Surnames:
Finkel
Finkelstein
Weinstein
McGillicuddy
Kanjanavaikoon
Two Bears
Place names:
Wa Wa Wai, WA
Walla Walla, WA
Pompano, FL
Kissimee, FL
Honeyoye Falls, NY
Germantown, PA
That’s 2 m’s in Kissimmee, FL.
Even better! 
Happy to help.
Um, would you mind explaining the thread?
List proper names that are fun to say, funny, or just plain weird. Seriously, try saying Wa Wa Wai Washington five times real fast. Do so out loud. At the office.
Chargoggagoggmanchaugagoggchaubunagungamaugg is the name of a lake in Massachusetts.
Okey dokey, I get it.
Here are some more. Bonus points to anyone who can pronounce them correctly. 
Clatskanie, OR
Yachats, OR
Molalla, OR
Boring, Oregon (hee!)
Herkimer, NY
Okeechobee, FL
Wow, totally cool. I must get there this summer. Where exactly is Webster?
New entry: Fucking, Austria
. It isn’t all that far from I live all things considered.
All in Pennsylvania:
Altoona
Beaver
Big Beaver
Blue Knob
Covode
Desire
Intercourse
Kishacoquillas
Kittanning
Punxsutawney
Gobbler’s Knob
Kalamazoo (Michigan)
Ougadougu (Burkina Faso)
Cat Brain Hill (England)
Douro-Dummer (Ontario; I just now noticed it on a map on my wall)
Trawsfynydd (Wales; it’s quite lovely for a word with so few vowels. Hint: “dd” is pronounced “th”)
Shagnasty, thanks for that. It’s a leetle far for me.
NY:
Irondequoit
MA:
Chicopee
Mashpee
Beetlebung Corner
Gay Head
[Joyless, Wet-Blanket Nitpick] I count four vowels. A, W, Y, and Y again. [/Joyless, Wet-Blanket Nitpick] Carry on.
Knaw Bone, IN
Floyd’s Knobs, IN
French Lick, IN
Moonsville, IN
Lapel, IN (named for the original shape of the town map)
Rabbit Hash, KY
Patoka Lake, in IN. Near as I can figure, “Patoka” is an old Native word for “Rains every time I camp here.”
You can go to a lot of exotic places without leaving Indiana.
Mexico
Brazil
Peru
Hobart
Versailles
Edinburgh
New Castle
Frankfurt (Frankfort, actually)
Florida Station
Native American surname I always liked – Everybodytalksabout.
Another Washington State name isn’t particularly good until you say it – Puyallup isn’t funny but – Pew-all-up kinda is.
My great great (I think that’s enough greats) grandmother had a wonderfully fun name to say, but I have no idea how to spell it. I’ll try it more or less phonetically, and maybe a passing German speaker can fix it if they don’t die laughing at my ignorance.
Yes, in a family full of Hildegardes and Brunehildes, we hold a place of honor for Kuneygunda Schmaltzer.
Try saying it out loud. Isn’t it like choking on a seltzer bottle?
A major street in New Orleans is Tchopotoulis. Even people that have lived there all their lives sometimes can’t spell it. Visitors usually can’t say it (Chop - O - Tool - is).
That spelling makes perfect sense. In French.
A few from Ontario:
Omemee. (One of my favourite names to say).
Yelverton. (The perfect rural hick town name, in my opinion, even though it is actually little more than a named crossroads northeast of Oshawa).
Mississauga. (Four S’s. 650,000 people).
A few from upstate New York:
Tonawanda
Canandaigua
Schenectady
Lackawanna
Irondequoit
Cheektowaga
Manlius