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VIDEO · SAILING

Sailing the Florida Keys - The Sandbar Sail

With Matt Sexton, owner and US Sailing instructor since age 16 · July 20, 2026 · 2 min 45 sec

Matt Sexton walks through the Sandbar Sail at Grassy Flats: a three-mile Hobie Cat sail to the Valhalla Sandbar, with the guides handling the boat while you bring the cooler. He also explains why sailing here feels different. Hawks Channel gives you four protected miles between the shoreline and the reef, with calmer water than an open-ocean sail.

What's in this video

0:00: Meet Matt and the fleet

0:11: Why a Hobie Cat is so much fun

0:34: The Sandbar Sail

0:45: Out to the Valhalla Sandbar and what to bring

1:00: Matt's sailing background

1:33: Learn to sail, or let the captain do the work

1:45: Is the Florida Keys a sailing destination?

2:05: Hawks Channel and why it stays sheltered

2:34: The price quoted in the video and how to book

Transcript

The Hobie Cat fleet Hey guys, this is Matt at Grassy Flats. I want to let you in on one of my favorite little secrets about this place. This little fleet behind me is probably one of the coolest ways to get on the water. No matter what, where I go, one Why a Hobie Cat is so much fun Of the most fun boats that you can get back on to is always going to be a Hobie Cat. This thing looks like a Playmobil sailboat, but I kid you not, you will have pure childhood joy out there on the water ripping it up. Probably the coolest trip we offer is called our sandbar sail. So, whether you're a couple looking for a fun romantic day trip or you got a family of four want to get out on the water, we can load up a bunch of people on these two boats and The Sandbar Sail Our guides are going to take you to the Valhalla sandbar, which is 3 miles away. Bring some sodas, bring some waters, maybe a bottle of rosé or some beers, and we're going to take you out there, Out to the Valhalla Sandbar and what to bring Show you a phenomenal way to see the Florida Keys from the water on a sailboat. At 16 years old, I became a US sailing instructor. I actually helped run one of the largest youth sailing programs in the world. We did about 5,000 kids a summer and taught everything from the state boaters Learning from an experienced sailing instructor License course for the state of Connecticut all the way up to advanced race tech theory and open ocean navigation. Since then, sailing's taken me all over the world to the Virgin Islands, to the Bahamas, pretty much everywhere in the Caribbean, Central America, South America, and a lot of Europe. That being said, the boats that we have right here at Grassy Flats are some of the most fun things you can get on the water with. So, whether you want to learn how to do a basic sailing lesson so you might go on a vacation and take a sailboat out yourself, or you want to let us do the work and grab a couple beers and we'll do a sandbar sail, we've got you covered to get on Learn to sail, or let the captain do the work The water on our sailboats. The Florida Keys is not actually known as a sailing destination, but is 100% a sailing destination. Compared to going to different parts of the world where you've got this deep Is the Florida Keys a sailing destination? Water, heavy waves, you're going to be on a boat rocking back and forth wondering if you brought your Dramamine, that is not this experience. We have this beautiful calm water right here in Hawks Channel, which is our 4-mile channel between the shoreline and the reef, which is going actually all the way out 4 mi before the water gets deep and starting to get really rough. So, we can put you on these sailboats Hawks Channel and why it stays sheltered Even on a cranking windy day, and you're going to only have about 1 to 2-ft seas on our way to the Valhalla sandbar. So, sailing in the Florida Keys is going to be different than other locations because of that. You've got calm water, you've got steady consistent winds, and you've got one of the best places to get out for a simple cruise or learn how to sail for your first time. Our sandbar sails run $249 and are going to be a guide like myself oftentimes. Any chance I have to sign up to be the coach and the captain on a sandbar sail, I'm going to take it because to this day Sandbar Sail pricing and how to book It's still one of my most fun activities we can do here. So, go online floridakeyswatermanscompany.com or call up the front desk at Grassy Flats, book your sandbar sail today.

Quick answers

What is the Sandbar Sail?
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A captain-guided Hobie Cat sail from Grassy Flats to the Valhalla Sandbar. The video describes it as a three-mile trip where guests can bring drinks and spend time in the shallow water.

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Do I need sailing experience?
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No. You can take a hands-on sailing lesson or let a captain handle the boat during a Sandbar Sail.

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Why is sailing calmer here?
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Grassy Flats sits on Hawks Channel, with roughly four protected miles between the shoreline and the reef before the water becomes deeper and rougher.

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What should I bring on the Sandbar Sail?
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Bring water, sodas and any other drinks your group wants for the sandbar. Confirm the current food-and-beverage rules with Grassy Flats before departure.

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How much does the trip cost?
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Matt quotes $249 in the video. Use the live sailing page to confirm the current price, passenger limit and availability before booking.

READY WHEN YOU ARE

Sail to the sandbar

Learn the boat yourself or let a captain handle the sail while your group enjoys the ride to Valhalla Sandbar.

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