Contributor - Jack Bartholet | Head of Events & Experiences • 9/18/25

The idea that boating ends with Labor Day is one of those myths ready to be retired. In truth, fall is when locals reclaim the water. The days are still long enough to savor, and the cooler nights only add to the romance. Watching shoreline leaves turn from the deck of a yacht is proof that boat rides are just as beautiful in September and October as they are in July. This month, we’re featuring Joe Ialacci’s company, Yacht Hampton as an experience you’ll want to consider.

September is prime time to climb aboard and see the East End from the best vantage point: the deck of a yacht.

Autumn sails mean less boat traffic, calmer waters, and secluded coves all to yourself. There’s also greater availability; you’re more likely to secure the exact boat you want. We love assisting our members in customizing excursions by boat type, destination, and activity.

Joe’s marina in Sag Harbor boasts an impressive fleet of 25 boats and yachts ranging from 22 to 62 feet. Four Hundred has a longstanding relationship with Captain Joe, and he’s the kind of insider you want guiding your day. He’s not only a seasoned captain but also a true host, curating itineraries that blend discovery with indulgence.

WHY SEPTEMBER SAILING IS SPECIAL

The sky feels wider, the water calmer, and the sunsets more vivid. Beaches are blissfully quiet, coves more accessible, and the whole experience more intimate. Autumn doesn’t just extend summer, it creates its own quieter and richer rhythm.

CAPTAIN JOE’S ITINERARY HIGHLIGHTS

Joe has designed itineraries that make the most of a day on the water, each one shaped by the mood you’re in. For a leisurely afternoon, he might suggest the Sandbar Circuit, anchoring off a hidden stretch of beach where you can swim, lounge, and treat the yacht like your own seaside villa. For those craving more movement, there’s the Harbor Hop: a cruise through Sag Harbor, Shelter Island, Montauk, or Greenport, with a stop ashore for oysters before returning to cocktails on deck. And if you’re simply chasing a perfect moment, nothing compares to a sunset sail with champagne in hand, watching the horizon soften into pinks and golds as the season itself seems to exhale.

If you already have a favorite cove, swimming spot, or restaurant in mind, Joe will happily build the day around it. That’s the beauty of insider access.

WATERSPORTS AND ONBOARD FUN

While peak watersports season is summer, it’s never too early to start dreaming about next year’s adventures. Joe’s fleet is stocked with nearly every toy imaginable, from Seabobs and paddleboards to hydrofoils and electric surfboards. Families love the variety, and groups of friends often turn it into a spirited competition. One moment you’re diving into clear water, the next you’re racing across the bay, and before long you’re back on deck with sushi platters and rosé, laughing about who wiped out first.

For those who prefer a slower pace, there are floating lily pads, loungers, and snorkeling gear. And if speed is more your style, wake sports and Jet Skis can be arranged. Joe can even capture it all with drones or onboard cameras—because sometimes the only thing better than living the moment is replaying it later.

THE MARINA SCENE

Here’s where the experience gets especially Four Hundred. Captain Joe’s chic marina is not just a departure point, it’s a destination. He has hosted birthday dinners there for our members, transforming the docks into candlelit lounges where champagne flows and DJs spin under the stars. It’s Hamptons glamour without the velvet rope. For those who want something beyond the restaurant circuit, the marina offers a fresh and unforgettable alternative.

DINING AFLOAT

Fall on Long Island means oysters at their peak, pumpkins, and local apple cider. Dining on the water is always memorable, but this season brings the chance to build menus that feel rooted in the local landscape. Warm soups, cider-glazed vegetables, or a platter of Montauk seafood served with warm bread and local cheeses.

Four Hundred can work directly with Yacht Hampton to curate these meals so they feel both seasonal and personal. We can arrange everything from a casual lobster roll lunch to a chef-prepared autumn tasting menu. The goal is simple: food that reflects the best of Long Island, served in the setting that makes it unforgettable.

CELEBRATIONS ON THE WATER

There’s hardly an occasion that can’t be made more memorable afloat. We’ve seen everything from birthday dinners and anniversary toasts to proposals, photo shoots, and even thoughtful memorials take shape on Joe’s yachts. The setting adds a kind of magic you can’t manufacture—whether it’s a bride-to-be surrounded by friends with music spilling across the bay, or a family raising a glass at sunset to mark a milestone.

Captain Joe, the Yacht Hamton Team and Four Hundred collaborate closely to ensure these moments feel personal and effortless. The yachts become floating venues, both intimate and glamorous, with every detail: food, music, all curated for the occasion. It’s a reminder that the most meaningful celebrations often unfold away from the ordinary world, with nothing but open horizon around you.

EXTEND THE SEASON

Don’t overlook October. The foliage views from the deck are unforgettable, the air is crisp, and the sense of having the water to yourself makes every sail feel private. Whether you slip in one more outing this year or start planning next summer’s adventures, Four Hundred and Captain Joe are ready to craft the perfect experience.

Contributor — Jack Bartholet | Head of Events & Experiences

Jack effortlessly transitions from the entertainment industry to the world of luxury hospitality and travel, bringing a rich background of collaboration with celebrated artists and extensive personal travel experiences. When not consulting, he can be seen onstage with cabaret and theatre performances. Jack's enduring passion centers on fostering a sense of belonging for LGBTQ travelers wherever their journey takes them.

SAVORING THE SEASON: YACHTING INTO FALL