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Explore the stunning waters of the Gulf of Mexico and Pine Island Sound on a private, fully customizable boating adventure. Guided by Captain Jenni, the island’s only female captain, you'll visit secluded islands accessible only by boat, search for marine wildlife, snorkel in crystal-clear waters, and collect shells along pristine beaches.
Customize your day with a stop at the waterfront restaurant on Cabbage Key, discover hidden coastal gems, and learn about the area's fascinating history and local culture from a lifelong resident. Perfect for families, couples, and adventure seekers of all ages, this unforgettable experience combines sightseeing, wildlife, relaxation, and exploration in one memorable day.
Service animals allowed
Not recommended for travelers with poor cardiovascular health
Suitable for all physical fitness levels
The boat we use is easily accessible from the dock or the water with a ladder
Spend six unforgettable hours exploring the beautiful waters of the Gulf of Mexico on a private charter tailored to your interests. Cruise to secluded islands accessible only by boat, search for marine wildlife, stroll shell-covered beaches, swim, snorkel, and discover hidden coastal gems along the way. Your adventure is led by Captain Jenni, a certified captain and lifelong island resident who shares fascinating local history, folklore, and insider knowledge throughout the day. You can also customize your experience with a visit to destinations like Cabbage Key or Boca Grande. The boat is equipped with a cooler filled with ice, sanitized snorkeling gear, and all required safety equipment, ensuring a comfortable and memorable day on the water.
All Safety Equipment is provided
Sanitized Snorkeling equipment is provided or feel free to bring your own
The boat will have a large cooler with ice and a couple of waters, Please feel free to bring your own as well
Feel free to bring drinks (alcohol is permitted) and snacks, preferably in non staining colors
For a full refund, cancel at least 24 hours before the scheduled departure time.
11 đánh giá
Tổng số đánh giá và xếp hạng từ Viator & TripAdvisor
X9316RQrayh,12 thg 6, 2026
- Đánh giá từ Tripadvisor
The most amazing and fun day ever with Capt Jenni! She took us shelling on Cayo Costa island, and on the way out she told us about the history of what we were seeing, and then there were dolphins everywhere! A stop for lunch on Cabbage Key, and then off to a secret sandbar to jump in the water and where Capt Jenni told us all about the amazing sea creatures that we were seeing, and shells with little critters inside. Capt Jenni made us feel like we were family, and we so enjoyed every minute of our excursion. Book your trip now. You won’t go wrong with Capt Jenni at the helm!
jofA4736HS,3 thg 6, 2026
- Đánh giá từ Tripadvisor
Spending 6 hours with Captain Jenni was so amazing. The knowledge of nature and history was great. We all felt welcomed and comfortable. I would recommend the 6 hour charter. Snorkeling, shelling, manatee watching and so much fun. Thanks again Captain Jenni. Jo and family
mamalovestravel,20 thg 4, 2026
- Đánh giá từ Tripadvisor
We had a phenomenal day on the water with Captain Jenni! We were six adults and there was plenty of room for all of us to enjoy the sights & sounds of the islands. Her boat had plenty of comfortable seating as well as dry storage and a cooler for our beverages. We have been visiting Sanibel for 30 plus years and wanted to take our friends out for the day. This was by far the best boat charter for a laid back, relaxing day exploring Cayo Costa, N Captiva and Useppa. Captain Jenni will customize your day as you wish. It was so much fun! I can't recommend Captain Jenni & Flipside Charters enough. You will not be disappointed!

rosimom,6 thg 3, 2026
- Đánh giá từ Tripadvisor
If you want the most incredible way to experience Sanibel and the islands around it, you have to go out with Captain Jenni at Flip Side Charter. Our family has been boating with her for years, and every trip somehow gets even better. Captain Jenni has spent her entire life on these waters around Sanibel, Captiva, Cabbage Key, Pine Island, and Useppa Island, and her knowledge of the area is amazing. She knows the history, the wildlife, the ecosystems, and the people. It feels less like a tour and more like exploring with a lifelong local friend who truly loves and respects this place. She took us to a beautiful sandbar and a beach that felt like our own little tropical oasis. Along the way she pointed out dolphins, manatees, birds, and other wildlife and shared so much about the environment and sea life around Sanibel and the surrounding islands. It was fun, fascinating, and relaxing all at the same time. We also loved visiting the Useppa Museum to learn about the long history of the area, and, of course, stopping for lunch on Pine Island. Every stop felt special and authentic. One tip: ask if you can climb up to the flying bridge where the view is incredible. Beyond the amazing places we visited, what makes the experience truly special is Captain Jenni herself. She is warm, friendly, welcoming, and makes everyone feel completely safe and comfortable on the boat. You can tell she genuinely cares about her guests and about protecting the waters she grew up on. Going out with her has become a yearly tradition for our family and something we always look forward to. If you want to explore Sanibel and the surrounding islands the right way, we can’t recommend Captain Jenni and Flip Side Charter enough. We absolutely love her.







1969TKO,2 thg 1, 2026
- Đánh giá từ Tripadvisor
Captain Jenni is AMAZING! She grew up in the area and knows so much about its history, history and we found hugh shells! What a wonderful day for me and my husband. Don't miss this one!
Coastal44268749167,1 thg 1, 2026
- Đánh giá từ Tripadvisor
Me and my family had the best time with captain jenni! she is lovely and we had so much fun with her! i caught my first fish. this will defiantly be a time to remember!
631daniw,1 thg 1, 2026
- Đánh giá từ Tripadvisor
Perfect day on the water! We saw dolphins, manatees, schools of mullet, 3 types of heron. Then started fishing. We each caught a fish-sheepshead anyone? What a fun day. Highly recommend!
johnlL7753MU,1 thg 1, 2026
- Đánh giá từ Tripadvisor
Captain Jenni made this experience one to remember! This was our first time fishing and she showed us all of the best spots! Such a funny and down to earth person. Highly recommend!
P9029WCdaniels,25 thg 12, 2025
- Đánh giá từ Tripadvisor
Our day on the water with Captain Jenni exceeded our expectations. Captain Jenni was a terrific host and resource for information. She helped us check all the boxes: from seeing dolphins and manatees to shelling and snorkeling at a secluded island. We wanted to have lunch on Cabbage Key and visit Useppa so she arranged that too. Along the way Captain Jenni pointed out lots of interesting animals, plants and local history. Thank you Captain Jenni. Dan, Priscilla, Alex, Michael, Sami and Kaz
deannacF3214PO,12 thg 12, 2025
- Đánh giá từ Tripadvisor
Oh my god….we love Jenni. This was the most epic adventure I’ve ever had. From the mudflat crown conchs to Jenni ordering me to catch a sick cormorant by hand to dolphins teaching baby to swim; and she has sexy boat. To be fair, I’ve had a lot of awesome adventures whitewater paddling, caving and those are different environments so I’m not trying to put down on those; but if had missed out on this adventure with Jenni, I would feel like one that got away; I would feel cheated in life. This is total bucket list event to participate in. Best money I’ve spent since I can remember. I love flip side tours of Goodland and appreciate Hemingway to keewaydin, but Jenni is the emirates airlines of gulf coast tours.








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