There are too many countries that you are interested in and that makes any suggestion almost impossible.
Why don't you narrow down your areas of interest first and then ask for advice from the forum?

Well you've thrown out alot of options and you don't have an extended amount of time but you could consider Italy / Amalfi Coast and Capri OR Spain / Barcelona or maybe San Sebastian and then for Monaco I'd suggest staying in Nice - many daytrip options including Monaco. Any of those should be pretty easy to get to from Philly - a Greek Island would be a bit more involved. IMO the other destinations offer a bit more to do besides just hanging out. If you mostly want sun and sand go to the Carribean (the beaches are not as good in most European locals) but for a mix of culture and sunning, head to one of the other options. (Let me add Bermuda is lovely too in May and has alot of English flavor thown in!)

Barbados or Bermuda.

I got it! Rent an apartment in Barcelona. Fly non-stop from Philly. Public transport in Barcelona is very good, beaches are beautiful, museums are top rated, food is fantastic, shopping is fun, many parks and pedestrian walkways to walk all day if you so wish and take it all in. Do it now because life gets a bit complicated later on and you will regret not getting to Europe when you were more free and had a chance Just beware of pickpocketers.

Have fun! Congrats!

viajero2 i definitely appreciate the suggestion! i actually studied abroad in spain and he had visited me there so we've done the city together... and funny thing you mentioned pickpocketers bc i was mugged in seville! i love spain though and was thinking about the canary islands since its one area ive never been.

Ambergris Caye, Belize. Fits every one of your criteria, not ridiculously expensive, safe, great people, great day trip options, good food, all kinds of pretty, and you don't have to exchange currency because the Belizeans accept US dollars.

It's also the only Central American country in which English is the official language (the Belizeans say "and Spanish is widely spoken" - this is a crock because Spanish is the official language in fact, not in law, but everyone speaks English to some degree). Easy flight options through Houston or Dallas (do NOT ever connect through Miami, especially coming back into the US) with a 15 minute puddle jumper connection to Ambergris Caye.

Canary Islands are aslo a great place to consider. I would recommend holiday-rentals.com or vrbo.com for rental properties in Europe. I think having a place to yourselves on a nice setting has the potential to take a honeymoon from nice to sublime! Have fun!

thank you bigruss! i will look into that further bc it sounds great!

You have said you want to relax - but does that mean the beach? Much of europe is too cold for the beach (you can walk, but not swim - in May).. Also many beaches in europe are not the type you find in FL or the carib -(wide pure white sand with no business nearby) many are pebbles versus sand and located in the center of town with boats and marinas/shops right nearby.

So - if yuo want to swim in mid May in europe probably your best choices are southern Spain or Sicily. If you want history, art, and you can get countryside and seaside - just not swimming or pools.

And IMHO 7 days in europe you should go to one place (and Monaco should not be it unless you have a fortune to spend - it is really designed for the uber wealthy.)

ikies.com my fav in santorini.com best sunsets in the world

sargegna.com Costa Smeralda best beaches

Canaries in most areas too touristy...

Carib/Colombia best for me

Hawaii Kona 4 hours direct from LAX closer than Europe.

Venice-tourism.com is VERY Romantic bauervenezia.com

for me last there.. beach not as good...

Paris of course but will be pretty cool there

intercontinental.com right by the Louvre my fav there.