Sunset Sail

Hilton Head Island•easy

Difficulty

easy

Duration

2–2.5 hours

Fitness Level

Suitable for most fitness levels; comfortable seating and gentle sailing conditions.

Overview

Discover the beauty of Hilton Head Island during an exclusive sunset sail with Vagabond Cruise. Experience stunning ocean views, wildlife sightings, and peaceful evenings at sea in this private adventure tailored just for you.

Boat Tour

Sailing

Hilton Head Island, South Carolina

Sunset Sail

2 Hrs • All Ages • Evenings

Select participants and date

Date

Thu, Sep 25

Travelers

Adventure Photos

About This Adventure

Experience the thrill of sailing aboard the legendary America’s Cup – 12 Meter – Stars & Stripes, once captained by Dennis Connor. Enjoy a breathtaking sunset over Daufuskie Island and the saltwater marshes, whether you choose to participate in sailing or relax with a drink. An unforgettable adventure for all ages awaits!

#Book Online and Skip the Line!

Seats sell out fast! Advance purchase recommended. Book online now for fastest and most convenient check out.

#Sail aboard the real America’s Cup – 12 Meter – Stars & Stripes once skippered by the famous Dennis Connor!

Duration

2 Hours

About

Only on Hilton Head and only in Harbour Town can you sail aboard the real America’s Cup – 12 Meter – Stars & Stripes once skippered by the famous Dennis Connor!
Come sail away into the sunset and enjoy the breathtaking views of the sun as it slips into the backdrop of Daufuskie Island and the saltwater marshes.
This is the perfect way to end a day on Hilton Head Island.
It doesn’t matter if you are a novice to the art of sailing or an expert, a trip aboard Stars & Stripes will leave an everlasting memory! This is a great trip for anyone from 3yr-99!
Beverages available for purchase including beer & wine

Adventure Tips

Arrive early to secure the best viewing spot

Arrival 15-30 minutes before departure allows you to settle in and enjoy prime positions for sunset viewing.

Dress in lightweight layers

Evenings can be cooler on the water, so bring layers to stay comfortable during your cruise.

Bring your camera or smartphone

Capture the stunning colors of the sunset and scenic vistas during your sail.

Book in advance for private experiences

Private sunset sails fill quickly, especially during peak season, so reserve ahead to secure your preferred date.

Local Insights

Wildlife

dolphins
herons

History

Hilton Head Island has a rich maritime history, once serving as a crucial port and lookout point during the Civil War, and today offers wonderful opportunities for scenic sailing and wildlife viewing.

Conservation

Vagabond Cruise emphasizes eco-friendly practices, including responsible wildlife viewing and minimal environmental impact during their sails.