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Many guides to Sag Harbor will emphasize its past life as a major whaling town, but today’s Sag Harbor has evolved into a gorgeous seaside village with a thriving local culture. Nowadays, there are so many things to do in Sag Harbor to keep even the most active visitor interested.
In our opinion, Sag Harbor and its immediate surrounds feature almost all of the things that make the Hamptons such a joy (and not just in the summer). Sag Harbor has moved well beyond its past and invites visitors with a surprising amount of things to do and excellent restaurants, all within the quaint village of Sag Harbor with its beautiful architecture.
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Take a sunset cruise on the American Beauty II
One of the best things to do in Sag Harbor that thankfully still hasn’t made it to the mainstream is a sunset cocktail cruise aboard the American Beauty II. The boat is quaint and allows just the right number of guests to feel like you’re on a friend’s boat for the late afternoon. If you’re looking for the perfect Hamptons evening and dry land just isn’t cutting it anymore, book the sunset cruise on the American Beauty II.
The crew are renowned for pointing all of the interesting historical and natural landmarks which make this once-glorious whaling village such an unexpectedly interesting destination. Don’t be shy to ask questions. And if you need a little bit of confidence, the sunset cruise is delightfully BYOB so bring along your favorite beverages (and snacks) and enjoy the two-hour cruise on the bay.
There is something uniquely relaxing about experiencing the sunset aboard the American Beauty II. The team has finessed the experience they are delivering and they truly do deliver every time. In our view, the sunset cruise isn’t just one of the best things to do in Sag Harbor, it’s one of the essential things you must to do in the Hamptons.
Go for a walk along Havens Beach
Sag Harbor isn’t quite known for its beaches, but the experience of going for a simple walk along Havens Beach is a quintessential Sag Harbor experience. Havens Beach is located only a short 15-20 walk from the core of Sag Harbor. It’s the perfect place for a post-meal stroll following lunch at one of Sag Harbor’s delicious restaurants.
Havens Beach overlooks Sag Harbor Bay so you’ll get a gorgeous view of the whole area during your walk. You might find online that the beach is private but we can confirm that Havens Beach is a public beach, albeit slightly small.
Spend an afternoon at Kidd Squid Brewing
We don’t say lightly that a place has it all, but Sag Harbor sort of really does have it all – even a brewery. For a town this small, it’s surprising that there’s a brewery right in town. There’s no shortage of delicious beers for you to try. But even if that isn’t your thing, the outdoor area is beautiful and there’s plenty of games to keep you busy.
The owners take great pride in what they’ve created so they’re only too happy to take the time to explain their beers. We will probably get in trouble from Sag Harbor locals for including this hidden gem but it’s too lovely to keep to ourselves. We suspect Kidd Squid will become a much more popular spot in the Hamptons in the coming years for discerning visitors.
Watch a show at the Bay Street Theater
Sag Harbor does indeed boast its own theater. Bay Street Theater is located right in the heart of Sag Harbor and offers a surprisingly wide range of (usually quite eclectic) performances. There’s an old-world atmosphere that harkens back to a time when the theater was a critical component of socials life in a town.
Tickets do sell out fast so make sure to check the shows that are currently running and book yourself a ticket. Watching a show at the Bay Street Theater is one of the best things to do in Sag Harbor at least for its excellent selection of performances which certain punch above their weight. And because of the size and design of the theater, there really aren’t any bad seats.
Visit the Sag Harbor Whaling Museum
If you’re familiar with the northeast of the United States, you’ll know that whaling was the lifeblood of many a village and island in the area, including the ever-famous Nantucket. The history and importance of whaling is deeply interesting and is well worth spending the time to understand.
It might not be the first thing you want to do in Sag Harbor if the weather is good, but if you’re spending a few days in Sag Harbor or you get unlucky with the weather, a visit to the Sag Harbor Whaling & Historical Museum will not leave you disappointed. The museum is delightfully small so you only need a couple of hours to fully digest the interesting whaling history that made the town what it is today.
The collection within the museum is large and informative and you’ll no doubt be kept engaged for the duration of your visit. Ultimately, whaling is a unique and very historically significant endeavor, so it’s interesting to see how this now abhorred practice was the center of economic activity for a whole region.
Visit a former Presidential Summer White House
For the history buffs out there, Sag Harbor boasts the “Summer White House” of former President Chester Arthur. Located at 20 Union Street, the house is objectively beautifully designed and is well worth walking by. It has now been completely renovated and redesigned, but the magic of the place remains.
The house is still used as a private residence today, so unless you happen to know the right people, you’ll only get to appreciate it from the outside.
Shop the boutiques
We’re glad that residents of Sag Harbor are unyielding in their support of local business. This means that, unlike main streets in so many other towns, virtually all of the shops in Sag Harbor are boutiques, whether clothing or home furnishings. A town that doesn’t have mainstream brands lining its best streets and boulevards is, in our opinion, a much more enriching and enjoyable experience – and Sag Harbor is just that.
We recommend Donna Karen’s Urban Zen which sits just beside one of the best restaurants in Sag Harbor. We’re also big fans of Road to Nowhere which currently only has boutiques in Sag Harbor and Montauk. Sag Harbor also boasts goop’s flagship store – and it’s absolutely worth a visit.
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