The Escape: From Westchester Carpools to Nantucket Cobblestones in 36 Minutes

Active & outdoors

• Impromptu island bike ride: Rent wheels in town and log a 20+ mile ride across the island's excellent bike paths for a fast, scenic way to scout different beaches.

• Jetties Beach: Spend time enjoying the endless shoreline, grab a bite with live music from 3–6 p.m. at the Sandbar patio, and check out the amazing beach boutique right on site.

• Stroll by Sankaty Head Light: Take a walk out toward this historic lighthouse in 'Sconset, which features beautiful coastal paths that cut right along the edge of a scenic golf course.

Morning fuel & workouts

• Bike to breakfast at Island Kitchen: Take an easy morning ride out to this mid-island favorite for an exceptional, casual breakfast or brunch on their great outdoor patio.

• Pilates at HotHaus and breakfast at Lemon Press: Pair a high-intensity morning workout at HotHaus with a fresh, health-forward breakfast or green juice just down the street at Lemon Press.

Shopping

• Main Street and wharf boutiques: Dedicate an afternoon to browsing the high-end shops and unique local storefronts, as shopping remains a premier and highly rewarding island activity.

Casual waterfront & day bites

• Harbor relaxation at Old South Wharf: Relax right along the harbor just outside The Cottages, which offers a picturesque and quintessential waterfront location to unwind.

• Afternoon sushi at Old South Wharf: Head down to the wharves near The Cottages for a perfect afternoon mid-day bite of fresh sushi paired with an Aperol spritz right on the water.

• Late lunch at Sandbar at Jetties Beach: Grab a solid lobster roll and a drink right on the sand at Jetties Beach, which features great live music and a casual, high-energy patio vibe.

• Grab-and-go lunch at Provisions: Skip the sit-down wait times and grab high-quality, famously packed sandwiches from this Straight Wharf staple, perfect for bike trip fuel.

Dinner & nightlife

• Dinner at Black-Eyed Susan’s: Booking a dinner table at this cozy, widely known morning spot offers an exceptional evening menu with the added bonus of a BYOB policy.

• Sunset and dinner at Millie's: Head out to Madaket for a casual, Mexican-style seafood dinner and catch one of the most reliable and spectacular sunset views on the entire island.

• Drinks at The Gazebo Bar: Stop by this iconic harbor-side spot for their famous mudslides before the current operator's historic lease wraps up at the end of the 2026 season.

• Evening drinks at Tree Bar: Start your night at this sophisticated, gorgeous outdoor patio bar tucked right on Main Street for excellent cocktails and people-watching.

• Cisco Brewers: Catch live music while sampling fresh local oysters and visiting gourmet food trucks at this iconic brewery, which easily mimics a mini music festival atmosphere.

• Late-night laughs at The Chicken Box: Head to this legendary, unpretentious mid-island music venue and dive bar for great live bands, high-energy crowds, and a great late-night dance floor.