One day in Venice

Decide where you'll end your night after you've finished your "must do" stops. Don't be surprised if things take longer than you estimate so prioritize.

@KBK ^^^ that is sort of what I am asking in my post....?

Your plan sounds fine. The canal ride and the walks will probably be the highlights. But most these areas will be mobbed with tourists. When you walk back to Piazzale Roma from Rialto be sure NOT to take the "main drag" (and most direct route) along Strada Nuova. This route is really touristy, and by the time you walk back, you'll probably be sick of the crowds. But you can alternately walk back along the opposite side of the canal. I don't remember all the neighborhood names - but...if you look on a map and find Rialto, you want to walk back on the south side of the Grand Canal (to Santa Croce I think) not the northern side (Strada Nuova). The walk on the south side is a bunch of zig-zags through piazzas and over a bunch of little bridges...but if you look up for the yellow arrows pointing toward "Per Ferrovia" (to the train station) or maybe signs toward nearby Piazzale Roma, you'll get there sooner or later. It's a much more atmospheric walk with fewer tourist crowds (best in the morning! I know you can't go then.) Give yourself time to enjoy this walk, not when you are exhausted and just want to get back to your hotel.

How about checking into your hotel and then follow the crowd to Rialto Bridge and San Marco Square. You cannot go wrong if you stay on the beaten path. At dusk hop on a vaporetto (water bus) to your hotel so you can see the illuminated foyers of the gothic palaces and not the decay that line the Grand Canal.

Check the opening and closing times of the places you want to get into. I think the Academia is closed on Monday, not sure it that would affect you. Also, they limit the number of people allowed in at a time, so it is better to reserve a time in advance. If you just walk up, you may not be able to get in. The Doge’s Palace is easier to get in, especially later in the afternoon. We walked up around 4 pm and there was no line up. But, to do it justice you should allow yourself about an hour and a half. With such an early flight you may want to stay closer to the train station to cut your travel time to the airport. I took an Alilaguna to the area near Rialto, and I think it took 45 minutes.

Thank you everyone for the input!

I guess truly I am just wanting opinions on which I should do first.. Should I start with Rialto bridge and make my way down to San Marco and eat dinner and hang out here till we go back to hotel? OR should I start in San Marco and hit the spots and finish by Rialto bridge and eat dinner here?
(Basilica closes at 5:15pm while we are there and Doge's Place 6:30pm)

I am now leaning more toward hit Rialto area first, and then end around San Marco (getting there around 4 to get in in time, and then Doge after). Does this sound okay? If so, what are your favorite dinner spots or hang out evening spots in this area?

I think dump your bags at your hotel, and make your way to Rialto by way of San Polo and Santa Croce ( both are on the side of the Grand Canal away from the station and P. Roma).
Walk past the Basilica de Frari, maybe take a look inside; it is very special. Pure soaringknock your socks off soaring Gothic, and Canova’s ptramid monument is great. Titian’s Assumption of the Virgin is one of the world’s great paintings.

Just over the bridge in front of the Frari is the bar Al Archivo, grab some chicetti and a spritz for lunch. Follow the signs from there to Rialto, look for “per Rialto” directions.

Have a poke around Rialto, the department store just to the left of the Rialto bridge, the Fondaco Tedeschi is quite something if you want to give your Amex a workout.

Head towards the CamponSan Stefano, take a look at the Academia bridge for a great view down the Grand Canal towards the Salute. Then head towards San Marco.

Maybe do the Doges Place, although to do it justice it does need at least a couple of hours. Maybe the Basilica if the line is not too long, maybe you can buy timed entry tickets.

Head down towards Castello, find a place to eat. The food atvthe places fronting the GC is avoidable.

Head back to the Piazza, have a drink at any of the cafes - Florians, Quadri, they are all the same. Get a vaporetto from San Marco to P. Roma after dark.

Just one other suggestion. DO BUY A PAPER MAP. Venice is like a rabbit warren, tiny streets leading to even more tiny streets. Phone navigation in Venice is really crap, you cannot get a picture of where you are, and if you ask for help, people cannot point to your phone and say “you are here”.
Spend the three or four euro,it might save you an hour of your precious time.

I have spent a lot of time in Venice, and I still carry a map. The phone, not so much.

I actually really like your first plan to take the vaporetto down the Grand Canal and get off at the Accademia bridge area. You could walk in Dorsoduro to Zattere Fondamenta and have lunch outside on the waterfront at Ristorante Pizzeria Alle Zattera and even get gelato near there. Then you could take the vaporetto to the San Marco area or walk there. Be sure to see St. Mark's Basilica and Doge's Palace before you are too tired. It is a majestic area and a beautiful part of Venice, so allow time to enjoy it. Also walk along the Riva degli Schiavoni. Then you could end at the Rialto Bridge area which we felt was crowded and our least favorite part of Venice. I agree that a paper map of Venice is very helpful and worthwhile to have.

I would go to the San Marco area first since both the Basilica and the Palace may have lines (even long) to enter. Then you'll spend time inside each. The Bridge can be viewed/crossed anytime.

It's easier than you think to make a wrong turn and end up at a dead end, especially on the Santa Croce/San Polo side of the Grand Canal. I know, it happened to me several times yesterday and today! Using your phone's GPS/google maps/whatever doesn't always work because service is sketchy in the narrow streets lined with 3-4 story buildings. Sometimes street signs are non-existant and sometimes the names don't quite correspond to the maps.

There aren't a lot of tourists here in Venice right now (I'm one of them) so there are no lines for the vaporetto and most sights. This morning at 10.30 there was a long line to buy tickets for the Basilica and a short one for the Doge's Palace. The Basilica tried to set up a website for tickets. I'm told they took it down after 3 days of its not working properly and nothing's been heard from since. Currently the Basilica opens at 9.30 - except Sundays when visits are limited because of services. It sounds like your hotel isn't far from the train station. Maybe take the vaporetto all the way to San Marco and then walk to the Accademia and on to Rialto. There are lots of good restaurant choices in the Dorsoduro and San Polo, less touristy than around San Marco. I'm told that on Fondamenta Misericordia (past the train station in Cannaregio) it's quite lively until the wee hours . . .