(941) 284-3694



To provide our Customers with an Experience of a beautiful Waterside View of the exotic Siesta Key

Our beaches and sandbars are covered in soft, crystal-white sand that, even on the hottest days, is cool to the touch.

You can enjoy Siesta Key and the surrounding waterways without being packed like sardines on larger charter services. By choosing one of our tours, you can maximize an experience tailored to your group’s interests.
Years of Experience
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Our Captain

Meet Captain Joe

Joe is a USCG-licensed captain with the skill, knowledge, and passion to provide you with the finest experience the area has to offer while safely under his care. Captain Joe began his journey as a young boy fishing with his father and grandfather on the Great Lakes while living in Michigan. He took his first boating safety class at 12 years old and began motoring around on small vessels exploring the waters and building skills.

As a teenager, he explored and worked in the marinas helping with small charters, sanding and painting boats, and traveling as the first mate with friends and customers from the marina. He graduated to larger vessels with large parties as a crew member working under a respected captain at the marina, honing his skills and love for boating culture. As an educator for over 20 years, Capt. Joe has the heart of a teacher and loves to share his knowledge. 

Exploring the waters surrounding Siesta Key and offshore became an obsession for this Captain, who learned all about the area by water. Take an adventure with a very knowledgeable and passionate captain who will share his love of the water with you, your friends, and your family.



Siesta Key is known for its beautiful sunsets, thriving sea life, and crystal white sand on our beaches and sandbars.

Our tours are perfect for small groups, couples, or families looking to escape from the large crowds and enjoy a relaxing, stress-free journey into all the beauty Siesta Key has to offer.

We are more than happy to help you enjoy all the area waters have to offer, and we will be happy to do all the work.


Join Us


We often get asked what sets us apart from other boat tour providers in Siesta Key. We think our personalized approach, knowledgeable crew, and commitment to delivering an exceptional experience make us the top choice for your Siesta Key adventure.

One of the key aspects of The Happy Go Lucky Difference is our personalized approach. Unlike mass-market tours on crowded boats, we offer private charter boat tours with a luxury boat that accommodates just your party of up to six people, plus our captain. This allows us to tailor the tour to your interests, making your dream vacation a reality. Whether you’re looking for a family-friendly adventure, a romantic getaway, or a fun-filled trip with friends, we can make it happen.

Our knowledgeable crew is another highlight of The Happy Go Lucky Difference. Captain Joe, our USCG-licensed captain, has years of experience exploring the waters surrounding Siesta Key and offshore. His passion for boating and love for the water shines through as he shares his knowledge and expertise with our guests. Our crew members have also acquired skills through years of exploring the area, and they are well-versed in the best spots to maximize your beach vacation experience, such as Egmont Key and Jewfish Key, near Sarasota.

Furthermore, we are committed to providing a stress-free and fun experience. We understand that our guests want to relax and enjoy the beautiful Siesta Key scenery, and we take care of all the details so you can sit back, relax, and have a memorable trip. From dolphin tours to sightseeing in Sarasota Bay to sunset cruises, we are here to make your Siesta Key adventure truly special.

Choose The Happy Go Lucky Difference for the best boat tours in Siesta Key. Experience the personalized approach, knowledgeable crew, and stress-free adventure that sets us apart from the rest. Join us for an unforgettable journey into the beautiful waters of Siesta Key and create lasting memories with your loved ones.


Sarasota, Florida, located on the Gulf Coast, is a vibrant community known for its beautiful beaches, thriving arts scene, and rich cultural heritage. One of the most popular destinations in Sarasota is Siesta Key, a barrier island that boasts stunning white sandy beaches, turquoise waters, and abundant wildlife.

Siesta Key is famous for its crystal white sand that stays cool to the touch even on the hottest days, making it a perfect destination for beachgoers seeking relaxation and fun. The soft waves and powdery sand of Siesta Beach provide an idyllic setting for swimming, sunbathing, and water sports. The area is also known for its thriving sea life, including dolphins, manatees, and a variety of fish and birds, making it a paradise for nature lovers.

At Happy Go Lucky Siesta Key Boat Tours, we are passionate about showcasing the beauty of Siesta Key and the surrounding waters. Our private charter boat tours are designed to provide our customers with an unforgettable experience tailored to their interests. Our knowledgeable and experienced captain, Captain Joe, is a USCG-licensed professional who has a deep love for the water and a heart of a teacher, eager to share his passion with our customers.

Whether you’re looking for a family getaway, a romantic sunset cruise, or a sightseeing adventure with friends, our small group tours offer a stress-free and enjoyable way to explore Siesta Key and the Gulf Coast of Florida. 

We strive to provide the best boat tours in Siesta Key, offering personalized service, luxury accommodations, and a commitment to making your trip a memorable one.

Come join us at Happy Go Lucky Siesta Key Boat Tours, and let us show you the breathtaking beauty of Siesta Key and the surrounding waters.

Frequently Asked Questions

It has a flushable marine toilet for liquids only. The boat also has fresh water so you can rinse yourself from salt water.

To some extent – yes. Sometimes we will have to because the weather isn’t always ideal and we want to stay in shallow, calm waters to keep the trip enjoyable.

If you feel like you had a great experience gratuity is much appreciated, but not expected!

No. All our trips are private. Just you, your loved ones and our captain.
Absolutely. Our boat has a premium amplified 9-speaker audio system and you can play music from your phone via Bluetooth.

We have a refrigerator with bottled waters and sodas. You’re welcome to bring your own drinks, beers and snacks.