Chart your course

Story by Lance Hanlin

If you’ve got a sailboat and a weekend, Hilton Head Island makes a great starting point. With steady breezes, shifting tides and a winding network of creeks, rivers and sounds, it’s both a proving ground for new sailors and a playground for experienced ones. Once you’ve found your rhythm, it’s time to explore. From tucked-away sandbars to storied harbors, these seven routes offer a satisfying mix of challenge and calm. While a motor comes in handy for tight or shallow spots, each journey includes open stretches where you can cut the engine, hoist the sails and let the wind take over. 

Close to home

No cars, no problems

Daufuskie Island

Sailing time: 1-2 hours (5 nm) 

Sail across Calibogue Sound, watching for shallow spots, oyster beds and shifting bars as you near the Cooper River. Dock at Freeport Marina, the more remote county dock or anchor in the river. With no cars on the island, you’ll hop in a golf cart and ease into island time. Explore the old church, lighthouse and local art, then grab lunch at the Old Daufuskie Crab Company. Don’t skip the beach: three miles of wild shoreline await.

Sailing difficulty: Tide taster (2/5). A mellow cruise with a few skinny spots. Mind the oyster beds and keep an eye on the depth as you near shore.

Low tide, high spirits

Bluffton

Sailing time: 1-2 hours (9 nm) 

Sail into the May River and drop anchor near the sandbar locals call the “Redneck Riviera.” At low tide, it becomes a party spot with grills, games and good vibes. Prefer solid ground? Dock at the Bluffton Town Dock at Palmetto Bluff for dining and riverfront strolls, or head to the Calhoun Street Dock to explore Old Town Bluffton’s restaurants, shops and art galleries.

Sailing difficulty: Easy breeze (1/5). A short hop that’s hard to mess up, unless you forget to check the tides and end up stuck near a sandbar.

Stretch your sails

Anchored in charm

Beaufort

Sailing time: 3-5 hours (16 nm) 

Follow the Intracoastal Waterway north from Hilton Head through Skull Creek and across Port Royal Sound, then veer into the Beaufort River. It’s a scenic and rewarding day sail with shifting shoals and strong currents near the inlets, so stay alert. Dock at the Downtown Marina and step right into Beaufort’s historic core, where live oaks, waterfront views and charming local shops line the streets. For a quieter stop just south of town, Port Royal Landing Marina offers solid amenities and easy access.

Sailing difficulty: Mind the markers (3/5). Straightforward but it’s not a sleepwalk. Tidal currents pick up near bridges and shoals don’t forgive sloppy chart work.

Go with the flow

Tybee Island

Sailing time: 3-5 hours (15 nm) 

Sail offshore via the Port Royal Sound or take the slower Intracoastal route to reach Tybee. The offshore path is faster but exposed, with strong currents and busy traffic near the Savannah River. Tie up at Lazaretto Creek Marina or anchor in the calm waters of the Back River. Once ashore, explore Tybee’s wide beaches, laid-back charm and off-the-beaten-path spots like the “secret beach” on the southwest tip.

Sailing difficulty: Currents ahead (3/5). Scenic and mostly smooth, but the inlets and river mouths like to keep things interesting. Stay alert and ride the tide when you can.

History on the horizon

Savannah

Sailing time: 3-5 hours (17 nm) 

Sail south via the Intracoastal and cut west into the Wilmington River. The winding route ends in the busy Savannah River, where tugboats and massive ships share the water. Dock along River Street and you’re steps from historic squares, live music and riverside dining.

Sailing difficulty: Mud and massive ships (4/5). Expect tight turns, strong currents and close encounters with big boats and ships. Gorgeous payoff, but not for the distracted.

Beyond the horizon

Drift and disconnect

Edisto Island

Sailing time: 5-7 hours (32 nm) 

Head north along the Intracoastal winding through rivers, creeks and sounds to the South Edisto. The entrance to Big Bay Creek can be tricky, especially at low tide. Stay vigilant for markers and natural indicators of the creek’s path. Use your VHF radio to contact Edisto Beach Marina for docking instructions and local advice. They monitor VHF channel 16. Enjoy the island’s unhurried charm, quiet beaches and local flavor.

Sailing difficulty: Skinny water warning (4/5). A beautiful route with a few tricky cuts and a shallow approach that demands smart timing. Don’t try it on a falling tide.

Port of style

Charleston

Sailing time: 10-12 hours (55 nm) 

This full-day sail offers two routes: the protected but winding Intracoastal or the faster offshore path for experienced crews. Along the ICW, you’ll pass rivers, sounds and cuts before reaching Charleston via the Ashley River. Offshore, enter the harbor between the jetties near Fort Sumter. Whichever way you go, the journey is long, scenic and unforgettable.

Sailing difficulty: Full sail required (5/5).  A long, rewarding run through shifting currents, narrow passages and one of the busiest harbors in the South. Bring your A-game and backup plans.