Sit Back And Enjoy The Sarasota City Skyline

Happy Go Lucky Siesta Key Boat Tours

Experience beautiful sunsets, thriving sea life, and crystal white sand on our beaches and sandbars.

About Our Tours

We offer a wide range of tours of the amazing Siesta Key and Sarasota. From bar hopping tours to dolphin-watching tours, we have great adventures for tourists, locals, families, couples, and just about everyone else! Check out our full list of boat tours to learn more!

Welcome To Adventure On Florida’s Famous Gulf Coast!


Come explore the sea life, turquoise water, and sandbar swimming with us on our Siesta Key boat tours! Our private charter boat tours are customized to deliver your dream vacation. We are not a mass-market tour on a crowded boat. We offer a luxury boat, with just your party of up to six people plus our captain.

If your perfect day includes exploring the mangroves with your family and spotting wild dolphins, let us take you on our epic dolphin tours. Perhaps you would like to go sightseeing in Sarasota Bay with a few friends or play in the sand on Lido Key or Siesta Key. We can make it happen.

You know that Happy Go Lucky, Siesta Key Boat tours are the perfect friends’ trip or family getaway. Do you also know they plan romantic trips for couples? From our North Siesta Key location, we’ll take you to the quiet, out-of-the-way spots. If a sunset cruise is on your bucket list, we know where to go. You can sit back on our luxurious boat with a drink in hand and watch an epic sunset.


Our Siesta Key Boat Tours

Immerse yourself in the beauty of Siesta Key with our private boat tours.

Siesta Key Sunset Cruises

Starting at $375 USD

Close out a perfect day by joining us for a breathtaking sunset and a chance to see that elusive green flash while sipping your favorite beverage.

Duration :  2 hours 30 minutes

Group Size :  Up to 6


Siesta Key Dolphin Watching

Starting at $375 USD

We will adventure our way through the mangroves and tour the wildlife areas around Siesta in search of our favorite creatures. We will take in the views of the area as we watch dolphins play…

Duration :  2 hours 30 minutes

Group Size :  Up to 6


Adventure in the Sun (Half-Day Package)

Starting at $500 USD

Best way to enjoy the keys as the local. Snorkel, explore one or two different sandbars, watch dolphins play, explore sea life, and stop at the local restaurant for a bite to it.
Duration : 4 hours

Group Size :  Up to 6


Realtor Special Property Boat Tours

Starting at $250 USD

You will show your clients waterfront properties from the comfortable seating of our high-end vessel (28 ft. Axopar with twin 200hp with a bathroom on board).
Duration :  1 hour 30 minutes

Group Size :  Up to 6

The Best Boat Tours In Siesta Key!

Why choose us?

We are a friendly team of highly trained professionals who know the best places to explore. We specialize in small group tours, and our luxury boat has a capacity of six people plus the captain. We want to provide you with a memorable trip that is stress-free and fun.

Perfect Destination

Once you feel the refined-crystal powdery sand between your toes and experience the soft waves and the abundance of sun & fun at gorgeous Siesta Beach, you will realize that you are in the perfect place to relax, chill out, and enjoy.


Knowledgeable Crew

Our crew members have been exploring the waters surrounding Siesta Key for years, where they have acquired their skills. They are knowledgeable of the different beautiful spots to go where you can maximize the best of your beach vacation.



Our beach adventures are perfect for family getaway vacation destinations where you can enjoy dolphin watching, sightseeing, and sandbar swimming. It is also perfect for romantic lovers who love sunset-watching while on the waters.

Exploring The Florida Gulf Coast


Florida sits on a peninsula surrounded by the Gulf of Mexico to the west and the Atlantic Ocean to the east. Dotting the coastline are several island keys, small islands sitting atop an ancient coral reef. Visitors are surprised to find sparkling, powdery white sand. This crystal sand is the result of crushed quartz pounded by the ocean. Even on the hottest summer day, this sand stays cool to the touch.

Sarasota is a lively community of hotels, condos, boutique shops, and restaurants. The area was once the seasonal home to Ringling Brothers Circus. The Ringling Circus Museum offers a look into the history of one of America’s favorite forms of entertainment. On exhibit are intricately carved parade wagons, posters, costumes, and props.

Book Your Next Sea Adventure Now.

Enjoy Siesta Key and the surrounding waterways of Sarasota, Florida.

Most frequent questions and answers

Frequently asked questions

Does the boat have a bathroom?
It has a flushable marine toilet for liquids only. The boat also has fresh water so you can rinse yourself from salt water.
Can we modify existing itineraries?
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.
Should We Extend A Tip?

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

Are there going to be other people on the boat with us?
No. All our trips are private. Just you, your loved ones and our captain.
Can we play our own music on the boat with us?
Absolutely. Our boat has a premium amplified 9-speaker audio system and you can play music from your phone via Bluetooth.
Are drinks included? Is there a cooler on the boat?

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


Latest News

Join us on an exciting journey as we share insider tips, local insights, and firsthand experiences of exploring the stunning island of Siesta Key and its surrounding waters