There are beautiful places to propose in Newport. And then there is this: out on the water, the harbor behind you, the coastline of one of New England’s most storied sailing cities opening up as you move into Narragansett Bay. A private sail sets a stage that no restaurant table or cliff walk can match. It is unscripted, unrepeatable, and entirely your own.
Sightsailing offers two vessels for engagements in Newport, RI, each suited to a different vision of the moment. Starlight is by far, our most popular boat for engagement charters and may be booked online. Starlight is our intimate O’Day 34 yacht — designed for just the two of you and your captain, quiet, private, and built for exactly this kind of occasion. Sightsailer is our spacious 46-foot sailboat, perfect for those who want to share the celebration with close friends and family the moment the answer is yes.
Both depart from Bowen’s Wharf in the heart of Newport’s waterfront district, and both sail through Newport’s iconic harbor, out into Narragansett Bay, and along the Ocean Drive coastline. Bring your favorite drinks, a small picnic, and the ring. We’ll handle the rest.
A private sail through Newport Harbor sets the stage for a one-of-a-kind engagement against one of the most beautiful coastlines in New England. No two sails are exactly the same, and neither is the moment.
On Starlight, it is just the two of you and your captain. No other guests, no shared experience, no audience. The boat, the harbor, and the moment belong to you alone.
Bring your favorite drinks and a small picnic to make the moment feel exactly right. Take the wheel if you want to. Or simply sit back together and let Newport do what it does best.
Every engagement charter sails from Bowen’s Wharf in downtown Newport — one of the most walkable, well-known locations on the waterfront, close to hotels, restaurants, and parking. The sail takes you through Newport’s iconic harbor, out into the protected waters of Narragansett Bay, and along the Ocean Drive coastline. Your captain knows these waters and knows how to make the experience feel effortless. You focus on the moment. Everything else is handled.
It depends on what you’re envisioning. Starlight is our intimate O’Day 34 yacht — designed for just the two of you and your captain. It’s the ideal choice if you want a private, secluded proposal with no other guests around. Sightsailer is our 46-foot sailboat and accommodates up to 13 guests — perfect if you want close friends or family there to celebrate the moment with you.
Yes. Starlight can be booked online now through our booking page. For Sightsailer, please complete a Private Charter Inquiry form and we’ll be in touch with availability and details.
Absolutely. You’re welcome to bring your own beverages (just no hard liquor) and a small picnic to make the experience your own. This is your charter, personalize it however you would like!
Yes. On Starlight, you’re welcome to take the wheel and steer if you’d like that to be part of the moment. Your captain will be there to guide you, and there’s no experience required.
All charters depart from Bowen’s Wharf in Newport, RI — right in the heart of the waterfront district, steps from downtown Newport’s hotels and restaurants.
Not at all. Your captain handles all the seamanship. You’re free to relax, take in the scenery, and focus on the moment you’ve been planning.
You’ll sail out through Newport’s iconic harbor, into Narragansett Bay, and along the Ocean Drive coastline — some of the most beautiful water in New England. The exact sail depends on wind and conditions, but the scenery is spectacular in every direction.
There is no single way to see Newport, so we offer them all. Step aboard for a sightseeing cruise, a hands-on sailing lesson, or a celebratory special event. Browse our daily departures below and secure your spot on the water.
