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You're in good hands

Book your trip with confidence — We only work with the best local guides that know the area like the back of their hand.

About Your Trip

Type

Boat Cruise, Dolphin Watching

Skill Levels

Beginner, Intermediate, Advanced

Weather

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

About Your Trip

Set sail on Florida’s Treasure Coast with Captain Troy for a private sailing experience that’s all about great wind, beautiful views, and total relaxation. Whether you’re a first-time sailor or a seasoned sea-goer, Captain Troy brings a warm, safety-forward approach that makes everyone feel right at home—from the Fort Pierce Inlet to the hidden coves behind Hutchinson Island.

As a USCG-licensed captain with deep local knowledge, Troy knows how to make the most of your time on the water. He’s friendly, professional, and just the right amount of obsessed with catching a perfect breeze. From learning to tack and trim to simply sitting back and soaking up the salt air, your day will be tailored to fit exactly what you’re looking for.

You’ll be sailing aboard a capable and comfortable 39-foot Catalina cruising sloop, designed for both performance and ease. With a spacious shaded cockpit, three cozy double berths below deck, a marine head, and plenty of room to stretch out, it’s the ideal vessel for couples, families, or small groups looking for a private and peaceful escape.

Captain Troy offers two charter options to match your schedule and sense of adventure:

Half-Day Sail (4 Hours)

A relaxed outing with plenty of time to feel the breeze, spot dolphins, and either take the helm or unwind in the shade. It’s the perfect intro to sailing or a refreshing break from the bustle of the land.

Full-Day Sail (8 Hours)

Set off for a full coastal adventure—sailing offshore along the Treasure Coast or cruising down the Intracoastal Waterway to Stuart and back. With a full day on board, you can explore more, anchor for a swim, enjoy lunch on the water, and truly settle into the rhythm of the sea.

These charters are all about custom experiences—whether you’re celebrating a special occasion, introducing the family to sailing, or just looking for a quiet day away from it all. Captain Troy keeps the atmosphere easygoing, the itinerary flexible, and the focus right where it should be: on you enjoying your time on the water.

All safety gear and sailing equipment are included—just bring your favorite drinks, snacks, sun protection, and a sense of adventure.

Book your private sailing trip today and let Captain Troy show you why the Treasure Coast is one of Florida’s best-kept secrets for a day under sail.

Amenities

Type

Boat Cruise, Dolphin Watching

Skill Levels

Beginner, Intermediate, Advanced

Beer

Feel free to enjoy responsibly, but please no glass.

Boat Restroom

This boat has a restroom.

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 3 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	$595.00	$1,150.00
2 People	$595.00	$1,150.00
3 People	$595.00	$1,150.00
4 People	$595.00	$1,150.00
5 People	$595.00	$1,150.00
6 People	$595.00	$1,150.00

Pay 50% of the price as a deposit today, with the balance due on the day of the trip.

About Your Guide

Troy T.

Independent Guide

Meet Captain Troy: Friendly, safety‑forward, and obsessed with good wind. Captain Troy knows these waters—from the Fort Pierce Inlet to quiet coves behind Hutchinson Island. Whether it’s your first sail or your hundredth, you’ll feel right at home. Troy is happy to do hands-on sailing or a pure relaxation trip, whatever you'd prefer. He can tailor the itinerary for couples, families, and small groups. Troy is a USCG licensed captain and knows all the local...

About Your Guide

Troy T.

Independent Guide

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Start Location & Lodging Options

Fort Pierce, Florida

About Your Boat

Boat Type: Sailboat
Boat Manufacturer: Catalina
Boat Length: 39'
Boat Restroom: Yes

About Your Boat

Boat Type: Sailboat
Boat Manufacturer: Catalina
Boat Length: 39'
Boat Restroom: Yes
Engine Manufacturer: Yanmar
Total Horsepower: 40
Number of Engines: 1

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Trip Details & Amenities

Type

Boat Cruise, Dolphin Watching

Skill Levels

Beginner, Intermediate, Advanced

Beer

Feel free to enjoy responsibly, but please no glass.

Boat Restroom

This boat has a restroom.

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 3 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 3 days before the trip and receive credit back to your account. Cancelling within 3 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.