You can rent a boat in Chincoteague but I don't think you will find one big enough to do any real offshore fishing. Most of the boats are pretty small to medium. Now having said that, if you get a good day, you could head out to sea to the artificial reef sites (railroad cars) that are approximately 5 or 6 miles NNE out of the inlet. There you will find flounder, possibly spadefish, and who knows what else. The fishing in the channels hold some croaker & flounder but both will probably be small. Check on the VMRC site (Virginia Marine...) and they should have the coordinates for the artificial reef sites. Now you will need to bring a handheld GPS to get you there as the rental boats will not have GPS or any other electronics for that matter. I would bring a handheld VHF as well.
As for the crabbing, it was pretty slow last year. Haven't been down there this year. There are plenty of places to crab in the creeks. Just stop in at the local bait stores and they'll send you in the right direction. They may also help with the reef site numbers if you can't find them online. Claming can be good but the ones I got last year were big chowder clams and if you don't know how to cook them (and I didn't) they can be tough.
Have fun, Chincoteague is one of my favorite places. By the way, there are charters to be had at the main public dock.
Offshore check out charters for Capt. Perry Topless, Shammy capt Glenn, Capt. Glenn does make up trips so you don't have to charter the whole boat. Good luck
based on johnrogers latest trips I'd book him!!!! Seriously though, he mentioned a couple great boats w/superb crews so definitely look them up. Like he said, Shammy is doing make ups and Perry and Kyle (Topless) are great fishermen, perhaps if u contact them u can work something out.
If you're going "offshore" I would strongly recommend NOT trying to rent a boat yourself - do the charter thing. A buddy and I went out in his boat trying to find wreck fish such as sea bass. The first time out we used some coordinates from a tackle shop and found a wreck and caught lots of sea bass. The second time out that wreck had been overfished and no keepers were left. So we had a backup plan - we would find another wreck using a list of wreck coordinates we found online. We tried finding any one of 9 other wrecks, ran about 70 miles, and found ZERO of them (even using sonar and zig zagging / circling around the coordinates). The closest wrecks or structure are 8-10 miles out. If you're going farther offshore (for tuna, etc) count on going 30-40 miles out. I would stongly recommend against running that far in a rental boat for safety reasons, even if you could find one. My buddy and I have caught tuna, cobia, and dolphin at Lumpy Bottom this year but the tuna bite slowed down in recent weeks.
Captain Bob's ramp is a good location for bay fishing in Chincoteague Channel/Queens Sound and Donna rents small boats.
No special fishing license is required for boat fishing if you've got a VA saltwater fishing license (or MD saltwater license, as it's reciprocal). If you were trailering a boat you'd need a town boat ramp license to use any of the public ramps. Tuna fishing requires a federal HMS boat permit but that's not an issue if you go on a charter.
In the back bays this has been a great year for flounder but the larger ones are mostly gone now. Remember flounder is 19 inch minimum in VA. Spot and kingfish are in heavy right now, and the croaker have finally moved in also. There are also a zillion little sea bass. All of these can be found in Chincoteague Channel and Queens Sound although kingfish tend to stay nearer to the inlet where it's sandy. If you're looking for action and don't mind smaller fish the action is excellent right now. Bloodworm flavored FishBites on small hooks will keep any children entertained even if they have been diagnosed with A.D.D. If you fish deeper than 12 feet or so it will minimize the seaweed and sea bass - two big annoyances.
Crabbing is pretty good in Assateague Channel, and some fish get back there also. A couple of weeks ago I put out some pots and the keeper ratio was 1 in 3 or 1 in 4 with some larger ones/jumbos mixed in. Still only got 8 keepers using 4 pots and it wasn't worth the effort, especially cleaning the seaweed from the pots off my boat. Next time I'll use hand lines which is more fun anyway.
Running from Chincoteague Channel into Assateague Channel can be tricky - you can run up on an oyster bed if not careful - follow another boat if it's your first time.
Actually that's a general warning about boating in Chincoteague: be careful of sand bars/mud flats. There are many places where it gets shallow in a hurry. You can easily run aground even getting out to the ocean on either side of the main channel if you get on the wrong side of the buoys by even 100 feet. There is even a sandbar in Chincoteague Channel that you need to be aware of if launching from Captain Bob's.
Haven't tried clamming in Chincoteague, but have seen a couple clams being dropped by seagulls onto the pavement. It's a mystery of life how they dig those up (or maybe just steal them from clammers' baskets?) but they're clever birds to use the pavement as a tool. I don't know how a seagull can even grip a large and heavy 4 or 5 inch quahog, but they do.
I won't post the links here, but search for Captain Steve's and Captain Bob's web sites for fishing reports and more info - those are the two main tackle stores. Captain Steve's has the best tackle selection on the island. They both have plenty of bait and ice.
i was just down there this past week and i did very well on croacker drifting right in front of inlet view campground, i was actually fishing off of my jetski since my boat is out of commision, i will be back down there this week as well probably going to go out on the jet ski fishing again, i have a place in toms cove campground and go down dam near every other weekend, its a blast and renting a boat for the day will be a great time..LIKE THEY SAID MAKE SURE YOU READ YOUR MARKERS CORRECTLY OR YOU WILL HIT A SAND BAR i cannot stress that enough, and one other thing that alot of people forget to realise down there is if you do beach your boat on purpose to walk around the sandbar or whatever the case maybe remember that if the tide is going out you are going to have to wait a long time before the water will be high enough again to get the boat back floating, other than that enjoy have fun chinco is the best place on the planet