Osprey Boat Tours

The best out of 98 boat tours in Osprey - enter dates to check availability

Osprey Boat Tours

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Top Boat Tours in Osprey

Osprey: 98 boats available

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Meet the Captain
23 ft
Up to 11 people
Beach Bum Charters SunDancer
4.9
/5
(12 reviews)
Sarasota (6 min drive from Osprey)
Set your own pace on the water with Beach Bum Charters SunDancer, offering fully customizable start times to fit your perfect Sarasota adventure.

"The boat chartered by Captain Clif was amazing! Very friendly and accommodating staff." —⁠ Tessa,
+9
trips from
US $800
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26 ft
Up to 6 people
Casey Key Water Taxi Tours
4.9
/5
(4 reviews)
Osprey
Set sail on Casey Key Water Taxi Tours aboard a beautifully restored 2006 Bennington 26 Pontoon (2025) from Osprey. Perfect for up to six guests, this spacious pontoon is powered by a 150 HP Yamaha outboard, cruising comfortably at 25 knots.

"Captain Steve was very knowledgeable and interesting about Casey key and Venice." —⁠ Linda,
+5
trips from
US $290
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23 ft
Up to 6 people
Get Salty Charters
5.0
/5
(63 reviews)
Sarasota (13 min drive from Osprey)
Get ready for an unforgettable experience with Get Salty Charters, a premier boating adventure based in beautiful Sarasota! Step aboard our 2015 Southwind 239L Deck Boat, designed for comfort, style, and fun on the water.

"We felt very fortunate to have Captain Logan take us out on our charter." —⁠ Pam,
trips from
US $300
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22 ft
Up to 9 people
Beach Bum Charters Tipsy Tiki
4.9
/5
(6 reviews)
Sarasota (7 min drive from Osprey)
All of our trips have customizable start times, just ask, please note groups over. Step aboard Beach Bum Charters, a freshly restored 2004 Hurricane FD-218R Deck Boat, and experience the best of Sarasota by water.

"What a fantastic experience we had. My family and I decided to book this somewhat last minute, they had availability and we’re eager to get us on the water." —⁠ Anne,
+10
trips from
US $800
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34 ft
Up to 12 people
Casey Key Tiki Tours
4.9
/5
(12 reviews)
Nokomis (4.8 miles from Osprey)
Experience the ultimate Florida boating adventure aboard Casey Key Tiki Tours. Our unique 2024 Tiki Kai Pontoon will serve your needs on the water and stand out in the crowd. We have 2 locations: Casey Key in Nokomis and Evie’s at Spanish Point.

"We had such a great time with our Casey Key Tiki Tours crew." —⁠ Natalia,
+9
trips from
US $140
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Meet the Captain
29 ft
Up to 6 people
SRQ Boat Charters LLC
5.0
/5
(29 reviews)
Sarasota (18 min drive from Osprey)
Come for an unforgettable adventure with SRQ Boat Charters LLC, featuring a 2008 Century 2901 Center Console, based in Sarasota.

"We had yesterday our trip with Captain Rob, two adults and two little kids." —⁠ Andreas,
+2
trips from
US $460
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23 ft
Up to 6 people
New Wave Boat Charter
5.0
/5
(9 reviews)
Sarasota (3.3 miles from Osprey)
At New Wave Boat Charters, we believe the best way to experience Sarasota is from the water. Create lasting memories with safe, laid-back, and personalized boat tours in Sarasota and surrounding areas.

"WOW!  We had such a great time with Captain Raphael and Simone!" —⁠ Denise, Florida
+2
trips from
US $300
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31 ft
Up to 6 people
Sarasota Sunset Charters
5.0
/5
(8 reviews)
Sarasota (20 min drive from Osprey)
Experience the beauty of Sarasota from the water with Sarasota Sunset Charters aboard a 2014 True World Marine TE288 Cruiser, beautifully restored in 2024.

"i booked a sunset excusion with Captain Pat and had the best evening." —⁠ Jacqueline,
trips from
US $499
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24 ft
Up to 6 people
Tortuga Boat Adventures
5.0
/5
(8 reviews)
Sarasota (11.0 miles from Osprey)
Step aboard Tortuga Boat Adventures’ sleek 2018 Nauticstar 243 DC and experience Sarasota from the water in comfort and style.

"We had an amazing day with Tortuga Boat Adventures! From start to finish, the trip exceeded our expectations." —⁠ Rachel,
+3
trips from
US $450
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26 ft
Up to 6 people
Sarasota Bike Tours – Sabrina's Buoy
New
5.0
/5
(1 review)
Sarasota (8.1 miles from Osprey)
Sabrina’s Buoy is a comfortable and fun 2005 Catamaran Cruiser Party Barge pontoon based in Sarasota, perfect for relaxed cruising and unforgettable days on the water.

"There are moments when you truly can call it a perfect day. This trip with Sabrina’s Bouy was one of those idyllic days in paradise." —⁠ Norma,
+9
trips from
US $300

Frequently Asked Questions about Boat Tours in Osprey

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Boating in Osprey

Discover why Osprey is a favorite launch point for exploring Florida’s Gulf Coast. Nestled on Little Sarasota Bay along the Gulf Intracoastal Waterway, Osprey offers calm, protected waters ideal for sightseeing cruises, family-friendly excursions, wildlife watching, and inshore angling. With Osprey boating charters, you can trace scenic shorelines, slip into quiet coves, and enjoy panoramic bay views with the Gulf just beyond the passes to the south and north.

A signature landmark is the historic, one‑lane Blackburn Point Swing Bridge, which links the mainland to Casey Key. Cruising beneath or near this storied crossing sets the tone for a classic “Old Florida” outing, followed by shoreline cruising along Casey Key’s natural stretches and serene residential waterfronts. Sunset rides often reward guests with glowing skies over the barrier island.

Nature lovers can pair a charter with paddling or tender adventures around nearby mangrove-lined waterways. South Creek at Oscar Scherer State Park flows toward the bay, offering a peaceful route for kayaks and a chance to spot native birdlife. Freshwater and saltwater options sit side by side here: Lake Osprey provides a family-friendly freshwater setting, while the bay invites light-tackle action and relaxed sightseeing.

Whether you’re planning a half-day cruise, a wildlife-focused tour, or a laid‑back beach-and-bay hop, Osprey boating charters put you close to everything that makes this corner of Southwest Florida special—protected waters, a storied bridge, pristine barrier‑island scenery, and easy Intracoastal access for smooth, memorable days on the water.

What people said about boating in Osprey

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How people rated boat trips in Osprey

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