Stay Afloat. Wake to Sunrise

Luxury overnight Hamptons getaways • one, or up to seven night custom itineraries.

Set sail for an unforgettable escape. Elysian Sailing’s overnight sailing charters offer the perfect way to slow down, reconnect, and experience the beauty of the Hamptons and beyond — all from the comfort of your private catamaran.

Anchor in a quiet cove. Dine under the stars. Fall asleep to the gentle sway of the sea. Wake to sunrise on the water. Whether it’s a romantic getaway, a weekend with friends, or a special celebration, your overnight sailing adventure is fully tailored to you.

A sunset over the ocean with a sandy beach in the foreground, scattered rocks, and a large driftwood log.
A narrow dirt path running through tall green grass and bushes in a natural outdoor setting under a clear blue sky.

Life Aboard.

  • Private Lagoon 450 catamaran with Captain

  • 3 queen size with full shower/bathroom ensuite cabins for use

  • Swim stops & water toys (as conditions allow)

  • Coffee, tea, soft drinks, water

  • Fully equipped galley

  • BBQ Grill

  • Bluetooth sound system

  • BYO food & beverages welcome (premium catering available upon request)

  • Wakeboarding

  • Floating inflatable lounge platforms

  • Paddle boards

  • Snorkle gear

  • Custom itinerary meal planning assistance

Your Escape, Your Way

Every Elysian overnight charter is fully tailored to your style — whether you want to swim and sun, explore hidden coves, hike island trails, or sip rosé on deck. Here are just a few ways our guests love to sail. Your custom itinerary starts the moment you step aboard.

Unplug • Indulge • Reconnect

Day 1: Step aboard Elysian in Sag Harbor for a late morning departure. Sail through the sheltered waters of Shelter Island Sound, with a leisurely stop at a secluded Hamptons beach — perfect for swimming, sunbathing, and champagne on the sand. In the afternoon, sail to a dockside destination for a long, indulgent seafood lunch at one of the area’s top waterfront restaurants. As the sun dips low, cruise to a quiet anchorage. Toast the sunset with cocktails on deck, dine under the stars, and drift off to sleep aboard your private yacht.

Day 2: Wake with the sunrise, enjoy coffee and a leisurely breakfast on deck. Take a refreshing morning swim, then sail back to Sag Harbor at your own pace — relaxed, restored, and inspired.

Sail Farther • Explore Deeper • Make It Epic

Day 1: Depart Sag Harbor in the late morning and sail along the Hamptons coastline. Drop anchor off a favorite beach — swim, sun, and savor a catered onboard lunch. Afternoon sail to Montauk Harbor; dock for dinner at a classic Montauk seafood spot and enjoy the vibrant harbor scene. Spend the night anchored just outside the harbor or moored at the dock.

Day 2: Early departure for Block Island. Enjoy an exhilarating open-water sail and arrive mid-day. Anchor in the Great Salt Pond. Head ashore to explore Block Island’s dramatic bluffs, hiking trails, and charming town. Return to Elysian for sunset and an al fresco dinner on deck. Overnight at anchor under the stars.

Day 3: Spend the morning at leisure — swim, paddleboard, explore hidden beaches. Sail to Shelter Island in the afternoon. Drop anchor for a final night in a peaceful cove, complete with onboard dinner and stargazing.

Day 4: Slow morning aboard with breakfast on deck, final swim, and a relaxed sail back to Sag Harbor.