OM Sailing Charters: What to Expect on the Water

OM Sailing Charters operates from Charleston's waterfront with skippered and bareboat options

OM Sailing Charters is based in Charleston and offers both skippered sails—where a captain runs the boat—and bareboat rentals for sailors who want to take the helm themselves. The company operates from the Charleston City Marina, putting you within reach of the harbor, nearby islands, and the Intracoastal Waterway. Whether you're looking for a guided afternoon on the water or a multi-day voyage, the charter type and boat size determine what you'll pay and what experience you'll have.

The boats range from smaller day-sailing vessels to larger cruising sailboats equipped for overnight trips. OM maintains its fleet regularly, and each boat comes with safety gear and navigation equipment. If you're chartering bareboat, you'll need to demonstrate sailing experience—most bareboat operators require proof of competency, either through a sailing certification or a checkout sail with the company.

Key Takeaways

• OM Sailing Charters operates skippered charters where a captain handles the boat and bareboat rentals where you sail it yourself from Charleston City Marina.
• Bareboat charters require proof of sailing experience, usually a certification card or a successful checkout sail with OM staff.
• Skippered charters work well for groups or sailors who want instruction and don't want to navigate; bareboat suits experienced sailors planning their own route.
• Pricing varies by boat size, season, and charter length—day sails cost less than multi-day cruises, and larger boats command higher rates.
• Charleston's harbor and nearby barrier islands offer protected waters for day trips and open-water routes for longer voyages.

Skippered charters: Captain handles navigation and sail trim

On a skippered charter, OM provides the captain, who manages the boat, sets the sails, and navigates. You and your group are passengers and crew—the captain will teach you to help if you want, or you can simply enjoy the ride. This option works well for groups with mixed sailing experience, corporate outings, or anyone who wants a guided tour of Charleston's waters without the responsibility of running the boat.

Skippered charters typically run as half-day or full-day sails, though OM can arrange longer trips if you book in advance. The captain chooses the route based on wind and weather, so you might sail out to Folly Beach, around the harbor islands, or up the Intracoastal depending on conditions. You'll see the same water a bareboat sailor would, but with someone else making the decisions.

Bring sunscreen, a hat, and water. The boat provides life jackets and safety equipment. If you're prone to seasickness, take medication before you board—the harbor is relatively protected, but open-water sections can have chop depending on the day.

Bareboat charters: You navigate and sail the boat yourself

Bareboat means you rent the boat without a captain and sail it yourself. OM will want to see proof that you know what you're doing—either a sailing certification (like ASA or RYA credentials) or a passing score on a checkout sail. The checkout is a short sail where OM staff observe your boat handling, anchoring, and decision-making. If you pass, you're cleared to take the boat out.

Bareboat charters give you freedom to set your own itinerary. You might sail to Shem Creek in Beaufort, anchor off Hunting Island, or spend a night at one of the barrier islands. You're responsible for navigation, weather decisions, and getting the boat back on time and in the condition you found it. OM provides charts, a GPS plotter, and radio communication; you bring the seamanship.

Bareboat rentals typically run by the day or week. A weekend charter (Friday evening through Sunday) is common for sailors planning a short cruise. Longer charters let you explore farther—the Intracoastal runs north to Georgetown and south toward Savannah, both within reach of Charleston.

Boat sizes and what each is suited for

OM's fleet includes boats ranging from around 30 feet to 45 feet or larger. Smaller boats are nimble in tight anchorages and cost less to rent; they're good for day sails and sailors comfortable in a cozier cabin. Larger boats have more cabin space, better galley facilities, and more stability in open water—they're worth the extra cost if you're cruising overnight or have a group that needs room to move around.

Day-sailing boats might be 30 to 35 feet, with a small cabin and minimal overnight gear. Cruising boats are typically 35 to 45 feet, with a full galley, multiple cabins, and systems for longer passages. Ask OM what's available for your dates and what each boat includes—some come with a dinghy, some with a generator, some with air conditioning. Those extras matter on a multi-day trip.

Charleston waters and where you can sail

The Charleston harbor is protected by barrier islands and relatively calm—good for learning or for sailors who prefer sheltered water. From there, you can sail out to Folly Beach, around the Morris Island Lighthouse, or across to James Island. The Intracoastal Waterway runs north and south, offering a scenic, protected route with stops at small towns and anchorages along the way.

Beaufort, South Carolina, is about 45 minutes north by water and a popular overnight destination. Hunting Island State Park offers good anchorages and a historic lighthouse. Farther south, the waters around Edisto Island and Calibogue Sound (near Savannah) are beautiful but require more experience and attention to tides and shallow spots. OM can advise on routes that match your skill level and the time you have.

Wind and tide matter. Charleston's harbor has strong tidal currents, especially near the jetties. The best sailing is usually in spring and fall when the wind is steady and the weather is mild. Summer can be hot and still; winter brings stronger winds but colder water and shorter days.

What to bring and what OM provides

OM provides the boat, safety gear, life jackets, navigation equipment, and basic tools. For a day sail, bring sunscreen, a hat, sunglasses, a light jacket (it's cooler on the water), and water or snacks. For an overnight charter, you'll need to provision the galley—OM can tell you what's already aboard and what you need to buy. Bring medications, toiletries, a change of clothes, and any special food or drinks you want.

The boat has bedding, but bring your own pillow if you're particular. Bring a headlamp or small flashlight for moving around the cabin at night. If you're bareboat chartering, bring charts or load them into your phone or tablet—OM will brief you on navigation tools and radio protocols before you leave the dock.

Booking, pricing, and cancellation

Contact OM Sailing Charters directly through their website or phone to check availability and get a quote. Pricing depends on the boat size, the season, and how long you're chartering. A half-day skippered sail costs less than a full day; a bareboat day rental costs less than a week. Peak season (spring and fall) is busier and may cost more than summer or winter.

Ask about cancellation policies when you book. Weather can force changes—if wind is too strong or a storm is coming, OM may reschedule your charter or offer a refund. Confirm what's included in the price: fuel, dockage, provisioning, insurance, and any extras like a dinghy or fishing gear. Some charters include a skipper's briefing or a navigation lesson; others don't.

Book as far in advance as you can, especially for weekends or multi-day trips. Summer weekends and holiday weeks fill up quickly. If you're flexible on dates, you may find better availability mid-week or in shoulder seasons.

Frequently Asked Questions

Do I need sailing experience to book a skippered charter?

No. On a skippered charter, the captain runs the boat, so you don't need any experience. You can participate in sailing the boat if you want, or simply relax and enjoy the ride. OM will brief you on safety before you leave the dock.

What happens if I don't pass the bareboat checkout?

If you don't pass the checkout sail, OM may offer a skippered charter instead, or you can book a lesson to build your skills and try again later. Some sailors book a skippered sail first to get comfortable with OM's boats and procedures, then move to bareboat.

Can I bring my own food and drinks?

Yes. Most charters allow you to bring your own provisions. For overnight trips, you'll stock the galley with groceries. Ask OM what cooking equipment is aboard and whether there's a cooler or refrigerator. Some charters include ice or basic supplies; others don't.

What if the weather is bad on my charter date?

OM monitors forecasts and will contact you if conditions are unsafe. You can reschedule to another date, receive a refund, or sometimes sail a shorter route in protected waters if the wind is strong but manageable. Confirm the weather policy when you book.

How far can I sail on a bareboat charter?

That depends on your experience, the time you have, and the boat. A day charter keeps you close to Charleston—the harbor and nearby islands. A weekend or week-long charter lets you reach Beaufort, Hunting Island, or farther down the coast. OM will help you plan a realistic itinerary based on your skills and the boat's capabilities.