Our fall escape to Shelter Island was one of those rare weekends that felt both restorative and full of adventure. The kind of trip that reminds you how magical family travel can be when everything just flows. There’s something special about a place that makes traveling with little ones feel easy, because we all know that traveling with kids can be anything but. And The Pridwin in Shelter Island is that place. Where the kids are entertained, the parents can unwind, and everyone leaves feeling recharged. It’s a family-friendly haven with a nostalgic spirit and all the modern comforts you could hope for. Days here unfold effortlessly: s’mores by the fire pit at dusk, bike rides under the turning leaves, crafts and watercolor painting in The Nook, and outdoor movie nights that stretch into cozy evenings wrapped in blankets under the stars. Every detail feels intentional, every moment invites connection, and the pace of island life seems to slow just enough to let you really savor it. Although we were there for their final weekend, The Pridwin reopens for the season Friday, May 8, 2026, and it’s the kind of destination you’ll want on next summer’s list, whether you’re coming for a long weekend, a family getaway, or just to breathe in that coastal calm.

If you’re coming from Connecticut, I’d recommend the Bridgeport to Port Jefferson ferry. Driving the car right onto the boat was such a highlight for the girls (and honestly, for us too!). It’s easy, scenic, and such a fun way to start the trip. Be sure to book tickets in advance, then enjoy the breezy ride across the Long Island Sound before heading east toward Shelter Island. The drive from Port Jefferson winds through Long Island’s charming North Fork, dotted with roadside farm stands overflowing with seasonal produce; think apples, pumpkins, squashes, and cider donuts at every turn. It’s one of those quintessential fall drives where you’ll want to pull over just to take it all in. The final ferry to Shelter Island is a quick ten minutes and doesn’t require a reservation, making the journey just as effortless as the destination itself.

One of the standout moments from our trip was dinner at Léon, the island’s buzzy, wood-fired restaurant that feels equal parts coastal and cosmopolitan. We were seated at a small table in front of their hearth style-open-fire oven, where the glow from the open kitchen and flickering firelight made the whole space feel impossibly romantic. Everything about Léon feels intentional, from the open-fire cooking to the artful simplicity of the menu. It’s the kind of meal that unfolds slowly, with a glass of wine in hand, as you watch the chefs at work and the sun sink low outside. The food is seasonal, rustic, and deeply flavorful, the kind of cooking that makes you appreciate the ingredients as much as the artistry. It’s a must for any visit to Shelter Island, whether you’re there as a couple, with family, or for a girls’ weekend escape.

The next morning, we took the ferry from Shelter Island over to Sag Harbor, one of our favorite nearby towns to explore with the girls. The crossing itself is short and scenic, and once you arrive, you’re met with streets lined with charming boutiques, coffee shops, and bakeries. We strolled through the harbor, browsed local shops, and grabbed lunch before heading back to the island for one last evening by the water. Sag Harbor is the perfect complement to Shelter Island, a little more bustle, a touch of glam, and plenty of ways to spend a leisurely afternoon. If time allows, it’s well worth adding to your itinerary.

For anyone looking to recreate our trip, here’s the exact itinerary that worked beautifully for our family:

Day 1:

  • Morning: Ferry from Bridgeport to Port Jefferson (book in advance)
  • Afternoon: Drive through the North Fork with farm stand stops
  • Late Afternoon: Arrive at The Pridwin Hotel, check-in, unwind by the pool or fireside with stores
  • Evening: Evening boat ride arranged by The Pridwin, Dinner at Léon

Day 2:

  • Morning: Breakfast at The Pridwin, kayaking or bike rides with the kids
  • Afternoon: Tennis, Crafts in The Nook, lawn games, or a dip in the pool
  • Evening: Family outdoor movie under the stars

Day 3:

  • Morning: Ferry to Sag Harbor, stroll and shop downtown
  • Afternoon: Lunch in Sag Harbor, explore the marina
  • Evening: Return to Shelter Island, enjoy sunset on the dock

Shelter Island has a way of feeling untouched, like a world apart from the rush of everyday life. Between The Pridwin’s warm hospitality, the kid-friendly experiences, and the easy rhythm of coastal living, it’s the kind of place that lingers with you long after you’ve unpacked your bags. Whether you’re planning a summer getaway or a cozy fall retreat, this little island will charm you, one s’more, ferry ride, and farm stand stop at a time.