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HC Travel Guide to Sag Harbor

by habituallychic

06 . 18 . 18

I have a bad habit of going on a trip and posting all my adventures on Instagram but never following up with a travel guide on the blog. Well, those days are changing. I am going to try to post a recap after every trip and go back to some of my old travels but first up is a guide to Sag Harbor, my favorite place out east.

Sag Harbor is the least Hamptons-y town in the Hamptons and that’s exactly why I like it. The former whaling port is also less seasonal so you can visit all year round. I usually go out in June but I’ve also gone out in April and all the stores and restaurants were open which makes it a nice any time escape from New York. While East Hampton and Southampton are filled with all the latest designer shops, Sag Harbor still has a quintessential small town American Main Street with a hardware store and family owned businesses.

Of course, new stores pop up each summer but they still manage to fit in with the low key feeling. Sag Harbor also has a quite a few stores popular with decorators which makes it a great destination for design lovers. And while some of the former homes of ship captains have been renovated, there is still a lot of authentic architecture that make Sag Harbor the most charming town.

The hours of some restaurants and stores will change according to the season or their owner’s whims so make sure you double check before you set out. If you have your heart set on a certain place, you may also want to call ahead just in case.

The iconic Sag Harbor Cinema that represented the town in my first photo had a devastating fire in December 2016. They are very far from reaching their goal to rebuild so please consider making a donation whether you visit Sag Harbor or not.

How to get to Sag Harbor:

You can drive to Sag Harbor which is great if you would like to explore other towns but what I like best about Sag Harbor is that you can walk everywhere in town so I take the Jitney Ambassador. It’s the nicer bus that has two seats on one side and one seat on the other, assigned spacious seating, outlets to charge your phone, and drinks and snacks. The regular Jitney is cheaper and first come first serve on seating. Both Jitneys pick up all over Manhattan and make stops in towns in the Hamptons and the North Fork on different routes.

Where to stay in Sag Harbor:

Baron’s Cove – I have stayed at Baron’s Cove (above) four times in four different types of their 67 rooms since they opened in 2015. It’s a boutique hotel on the waterfront with a pool, restaurant, bikes, and a small spa and gym. The decor is a chic take on traditional nautical design by Colleen Bashaw that also includes a few dog friendly rooms. They also offer live music on the porch which is a big draw for people not staying at the hotel and some last minute offers can be found on Hotels Tonight app. In the interest of full disclosure, I have been comped in the past but I paid for my room on my most resent trip.

American Hotel – The Jitney drops off passengers right in front of the American Hotel which makes it a convenient location right on Main Street. I’ve yet to stay at this very traditional hotel but I might try to book a room for my next trip. Unlike Baron’s Cove, you have to call to make a reservation which they write in a book. That makes it hard to check for last minute availability of their eight rooms. The website says they are usually fully booked for summer by the end of March so plan ahead. They also have a restaurant with seating on the front porch with is a big draw.

Where to eat in Sag Harbor:

There are so many great places to eat in Sag Harbor which is another part of the appeal. You can just walk up and down Main Street reading menus until you find something that appeals to you but here’s a little help.

Baron’s Cove – They do offer breakfast and lunch but dinner is the big draw. Definitely order the fish of the day special since it’s bound to be fresh in a harbor town.

Le Bilboquet – The New York institution popular among a very chic crowd has just opened at the Sag Harbor wharf. Definitely order the cajun chicken. It’s their signature dish.

Page at 63 Main – This is one of my favorite places in Sag Harbor for healthy options sourced from local ingredients in a beautiful setting. The Main Street restaurant also offers outdoor seating perfect to see and be seen.

Tutto il Giorno – The popular Italian restaurant by Gabby Karen de Felice has just moved to a new building on Main Street and also includes Urban Zen store by her mother Donna Karen.

Wolffer Kitchen – The decor of this Main Street restaurant is too sleek and modern for my taste but the cuisine from the family behind Wolffer Estate Vineyard makes it a great choice.

Sen -Very popular Japanese restaurant on Main street currently closed for renovations. Not sure why they didn’t do this in the winter but check them out when they reopen.

Lulu’s – I’ve never eaten at this restaurant centered around dishes cooked in their wood burning oven but it looks cute.

There are also a lot of other casual places, a burger spot, a pizza place under renovation, and an ice cream shop on the wharf. 
What to wear in Sag Harbor:

You really can’t go wrong with white jeans and anything in my recent What I’m Packing post. Make sure you pack a sweater and/or wrap for evenings when the temperature can drop. Sag Harbor is more casual than other towns but I’d dress up for dinner since those from East Hampton and Southampton often frequent Sag Harbor restaurants. 
What to See in Sag Harbor:

Custom House – I’ve never been to the Custom House since it’s always closed when I walk by but the historic building is worth a visit to get a sense of the importance of Sag Harbor as a busy port in the late 1700’s.

Hannibal French House – This Main Street home is private and not open to the public but it’s definitely worth walking by for a photo for Instagram. The former home of “one of the more illustrious whaling and ship owning families” is the most beautiful house in Sag Harbor.

The Sag Harbor Whaling & Historical Museum – I visited once and found it fascinating and had a lovely chat with the men working the desk. It’s definitely worth a visit to learn more about the whaling industry. This is a great rainy day activity for kids too. Baron’s Cove copied art and maps for the hotel from prints found at the museum too.

One of the nicest things to do is just stroll down Main Street and admire the houses. Go all the way down to Canio’s Books and Cove Deli and check out all the side streets between Main Street and Baron’s Cove. Steven Gambrel renovated quite a few of them. Head back behind the Library for more charming homes.

Just one of the old fashioned store fronts on Main Street.

Where to shop in Sag Harbor:

Walk up and down Main Street for the majority of the stores but make sure you head over to Madison Street for Bloom and Monc XIII, Washington Street for Ruby Beets, Bay Street for the Goop Pop Up, and Division Street for Sage Street Antiques.

Bloom – Long time readers know that Bloom is one of my favorite stores. Owner Mona Nerenberg fills it with new finds and antiques from France and Belgium. The back building is dedicated to Astier de Villette and the center garden is perfect for taking a rest. She doesn’t have a website or Instagram.

Monc XIII – An expensive and refined interior design store if you aren’t into beachy decor.

Love Shack Fancy – Fashion and accessories for the super romantic and bohemian woman.

Neo Studio and AYR at 25 Madison Street.

Ruby Beets – This store on Washington Street has a very eccentric owner but it’s filled to the brim with new and vintage treasures. Just make sure she’s open or call for an appointment.

Sag Harbor Florists – I was very excited to finally stop by this well known floral shop on Sage Street. Too bad they were rude and unwelcoming. But if you need to pick up flowers or send an arrangement, this is the place. Just hope they are nicer to you.

Goop Pop Up – The latest Goop outpost has taken over the old Urban Zen space at 4 Bay Street is filled with everything you need for summer including fashions, accessories, homewares, beauty products, and food.

Sage Street Antiques – This is another shop on Division Street that is always closed when I visit. I peeked through the windows and it definitely looks like it’s filled with some good stuff.

Cavaniola’s Gourmet – Mona at Bloom recommended I stop by years ago but it’s also a favorite of Ina Garten. The Cheese Shop on the left is filled with cheeses, dried fruits, spices and condiments while the Kitchen on the right has delicious prepared food, coffee, and desserts. Everything I’ve ever tried has been amazing.

Cavaniola’s Gourmet Kitchen

Cavaniola’s Cheese Shop

Another look at Main Street. Make sure you stop by Harbor Books at 20 Main Street for something good to read or a book signing.

The chicest new addition to Main Street is Onda Beauty, a natural beauty store and spa. The woman working there could not have been nicer and I met one of the three owners that include actress Naomi Watts. They also have a location in Tribeca in the city.

This is a look at Tutto il Giorno and Urban Zen space.

This is one of the houses renovated by Steven Gambrel. Some homes are for rent in Sag Harbor if you would like to plan a longer strip.

I usually visit in June which is before high season starts and the weather really warms up so I don’t go to the beach but that’s another thing to do out east. Baron’s Cove offers a beach shuttle with chairs, umbrellas, and chairs to town beaches as well as beach passes for Sag Harbor and Southampton.

If you drive, you can also take the ferry to Shelter Island and explore their shops like Beall & Bell.

Hopefully, you can see why I love Sag Harbor. New York City can be stressful and it’s always good to get away whether it’s at the height of summer or just a winter weekend and Sag Harbor is great option. They also have some of the most beautiful sunsets I’ve ever seen. Perfect posting on Instagram.

All photos by Heather Clawson for Habitually Chic.