Set Sail With Captain Harry

NEW Dunedin, FL 1 - 6 People 4 - 8 Hours From $400 Trip #11158
Fishing in Destin
Fishing in Destin
Fishing in Destin
Fishing in Destin
Fishing in Destin
Fishing in Destin
Fishing in Destin
Fishing in Destin
Fishing in Destin
Fishing in Destin
Fishing in Destin
Fishing in Destin
Fishing in Destin
Fishing in Destin
Fishing in Destin

About Your Trip

Type

Eco Tour, Boat Cruise

Skill Levels

Beginner, Intermediate, Advanced

Weather

You won’t lose your deposit if the trip is canceled due to weather.

Looking for a unique way to experience Florida’s Gulf Coast? Join Captain Harry for a private sailing adventure through the stunning waters surrounding Dunedin. Whether you're after a relaxing escape, an eco-focused wildlife tour, or hands-on sailing instruction, this personalized charter offers the perfect way to explore the area’s natural beauty—without the crowds.

Your day begins aboard a spacious 41’ Morgan Out Island Ketch, designed for comfort and smooth cruising. With trips limited to just...

About Your Trip

Looking for a unique way to experience Florida’s Gulf Coast? Join Captain Harry for a private sailing adventure through the stunning waters surrounding Dunedin. Whether you're after a relaxing escape, an eco-focused wildlife tour, or hands-on sailing instruction, this personalized charter offers the perfect way to explore the area’s natural beauty—without the crowds.

Your day begins aboard a spacious 41’ Morgan Out Island Ketch, designed for comfort and smooth cruising. With trips limited to just six guests, you and your group will have the boat to yourselves for a tailored experience built around your interests.

Half Day Sail

This four-hour cruise is perfect for those wanting a taste of sailing through the calm waters of St. Joseph Sound. Keep an eye out for dolphins, enjoy the coastal breeze, or hop off to explore one of the nearby spoil islands. Whether you're looking to relax or take the wheel for a bit, Captain Harry is happy to guide the experience at your pace.

Full Day Cruise

Spend a full day sailing to some of the Gulf Coast’s most beautiful destinations. From the white sands of Honeymoon Island and Caladesi Island to the remote beauty of Anclote Key and its historic 1887 lighthouse, you’ll have the chance to anchor, explore, and unwind. Prefer to stay aboard and enjoy the rhythm of the wind and water? You can do that too. It’s your day—set the course however you like.

Eco Tour (Full Day)

Nature lovers will appreciate this guided ecological experience led by Captain Harry, a certified Florida Coastal Naturalist. As you sail through grass flats, mangroves, and bird rookeries, you’ll spot a variety of local wildlife, including bald eagles, ospreys, rays, and dolphins. Kayaks are available upon request for guests who want to paddle into the shallows and get an even closer look at these thriving ecosystems.

Want to Learn to Sail?

No matter your experience level, Captain Harry offers hands-on instruction for those interested in learning the basics or brushing up on their skills. Just let him know you're eager to learn, and he’ll tailor the trip accordingly.

All charters are private, and everything you need for the day is provided. Just bring your favorite snacks, drinks, sun protection, and a sense of adventure.

Set your course for an unforgettable day on the water—book now and experience Dunedin like never before.
Amenities

Type

Eco Tour, Boat Cruise

Skill Levels

Beginner, Intermediate, Advanced

Beer

Feel free to enjoy responsibly, but please no glass.

Weather

You won’t lose your deposit if the trip is canceled due to weather.

Kid Friendly

This trip can cater to small children.

Flexible Cancelation

This trip can be canceled up to 14 days before the trip.

Disability Friendly

This trip is not suited for those with disabilities.

Lunch

Please provide your own food / snacks.

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Pricing Matrix

4 hours 8 hours
1 Person
$400.00
$800.00
2 People
$400.00
$800.00
3 People
$400.00
$800.00
4 People
$400.00
$800.00
5 People
$400.00
$800.00
6 People
$400.00
$800.00
Pay 15% of the price as a deposit today, with the balance due on the day of the trip.
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About Your Guide

Harry

Independent Guide
Born and raised in Dunedin, Captain Harry knows the shores of Dunedin/Clearwater Bay like the back of his hand. A fourth generation native Floridian and sailing since he was a child; he has decades of experience navigating the Florida waterways and the Gulf of Mexico. Captain Harry is a retired teacher who brings his knowledge and gift of sharing to each charter.

About Your Guide

Harry

Independent Guide
Born and raised in Dunedin, Captain Harry knows the shores of Dunedin/Clearwater Bay like the back of his hand. A fourth generation native Floridian and sailing since he was a child; he has decades of experience navigating the Florida waterways and the Gulf of Mexico. Captain Harry is a retired teacher who brings his knowledge and gift of sharing to each charter.
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Start Location & Lodging Options

Dunedin, Florida

About Your Boat

Boat photo for Set Sail With Captain Harry
Boat photo for Set Sail With Captain Harry
Boat Type
Sailboat
Boat Manufacturer
Out Island Ketch
Boat Length
41'
Boat Restroom
No

About Your Boat

Boat Type
Sailboat
Boat Manufacturer
Out Island Ketch
Boat Length
41'
Boat Restroom
No
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Trip Details & Amenities

Type

Eco Tour, Boat Cruise

Skill Levels

Beginner, Intermediate, Advanced

Beer

Feel free to enjoy responsibly, but please no glass.

Weather

You won't lose your deposit if the trip is canceled due to weather.

Kid Friendly

This trip can cater to small children.

Flexible Cancelation

This trip can be canceled up to 14 days before the trip.

Disability Friendly

This trip is not suited for those with disabilities.

Lunch

Please provide your own food / snacks.

Everything Else to Know

Everything is included, but we also recommend bringing sunglasses, sunscreen, weather-appropriate clothing, and anything else you might want on the trip.
We use a cashless autopay system. We'll send you a boarding pass, and on the day of the trip, your guide will scan your boarding pass to automatically transfer the remaining balance. The only cash needed is to tip your guide (we recommend 20%).
Cancel for free up to 14 days before the trip and receive credit back to your account. Cancelling within 14 of the trip will forfeit your deposit to the guide. Day-of cancellations and no-shows will be charged the full balance of the trip to their card.
In the event of inclement weather you'll be covered by out 100% Weather Guarantee and will not lose your deposit.

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First Time Booking with Us?

Captain Experiences is home to thousands of quality, vetted fishing, hunting, and other outdoor sports guides across the US and beyond. Our mission is to Unlock the Outdoors by making it quick and easy to book the trip of a lifetime every time with our Damn Good Guides.
We vet our guides and only partner with the best of the best. Our guides do their very best to keep you safe, show you a great time, and send you home with a memorable experience shared with family and friends.
Once you've paid your deposit at checkout, we'll send you a QR Code boarding pass. Just show your guide your boarding pass on the day of the trip, they'll scan it, the remaining balance will transfer automatically, and you'll be all set to get out there. Just make sure you bring a cash tip for the guide!
In the event of inclement weather, our guides will check the conditions and make the final call on whether its safe to go on the trip. If they decide the trip needs to be postponed, we'll work closely with you to reschedule or provide a credit for the full deposit, which can be applied to any of our trips in the US and beyond.
Each trip's price is determined by the guide and reflects all associated costs. A significant factor in pricing is often the type of boat and the corresponding fuel expenses. Additional costs may include leases, marina or slip fees, and the expenses involved in providing and maintaining the necessary gear for your trip.
After booking your trip, we'll connect you directly with your guide to discuss additional details. In the meantime, our team is here to answer any questions via email, text, or phone.
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