Private Hilton Head Sunset Sailing Tour with Dolphin Watching

If you’re dreaming of a peaceful yet engaging way to enjoy Hilton Head Island’s natural beauty, this private sunset sailing tour might just be your perfect match. It promises a leisurely two hours where you can relax on a beautifully maintained sailboat, watch playful dolphins, and take in one of the most spectacular sunsets the Lowcountry has to offer.

Our review covers everything you need to know—what makes this tour special, what to expect along the way, and some practical tips based on dozens of glowing traveler reviews. We love how personalized and intimate the experience is, with only your group aboard, and how flexible the crew is about involving guests in the sailing process.

One possible thing to keep in mind is that the tour operates on good weather days; if the weather turns, the trip could be canceled. But with the option to reschedule or get a full refund, it’s a low-risk, high-reward way to enjoy Hilton Head’s waters.

This tour fits best for couples, families, or small groups seeking a memorable, authentic sailing experience with plenty of wildlife viewing and sunset photography. If you’re after a fun, relaxing adventure that combines education, nature, and gorgeous scenery, this private sail will likely delight you.

Key Points

• Personalized Experience: Only your group sails together, making it intimate and flexible.
• Wildlife Watching: Dolphin sightings are frequent, with some reviews mentioning up to six dolphins.
• Sailing Involvement: Guests can participate in sailing activities or simply relax and enjoy the ride.
• Stunning Views: Expect remarkable sunsets and great photo opportunities with sails against the colorful sky.
• Knowledgeable Crew: Guides are friendly, informative, and eager to share insights about local wildlife and sailing.
• Good Value: At $525 for up to six people, the experience offers a memorable, private outing that many find well worth the cost.

An In-Depth Look at the Hilton Head Sunset Sailing Experience

This private tour, offered by Anchors Away Sailing Charters, provides an opportunity to enjoy Hilton Head’s stunning coastal scenery from a comfortable sailboat. The two-hour trip begins at the Safe Harbor Skull Creek marina, a convenient starting point in Hilton Head Island. The boat itself is described as beautiful and clean, with attentive crew members ready to make your trip special.

What the Itinerary Looks Like

The core of the experience is sailing in calm waters just a few minutes from the marina—no long motor rides or crowded group tours here. Once in the sailing zone, the crew will raise the sails and turn off the motor, allowing you to feel the true rhythm of sailing. For some, this is the highlight—the peaceful, quiet glide over the water with only the sound of wind and waves.

Throughout the trip, the crew is committed to making your experience both fun and educational. They’ll tell stories about local wildlife, including dolphins, manatees, and various bird species. Several reviews mention how guides like Captain Andy, Jude, and others are not only friendly but eager to share their knowledge, making the trip enjoyable for kids and adults alike.

Sunset and Wildlife

As the boat approaches sunset, you’ll have plenty of opportunities for stunning photos with the sails silhouetted against the late afternoon light. Many travelers comment on how spectacular the sunset is—one reviewer even calls it “the most beautiful sunset we saw while in Hilton Head.” The crew often stows the sails as the sky turns vibrant hues, and you can watch the sun dip below the horizon from a comfortable vantage point.

Dolphin sightings are a frequent highlight—several reviews mention seeing dolphins up to six times during their sail. The crew maintains an attentive eye on the water, and guests often get to see playful pods swimming alongside the boat.

How Involved Can You Be?

One of the most appreciated aspects of this tour is its flexibility regarding guest participation. If you’re interested, you can learn sailing tips, steer the boat, or help with the sails. For those who prefer a relaxed approach, simply sitting back and soaking in the scenery is equally welcomed. This balance makes it suitable for a wide range of travelers, from eager learners to those seeking serene escape.

Practical Details and Considerations

The price of $525 covers the entire boat for your group—up to six people. Many reviews emphasize that this price is quite fair considering the intimacy, personalized service, and memorable experience you get. The tour is most often booked about 35 days in advance, suggesting it’s popular, especially during peak season.

The tour is offered in English and requires only most travelers to participate, including service animals. It’s near public transportation, making it accessible for visitors staying around Hilton Head.

Remember that cancellation is free up to 24 hours before the scheduled start. If the weather turns poor, the tour will be canceled or rescheduled, with full refunds or alternative dates offered. This policy minimizes risk, but it’s worth noting that you might find weather-dependent sailing a little unpredictable.

What Travelers Say

The reviews consistently praise the knowledgeable crew, mentioning how friendly and professional guides like Captain Randy, Paul, Kevin, and Jude make the trip enjoyable and safe. Many travelers highlight how much they appreciated the dolphin sightings—some even note seeing dolphins multiple times during their sail.

Several reviews mention how the experience appealed to families, including children as young as 7 or 8, who are able to help with sails or steering, making it engaging for all ages. The sunset views, combined with the chance to see local wildlife, make it a “must-do” activity for many.

Value for Money

Considering the private nature of the tour, the personalized attention, and the opportunity to see dolphins and beautiful sunsets, most guests feel the cost of $525 is justified. The reviews reflect a strong sense that this experience provides excellent value, especially for special occasions like birthdays or romantic outings.

The Sum Up: Who Will Love This Tour?

This private sunset sailing trip is ideal for small groups or couples who want a tailored, intimate experience that combines wildlife viewing, sailing, and stunning scenery. It’s perfect if you appreciate expert guides who can share local stories and answer your questions, and if you’re seeking a relaxing yet engaging way to enjoy Hilton Head’s coast.

Families with children who are interested in learning about sailing will find it especially rewarding. The flexible participation options—whether you want to steer or just relax—make it accessible and fun for everyone.

If you’re celebrating a special milestone or just want a peaceful escape to unwind at sunset, this tour offers an authentic and memorable way to experience Hilton Head’s natural beauty. The combination of dolphins, sunsets, and personalized service ensures it’s a highlight for many travelers.

Frequently Asked Questions

How long is the tour?
The tour lasts approximately two hours, starting from the marina and ending back there.

What is included in the price?
The price covers the entire boat for your private group—up to six people—and the guided sailing experience.

Can I participate in sailing activities?
Yes, guests can choose to get involved with sailing tips, steering, and handling sails, or simply relax and enjoy the ride.

What happens if the weather is bad?
The tour requires good weather. If canceled due to bad weather, you’ll be offered a different date or a full refund.

Is the tour suitable for children?
Most travelers can participate, including children, and some reviews mention kids helping with sails or steering, making it family-friendly.

What do I need to do to get into Hilton Head Plantation?
You should tell the guard that the marina called in a pass for you and show a photo ID; the pass will be under the name of the person who booked the tour.

This sailing adventure offers a unique blend of relaxation, wildlife, and scenic beauty—perfect for those looking to enjoy Hilton Head’s waters in a personal, memorable way.