Every summer I spend the season on the East End, and there's nothing quite like a day on the water out of Sag Harbor. Sunset off Shelter Island, lunch at anchor, and a run along the coast with friends.
A charter is the easiest way to enjoy it without owning a yacht. Here's what you should know before you book, including the Coast Guard rules that keep you safe.
When to book
The Hamptons season is short and busy, centered on the summer months and holiday weekends. The best yachts and dates go first, so I recommend reaching out as early in spring as you can, especially for July and August weekends.
Crewed, captained or bareboat?
Most luxury charters are crewed: the yacht comes with a licensed captain (and crew on larger boats) who handle navigation and safety while you enjoy the day. A bareboat charter means you take full command and responsibility for the vessel. It's a very different legal arrangement, and only suitable when you have the experience and the paperwork is done properly.
The Coast Guard rules every charter guest should know
In the U.S., the number of paying guests a yacht can legally carry depends on how the charter is set up and whether the vessel has been inspected by the Coast Guard. Based on Coast Guard guidance:
- A yacht carrying more than six passengers (with at least one paying), or chartered with crew and carrying more than six passengers, generally must be Coast Guard inspected and hold a Certificate of Inspection (COI). On uninspected vessels of 100 gross tons or more, the limit is 12.
- An uninspected "six-pack" charter can carry up to six passengers for hire, and the captain must hold at least an OUPV (Operator of Uninspected Passenger Vessels) credential.
- A true bareboat charter (no crew provided by the owner, with the charterer in complete control and providing fuel, food and stores) can carry up to 12 passengers before inspection is required.
- Every vessel carrying passengers for hire must be under the direction of a mariner holding a Coast Guard-issued Merchant Mariner Credential.
How to spot an illegal charter
The Coast Guard regularly warns about illegal charter operations, which often skip the safety equipment, inspections and licensing that protect passengers. Its advice before you pay and board:
- Ask the captain to show their Merchant Mariner Credential.
- For more than six passengers, ask to see the Certificate of Inspection.
- Be wary if the price is far below everyone else's.
- Read the contract. In a so-called bareboat arrangement, you should be free to choose your own captain and crew, and the owner shouldn't be the operator.
If the Coast Guard terminates an illegal charter, passengers can lose the money they paid, and more importantly, the day. I only work with operators who can show the right credentials.
What's included
Charter terms vary by yacht and operator, so read what the fee covers. Typically the charter fee covers the yacht and crew, while costs like fuel, food and drink, dockage and gratuity are either included at a stated rate or billed separately. On longer, larger-yacht charters under the MYBA agreement, an Advance Provisioning Allowance (APA) is paid up front to cover running costs such as fuel, food and drink, and berthing. The captain accounts for it and returns any unused balance. I'll make sure you see exactly what's included before you commit.
Where to go
Sag Harbor is a perfect base. Within an easy run you have the protected waters of Gardiners Bay and Shelter Island, quiet anchorages for a swim and lunch, and the village waterfronts around the Peconic bays. On a longer day, Montauk is a classic destination, and with the right yacht and the right weather, some groups make the run to Block Island.
Your captain will suggest a route based on the forecast, the tide and the size of the yacht. Some of the nicest days are the simplest: a slow cruise, a long lunch at anchor and a sunset ride back into Sag Harbor.
Why book through a broker
Booking through someone who knows the local fleet saves you time and protects you. I match the yacht to your group and your plans, confirm the vessel and captain are properly credentialed, make sure the contract spells out what's included, and handle the details so you just show up at the dock.
Planning a great day out of Sag Harbor
- Pick the right yacht for the group. Comfort and shade matter as much as speed on a summer day.
- Have a weather plan. The captain has the final say on safety, and a flexible plan makes for a better day.
- Tell us the occasion. Birthdays, client entertaining and family days call for different routes and menus.
- Pack light. Soft bags, boat shoes or bare feet, sunscreen and a layer for the evening run home.
If you're thinking about buying, a charter is also a great way to try a style of yacht before you commit.
