Summer in Sag Harbor on Rhyme & Reason

Summer in Sag Harbor

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Sag Harbor holds such a special place in my heart because I’ve been going every summer for awhile now. My aunt and uncle have a house out there and graciously have me every year! It is truly always one of the highlights of my summer so I am beyond grateful for the invitation! Summer in Sag Harbor is such a magical time because the little town comes alive and is bursting with families and people out from New York City. I’ve got the perfect trip down to a science so keep reading to hear how I like to experience summer in Sag Harbor.

Summer in Sag Harbor on Rhyme & Reason

Summer in Sag Harbor Bucket List:

Start your morning with coffee at Sagtown and donuts at Grindstone

Eat steamers and lobster rolls at Dockside Grill for lunch or dinner

Embrace summer with an ice cream cone at Big Olaf’s

Go kayaking or sailing around the harbor

Shop in town at Goldie (clothing), Ruby Beets Old & New (antiques), Fishers Home Furnishings (furnishings, home textiles, interior decor), AYR Beach House (clothing), Monc XIII (Furnishings, home textiles, interior decor), Harbor Books (bookstore), Addo (clothing), Goop (a mix of everything), and Love Shack Fancy (clothing).

Visit the Serena & Lily Beach Market just outside of town

Stroll around the surrounding neighborhood streets of town for shingled homes, adorable doorknockers, and cotton candy colored hydrangeas

Wine taste just outside of town at Wölffer Estate Vineyard or Wine Stand (the Wine Stand holds a sunset event every Friday and Saturday through September)

Take a car and roll the windows down for a drive out to Sagg Main Beach

Pick up fresh seafood from Serene Green Farm Stand, fresh produce & the best guacamole at Country Garden, and fresh corn from Pike Farm Stand to cook (if staying at or renting a house)

Sip on sunset drinks at Baron’s Cove (p.s. stay here or at The American Hotel on your trip)

Drive your car on the ferry to neighboring Shelter Island for drinks and dinner at Sunset Beach

For more exploring of the different towns in the Hamptons, take a car and visit all the musts in my Hamptons Travel Guide

Snag our Sag Harbor wardrobes:

Reward Style Loads


As always, email me at if you are planning a trip to Sag Harbor or somewhere else in the Hamptons and have any questions! I’d love to help! xx

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  1. Summer is not complete without your visit which is a highlight! We’re so glad you love Sag Harbor and your itinerary of things to do in Sag is great. love, Aunt Patty and Uncle David

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