There is a big difference between a 26 and 38 ft boat. You need to narrow it down some to get a good answer. 26 ft = no problem with a 3/4 ton truck. 38 ft = no way with that truck.
My recent experience was towing a 30' cabin
cruiser with a Ford F350 dually. Boat and trailer were 12,500 lb. Most of the time my boat stayed in the water. I did trailer it from SC to the FL Keys once. Also numerous times the 100 miles to the SC coast and various lakes from where we lived. Never had a problem towing with that rig.
Things to consider:
1. Towing capacity. I checked the ford web site and a 2014 F250 diesel truck has a 23,500 lb Gross combined weight incl truck, trailer and boat. 12,500 lbs towing capacity is the max for trailer and boat. 14,000 if 4x4.
2. Make sure the trailer is in good condition. Tires rated to handle the load, properly inflated, hubs/bearings greased, and brakes on all axles are absolutely necessary. Being able to stop the boat is more important than being able to start it.
3. Check with your state highway dept for whatever permitting is required. You want to be legal
, but honestly I've never been stopped while towing a boat.
4. Proper tongue weight is critical to maintaining control. If you want to know what the rig really weighs, stop at a truck scale. You can get the tongue wt on the truck scale - it will tell you the weight on each axle.
5. Heavy duty straps tying the boat to the trailer. You want to make sure that when the trailer stops, so does the boat. No kidding. Had a friend learn this the hard way.
6. Is your truck 4WD? With a heavier boat, you may want that when pulling the boat out of the water, especially if the ramp is steep or slippery.
7. Dually. With a heavier boat, I liked the stability of the dual rear wheels. Not necessary on a 26 footer, but if you are thinking over 30 ft, I'd start thinking dually for any long distance hauls.
At the end of the day, with an appropriately sized truck and trailer both in good condition, you'll have stress free trailering. With some practice loading and unloading, it's not that big a deal.
Edit: Oh yeah, don't forget a spare tire and a jack that will work
for the trailer.
Hope this helps.