Best Boat Rides St Augustine FL: Why We Love the Schooner Freedom

Looking for the best boat rides in St Augustine FL? We’ve found our favorite—and we keep going back.

The Schooner Freedom offers one of the most peaceful, scenic, and romantic boat rides in town. It’s the perfect way to experience St Augustine sailing tours and take in the beauty of the nation’s oldest city—from the water.

Thank you to Captain Jack and the Crew of the Schooner Freedom for another amazing view of Saint Augustine, Florida. Learn more below:

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Why Schooner Freedom Is One of the Best Boat Rides St Augustine FL

We’ve sailed on the Schooner Freedom multiple times. Every trip is relaxing, fun, and memorable.

This isn’t a loud party boat. It’s more like a floating escape—with cool breezes, wine, and bayfront views.

Here’s what makes it special:

• A real 19th-century-style tall ship
• Small group sail – never feels crowded
• Complimentary wine and soft drinks
• Friendly crew with local knowledge
• Great for couples, friends, or anyone who loves the water

If you’re looking for romantic boat rides in St Augustine, this is it.

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Is It Kid-Friendly?

We’ve brought our grandkids before, and they enjoyed it. But to be honest, we think this sail is better for adults.

The atmosphere is quiet and romantic, not geared toward children.

If you’re traveling with a partner or group of friends, it’s the perfect fit.

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Our Favorite? The Sunset Cruise

Hands down, we always choose the sunset cruise in St Augustine Florida.

Here’s why:

• Cooler evening air in the hot Florida summer
• Amazing sunset views across the water
• A glass of wine in hand and sails overhead

In winter, afternoon cruises are also lovely and a bit warmer.

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Our Rainy-Day Sailing Story

One of our most unforgettable rides was during a rainstorm.
Yep—we got soaked.

But honestly? It was one of the most fun times we’ve had in St. Augustine.
Steve and I laughed nonstop, and so did the other passengers.
(That free wine may have helped…)

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Schooner Freedom Sail Options & Prices

Here are some current options (check their website for updates):

🌅 Sunset Sail

• Departs: Around 6–6:45 PM (varies seasonally)
• Duration: 2 hours
• Price: ~$65/adult, $45/child
• Includes: Complimentary wine, soda, and water

☀️ Day Sail

• Departs: 12:15 PM
• Price: ~$55/adult

🌕 Full Moon & Specialty Sails

• Look for Wine Wednesday sails, full moon cruises, and other special events.

Check the official Schooner Freedom site here

Helpful Tips for Boat Rides in St Augustine FL

Planning one of the best boat rides St Augustine FL? These quick tips will help you get the most out of your experience aboard the Schooner Freedom or any other St Augustine sailing tour.

1. The Schooner Freedom Sailing is ranked as a top couples Activity, so Book early.

The sunset sail is the most popular and often sells out fast. If you’re adding this to your list of things to do on the water in St Augustine, reserve your spot early—especially during weekends and holidays.

2. Arrive Early for Schooner Freedom Boarding

The boat leaves exactly on time. Plan to arrive 20–30 minutes before departure so you can check in, find your seat, and get comfortable. There’s no waiting for late arrivals once the sails are up.

3. Check the Weather (But Don’t Panic)

Florida skies can change quickly. Don’t let a few clouds or a passing shower stop you. Some of our favorite memories sailing in St. Augustine happened in the rain.

4. Dress in Layers for a sunset or moonlight sail.

Even on hot summer days, it can feel chilly out on the water. Sunset cruises get breezy once the sun goes down. Bring a light sweater or jacket to stay warm and comfortable during the sail.

5. Leave the Cooler at Home

No need to bring your drinks. Complimentary wine, soda, and water are included in the price of your sail. Just sit back, sip, and enjoy the view.

6. Wear Sunscreen and Sunglasses

Daytime sails can get sunny and bright. The sun reflects off the water, making it even stronger. Be sure to wear sunscreen. Bring sunglasses or a hat to protect your eyes and face. A little shade goes a long way on the open water.

7. Bring a Small Bag for Essentials

Space is limited on deck, so skip the bulky bags. A small crossbody or tote is perfect for carrying your phone, sunscreen, and layers.

8. Secure Your Belongings

This is important—be sure to secure your phone, sunglasses, and other small items. The wind can kick up fast, and once something goes overboard, it’s probably gone for good.

9. Accessibility Notes for Boat Rides in St Augustine FL

If you’re planning one of the popular boat rides in St Augustine FL, it’s good to know what to expect when boarding.

To access the Schooner Freedom, there is a metal gangway with a slight incline that leads down to the dock. From there, it’s a short walk to the boat.

The crew was very kind and seemed helpful to passengers as they stepped onto the schooner. However, the incline on the metal walkway may be challenging for older adults or those with limited mobility—especially on hot or rainy days when surfaces may be slick.

If you or someone in your group has accessibility concerns, we recommend calling ahead to ask questions. The staff is friendly and may be able to assist or provide more details based on your needs.

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Want even more ways to enjoy the water in Florida’s oldest city? Don’t miss our guide to the best sunset cruises and boat tours in St Augustine, FL!

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Other Top Boat Rides St Augustine FL

If the Schooner Freedom is booked, here are a few other boat tours in St Augustine FL to consider:

• St. Augustine Scenic Cruise – narrated and shaded
• Florida Water Tours – dolphin tours and private charters
• Black Raven Pirate Ship – a fun option for kids

Each offers a unique way to enjoy things to do in St Augustine on the water.

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Final Thoughts: Is It Worth It?

Absolutely. The Schooner Freedom is one of the top-rated boat rides in St Augustine FL for a reason.

The views. The peaceful vibe. The friendly crew.
And yes—the wine.

💡 Tip: Not all boat rides St Augustine FL offer wine, small group sizes, and a peaceful vibe. That’s why we keep choosing the Schooner Freedom.

Every time we’re in town, we make this part of our trip.
It’s the perfect way to end a day exploring the city.

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🧭 Plan Your Own Easy USA Trip

We keep going back to St. Augustine because there’s always something new to discover. We’ll show you the hidden gems, from old-school ice cream parlors to breezy garden paths.

Explore more of our favorite things to do in St Augustine

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