Private Boat for 20: Island Hopping, Dolphins, + Swimming

Imagine cruising through the calm, dolphin-filled bay of Clearwater on your own private boat, with room for up to 20 people. For just $748, your group can enjoy a tailored 2-hour adventure that combines island hopping, dolphin watching, and a refreshing swim on a tiny sandy beach. The experience is hosted by Paddle Pub Clearwater LLC, and it’s ideal for birthdays, bachelorette parties, corporate outings, or simply a fun day on the water with friends and family.

What makes this trip especially appealing are two key features. First, the private nature of the boat — no strangers, just your group, creating a relaxed, personalized vibe. Second, the ability to bring your own food and drinks, turning it into a true floating party. The lively Bluetooth music system and floats add an extra layer of fun.

One potential consideration is the duration—just two hours—so if you’re craving a full day of exploring, this may feel a bit short. Still, the quick pace and intimate setting make it perfect for a half-day escape.

This tour suits travelers who appreciate a blend of adventure, socializing, and relaxed beach time. If you’re looking for a lively, customizable experience with lots of opportunities for dolphin sightings and beach walks, this private boat tour in Clearwater could be just what you need.

Key Points

• Private Experience: Tailored for your group, offering exclusivity and flexibility.
• Dolphin Watching: A highlight with frequent sightings in the bay.
• Island Hopping: Stop for swimming and a walk on a picturesque tiny beach.
• BYOB Friendly: Bring your favorite drinks and snacks — perfect for a laid-back party.
• Lively Atmosphere: Bluetooth music and floats enhance the fun onboard.
• Short & Sweet: 2-hour tour, ideal for a quick yet memorable outing.

You can check availability for your dates here:

A Detailed Look at the Clearwater Private Boat Experience

Setting the Scene: A Private Boat in the Heart of Clearwater

When you book the Private Boat for 20: Island Hopping, Dolphins, + Swimming, you’re stepping into a scene that combines the freedom of the open water with the comfort of your own group. At $748 per group (up to 16 guests, but the boat can hold 20 plus crew), this is a surprisingly good deal for a personalized adventure.

The boat itself is spacious—large enough to comfortably accommodate everyone, with a Bluetooth sound system ready for your playlist, and coolers to keep your drinks chilled. The crew, based on one positive review, is described as “friendly and fun,” making the entire experience feel warm and welcoming.

The Itinerary: What to Expect from Start to Finish

The tour begins with a simple walk through Papaya Street Plaza to reach the docks, conveniently located behind the Marriott. Once aboard, your group will set sail through Clearwater Bay, a known habitat for playful dolphins. It’s common to spot these intelligent creatures, and many guests find dolphin sightings to be a highlight of their trip. Keep your eyes peeled — the bay teems with these playful swimmers.

The main activity is island hopping, where the boat anchors at a tiny, sandy island right in the middle of the bay. You’ll get off the boat to walk along the small beach, take a dip in the inviting waters, and relax on the sand with a float or two. The shallow waters and gentle waves make swimming safe and enjoyable, especially on a warm Florida day.

Music is always onboard, with Bluetooth connectivity allowing you to crank up your favorite tunes, turning the experience into a floating party. Guests are encouraged to bring their own food and drinks, so you can pack a picnic or cocktails — a big plus for groups wanting to celebrate or just chill out without extra costs.

Highlights That Make This Tour Unique

One of the most praised aspects, based on reviews, is the stunning views and the fun, lively atmosphere. Holly from the United States shared, “The staff was friendly and fun! Took lots of pictures for us and shared fun facts about the area.” Her review underscores how the crew not only facilitates the tour but also enhances the overall enjoyment with helpfulness and good humor.

The beach stop is especially memorable; walking onto the small island feels like a private getaway, far from the crowds. The calm waters and soft sands make it a perfect spot for a quick swim and some sunbathing. Plus, the floats and music keep the mood light and festive.

More Great Tours Nearby

Practicalities and Considerations

Since the tour is only two hours long, it’s ideal for those looking for a quick but fun escape. If you’re seeking an extended adventure, you might find this duration somewhat limiting, but for most, the compact schedule keeps things lively and engaging. The group size—up to 20 people—means you’ll enjoy a sociable vibe but not overcrowded, and the private nature ensures personalized attention.

A key convenience is the flexible booking and cancellation policy—you can reserve now and pay later, with the option to cancel up to 24 hours in advance for a full refund. This makes it easy to fit into your plans without stress.

Authentic Experience and Tips to Maximize Your Day

Based on the review, Holly’s experience was very positive; she appreciated the crew’s efforts and the photo opportunities. To make the most of your trip, consider bringing a waterproof camera or phone case to capture the scenic views and playful dolphins.

Pack essentials like sunscreen, towels, snacks, and water—though you can also bring your own drinks to sip while relaxing on the water. The shallow bay and calm waters are perfect for swimming, so don’t forget your swimwear and towel.

For a memorable experience, arrive early to enjoy the peacefulness of the bay before the crowds arrive, and be ready to spot dolphins and enjoy the gentle waves.

Who Should Consider This Tour?

This private boat experience is perfect for small groups wanting a personalized, relaxed outing. It’s especially suited for those celebrating special occasions or simply wanting a fun, social day on the water. If you’re an animal lover, dolphin sightings make this trip particularly rewarding.

Those who like to bring their own food and drinks will appreciate the BYOB policy, making it a flexible, budget-friendly way to celebrate. If you prefer a longer, more extensive cruise or a guided tour with a more structured itinerary, you may want to look elsewhere.

This tour offers a delightful combination of adventure, relaxation, and a touch of party atmosphere—ideal for travelers who value authentic, small-group experiences with a splash of fun.

Frequently Asked Questions

How many people can the boat accommodate?
The boat can hold up to 20 people plus 2 crew members, making it suitable for private groups of up to 16-20 guests.

Is the tour suitable for children?
Yes, the trip involves swimming, relaxing, and dolphin watching, which families often find enjoyable. Just ensure children can handle a boat ride and swimming in the bay.

What should I bring?
Bring swimwear, towels, snacks, drinks, sunscreen, water, and a scarf or hat for sun protection. You might also want a waterproof camera if you want to capture the scenery and dolphins.

Can I bring my own food and drinks?
Absolutely. The tour is BYOB, so you can pack your favorite beverages and snacks for a more personalized experience.

What is the duration of the tour?
The tour lasts about 2 hours, typically available in the morning and afternoon. It’s a quick but action-packed escape.

Where do I meet the boat?
The meeting point is at Papaya Street Plaza, behind the Marriott. The crew will meet you at the gate, and it’s a short walk from the main area.

Is there any cancellation fee?
You can cancel up to 24 hours in advance for a full refund, giving you flexibility if your plans change.

Final Thoughts

For anyone seeking a private, fun-filled water adventure in Clearwater, this boat tour hits many sweet spots. Its intimate setting, dolphin sightings, and beach stop create a memorable mini-getaway. The ability to BYOB and the lively atmosphere make it a fantastic option for groups wanting a flexible, customizable experience.

While the two-hour duration might be short for those craving a full-day excursion, it’s perfect for a quick, energetic escape that leaves plenty of room for planning other activities nearby. The friendly crew and the stunning views make this tour a standout choice for those who prioritize authentic, small-group adventures with a lively twist.

If you’re celebrating a special occasion or just want to enjoy Clearwater’s waters in style, this private boat tour offers a practical balance of fun, flexibility, and beautiful scenery—an experience worth considering for your next trip.

You can check availability for your dates here: