Sag Harbor is a sailor’s oasis nestled in the middle of the Hamptons. With a calm, protected bay and deep water, sailing in Sag Harbor will be a wonderful way to spend a long summer day. The history of this small village dates back to the 1700s when it was a whaling town.
Walking through town you’ll be surrounded by pastel Victorian houses. We pulled together the top local destinations to visit on a boat rental in Sag Harbor.
Anchor at Barcelona Point
Hop aboard your boat rental in Sag Harbor and raise the mainsail. Once you make way out of the breakwater in Sag Harbor, head east towards Barcelona Point. With the wind filling your sail, it’s a short and lovely journey to Barcelona Point. A favorite spot of locals, Barcelona has sandy bluffs that reach from the crystal clear water to the cloudless sky. The name dates back to the whaling history of Sag Harbor.
Sailors who used to transport whale oil across the Atlantic saw similarities between the bluffs welcoming them in Sag Harbor and Barcelona, Spain. Barcelona Point stuck through generations and is a quiet and calm spot to spend the day. Anchor your sailboat off the bluffs, swan dive into the water and head to shore to explore.
Pick Up Dinner at the Dock House
Sailing in Sag Harbor during sunset is a wonderful time to explore the area. Before you head to the water, pick up Wolffer Estate’s Summer in a Bottle, a classic rosé summer staple in the Hamptons.
Then, stop by the Dock House to pick up dinner. This no-frills establishment located on the wharf in Sag Harbor offers delectable and fresh seafood. Pick up a couple of lobster rolls for the family and head to your boat rental in Sag Harbor.
With a steady breeze, calm waters and fresh seafood, you are set up for a delightful evening on the water.
Sail around Cedar Point Lighthouse
For a nice afternoon sailing destination with the family, secure a boat rental in Sag Harbor and make way for Cedar Point Lighthouse. With the kids manning the jib lines, head northeast towards Shelter Island.
You will pass the lush, green landscape of Shelter Island on your port side. As you pass Shelter Island, you will start to see the Cedar Point Lighthouse off your bow. This lighthouse sits on the end of a sandy peninsula that was once used to guide the whalers through the tricky navigation of coming back to port.
Watch a Regatta from Your Boat Rental
Wednesday nights bring sailors from all over the east end to compete in a friendly regatta during the summer. If you are sailing in Sag Harbor on a Wednesday night, find a quiet spot to watch the regatta from a distance. You can watch the nail-biting start line as 38 foot boats come inches within each other to cross the line.
Follow the regatta to the downwind leg and watch the colorful spinnakers pop across the sky like hot air balloons. Be sure to snap a few pictures of the colorful sails as the sun sets behind them.
Walk through the Historic Town
After you spend a lovely day sailing in Sag Harbor on a Sailo boat rental, spend some time exploring the quaint whaling town. When you walk through the marina you will pass large and exquisite yachts.
Make your way through the town and admire the Victorian houses with gingerbread trim. As you walk through the town, it’s easy to imagine wives pacing on the widow walks looking out to sea for their returning husbands.
We hope you had a lovely time on a boat rental in Sag Harbor and we hope to see you again soon!