I spent a month in The Hamptons in July of 2021 with my family – myself, my wife and our two children (ages 6 and 3). We stayed for a month to work remotely (not as a vacation as we did last year). The Hamptons was perfect again because it is a relatively short drive from Manhattan (our accommodations were about a 2-hour drive) and the surroundings (beaches, towns, activities) were unique enough vs. our day-to-day to feel like it was a getaway. Yet the home environment allowed us to work with no issue. The weather was perfect during this period (high70s/low 80s every day) as it is slightly cooler than the warmer NYC temperatures and the restaurant and activity scene was in full swing – even moreso than last summer when coronavirus concerns were more acute. The extended stay was wonderful and we hope to make this an annual tradition.
We stayed in East Hampton again for this trip in an Airbnb home. The Hamptons – as I think of it – stretch from Westhampton Beach to Montauk and East Hampton is closer to Montauk. It is a beautiful community with a vibrant downtown (Newtown Lane), wonderful beaches, fun activities and it is near many other wonderful towns like Sag Harbor, Amagansett (with Soutthampton, Water Mill etc. not too far away). The Airbnb experience was also wonderful – we stayed in the East Hampton Springs neighborhood in a beautiful home with a grill, heated pool, basketball etc. It is a nice blend of being secluded but this year our home was also quite close to the town and main beaches
o East Hampton – Our regular favorites here were Mobys for Mediterranean (awesome outdoor seating, great food) and Fierro’s Pizza (Grandma’s is amazing and gluten free is popular) and Pepperoni's (amazing crusts) for the best pizza. For Brunch and mornings, we loved Babette’s (awesome brunch on main strip), Goldbergs (best bagels etc.), Springs General Store (generally low key and great coffee and breakfast sandwiches in EH Springs) and Round Swamp (great Farmers Market with awesome baked goods, pies); for Ice cream, sadly Scoop De Jour has closed but our favorite Moo Moo’s Ice Cream is still going strong (fewer but still many great flavors, no lines shockingly, and a seating area). On this trip, we added East Hampton Grill and The Palm East Hampton for American (delivery), Serafina & Nick & Toni’s for Italian on their outdoor patios and SiSi for Mediterranean on their awesome terrace.
o Sag harbor – Our favorites included Tutto il Giorno Sag (wonderful ambiance, great italian & seafood and cocktails and kids options) and II Capuccino (best chicken and eggplant parmesan and signature garlic bread was a huge hit). We also loved Yummylicious for Ice Cream (cookie doughlicious was a hit). This year we added an awesome outdoor dinner at DOPO La Spiaggia for Italian. Next time we may time some recommendations to Estia's Little Kitchen (Latin), Beacon (American), K Pasa (Spanish Tapas), Bell and Anchor (Seafood) and Le Biboquet (French) – we will check them out on a future visit.
o Amagansett – Our favorite here is La Fondita for Mexican (love their burritos, quesadillas and nachos; nice outdoor seating and great for takeout); coffee lovers will love Jacks. On this visit we also added Rosie’s for the best breakfast burrito at brunch and Hampton Chutney for the best dosa in town!
o Southampton – Given we were in East Hampton, we didn’t try much here. Our favorite was Saaz (Indian) and they deliver across a huge area including East Hampton.
o Water Mill – This being our first visit, we loved dinner at Calissa for Mediterranean and will go back!
• Activities: Our favorites included Wolffer Estate – Wine Stand for great wines, snacks and a perfect play area for kids; Paddle Diva for awesome kayaking; this time we visited East Hampton Main Beach (busy with concession) and Georgica (more secluded and peaceful) for beach fun and Ishan did a wonderful camp at Sportime in Amagansett. On a future trip, we may try Sunset Cruises and Charters with American Beauty Cruises or Sag Harbor Charters (very pricey but highly recommended)
We will certainly consider a future extended visit for a Hamptons workcation next year and beyond given the wonderful experience. The summertime continues to be among the busiest time but the beauty of renting a house and knowing where to go and what to do can make the experience as unique and relaxing as one would like. It is also an interesting reminder that even brief escapes there can be nice given the close proximity to the city. As always, for any of the recommendations above, make sure to make reservations well in advance and beach parking is only free after 6p (unless u get a permit) - enjoy!