Day 1: Exploring East Hampton Village

Morning:
Start your day with breakfast at The Golden Pear Café, a local favorite known for its fresh pastries, smoothies, and quality coffee. Enjoy a light meal to energize yourself for a day of exploring.

After breakfast, take a walk around East Hampton Village, where you’ll find a mix of high-end boutiques, art galleries, and charming shops. Be sure to stop by BookHampton, a quaint independent bookstore, and Clic, which offers stylish home decor and photography books.

Midday:
Head to Main Beach, just a short distance from the village center. Soak up the sun, go for a swim, or simply relax on the sand. Main Beach is one of the most popular beaches in the Hamptons, so arriving early is key to securing a good spot.

For lunch, visit The Maidstone Hotel for a laid-back meal. With its cozy interiors and Scandinavian-inspired design, it’s a lovely spot to enjoy a fresh salad or sandwich. Also, Cittanova and Sant Ambroeus are great spots for lunch.

Afternoon:
Drive over to Amagansett, a nearby hamlet that’s brimming with local character. Stop by Amber Waves Farm for fresh produce and homemade goods, or visit Jack’s Stir Brew Coffee for a midday caffeine boost. If you’re interested in history, don’t miss the Amagansett Historical Association for a glimpse into the area's past.

Evening:
End the day with a dinner reservation at Nick & Toni’s, an iconic restaurant that’s been serving Mediterranean-inspired dishes to locals and celebrities alike for decades. The wood-fired oven specialties are a must-try. A second choice would be East Hampton Grill, which offers a great ambiance for a date night along with amazing food and drinks. If you’re up for some nightlife, The Clubhouse or Stevens Talkhouse offers cocktails and live music for a fun night out.

Day 2: Outdoor Fun and Cultural Gems

Morning:
Begin your second day with a peaceful visit to Two Mile Hollow Beach, a quieter spot that’s great for morning walks or yoga by the water. The relaxed atmosphere here provides a refreshing start to your day.

Midday:
Make your way to Springs to visit the Pollock-Krasner House and Study Center, where Jackson Pollock and Lee Krasner lived and worked. This historic site offers a fascinating look into the lives of two major figures in American art.

For lunch, grab some seafood at Bostwick’s Chowder House. Whether you’re in the mood for a lobster roll, clam chowder, or a fish sandwich, this laid-back eatery is a Hamptons staple.

Afternoon:
Spend the afternoon at Guild Hall, East Hampton’s premier arts and cultural center. From contemporary art exhibits to theatrical performances, there’s always something interesting on display. If shopping is still on your agenda, make your way back to East Hampton Village for some last-minute retail therapy.

Evening:
For your final dinner, try The Palm East Hampton, a classic American steakhouse with a sophisticated yet welcoming atmosphere. If you’re craving something lighter, 1770 House offers a refined setting and delicious seafood options to end your trip on a high note.

Where to Stay

Consider booking your stay at The Maidstone Hotel, a charming boutique hotel near the village, or Gurney’s Montauk Resort & Seawater Spa, which offers beachfront accommodations and an indulgent spa experience. Both options provide easy access to all the activities and attractions on this guide.