There is no better way to experience Siesta Key than from the water. A Siesta Key boat charter with Siesta Funship puts your group on a spacious, shaded boat with a local captain who knows this bay the way most visitors never will. No crowds, no strangers, no fixed route — just the Gulf, the sandbars, and the people you choose to bring. Our private charters are designed for groups of up to six, and every trip is built around what you actually want to do. Siesta Key is beautiful from the beach. It is extraordinary from the water.
Staying on Siesta Key? We offer 3 convenient pickup locations around Sarasota, FL.
946 Siesta Dr, Sarasota, FL 34242
1708 Ken Thompson Pkwy, Sarasota, FL 34236
1059 N Tamiami Trl, Sarasota, FL 34236
A public tour boat puts you shoulder-to-shoulder with strangers on a set schedule. A kayak rental leaves you paddling against the current. A private boat charter is something different entirely.
When you book with Siesta Funship, your group has the boat to yourselves. The captain is not narrating for 30 people — he is guiding your crew to spots that rarely show up on tourist maps. You set the pace, pick the stops, and stay as long as you like.
Siesta Funship’s captain has spent years exploring Sarasota Bay and the Gulf. He knows the tides, the sandbars, the wildlife patterns, and the hidden inlets that take most people years to discover. That local knowledge is what makes this trip different from anything else you can book on the island.
Our home waters give you access to some of the most varied and beautiful spots on Florida’s west coast. Here are the highlights:
Big Pass is a wide, shallow sandbar that emerges between Siesta Key and the Gulf of Mexico. At low tide, you can step off the boat and stand in knee-deep warm water with open sky in every direction. It is the kind of place that makes people put their phones down. Dolphins are frequently spotted working the channel just beside it.
Midnight Pass sits on the southern tip of Siesta Key and is only reachable by boat. There is no public access, no parking lot, and no crowds — just a quiet stretch of sand that feels like a private island. Most visitors to Siesta Key never know it exists. Your captain will bring you right to it when weather permits—ideal for longer day trips.
Beer Can Island sits at the northern tip of Longboat Key and has the kind of old-Florida charm that is getting harder to find. Seabirds nest in the Australian pines. The water around it is calm and clear. It is a great stop for families or anyone who wants a few minutes off the boat on actual ground.
Jewfish Key is a small, undeveloped island in Sarasota Bay surrounded by calm, shallow water. The sandbar here is ideal for wading, swimming, or simply floating while the captain drops anchor. The isolation feels disproportionate to how close it actually is to shore.
Point of Rocks sits at the south end of Crescent Beach and is one of the few natural rock formations on Florida's Gulf Coast. The ledges and crevices attract reef fish, sea grass, and the occasional sea turtle. If your group wants to snorkel, this is the stop.
A Gulf sunset from the water is a different experience than watching it from the beach. With no shoreline crowd around you, the light hits the water in a way that is hard to describe until you have seen it. Sunset charters are among the most popular trips we run, and for good reason.
A Siesta Key boat charter is a private boat trip on Sarasota Bay and the Gulf of Mexico, guided by a local captain. Unlike a group tour, a charter means your party has the boat to yourselves. You choose the destinations, set the schedule, and the captain handles navigation, safety, and local knowledge. Siesta Funship runs private charters for groups of up to six people.
Siesta Funship’s private charters accommodate up to 6 guests per trip. Every booking is exclusive to your group — there are no shared tours or added strangers. If your party is larger than six, reach out to discuss options.
Yes. Siesta Funship is BYOB and BYOF — bring your own beverages and food. Pack a cooler with whatever your group likes. There is room on the boat for it, and having your own refreshments is part of what makes a private charter feel like your own trip.
The most popular stops include the Big Pass sandbar, Midnight Pass (a hidden beach only reachable by boat), Beer Can Island, Jewfish Key sandbar, and Point of Rocks for snorkeling. Sunset cruises over the Gulf are also a favorite. Your captain will help you build an itinerary based on tides, time of day, and what your group wants most.
For most visitors and locals, yes. Siesta Key’s coastline and surrounding waters have spots that simply cannot be reached on foot or by kayak. A private charter gives you access to hidden sandbars, calm snorkeling areas, and open Gulf waters — with a captain who knows where to go and when. Siesta Funship has earned 175+ five-star reviews from guests who came back and told their friends.
For peak season and weekends, booking at least a week in advance is recommended. Popular time slots — especially sunset charters and weekend mornings — fill up quickly. If you are planning a trip around a specific date or event, book as early as possible to secure your preferred time.
Siesta Key is one of the most beautiful places on Florida’s Gulf Coast, and a private charter is the best way to see the parts of it that most people miss. Siesta Funship has 175+ five-star reviews from families, couples, and groups who came back from the water with stories worth telling. Your captain is ready whenever you are.