Sail the historic Stars & Stripes into a Hilton Head sunset
2 Hours
Up to 29 people
Private sail, taxes, service charge
Sail aboard the America’s Cup 12 Meter Stars & Stripes for an evening on the water from Harbour Town. Take in views toward Daufuskie Island and the surrounding saltwater marshes as the sun sets.
Receive a full refund when you cancel at least 48 hours before departure. No-shows are charged the full price. Receive a full refund if the operator cancels due to weather or other unforeseen circumstances. If the minimum passenger count is not met, select another cruise or receive a full refund.
Product ID: 6G4KHQ
Wear comfortable clothing and non-slip shoes; avoid heels. Bring a light jacket or sweater for cooler breezes, plus sunscreen, a hat, and sunglasses for sunny conditions.
Yes. The boat has a small restroom, called a head, reached by a set of steps.
Guests typically stay dry, but wind conditions and sea spray may leave you a little damp. Bring a light jacket or waterproof layer for your private sail.
This cruise operation clearly has its act together when it comes to hospitality and wildlife viewing. The crew stands out as a major highlight across the board, with multiple guests praising Captain Windows and Captain Peter by name for their warmth, knowledge, and genuine passion for what they do. Whether you're on the Dolphins and Donuts morning cruise, a sunset dinner sail, or one of their day trips to Savannah or Daufuskie Island, the staff consistently checks in on passengers and creates a welcoming atmosphere. Dolphin sightings are practically guaranteed, with some groups spotting over 20, and the crew takes time to educate guests about the marine life while ensuring everyone gets good photo opportunities. The food on dinner cruises gets mixed feedback. Most guests are pleasantly surprised by how good the salads and desserts are, but one detailed review noted that all the protein options came out dry and disappointing. The bigger consistent complaint involves comfort, specifically the heat and lack of adequate shading while the boat is docked or during sunny portions of the journey. Missing or insufficient window shades became an issue for multiple passengers. Drink prices also raised some eyebrows. Still, the overall experience seems to win people over, especially families and repeat customers who return year after year for specific routes. Just book early if you're eyeing that afternoon Daufuskie trip, as it fills up fast.
This was our 2nd cruise with Vagabond. We did the dinner cruise on our last visit and it was awesome. Our sunset dolphin cruse with Captain Mike was everything promised and then some. We got to see dolphins in their natural habitat and the sunset was spectacular. The narrative provided was funny, entertaining and informative. What more could you ask? Would do it again.
Joyce Williams
July 7, 2026
This was our 2nd cruise with Vagabond. We did the dinner cruise on our last visit and it was awesome. Our sunset dolphin cruse with Captain Mike was everything promised and then some. We got to see dolphins in their natural habitat and the sunset was spectacular. The narrative provided was funny, entertaining and informative. What more could you ask? Would do it again.
Joyce Williams
July 7, 2026
Learn how shrimp are caught and take home part of the catch on this 2-hour educational cruise.
Watch Hilton Head's vibrant sunset while relaxing or helping crew aboard the historic Stars & Stripes
Explore Daufuskie Island with a narrated ferry ride and time ashore
Join the crew or relax on a 1.5-hour Hilton Head coastal sail aboard a historic America’s Cup yacht
Narrated Ferry Cruise With Time to Explore Daufuskie Island
Cruise Calibogue Sound on a 90-minute narrated dolphin tour