near-shore grouper and snapper fishing as well as redfish, trout and snook fishing around the harbor. “What I really like to do is take a family fishing for ‘what’s biting’ for a few hours then island hop to a nearby restaurant or go shelling on Cayo Costa,” says Capt Chapin. “I find a few hours of fishing where the kids and parents can catch fish together, then go on to the next adventure, is a wonderful way to spend a day day on the water.”

“I find a few hours of fishing where the kids and parents can catch fish together, then go on to the next adventure, is a wonderful way to spend a day on the water.”

Captain Roger Chapin, Lady Grey Charters

Too Many Great Spots to List Them All

These are just a few of the wonderful and unique opportunities to enjoy a Boca Grande boat tour of the surrounding islands, beaches and restaurants. Lady Grey Charters is uniquely qualified to take full advantage of the waters of Boca Grande, Charlotte Harbor, Pine Island Sound, Cayo Costa, Captiva and more! Drop Capt Roger an email via or contact him via his website today to schedule your custom charter on your next visit to Boca Grande.

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