Speakers - Your "Safest" Choice

How about a pretty economical trip to the Florida expo in February. (For me about $800, flights, hotel, tickets to the event, 1 free for my beloved…) then go talk to madman Greg of Volti Audio, have a listen to what he brought to the show. After a good listen there, head to other rooms and compare. I’m fairly confident you’ll head back to see Greg. His passion is infectious, his creations are amazing. Yes you can call me a devoted fan, or fanatic… but I’d put my Volti Razz up against anything south of $20k, they are that good to my ears.

I can't picture a trip to NY for a "few days" including airfare, hotel, transportation and food for under 5 K

Drive (if you're close enough); then if you happen to find speakers you really like, you can take them back with you (and save on shipping).

Don't stay in Manhattan. NJ, maybe. Look for unpopular dates and for deals. Even in Manhattan, you could stay in a Pod for ~ $120/night (incl. taxes & fees).

Eat street food (or bring something along).  You should be able to get a panful of rice rolls in Chinatown for < $5. Big Tray Chicken at Spicy Village (Chinatown) < $20, enough for 2. 

I would think you could have an enjoyable experience for about $250/day. Frugal, but not spartan.

Focal all the way

Hi, $20 k is in the perfect range of the OMA ´s Fleetwood Deville SQ. They are beautiful, not to big , floor stand speakers that sound very musical with the tiniest details and amazing voices.I truly suggest giving them a listening demo before making up your mind, I love them and could listen for hours as the speakers disappear and the musical magic is all around you.

@OP - The suggestions for B&W, Sonus Faber, Wilson and Focal and Magico are all on the money.

A pair of Wilson Sabrina Xs is in your budget range. Some people are put off by their diminutive size, but they sound bigger than they look.

My personal preference would be between Wilson and Sonus Faber but you should really try to hear comparably priced models from all of those firms.