Stay & Play Clearwater Beach Charters: Luxury and Adventure at Sea

Embark on a journey through Florida’s nautical paradise, a haven where the sea tells tales of adventure and serenity. Florida’s coastline, renowned for its diverse marine life and crystal-clear waters, invites you to explore its rich maritime history. From the playful dance of dolphins to the gentle glide of manatees, the ocean here is a living tapestry of wonders. The charter services we partner with offer you a front-row seat to this aquatic spectacle, where every wave whispers stories of the sea.

Clearwater Beach is well known as a jewel in Florida’s coastal crown, offering more than just a beach experience; it’s a sensory delight. Here, the beaches are pristine, the sunsets are stunning, and the waters of the Gulf of Mexico are tranquility itself. You can feel the soft, white sand under your feet, watch the sky paint itself in vibrant hues as the sun sets, and let the gentle rhythm of the waves soothe your soul.

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Caladesi Island

Caladesi Island State Park is a unique Florida State Park located on Caladesi Island in the Gulf of Mexico, north of Clearwater Beach. Although not a separate island, Caladesi Island shares its island geography with Clearwater Beach. Accessible by passenger ferry or private boat, this three-mile-long island boasts some of the most stunning beaches in the United States. The Caladesi Island beach has been listed multiple times among the best beaches in the country. A 1921 hurricane cut Hurricane Pass to divide the larger island into two parts, creating Caladesi and Honeymoon Island. Homesteader Henry Scharrer and his daughter Myrtle lived on the island in the 1880s.

Three Rooker Island

Three Rooker Island is a relatively new island in Pinellas County, Florida, accessible only by boat. South of Anclote Key and north of Honeymoon Island, Three Rooker Island emerged in the 1980s as water currents built up the sandbar above sea level. By the 1990s, vegetation had established itself on the newly formed island, making it more resistant to washing away. Part of the Anclote Key Preserve State Park, Three Rooker Island is partially protected for nesting seabirds while also being a popular place for local boaters. Its shape and size often change from interaction with ocean currents, providing a unique landscape.

Our charter partners are your gateway to experiencing this beauty up close in a way few get to. From the sun-kissed shores of our local islands to spotting majestic dolphins in the open sea, Florida’s natural beauty ensures that every aspect of your Clearwater vacation is spectacular.

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Why Choose Our Partnered Charter Services

When you choose Stay & Play Clearwater, you’re not just selecting a vacation spot; you’re opting for an experience that goes beyond the ordinary. We take this a step further with our charter service partners. These charters want to stand out as the luxurious peak of the “play” activities offered. You’ll find an exclusive blend of luxury, adventure, and personalization that you won’t find anywhere else on Clearwater Beach.

Unlike jet skiing or parasailing, which offer a quick thrill, charters invite you to savor the luxury of time and space. Onboard our partners’ fishing vessels, yachts, and catamarans; the ocean is your playground, and the horizon is the limit. Whether it’s the intimate setting of a sunset cruise or the joy of a day spent island-hopping, these experiences are about more than just activity—they’re about creating stories and memories.

The Bottom Line: An Unforgettable Experience

As the sun dips below the horizon and the stars begin to twinkle above Clearwater Beach, it’s clear that some experiences are simply irreplaceable. At Stay & Play Clearwater, we don’t just offer a place to rest your head; we offer a treasure trove of memories waiting to be discovered.

Whether it’s the gentle lapping of waves against the yacht during a sunset cruise or the joyous laughter of loved ones as you spot dolphins on an eco-tour, these moments are the ones that linger long after your footprints in the sand have faded. Choosing Stay & Play Clearwater for your charter services means making every moment count.

Don’t just dream about the perfect getaway; make it a reality. Book your charter experience today and set sail for a journey as boundless as the sea. Explore Clearwater Beach in style, and let the adventure begin.

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Caladesi Island

Caladesi Island State Park is a unique Florida State Park located on Caladesi Island in the Gulf of Mexico, north of Clearwater Beach. Although not a separate island, Caladesi Island shares its island geography with Clearwater Beach. Accessible by passenger ferry or private boat, this three-mile-long island boasts some of the most stunning beaches in the United States. The Caladesi Island beach has been listed multiple times among the best beaches in the country. A 1921 hurricane cut Hurricane Pass to divide the larger island into two parts, creating Caladesi and Honeymoon Island. Homesteader Henry Scharrer and his daughter Myrtle lived on the island in the 1880s.

Three Rooker Island

Three Rooker Island is a relatively new island in Pinellas County, Florida, accessible only by boat. South of Anclote Key and north of Honeymoon Island, Three Rooker Island emerged in the 1980s as water currents built up the sandbar above sea level. By the 1990s, vegetation had established itself on the newly formed island, making it more resistant to washing away. Part of the Anclote Key Preserve State Park, Three Rooker Island is partially protected for nesting seabirds while also being a popular place for local boaters. Its shape and size often change from interaction with ocean currents, providing a unique landscape.

Our Partners

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Blue Sky Yachts: Sailing in Luxury

Set sail with Blue Sky Yachts, where the horizon is not just a destination but the beginning of an unforgettable journey. With Blue Sky Yachts, you’re not just renting a boat; you’re claiming the keys to a personalized luxury experience on the waters of Clearwater Beach.

Preparing for Your Charter Experience

To ensure you have the most enjoyable and seamless charter experience, here’s a handy checklist of what to bring and how to prepare:
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Sun Protection: Florida sun can be intense. Bring sunscreen, a hat, and sunglasses.
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Comfortable Attire: Wear light clothing and bring a swimsuit for swimming or lounging on the sandbars.
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Footwear: Non-marking soles are preferred aboard yachts. For catamaran tours, bring something you can easily slip off.
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Towels: Pack a towel for drying off after a dip in the ocean.
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Refreshments: Feel free to bring snacks and drinks. Remember, the charterer provides all food and stores on bareboat charters.
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Camera: Don’t forget your camera or phone to capture the moments (waterproof casing is a plus).
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A Sense of Adventure: Most importantly, bring your enthusiasm for a great time!

As for policies and safety measures, we’ve got you covered for a worry-free experience:

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Safety Briefing: Before departure, your crew will provide a safety briefing and demonstrate the use of all safety equipment.
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Life Jackets: Our partners provide life jackets for all ages and insist on their use for children and non-swimmers.
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Weather Policy: Our partners monitor the weather closely and will reschedule or refund if conditions are unsafe.
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Crew Expertise: Rest assured, whether you choose a bareboat charter and select your own crew or join a charter with a crew, you’re in capable hands.
Crew Expertise: Rest assured, whether you choose a bareboat charter and select your own crew or join a charter with a crew, you’re in capable hands.

Policies & “Before You Book” Requirements

Before you book your parasailing excursion, there are some policies and requirements you need to be aware of. Cancellations made less than 24 hours prior to the reservation time will incur a 100% charge. In the event of inclement weather or water conditions that prevent you from participating, you may be moved to a different location or rescheduled. All participants must complete and sign a liability waiver, and anyone under the age of 18 must have a parent or legal guardian complete and sign the waiver.