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NOTICE: All Activities Require Online Reservation or Call Ahead

Small Boat. Big Fun.

Boat Rentals Oldsmar

Newest offering from Chadillac Adventures, we like to call it The Chadillac Experience. It’s our version of a private charter boat available to rent right on Clearwater Beach.

Let us take you to the islands and sandbars off of the beach (only accessible by boat).  We will fill your time with paddling, floating, snorkeling, finding dolphins, relaxing with a drink (or two!), swimming or whatever else your heart desires!

Available for 2 hour trips up to an all day adventure.  Comes with a captain, 110 gallon Yeti cooler, and, if you’re into it, a bumping sound system for a great atmosphere.

Remember, “The Ship don’t make the captain, the Captain makes the ship!”


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Chadillac Adventures Boat Slip Information

445 E Shore Dr Slip 42 Clearwater Beach, FL 33767

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Looking for a Sunset Cruise Adventure?

Come join us off Clearwater Beach on our shorter boat trips for the most beautiful sunsets in all of the world!

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Boat Rentals

Boat Rentals Oldsmar

Chadillac Adventures provides boat rentals in Oldsmar, boat charters in Oldsmar and boat tours in Oldsmar, allowing those visiting the area to explore its beautiful attractions.

People who take advantage of our boat rentals in Oldsmar are spending time in an area just off of the Intracoastal Waterway. It is also home to 2.5 miles of some of Florida’s softest sand, and we recommend enjoying that beach before and after you use one of our services, such as boat charters in Oldsmar.

Boat Tours Oldsmar also allow you to enjoy this community’s beautiful scenery. That is because boat tours in Oldsmar can feature, for example, the area’s marina and incredible sunsets across the Gulf of Mexico.

One of the most significant benefits of boat rentals in Oldsmar is being able to enjoy boating without the commitment and expenses that come with owning your own vessel as our boat rentals in Oldsmar allow for the removal of many of those hassles.

When you go to enjoy one of our boat rentals in Oldsmar, you can time it for when you want, noting that our boat rentals in Oldsmar should be reserved enough in advance of your desired time to ensure that this service will be available then.

Those who use boat rentals in Oldsmar can do so many activities. Boat rentals in Oldsmar allow you to look for dolphins, enjoy water sports, hop around the region’s islands and take in beautiful sunsets.

Boat Tours Oldsmar

Boat Charters Oldsmar is the way to go if you want to experience total comfort. That is because boat charters in Oldsmar allow you to take your mind off of everything. That includes operating the vessel as our boat charters in Oldsmar come with a captain.

You can also engage in numerous activities. For example, those who take advantage of our boat charters in Oldsmar often enjoy paddling, swimming, snorkeling and dolphin watching.

Boat charters in Oldsmar can also feature a sound system and a 110-gallon cooler for those who want some music and drinks while enjoying their day out.

No matter if you are enjoying boat rentals in Oldsmar, boat charters in Oldsmar or boat tours in Oldsmar, we can incorporate some exciting activities, depending on the details of the type of service that you have reserved.

For example, some of those who utilize one of our boat rentals in Oldsmar or boat charters in Oldsmar hold wedding parties. You can also involve your pets when you use many of our boat rentals in Oldsmar, boat charters in Oldsmar and boat tours in Oldsmar. Do check with us first while noting that it might even be possible to bring a cat along.

Where Locals Go

Regardless of if you are utilizing boat rentals in Sand Key, boat charters in Sand Key or boat tours in Sand Key, we can direct you towards where locals go and away from tourist-focused destinations. Or, of course, we could help you go towards the touristy locales with our boat rentals in Sand Key, boat charters in Sand Key and boat tours in Sand Key if you prefer that.

Simply put, the personalized services that come with our boat rentals in Sand Key boat charters in Sand Key and boat tours in Sand Key will get you somewhere that fits your preferences. Speak with us about what you desire out of this. We want everyone who uses our boat rentals in Sand Key, boat charters in Sand Key and boat tours in Sand Key to be happy with their choice.

Customer Reviews

Abdul Rahman
Abdul Rahman
May 11, 2024
I recently had the pleasure of going kayaking with Garrett from Chadillac Adventures, and it was an absolutely wonderful experience! The route we took was scenic and perfectly chosen, making the kayaking both enjoyable and memorable. Despite being just 17 years old, Garrett showed a level of professionalism and skill that surpassed all expectations. He was incredibly knowledgeable about kayaking techniques, ensuring that everyone felt comfortable and confident on the water. His customer service was top-notch; he was attentive, friendly, and genuinely cared about making the experience enjoyable for everyone. I strongly believe that such dedication and hard work deserve recognition. Therefore, I would kindly ask the owner to consider giving Garrett a bonus for his exceptional service. He truly enhances the experience for Chadillac Adventures’ customers and is a great asset to your team!
Isaiah Vargas
Isaiah Vargas
May 1, 2024
great spot to launch out, really good prices and amazing costumer service
Rebekah Rudd
Rebekah Rudd
May 1, 2024
Owner was awesome! Gave me a free pouch to keep my phone dry.
Lexi Buskirk
Lexi Buskirk
April 28, 2024
Perfect spot for paddle boarding through some awesome mangroves! There were a lot of sand bars and places to swim. We called ahead and asked about our dog joining us for the first time and they were super helpful.
Julius Martinkus
Julius Martinkus
April 23, 2024
Visited April 2024. Wonderful time! You will absolutely love the experience! When in Clearwater, visit Cadillac Adventures. You will love it. I've been doing it for a years!
Fran Lebel
Fran Lebel
April 22, 2024
Hidden gem in Clearwater, bought a Groupon and decided to use it last weekend and boy were we impressed. Nice area to kayak, they have a snack bar on site serving chicken wings, and also serve beer and wine. Staff was really friendly, Garrett provided us with information on were to go and what we would see depending on the journey. You do have to enter Cove Cay condo's by taking a right hand turn, stopping at the security booth, then you can enter the Marina a short distance by taking the first left hand turn, be careful because you could miss the turn off Frontage Road into the condo area. We had a beautiful day on the water and forgot our cooler in the snack bar area, we called up the next day, were told they had it and picked it up. They are very nice, honest, friendly, group of people. Don't hesitate to check them out, check Groupon for coupons as well, as they honor Groupon deals. Happy Kayaking
franck Kodjo
franck Kodjo
April 22, 2024
Very fun adventure
Elizabeth McMillion
Elizabeth McMillion
April 21, 2024
Lots of fun and worth every penny. Made lots of great memories with my family and it was a very stress free day. We will definitely be coming back in the future. Update 4/20/2024- Finally made our way back to this adventure! Had an amazing day out on the water celebrating 5 years of marriage. The gentlemen that helped us this time was super nice and informative! We had a blast and will continue recommending this place to friends and family! We will try to come again soon!
James Kelleher
James Kelleher
April 7, 2024
Chad was very professional, caring,and patient, helping my elderly parents get in and out of their kayak. Will 100% be back.