Physical Address
304 North Cardinal St.
Dorchester Center, MA 02124
Physical Address
304 North Cardinal St.
Dorchester Center, MA 02124

Experience authentic sailing on Hilton Head Island with a small-group afternoon cruise, dolphin spotting, and hands-on sailing on a modern, spacious sailboat.
Introduction
If you’re looking for a way to enjoy Hilton Head Island’s coastal waters that combines the thrill of sailing with a relaxed, intimate atmosphere, then the Exciting Public Afternoon Sail offered by Anchors Away Sailing Charters might just be your ideal afternoon adventure. This experience promises a small-group setting, which means more personalized attention from the captain and plenty of opportunities to get involved—or simply sit back and soak up the scenery.
What we love about this tour? First, the exclusive feel of having only six guests aboard our newest and largest sailboat. Second, the chance to actually participate in the sailing—hoisting sails, handling lines, and steering—truly puts you in control of your marine adventure. Still, a possible consideration is the timing; the tour starts at 5:15 pm, so it’s perfect for catching the sunset or winding down after a day of sightseeing. This experience suits travelers who appreciate authentic, hands-on experiences but also want a relaxed, scenic cruise with wildlife viewing.
Key Points:
– Intimate group size ensures personalized experience and fewer crowds
– Hands-on sailing appeals to those wanting to learn or actively participate
– Wildlife sightings like dolphins and local birds enhance the tour’s appeal
– Beautiful sunset views make it perfect for a romantic or peaceful outing
– Price of $153.85 offers good value for a private-like, authentic sailing experience
– Flexible participation allows you to relax or get involved as you prefer

When you arrive at the meeting point at 7 Waterway Lane, you’ll be greeted by the crew and given a safety briefing—an essential step ensuring everyone feels comfortable on the boat. Afterward, the vessel will motor out from the marina into the scenic waters of Port Royal Sound, a prime area for wildlife spotting and spectacular views.
The Sailing Itinerary:
The core of the tour involves raising the sails and then sailing without the motor, relying solely on the wind. This not only offers a genuine sailing experience but also a chance to witness firsthand how a well-handled sailboat responds to the elements. The captain encourages guests to participate—hoisting sails, handling lines, steering—making this more than just a cruise; it’s a hands-on adventure.
The route through Port Royal Sound is carefully chosen for its dolphin activity and abundant birdlife. We loved the way the captain expertly navigates the waters, slowing down at promising spots so guests can marvel at playful dolphins that often come close to the boat. As one reviewer noted, “This activity is perfect for all ages to enjoy,” highlighting its broad appeal.
Wildlife and Scenery:
Dolphin sightings are a highlight, especially during the transition from motoring to sailing, when the boat is in motion and the marine mammals often swim alongside or leap nearby. Birdwatchers will also appreciate the variety of local seabirds, adding to the natural charm of the trip.
Participation and Relaxation:
Whether you want to get hands-on or just relax and enjoy the views, the crew respects your choice. This flexibility ensures the experience remains comfortable for everyone, whether you’re eager to learn sailing techniques or prefer to sit back with a cool drink. The included sodas and bottled water help keep you refreshed during the trip.
End of the Trip:
Once the two hours are up, the sails are lowered, and the boat motors back to the marina. The return trip also offers chances for more dolphin sightings, making it a fitting conclusion to a memorable afternoon.

At $153.85 per person, this tour might seem on the higher end for a two-hour activity, but it’s important to consider what’s included. You get a small, private feel, personalized attention from an experienced captain, and a chance to actively participate in sailing—a rare opportunity in organized tours. Plus, the wildlife sightings and scenic views can make it well worth the investment.
Compared to larger, less interactive cruises, this tour offers genuine value for travelers seeking an authentic, hands-on sailing experience without the exclusivity or cost of a private charter. The inclusion of drinks is a nice touch, keeping you hydrated while you enjoy the coastal scenery.
Sailing fans have several other Hilton Head Island options to choose from

This experience is perfect for small groups, couples, families, or friends who want a relaxed yet engaging way to explore Hilton Head’s waters. It’s ideal if you’re curious about sailing or simply yearn for a peaceful afternoon in nature. Those who enjoy wildlife watching—especially dolphins—will find this tour particularly rewarding. Because it’s suitable for all ages and involves no strenuous activity, it’s a great outing for a wide range of travelers.


The Exciting Public Afternoon Sail offers a lovely balance of adventure, relaxation, and wildlife watching in Hilton Head. With limited seats, you’ll enjoy a more personal experience, and the opportunity to actively participate in sailing adds a unique touch many travelers cherish. Whether you’re a sailing novice, wildlife enthusiast, or simply looking for a scenic break, this tour provides a genuine taste of coastal life.
While the price may seem steep for a two-hour trip, the authentic sailing, friendly crew, and beautiful scenery make it a worthwhile investment. It’s especially suitable for those who want a memorable, hands-on experience that’s more intimate than larger boat tours. If you’re after a peaceful, engaging, and scenic way to spend an afternoon on Hilton Head’s waters, this tour deserves a spot on your list.
More ways to experience Hilton Head Island from the water include these boat tours

Is this tour suitable for all ages?
Yes, the tour is designed to be enjoyed by all ages. It’s a relaxed experience where everyone can participate at their comfort level, making it ideal for families and groups with children.
What should I wear?
Dress comfortably for the weather, preferably in layers. Since it’s outdoors on a boat, sunscreen and sunglasses are recommended to protect against the sun.
Can I get involved in sailing activities?
Absolutely. The captain encourages guests to get involved in hoisting sails, handling lines, and steering, but you can also choose to simply sit back and enjoy the scenery.
What wildlife might I see?
Dolphins are frequently spotted, especially during the transition from motoring to sailing. Birdwatchers will also enjoy observing local seabirds along the route.
What’s included in the price?
You’ll receive a 2-hour sailing adventure with a small group, along with sodas, diet Coke, Sprite, and bottled water.
Do I need to make a reservation?
Yes, booking in advance is recommended, especially since the tour limits participation to 6 guests and operates at a specific time—5:15 pm.
What if the weather is bad?
If weather conditions are poor, the tour may be canceled or rescheduled, and you will be offered a full refund or a different date.
Embark on this afternoon sailing trip for a genuine, relaxed, and fun adventure on Hilton Head Island’s waters. Whether you’re looking to learn, spot dolphins, or simply unwind with scenic views, this experience offers a memorable taste of coastal life that you won’t forget.