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I visited The Hamptons for an extended holiday during the last two weeks of August of 2020 with my family – myself, my wife and our two children (ages 5 and 2). We were joined for part of the visit by our close friends with two small children (ages 6 and 3). We rarely travel for two weeks during the year (except in december) but with all travel cancelled due to the Coronavirus pandemic, our whole family was in need of a break and an escape. The Hamptons was perfect 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. The weather was perfect during this period (low 80s every day) as it is slightly cooler than the warmer NYC temperatures and the restaurant and activity scene was in full (outdoor-focused, social distant) swing. The trip was wonderful and we are considering an extended visit again next year depending on the global travel climate. 

We stayed in East Hampton for this trip in an Airbnb home for the first time. 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 options 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, swings, basketball etc. The private beach access was a necessary and amazing perk of this trip given the need to be socially distant this summer. 

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East Hampton - Our favorites here were Mobys for Italian (awesome outdoor seating, great food) and Fiero’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, we loved Scoop De Jour (on the main strip, tons of flavors and great portions but long lines) and Moo Moo’s Ice Cream (fewer but still many great flavors, no lines shockingly, and a seating area - this was our preference). On a future visit, we will try Bostwicks for seafood, East Hampton Grill and The Palm East Hampton for American and Nick & Toni’s

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). We received strong recommendations for DOPO La Spiaggia (Italian), 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.

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 a future visit, we will certainly check out Wolffer Kitchen which has an eclectic menu and pours wonderful wines from the region. 

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. On a future visit, we will certainly check out Carbone South Hampton for Italian

Our favorites included Wolffer Estate – Wine Stand for great wines, snacks and a perfect play area for kids; Paddle Diva for awesome kayaking; Clearwater Bay Beach for private beach fun. 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 holiday next year and beyond given the wonderful experience. We typically go there to visit friends or for occasional events, but this unique circumstance whereby we did an extended trip allowed us to truly immerse ourselves in the community. The summertime tends 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 an of the recommendations above, make sure to make reservations and hope you enjoy! 



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