New York’s skyline fades into the background as we continue eastward. The light wind sail that was battered by the thunderstorm in Norfolk awaits us in Mamaroneck.

The sailmaker has repaired it properly. Thank goodness, because the growth on the hull is slowing us down considerably. Without the large sail, we would only be able to creep along. It helps to check the tide table for the Long Island Sound so that we don’t lose our new sailing power to the tidal current.

After two brief overnight stops in secluded spots, we arrive in the area where New Yorkers spend their summers: the Hamptons. Wide beaches, well-dressed people, plenty of lobster and rosé await us, all bathed in soft summer lightlightv— just like in a Ralph Lauren advertisement.

We start in Three Mile Harbor, whose large bay resembles an inland lake. Unfortunately, we don’t have enough time to visit the nearby Pollock-Krasner House and studio with its action painting splatters. Instead, we decide to visit the nearby tavern. After a few hundred meters along the main road through the forest, we turn onto idyllic paths lined with beautiful houses. The world seems impossibly peaceful here, with deer strolling undisturbed through open front yards. Abruptly, we enter another world. Immaculately dressed in white, the New Hamptoners — locals who live there year-round, as we are assured — sit with rosé and seafood, enjoying the fabulous evening weather. We try to blend in as much as possible.

The trip is a great introduction to Sag Harbor, a vacation hotspot for stressed-out, well-groomed city dwellers. The mouths in the Goop Store across from the harbor are, on average, a touch larger than usual. This small town has a lot of charm. There are small shops, a wonderful Art Deco-style cinema, museums, and restaurants. Even the temporary bad weather can’t spoil the mood. And how bad can a place be where John Steinbeck spent much of his life?

In East Hampton, on the opposite side of the island, where the Atlantic Ocean meets sandy beaches, the Hamptons feeling intensifies. The atmosphere is tranquil, the houses are picture-perfect, and the gardens are immaculate. From this idyllic setting, we board the bus again, which takes us back to the boat. The bus ride offers a glimpse behind the scenes. Because the people who work to keep things tidy and ensure that things run smoothly sit next to us. We also meet them in laundries, mini-markets, and front yards. Without their help, the clothes would probably be less white, and the gardens would be less perfect.

It’s time for a change of scenery. We want a smaller island, and Block Island comes highly recommended. On the way there, we are accompanied by the region’s typical fog. It creeps up on us, leading us into the unknown. Thankfully, the trusty radar is there to help. The tide calendar is also recommended for everyday use because the current can quickly become tricky here. As the water rises, we glide smoothly through the channel into the spacious, round bay.

The small harbor is bustling with activity as the annual Regatta Week is set to begin in a few days. Fortunately, there are still plenty of rental bikes available, so, despite the wind and fog, we set off on a tour of the island. The route takes us past lakes full of water lilies, old cemeteries, and lighthouses. One lighthouse had to be moved inland because the cliffs were eroding quickly. The fishermen’s warnings during construction were ignored.

Shortly before we reach the end of our tour, the thick fog lifts and the sun brings summer vibes. Over burgers and ice cream, we watch the ferries unload crowds of visitors. Without pause, bikes and cars swarm out and spread across the island. Unfortunately, we just missed one of the more exciting visitors.