Nataline,
Good news is that saltwater fly fishing for beginners can be had this time of year where you’re going to be. Bad news is a lot of guides are usually booked up months in advance.
Columbus Day weekend has always been my favorite weekend to fish in LI Sound around the CT or NY shorelines, and Montauk Point. The false albacore will have been around for about 3 weeks, and the striped bass start showing up in force. Another perk is large bluefish tend to be coming out of the western LI Sound and will be hungry and chasing the massive amounts of baitfish leaving the coolers waters of the Sound to school up and leave the sound near Montauk.
The alibi fishing can be tough for beginners with a fly rod. A guide will hopefully have small 1/2oz or 3/4oz tins or lures called Crippled Herrings or Deadly Dicks, so all is not lost if the wind gets over 10-15kts. Anchovy patterns in olive or tan over a white belly will work well. Same patterns for the stripers, but the retrieve is slow when they’re busting because anything faster than a slow pull will snag fish. Bluefish will destroy popper patterns, so Gurglers, Popovics Bangers, or hard body poppers will work. Plugs on spinning gear.
A 9-weight is perfect for fishing up there. Load up a reel with a 350gr intermediate shooting head for allies or stripers, or a floating line for bluefish.
Capt. Ian Devlin is in East Norwalk (45 minutes west of you) and a great guide. His # is
(203)451-9400.
Salt is fine for all ages.
Good luck!
R