What to Wear and Bring on a Sunset Cruise in New York City and the Hamptons

Welcome to summer and start sailing in New York! With clear blue skies, temperatures in the 80s, and a steady breeze, there’s no better place to be than a sailboat. Whether you rent a boat in NYC or captain a Hamptons boat rental, getting out on the water for a relaxing sunset cruise is the perfect way to destress and escape the heat.


From what to wear to what food to bring, we put together some helpful tips from our resident captain so you have the best experience watching the sun dip below the horizon.

What clothes should I wear?

Sunset cruises usually last between two to three hours. When you are on a Hamptons boat rental for a sunset sail, you should always expect it to be a few degrees colder on the water. As the sun makes its journey towards the edge of the water it can get chilly quickly, especially in the beginning and end of summer.


Be sure to bring layers such as a light sweater, sweatshirt or windbreaker to throw on when the sun starts setting. We recommend wearing comfortable and nimble clothing so you can easily move around the boat and venture to the bow with your sweetheart! For men, shorts and a t-shirt or long sleeve shirt would be best. Women would likely be most comfortable in shorts or loose-fitted pants. Dresses and skirts can be a bit difficult on boats as they get caught in the wind or could get caught on one of the many parts of your Hamptons boat rental.

What shoes should I wear?

It’s almost time to leave your house for the sunset cruise you’ve been looking forward to all week and you can’t decide, flip flops or top-siders? Toss those flip flops aside and slip on the topsiders!


On a boat, you should always opt for shoes with a white bottom. Shoes with colored bottoms can leave dark marks on the boat. When you rent a boat in NYC, we also recommend wearing close-toed shoes to avoid stubbing your toes. Flip flops can make it difficult to balance and get your sea legs! If you want to go au-natural, you can go barefoot which gives you a good grip on the boat. 

What should I bring to drink?

If your Hamptons boat rental doesn’t offer beverages we recommend bringing drinks in cans or plastic bottles. When you bring glass bottles on the boat, you could risk breaking the glass. Instead, pick up a couple of cans of beer from a local brewery to enjoy sipping as the sun sets. There are also many great options for wine or cocktails in a can these days. If you can’t live without your favorite bottle of rosé, bring a wine opener and plastic cups in case the boat doesn’t have one.


Once you settle onto your Sag Harbor boat rental, grab a cool drink and enjoy the pastel skies with your friends and loved ones.

What food should I bring?

Our last tip, and one of the most important, is what type of food to bring! When you rent a boat in NYC and have a strong wind, the boat will likely start keeling. This sailing word means the boat will start tilting with heavier winds. As the boat is keeling it can be difficult to eat something messy like a cheeseburger or chicken wings. We recommend bringing light snacks like nuts, cut fruit, crackers and your favorite brie! On a smaller boat it will be difficult to have a full cheese board but bringing items in separate dishes will be easy to snack on.


Whether you are renting a boat in NYC or taking out a Hamptons boat rental, you will have a wonderful time disconnecting from the world for a couple of hours and enjoying the beauty of watching the sky turn from blue to pastel hues. We hope you find our tips helpful and have a wonderful time sailing in New York with your loved ones!