• More about your oliver guide: Sabrina Eliasoph
• Trip type: Adult, Family, Group getaway, Beach
• Activity level: easy
• Ideal length of trip: 3 nights or however long as you can

to & from

Fly to NYC (LGA, JFK airports) and drive out to the East End; watch out though for traffic, can be brutal if leaving to go out on a Friday in the summer and returning on a Sunday evening…

And if coming from New England, Connecticut, etc., bring your car on the ferry to Port Jefferson from Bridgeport, CT – reservations in the summer are a must if traveling with your car (https://www.88844ferry.com/Default.aspx)

• Or take Blade Helicopter service out from NYC airports to East Hampton (https://blade.flyblade.com/flight_search)
• Or take Hampton Jitney bus from different NYC pick-up spots (https://reservations.hamptonjitney.com/hjmobile/)
• Or take the Long Island Railroad out to Hamptons (http://web.mta.info/lirr/hamptons/)
• And if coming from New England, Connecticut, etc., bring your car on the ferry to Port Jefferson from Bridgeport, CT - reservations in the summer are a must if traveling with your car (https://www.88844ferry.com/Default.aspx)

Where to Stay

Baron’s Cove  LOVE this awesome hotel, situated on the Peconic Side of Sag Harbor but within a 7-10 minute walk of Main Street. It is such a great hotel, with an awesome pool, very clean rooms that are nicely sized, a fun lobby/ bar scene, a yummy restaurant, AND such good service if you are choosing to go off campus to the beach. They will give you the parking permits for a few different Sag Harbor beaches and the hotel will set you up with chairs, towels, umbrellas, etc so you can go off and have a successful day at the beach without any hassle. Service was fabulous as well.

Where to Eat and Drink

• Dopo La Spiaggia Such an awesome restaurant with best atmosphere ever if you can sit outside in the garden. So romantic but vibey all the same and delicious food
• Wolffer Kitchen – restaurant from the local, beloved Wolffer winery, which in and of itself is a fun place to go wine-tasting. The restaurant in downtown Sag Harbor truly is pretty as can be, as are the rose bottles, and the food is yummy too.
• Fishes and Loaves – this is one of the most delicious places to pick up picnic foods but done-fancy… most delicious chicken and tuna salads, veggie salads, soups, breads, etc. It is a deli/ bakery but Hamptons style– so not just a typical place. Perfect place to stop and pick up lunch on the way to the beach but beware of long lines.
• Le Bilboquet- of the New York, Dallas, Atlanta fame, this is just a little French gem in a shingled single-story house serving up scene and some of the best moules frites around.

What to Do

Beach, beach, beach… so many of them! And you have your choice between beaches on the calmer, more mellow side of the Peconic Bay OR the wildly beautiful, vast Atlantic Beaches. The main beach at Sag Harbor is gorgeous; although if you find yourself nearby at Southhampton or East Hampton, the beach is the beach and they all share the same stretch of sand and surf. Be careful of heavy undertow though– these beaches have a strong current.

• Shopping.. between downtown Sag Harbor, Southhampton, East Hampton, think New York City at the beach.. and the shopping reflects that. There is a such a fun edge to all the boutiques out there on the East End.
• Museums- between the Parrish Art Museum and the Jackson Pollack- Lee Krasner House are just 2 examples but there are lots of cultural milestones and places to see)
• Biking- there are so many flat roads and trails and beautiful places to take in the scenery by bike
• Exercise- nearly every one of the great New York City exercise studios, like Soul Cycle, Taryn Toomey * The Class*, Tracey Anderson-- all have outpost studios in the Hamptons. The workout scene is nearly as good as it is in NYC. Definitely take a few hours to yourself pre-beach to hit one of the many fabulous studios to get your sweat on pre-beach.

inside scoop

• Parrish Art Museum – such a great place to spend a rainy afternoon; architecturally stunning and just such a complete cool collection of works of so many artists local to the region
• Drinks at the American Hotel in Sag Harbor– you will think they are copying Ralph Lauren’s Polo Bars in terms of atmosphere, but really this place is the real-deal; and has been around far longer than Ralph! 🙂
• Walking around is super easy and safe… we walked from hotel to town very easily back and forth each night.
• Certain beaches require permits so make sure to speak to hotel about which beaches they have access guests permits for.
• Farmers’ Markets- some of the best produce is grown out on the many farms of the East End of Long Island. The produce is fresh, delicious and so much fun to see in all of its summer glory at the various Farmers/ Fruit stands.
• Joey Wolffer: – This is an awesome boutique in Sag Harbor, owned by one of the family members of Wolffer Winery– eclectic cool finds, including clothing, home decor, gifts, etc.

skip it

Lulu Kitchen & Bar (http://www.lulusagharbor.com/index.php)- while some people had mentioned this as a good place for dinner, actually thought the place lacked charm and food was ok, but not great

What to Pack

Bathing suits & cover-ups for the beach

• Restaurants can be very chic, it is where many New Yorkers go after all, so definitely some fun dinner attire for which you'd even wear out in the city
• A sweater or light jacket- are you are out on the far point of Long Island, surrounded by water on all sides, it can be breezy night so bring a light jacket

more...

Be careful if you are going in off-season months to call and make sure any places you want to visit are actually open. Lots of people live out in the Hamptons year-round but high season is definitely summer. In the winter, many places close down.

Looking for some more Sag Harbor scoop? Check out summer local, Blythe Harris’ guide! 

• More about your oliver guide: Blythe Harris
• Trip type: Family, Beach
• Ideal length of trip: 5 DAYS

to & from

Fly into JFK and take the jitney, or Take the jitney from Manhattan. Rent a car (you likely will want one) at airport and head to the beach.

Where to Stay

• Barons Cove (Summer)- On the water with a pool, great bar and outdoor dining.
• The American (Winter) - Historic old hotel with a charming wood paneled bar.

Where to Eat and Drink

• The Beacon- right on the water, perfect for an adults night. Ask the bartender, Matty, for a Ruby Margarita.
• Murfs in Sag Harbor is a not-to-be-missed dive bar staple.
• Crows Nest In Montauk is a private beach on the bay where kids can explore while you wait for food.
• Town Line in Wainscott is perfect for kids and a casual night out.
• La Fondita in Amagansett has the best Mexican food. Try the tacos and the tostadas for lunch and let the kids run around the little lawn.
• We also love to take out lobster rolls from Fish Market in Sag Harbor and take them to Cameron Beach for a picnic.
• Sunset Beach on Shelter Island for cocktails and casual dinner-kids can play on the beach.
• Cavianolas in Sag Harbor- great takeaway salads and sandwiches.
• Bhudda Berry frozen yogurt shop in Sag Harbor is a crowd pleaser.

What to Do

• CMEE (Children's Museum of the East End) is a great resource-especially for an occasional rainy day.
• Barefoot Kids Camp is an adorable camp that takes campers by the week-very flexible and imagination based.
• We love going paddle boarding as a family on the bay in Sag Harbor.
• The Whaling Museum in Sag Harbor
• The John Jermain Library in Sag Harbor is really special, worth a visit.

inside scoop

• Cameron beach is the BEST beach!
• You need a parking pass to park at most beaches.

skip it

East Hampton is too crowded in August-skip it and go to Montauk, Amagansett or Sag Harbor instead.

more...

For a crash course on where to eat, drink and be merry in Sag Harbor, check out OG mega-contributor, Sabrina’a guide to this lovely town.

• More about your oliver guide: Sterling Boyd
• Trip type: Family, Beach
• Activity level: easy
• Ideal length of trip: HOWEVER LONG YOU CAN GO!

to & from

We live in New York so for us, travel to the Hamptons includes renting a car and leaving as early as we can to catch the afternoon rays at the beach. Otherwise, fly into JFK, rent a car and head out from there. Expect around two hours depending on traffic and where you are heading.

Where to Stay

• I always think the best option in the Hamptons is to rent a home with a pool. You get your own space and can balance beach going with lounging by the pool. Try airbnb, VRBO or splurge on Kid & Coe.
• If you are going for a short stay and need a hotel, our favorite is Topping Rose House. It is perfectly located in Bridgehampton close to Sag Harbor and Southampton.

Where to Eat and Drink

• Check out the local newspapers for the weekly listing of farmers markets. We particularly loved the farmers market in Sag Harbor and Southampton. Look for fresh fish, fruit, veg and delicious pies.
• Post beach, take the family to Bridgehampton Candy Kitchen for homemade ice-cream. It is DELICIOUS. Try the peach, coconut, mint chip, coffee...you get the drift. It is all good.
• We are always on the hunt for a good spot to have breakfast with the family post 6 am wake-ups. We love Estia's Little Kitchen. How can you not like a place where the infamous breakfast burrito is named "Big Al' after local Alec Baldwin. Get there early. It fills up and there are no reservations.
• When you marry an Englishman, you spend time researching where to find Fish and Chips. I'm happy to say that the Dock House in Sag Harbor is a winner. It is a tiny whole in the wall seafood shop that sells both fresh seafood and has about 20 bar chairs for a casual meal. You can also take your food and have a picnic on the pier. Super casual and local, but perfect for a night with the family.
• See "Do" for more food suggestions...

What to Do

• Friday night at Wolfers Wine Stand. Every Friday and Saturday at 5pm, you can bring your blanket, chairs and picnic food to enjoy live music in the vineyard at sunset. Check out the website for the music lineup and don't miss it. It is quintessential Hamptons and we love it every time.
• Beaches, beaches, beaches. If you have never been to the beaches in the Hamptons, you likely don't realize how beautiful they are. Make sure to spend some time exploring all the beaches in the area for a walk, dip or just the view. Our favorite is Sag Main Beach. If your children are young and scared of big waves, head to the Noyack Long Beach. It is on the Peconic side and is perfect for little ones to dip their toes. Some advice - do your research before you start your trip. Many Hamptons beaches are private and/or are only open for visitors on specific days. And most charge a fee. Make sure the house you are renting has access to a beach or check the beaches in your area to make sure you know when they are open to the public.
• On a really hot or rainy day head to Children's Museum of the East End. It is a perfect activity when you need a little break from the beach.
• Take a wander around the Hamptons towns - my favorite is Sag Harbor (although make sure you also do Southampton and East Hampton). My favorite shop in Sag Harbor is Stella and Ruby for kids clothes. They have some amazing brands and things you won't find anywhere else. They also have great interior shops. Stop at LT Burger with the family for milkshakes, burgers and fries. Always a winner.
• A day trip to the sleepy little town of Greenport on the Northfork. We generally stay in Sag Harbor, so this trip is just manageable for us with little ones. Take the ferry to Shelter Island and make a stop at Marie Eiffel Market where you can sit out on the dock for coffee or lunch. Take the ferry from Shelter Island to Greenport for a ride on the Antique Carousel and lunch at Lucharitos (tacos and killer margaritas for the folks not driving!).

inside scoop

Get wine shipped to your rental in advance. The local markup is about 20% – 25%.

skip it

Highway 27 at mid day. The traffic will kill you! Plan your day to get out early in the morning and then use the backroads in the afternoons. It will keep you moving and the kiddos happy.