Silly Lily
Fishing Charters
Step aboard our rugged and spacious 25' panga boat, purpose-built for shallow bay missions, inshore fishing, and long coastal runs. Based in Greenport and Sag Harbor, we offer personalized guided fishing charters across Long Island’s North and South Fork, targeting the top Northeast sportfish on fly and light tackle.
Join Captain Arek, a seasoned local guide with lifelong experience fishing the waters of Long Island Sound, Peconic Bay, and Montauk, for an exciting day on the water. Whether you're chasing striped bass, bluefish, false albacore, or bonito, we tailor each trip to your style and experience level.
From solo anglers chasing a personal best to families making lasting memories, our panga offers an intimate experience for up to four passengers. Depending on your departure time, complimentary drinks and snacks are provided to keep you energized and focused on the fishing.
Looking for something more adventurous? Book a long-range trip to Block Island, an offshore bluefin tuna charter, or a whale watching and wildlife tour.
The Fishing
Capt. Arek fishes exclusively with artificial lures and flies to deliver the most engaging and hands-on fishing experience on the water. Whether you're an experienced angler or brand new to fly fishing or light tackle, Arek provides all specialized gear and offers patient, expert instruction to help you master the techniques needed to fool the fish of a lifetime. Every catch is earned and unforgettable with Silly Lily Fishing Charters.
The seasons
Spring (April – June)
The season kicks off as striped bass and bluefish return to the Peconic Bay, feeding aggressively in the shallow flats and tidal rips. This is prime time for light tackle and fly anglers. May and June are peak months for landing large striped bass locally, and there’s always a chance at the elusive weakfish, the true crown jewel of Peconic Bay.
Summer (July – September)
When local waters slow down, trips shift to Block Island, the best spot in the Northeast to hook a 50-pound striper. In August, the offshore game heats up with bluefin and yellowfin tuna moving within 10–20 miles of the coast. Summer is also peak whale watching season, with guaranteed daily sightings of humpbacks and dolphins.
Fall (October – November)
The fall migration delivers explosive fishing in a short window. Striped bass and false albacore light up the waters around Orient Point, Montauk, and the North Shore surf. The season crescendos with epic ocean-side bass blitzes and late-season bluefin tuna crushing bait right through Thanksgiving.
3 Hour Trips $850
Perfect for dawn or dusk fishing. We’ll fish two to three productive spots, all within a thirty minute ride from your pick-up location. Great for kids, beginners, or the whole family!
5 Hour Trips $1000
More time to work different tides and locations. Ideal for anglers with some experience who want to dial in techniques and chase the best bite.
Full Day Trips $2600
Explore the region’s best waters over an extended day. This trip gives us the flexibility to follow the fish, travel farther, or switch to an entirely different area as conditions change.
Offshore Tuna / Whale Watching
Trips $3200
Just ten to twenty miles south of Montauk, we can encounter all sorts of marine mammals, and behind them, the prized bluefin tuna. These range from thirty pounds (perfect for fly fishing) up to several hundred pounds (we might just need a bigger boat!). This experience will most definitely be a memorable day on the open ocean, whether you’re after whales, tuna, or both.
Sunset Cruises
Step aboard for a relaxing evening on the water for the perfect sunset. Our evening cruises offer a front-row seat to nature’s nightly show, with breathtaking views of the sky ablaze in color over calm waters. Whether you’re celebrating a special occasion or simply unwinding at the end of the day, you’ll enjoy a peaceful, scenic ride with opportunities to spot local wildlife and coastal landmarks. Bring your favorite refreshments, sit back, and let's make memories that last a lifetime.
Sunset cruises are available at an hourly rate of $200.
