Assuming the same June start. I wish you had more like a March or April start.
I'm not going to make an assumption on where you buy the boat but just outline areas by the time of year. You'd have to adjust based on starting location.
The following areas are best for May through September.
I'd want a month in Massachusetts, between Cape Cod, Martha's Vineyard, Nantucket, Hyannis, and Boston and ending around Plymouth with a trip through the canal to perhaps North Falmouth, South Dartmouth and then to Newport RI. From Newport, I'd want to head to the Long Island Sound and spend at least a month between Newport, Long Island Sound and New York City. A couple of weeks along the New Jersey Coast from Atlantic City to Cape May, then to Ocean City. While Ocean City is a bit out of the way to what I'll suggest next, it's more than worth it. Then I'd take the Delaware and the canal with perhaps a stop in Chesapeake City and into the Chesapeake. That brings us to around 12 weeks.
There is so much to see in the Chesapeake. I would go to Baltimore, then Annapolis. Then you hit the smaller towns. The Eastern Bay, St. Michael's is a don't miss to me, Kent Island, Tilghman Island, Oxford and Cambridge, both on the Choptank, Chesapeake Beach, Solomons. That is at least 5 weeks. I'd want two weeks up the Potomac and to DC. Then one of my favorite stops is Cape Charles before going to the Tidewater area of Norfolk, Hampton, Portsmouth, Newport News. So that's 20-21 weeks I've labeled North of Virginia. This is the area you're going to want to see during the summer months and perhaps May and September.
For North Carolina and South Carolina you probably have two more months of pleasant boating. Now recognize you're going to have two summer periods to use if you start in June for 14 months.
Out of NC, SC, and GA, while we love them all, NC has more different spots to see. Between Beaufort and Portsmouth, VA, you have Coinjock, Belhaven, New Bern. Manteo, Elizabeth City, Washington, NC., Oriental, Wanchese, Hatteras, and Ocracoke. That's three weeks minimum. Total to this point 24 weeks.
Beaufort and Morehead City merit an extended stop. We're not a fan of the ICW between there and Wrightsville Beach but others are. I'd allocate at least 4 weeks for Beaufort, Morehead City, Wrightsville, Wilimington and the Cape Fear, Bald Head Island and Southport. Sub total 28.
South Carolina, the next stretch south is Myrtle Beach, Georgetown, and Charleston. Perhaps a couple of stops between. Beaufort, SC, Port Royal, Port Royal Sound, lead you to Hilton Head. I'd allow 4 to 5 weeks for SC. Sub total 33.
Georgia is interesting with islands like Tybee and Jekyll and St. Simons. Then there are two mainland towns I think of. Savannah is worth going up the river and into the downtown area and spending days. Brunswick is a nice water oriented small town. I'd allow 3 weeks for GA. Sub total 36.
I'm going to cover Florida's east coast in sections. First is Georgia Border to Melbourne. Fernandina Beach and Amelia Island are worth a couple of days. Then there is Jacksonville and the St. John's River. A couple of days for the city, a couple for the river. Next major stop is St. Augustine and it's worth the better part of a week. We like a day or two stop over in Palm Coast. Then two or three days in Daytona Beach. Perhaps a quick stop in New Smyrna and then you're to Titusville and Cape Canaveral and the Kennedy Space Center. I give that entire area of Northeast FL at least 3 weeks. Sub Total 39.
Now, Melbourne to the St. Lucie Inlet. Vero Beach and Ft Pierce are brief stops. However, the St. Lucie River brings you to Stuart and it brings you across to the West Coast of FL. At some point you'll probably want to loop South Florida taking the route around the Keys one way and the Okeechobee across the other way. So, we'll a week for this section of the coast and the trip across. Sub total 40.
From Jupiter to South Miami is continuous water pleasure. Between the Palm Beaches, Fort Lauderdale, Miami and the Biscayne Bay, I can't imagine spending less than a month. Then from Miami you have a multitude of sounds and islands, places like Key Largo, Tavernier, and Marathon Bringing you to Key West. Counting several days in Key West, I would allow 6 weeks for this section and we're to 46 weeks. I'd spend at least six of the remaining weeks in the Bahamas. You won't even touch them. Just hit on Bimini, the Berry's, Nassau, Grand Bahama, the Abacos, Eleuthera, Andros and the Exumas. That brings us to 52 weeks
For the remaining 8 weeks, I'd include the west coast of Florida and the gulf. We love Naples for 2-3 days, Sanibel for a brief stop, Ft. Myers for a couple, the Charlotte Harbor for 1, Venice for 2 or 3 at least, at least 2 or 3 in the Sarasota area, a brief stop perhaps at Longboat Key. Then you reach Tampa Bay. The better part of a week between St. Petersburg and Tampa and then a few more days at Clearwater. That's at least 4 weeks. That brings us to a total of 13 out of your 14 months.
Sadly, I don't think it likely leaves time for crossing to Carabelle, Panama City, Pensacola, Mobile, Gulfport and New Orleans if you're running under 10 knots and definitely not enough to fit Texas in.
It can be a wonderful trip. How does it compare to the trip around and through the Panama Canal? Both are wonderful. On the Panama Canal route you're seeing more countries, a greater variety of culture and scenery. But the price is that you're spending more time traveling on the water and not seeing things. Taking the East Coast trip, you see a tremendous portion of the US. You'll see the sights of history from much earlier than you've seen from the west coast. If you haven't traveled this area, you'll see places you're read about only in history books. I do not like reading history, but I like hearing the story of the lost colony in Manteo or seeing Plymouth Rock or the sight of the Boston Tea Party or Ellis Island and the Statue of Liberty or seeing where the Wright Brothers made their flight and where space travel originated in the US. Seeing the Capitol, Lincoln Memorial, and White House. So many different kinds of beauty to be seen. There's a lot similar and then so much different. Then toss in the Bahamas which are like a vacation to your vacation. I still can't believe that in moving to South Florida we got this playground right off our coast of hundreds and hundreds of islands.
Who knows. By the time you make your trip, you may even go 90 miles out of your way and visit Cuba.
I think either of the paths you've thought of would be great. It's really a matter of what would you and your family like most to see. It will definitely be a time you're never forget.