St Augustine: Shared Sunset Sailing Charter

Imagine drifting along the waters of St. Augustine as the sun dips behind historic landmarks, casting the sky in hues of orange and pink. That’s exactly what a 2-hour sunset sailing cruise in St. Augustine promises—an intimate, scenic experience that’s perfect for couples, small groups, or anyone craving a peaceful escape from the busy streets.

While we haven’t personally set sail on this specific tour, reviews and descriptions paint a vivid picture of what travelers can expect. We love how this experience combines stunning views with a relaxed, small-group vibe. The chance to glide past icons like the Castillo de San Marco, the Bridge of Lions, and the St. Augustine Lighthouse makes it a memorable way to appreciate the city from the water.

One thing to keep in mind: this tour is limited to 6 participants, which means it’s ideal for those looking for a more personal, less crowded experience. However, it’s not suited for non-swimmers or people prone to seasickness, so some travelers may need to consider that. Overall, if you’re after a peaceful, scenic, and small-group adventure—especially at sunset—this cruise could be just the ticket.

Key Points

• Short but Sweet: The 2-hour duration makes it a manageable and relaxing addition to your itinerary.
• Intimate Experience: Limited to 6 participants, ensuring a personalized journey.
• Iconic Views: Pass by major landmarks like the Castillo de San Marco, Bridge of Lions, and Lighthouse.
• Relaxing Atmosphere: Feel the wind in your hair and enjoy a drink while taking in the beauty.
• Flexible Cancellation: Full refund available if canceled at least 24 hours in advance.
• Ideal for Sunset Lovers: Perfect timing for those wanting to see the city’s architecture bathed in golden light.

You can check availability for your dates here:

What You Can Expect from the Sunset Sailing Experience

If you’re looking for a calm, scenic way to end your day in St. Augustine, this shared sunset cruise offers just that. The experience begins as you arrive at the marina a bit before your scheduled departure—being punctual is important, as you’ll want to be on time to set sail. Once greeted by the crew, you’ll board a comfortable boat suited for small groups, which enhances the intimacy and relaxed vibe of the tour.

As you set out, the crew will steer you past some of the most recognizable landmarks of the city. The Castillo de San Marco stands proudly on the waterfront, its star-shaped walls providing a striking backdrop in the late afternoon light. The Bridge of Lions, with its graceful arches and ornate details, offers a lovely view from the water, especially at sunset. The St. Augustine Lighthouse, perched on Anastasia Island, provides a dramatic silhouette against the colorful sky.

Throughout the cruise, you’re encouraged to sip on a drink—alcohol can be purchased prior to departure—and simply enjoy the breeze, the views, and the peaceful atmosphere. The crew aims to create a memorable moment, whether you’re celebrating a special occasion or just seeking a tranquil escape.

Once the sun dips below the horizon, the sky transforms into a canvas of pink, purple, and gold. Many reviewers mention that the views are absolutely stunning, with some describing it as a “breathtaking” way to see the city. After sunset, the boat gently heads back to the marina, leaving you with a lasting impression of St. Augustine’s beauty from the water.

Details That Matter

Duration and Group Size: At just 2 hours, this cruise strikes a nice balance between enough time to soak in the scenery and not overcommit. The limited group size (6 participants) makes for a more relaxed, conversational experience—ideal if you prefer a quieter, more personal outing.

Pricing and Value: While specific prices aren’t listed here, the focus on small groups and scenic views suggests this experience is geared toward travelers who value quality over quantity. If you’re seeking a peaceful, scenic end to your day, the cost per person is likely justified by the intimate setting and stunning vistas.

Cancellation Policy: With free cancellation up to 24 hours before, you can plan with confidence. The flexibility is especially helpful if your plans change or weather looks uncertain.

Accessibility and Restrictions: The tour isn’t suitable for non-swimmers or those prone to seasickness, so consider your comfort on the water. Pets, smoking, and sprays are not allowed onboard, and alcohol must be purchased beforehand. Also, note that the crew emphasizes arriving 10 minutes early and wearing shoes with non-marking soles.

COVID Measures: The experience adheres to current health guidelines, providing a safe environment for participants.

Why This Tour Works for Different Travelers

This sunset sailing tour is best suited for those who enjoy relaxing, scenic moments and want to see St. Augustine from a different perspective. It’s perfect for couples celebrating a special moment, small groups seeking an intimate outing, or solo travelers who enjoy peaceful, unobstructed views.

However, it’s not recommended for people who aren’t comfortable on the water or have mobility issues. Also, if you’re looking for a high-energy, lively experience, this might feel a bit too calm—though the tranquility is precisely what many find appealing.

The stunning vistas make this tour stand out, especially at sunset, as the city’s historic architecture is bathed in warm light. Combined with the gentle sway of the boat and the soft sounds of the water, it’s a wonderful way to unwind and appreciate St. Augustine’s charm.

The Sum Up

This shared sunset sailing cruise offers a peaceful and scenic way to experience St. Augustine’s most iconic landmarks. Its small-group vibe ensures a personalized experience, perfect for couples or small groups seeking quiet beauty over hustle. The views of the Castillo, the Bridge of Lions, and the Lighthouse, all set against a colorful sunset, are the highlights that make this tour memorable.

While it’s not suited for everyone—particularly those with seasickness or mobility issues—the overall value lies in the combination of stunning scenery, relaxed atmosphere, and intimate setting. It’s a great choice for travelers who want a gentle, picturesque end to a day in this historic city.

If you love spectacular sunsets and are eager for a smooth, unhurried experience on the water, this cruise offers a genuine, affordable way to see St. Augustine from a fresh perspective. Just remember to book in advance, arrive on time, and enjoy the peaceful beauty of Florida’s oldest city from the deck of a sailboat.

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FAQ

Is this tour suitable for non-swimmers?
This tour isn’t recommended for non-swimmers because it takes place on a boat, and comfort on the water is important. If you’re unsure, consider your comfort level around boats before booking.

How long is the cruise?
The cruise lasts approximately 2 hours, making it a manageable outing that won’t take up your entire evening but still provides ample time to enjoy the scenery.

Can I bring my own drinks?
No, all alcohol must be purchased prior to departure from the office. You’re welcome to sip a drink onboard, enhancing the relaxing atmosphere.

Are pets allowed on the boat?
No, pets are not permitted onboard, ensuring a comfortable environment for all guests.

What landmarks will I see?
You’ll enjoy views of the Castillo de San Marco, the Bridge of Lions, and the St. Augustine Lighthouse, all as the sun sets behind them.

Is this experience flexible in case of bad weather?
Yes, you can cancel up to 24 hours in advance for a full refund, which is helpful if weather conditions look uncertain.

This sunset sailing tour in St. Augustine offers a charming, peaceful way to admire the city’s beauty from the water. Whether you’re traveling as a couple, a small group, or a solo adventurer, it’s a memorable way to cap off a day of exploring this historic seaside town.