An Island Wedding by the Water: Marianna & Greg's Pridwin Hotel Wedding on Shelter Island
There is a moment on the ferry to Shelter Island when the rest of the East End seems to fall away behind you. The island sits between the two forks of Long Island, reachable by car only over the water, and that short crossing gives every wedding here the feeling of a place set slightly apart. Marianna and Greg married on Shelter Island on September 28, 2024, at The Pridwin Hotel, where the lawn runs right down to the water and sailboats ride at their moorings off the docks.
We photographed the weekend from Friday through the last dance. What we loved most was the shape of their day. They married on the lawn in the morning, poured brunch cocktails right after, and then let everyone loose to explore the island for a few hours before the whole group came back together for dinner and dancing. For a destination wedding on an island like this one, we can't think of a better schedule.
GETTING READY AT The Pridwin
For the ceremony Marianna wore a long white satin Ralph Lauren gown with long sleeves and a wrap front. It was simple and fluid, and it moved beautifully once we got her outside by the water. Greg wore a navy suit by Alan David.
A MORNING CEREMONY on the Lawn AT THE PRIDWIN HOTEL
The ceremony was on the hotel lawn, facing the water, with a wooded shoreline on the far side. Big white hydrangeas stood in planters along the aisle and around the front, with white folding chairs on both sides, so the whole space read as white and green against the water.
When it was over the guests rose to their feet, and Marianna and Greg walked back up the grass through a shower of petals and straight into brunch cocktails.
PORTRAITS on the Docks
Right after the ceremony we took Marianna and Greg out onto the wooden docks, past the white pilings and the moored sailboats, with the big white hotel and its flag behind them. Some of our favorite frames of the whole weekend come from that walk. The ceremony was behind them, the day had barely started, and the two of them were completely relaxed. From there we walked a gravel path along the harbor where the marsh grass grows up to the edge, and on past a bank of red flowers in the garden, where their dog wandered through while we worked.
We shot the portraits on digital and on film. We love how the film tones picked up the island's landscape that day, early fall on Shelter Island in every frame.
Shelter Island makes this part of the day a pleasure. Everything we wanted was a few steps from the lawn: water, boats, marsh and garden, and none of it needed any help from us.
THE Celebration
After a few free hours on the island, everyone came back for dinner at The Terrace Restaurant at the hotel, a room with dark green tablecloths, rattan-backed chairs, chandeliers and shelves of books and pottery along the walls. Missi Flowers did the centerpieces in white and cream with greenery, and each table had a hand-lettered number. It felt like dinner in a well-loved island house. Greg changed into a black Alan David tuxedo for the evening, and Marianna into a long-sleeved sequined Erdem dress.
They cut The Pridwin's three-tier white cake, dressed with berries and hydrangea, under a red-and-white striped awning with palms behind them. Their first dance was on the wood floor with their guests standing close around them, and Cosmo Baker kept that floor full for the rest of the night. Near the end of the night they stood for a portrait by the hotel's shield sign, which reads "The Pridwin Resort-Hotel Cottages," Greg in his tuxedo and Marianna in sequins, a fitting last frame for a wedding so tied to its place.
GETTING TO Shelter Island
The only way on by car is a ferry. The North Ferry runs to Greenport on the North Fork. The South Ferry runs to North Haven, by Sag Harbor, and its schedule says boats leave every 10 to 15 minutes, every day of the year, with no reservations. On Fridays and Saturdays the last South Ferry leaves Shelter Island at 1:45 a.m., worth knowing if guests are staying in Sag Harbor or East Hampton and the party runs late. Check both schedules before you set an end time. From New York City, plan on roughly two and a half to three hours of driving, plus the crossing. For guests who want to stay on the island, the hotel itself is the obvious choice.
For more on weddings out east, read our Hamptons wedding venue guide, and for more on planning a weekend away, see our destination wedding photographer page. If you are thinking about a September or October date, our notes on fall wedding photography are a good place to start.
THE Feeling
What stays with us from Marianna and Greg's wedding is how naturally it belonged to the island. The ferry, the harbor, the docks and the green dining room all became part of their day, and their guests seemed to settle into that slower rhythm the moment they arrived. A morning ceremony and a free afternoon gave everyone time to actually be on Shelter Island, and the evening was better for it.
CREATIVE Partners
Photography: by Trent Bailey (trentbailey.com) | @bytrentbailey
Venue and Cake: The Pridwin Hotel, Shelter Island (caperesorts.com/pridwin) | @pridwin
Planning: Erganic Design (erganicdesign.com) | @erganicdesign
Florals: Missi Flowers (missiflowers.com) | @missiflowers
Band and DJ: Cosmo Baker (cosmobaker.com) | @cosmobaker
Bride's Ceremony Gown: Ralph Lauren (ralphlauren.com) | @ralphlauren
Groom's Suit and Tuxedo: Alan David Custom (alandavid.com) | @alandavidcustomsuits
Hair and Makeup: Elite Bridal Beauty (elitebeautyny.com) | @elitebridalbeauty
Videography: Reel Brooklyn (reelbrooklyn.com) | @reelbrooklyn
PLANNING A WEDDING on Shelter Island?
We're Trent and Dara, and we've been photographing weddings out east since 2010, on 35mm and medium format film alongside digital. Our work has been featured in Town & Country and Over the Moon. More on how we work in the Hamptons is on our Hamptons wedding photographer page.
If you are dreaming of a wedding by the water on Shelter Island, we would love to hear about it. Tell us your date and a little about your plans, or write to inquire@trentbailey.com.