Private Hilton Head Sunset Sailing Tour with Dolphin Watching

The motor cuts off once you're under sail, and the engine noise disappears entirely.

A 2-hour private sunset sail on Port Royal Sound near Hilton Head where you raise the sails, watch for dolphins and manatees in the evening light, and lower them to watch the sunset from the water. You choose how involved you want to be: help trim the sails or sit back and let the crew manage everything. Soda and bottled water are included. The captain speaks English and meets you at the marina after a brief motor out to the sailing grounds.

The experience

What makes this different from a motorboat tour is that the engine actually stops. You motor out from the marina just a few minutes to Port Royal Sound on the north side of the island, where conditions are generally best for sailing. Once there, the sails go up and the motor shuts down. That silence (and the feel of the boat responding to wind instead of throttle) is what separates true sailing from a scenic ride. The crew invites you to be as hands-on as you want: help with the lines, trim the sails, steer if you're interested. Or don't. If you'd rather sit and watch, that works too.

You sail until sunset, which means the light is changing the whole time you're out there. The crew sets up for group photos with the sails and the sky behind them. Once the sun gets low, the sails come down and you watch from the deck as it drops into the water. That's when the wildlife tends to show up: dolphins, manatees, stingrays, birds. The evening is when they're most active. You'll also see Pinckney Island and Parris Island from the water, landmarks most visitors only see from land.

After the sun sets, you motor back to the marina and usually dock right around last light. The whole trip is 2 hours. Bring a photo ID for the gate pass into Hilton Head Plantation, which the marina will have called in for you before you arrive.

What’s included

• Soda and bottled water.
• a captain who speaks English and handles the boat.
• the choice to help sail or relax while the crew works.
• motor transport to and from the sailing grounds in Port Royal Sound.

Before you book

Days and timesEvery day except Friday and SundayDepartures at 15:45 and 17:15

Book up to12h before

GroupPrivate

Live guideEnglish

Meeting point and pickupNo hotel pickup: you go to the meeting point. Ends back at the starting point.

Cancellation and refundsFree cancellation up to 24 h before the start. After that, no refund.It may be canceled due to bad weather. If that happens, you're offered another date or a refund.

ConfirmationConfirmation within 48 h

Prices and times updated 17 days ago

Good to know

Low physical effortStroller-friendlyPets welcomePublic transport nearby

Operated by Anchors Away Sailing Charters

Is this one for you?The guide speaks English, so commentary and sailing instructions are clear for anyone who doesn't speak the language fluently. If you want to understand what's happening with the boat and the wildlife, this works. If you prefer to follow along without detailed explanation, that works too.

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Top questions

What happens if it rains?

It may be canceled due to bad weather. If that happens, you're offered another date or a refund. Free cancellation up to 24 h before the start.

Can I help sail the boat, or do I just sit and watch?

You choose. The crew encourages guests to be as involved in the sailing process as they'd like (help with the sails, trim the lines, steer), or simply relax and let the crew handle everything. Either way works.

What wildlife will I actually see on an evening sail?

Dolphins, manatees, stingrays and birds are common in Port Royal Sound during the evening hours, when they're most active. The timing of a sunset sail often means better chances of spotting them than a daytime trip.

How many people can fit on the boat?

The captain takes up to 6 people on a private sail, so it's your group plus the crew.

What's included in the price?

Soda, pop and bottled water are provided. Everything else (the sail, the captain's expertise, the motor out and back) is part of the trip.

What do I need to bring or know before I arrive?

Bring a photo ID. The marina will call in a gate pass for you at Hilton Head Plantation in the name of whoever booked the sail. Show the ID at the guard gate and you'll get in. The trip is suitable for all fitness levels, and infants and small children can come along.