At a planned average speed of 5.25 knots, your itinerary was pretty aggressive. My boat lets me try for an average of 6.0-6.5 knots, which greatly enhances my range. 40 miles on a day isn't bad if you have a couple of days in between trips, but cramming all that into a weekend is ambitious.
Don't turn your cruises into "pain missions" or the wife will stop coming.
One solution is to use more vacation time so that you have more time to travel. The other solution is to pair back your agenda a little bit.
Our approach is to plan for an average of 5 knots . Our range is generally 30 miles on direction. 6 hours of sailing / motoring is fine. It isn't a death March for my wife and I. We generally shove off by 9....after having breakfast , that way we are where we want to be by 3 which gives plenty of time for a nap/ dinghy ride/ swim and then a cocktail hour and dinner. We average 32 weekends a year so our total travel is 1800-2000 nm per year without vacation.
This lends itself to another criteria. Where is your marina in relation to your sailing grounds/ anchorages. You are in Baltimore so it's 9.4 miles before you hit the Bay. That's a long hike. One of the reasons we choose MYC was that. It put us in easy range of worton, still pond, sassafras, Chester, mogothy, Severn , and even South, West and Rhode. St Mikes and Wye we attainable.
Thats another reason we moved after 10 years there. Now Solomons, Choptank, Wye, Chester, Magothy, Severn, west, south , Rhode, Rock Hall and Worton are in that radius.
The trick is to get up earlier . Arrive earlier . Then you'll get you RandR .
The more time you spend on the boat the more you will relax while sailing too.
We are quiete comfortable having lunch under way and even set up the table and let the auto pilot steer us . That comes with time and is certainly harder to do if you choose to sail in a busier area.
Vacation is different. We go 50-80 miles per day the first few days and beeline to our furthest point usually taking our time coming back. Sometimes spending a few nights at a location. Those jaunts are 20 miles . Getting underway after breakfast by 9-10 arriving by 2.
On weekends when we return we are usually relaxed , don't try to get back by 2 Pm. Our last hour returning is the time to pack up the inside of the boat so when we get to dock ( where it's always warmer) much of the work is done. We also try and have a good snack like watermelon in the cockpit or in the air conditioning after we have Haleakula buttoned up before we wheel our stuff to the car.
We try not to rush home. Since we don't have little kids it's easier ( but we've been there and done that already) .
Not sure if this helps but it works for us and it makes this much more enjoyable for my wife and we are not worn out when we have to work Monday.
We always laugh that on our Sunday night showers st home we are still rocking.