I’m Doing This Backwards. Now That I’ve Booked For 5 Nights At Southernmost Beach…

Yes, for a wedding. The resort is ok, nothing special.

We did not particularly like it. We ate some good food, walked around, saw the "southernmost point" and did a fishing trip. I think Hemingway's house is there too.

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What are some of your favorite things to do in Key West that doesn’t involve a boat?

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About a year ago someone was in KW and listed all the things he had done and was going to be there a few more days. He was asking for recommendations. That post would be helpful if you can find it.

We there in February of last year for 3 nights and stayed around the corner from where you are. KW is very walkable; it's about a mile from the Southernmost Point area to the north side, Mallory Square.

Best things we did:
Mel Fisher Museum
Dessert at Better Than Sex restaurant; probably need reservations but we got lucky and someone cancelled just as we walked in.
Walking up and down Duval Street.
Mallory Square and Truman Annex areas
Butterfly Museum - it's small but it was worth it
Key Lime Pie at the restaurant at The Reach (where we stayed).

We did not do:
Truman Little White House - didn't seem worth the cost
Hemingway Home and Museum - it's was too crowded but will do that if we ever get back.
Lighthouse - didn't want to climb it.

There is a free circulator bus that I think goes right by your hotel. There is a website or an app that shows you where the bus is and about what time it will get to your stop. After a lot of walking the bus is nice. They did require a mask on the bus last year.

The best thing we did was a sunset cruise. Too bad that won't work for y'all. But a lot of people watch the sunset from Mallory Square or a nearby bar with outdoor seating on the water.

Another major attraction is Dry Tortugas National Park and a boat is one way to get there but I think there is plane that you can take also. We didn't do that because the boat was sold out.

IMO, 5 nights is probably more than you need in just Key West. If you're driving you might want to consider staying at one of the other keys a few days. We drove and did not move the car until it was time to leave KW; you really don't need a car there.

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Dry Tortugas National Park is closed

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OP is going mid April...the park should be back open in a couple of days

The plane to the Dry Tortugas is definitely the way to do it and take the first plane out. You'll beat the first ferry and once the boat arrives you would have already had the island basically to yourself for a couple of hours.

Snorkel the pilings for sure....probably the best snorkeling ive done anywhere in the world

Its not a bad property and it has a beach. Its a block from the iconic Southernmost Buoy. The Southernmost Mansion across the street has a cafe and is open to the public. Closest restaurants Banana Cafe (breakfast is really good), Martins (on Duval), and Louies Backyard (Dinner ocean side). Louies might be the best high end restaurant in town. I like the deck for day drinking. Since Ian they re-did the deck and it has more shade than it did prior to that. Most of the stuff is on the other end of Duval. I rarely travel past the 300 block.
The best things to do here are out on the water. The sandbars are great but depending on how fast your boat goes it is a hike.

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Great Cuban food and great drinks

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el siboney for Cuban food and the best sangria I’ve ever had. OP catch a ride to a rental place and rent bikes or mopeds for the week you’ll be glad you did, much easier to get around and park

What could go wrong with thousands of inexperienced scooter
riders riding from bar to bar looking for fun? We were there in October for 4 days. 3 would have been plenty...