Please help me think of a great vacation idea :-D

Hawaii! Go to the Big Island--stay a week on the Hilo side of the island and take in Volcano National Park (we stayed at Kilauea Lodge)--see the Observatory on Mauna Kea--the eruption of Kilauea crater--walk on black sand beaches. Then spend the next week on the Kona side of the island, soaking in the sun and beaches--or fly to another island. Oahu, Maui, Kauai--all are beautiful.

A few ideas... - Fly to New York and take your friend up on his offer. Spend at least a half day at The Met and a half day wandering the galleries of Chelsea. End or begin one day with a walk along the High Line. Have a proper New York dinner - Prune or the Spotted Pig or Fatty 'Cue or the bar at Marea. Spend a day walking - I'd do Wall Street and environs, Central Park, and Fort Greene, Brooklyn. See a show on Broadway. See a show off-off-Broadway at HERE, The Brick or Soho Rep or 59E59 or Bushwick Starr. After a couple days, rent a car and drive up the Hudson River Valley. Go see art at Dia:Beacon, stay a couple nights in Hudson, NY seeing old houses, galleries and touring the countryside. Eat the best farm-to-table food on the east coast. Hike. After a week has gone by, fly out of New York and spend a week somewhere warm; Puerto Rico, Key West, US Virgin Islands, Savannah, GA. - Fly to San Francisco and spend a few days there seeing art and eating. Then rent a car and drive south to Big Sur and avail yourself of the hiking. East the best farm-to-table food on the west coast. Stay at Deetjen's or Glen Oaks. Take a midnight hot springs soak at Esalen. Continue your trip south along highway 1, slow and steady and filled with side-trips. Wind up in LA, spend a couple days on a hiking/kayak trip out on the Channel Islands. Go to the Getty. See a show at IO West. - Rent a house or an apartment or a room through Airbnb or VRBO or what have you in New Orleans. Stay there for two weeks and see how much of a local you can become by the end of 14 days.

If I had no chance of bringing someone with me, but had two weeks otherwise free, I'd do something that I wouldn't likely be able to do with others (i.e., my wife and child) in tow, but I don't know how much this applies to you. This means I wouldn't go to Hawaii, because that'd be an easy trip to do with them. I'd do something like a bicycle tour of the California coast (which my wife would never want to do) or a camping/surf trip in baja. If I was doing a trip by myself, I'd want it to be a trip that was uniquely my own and not a compromise to satisfy everyone on the trip with disparate interests.

Thanks to everyone for their suggestions, especially deanc about checking passport validity requirements for destination countries. I wound up booking a package tour through a company called Contiki (http://www.contiki.com/), and took a 10 day tour of the UK (which doesn't require 6 months passport validity after your departure date). I had a great time on the tour, with the standard disclaimer that if you were to book through them (or a competitor for that matter), YMMV.

Miami or Malibu.

My vote would be for Hawaii too--it's in the US, so no passport issues, and offers nature, history, culture, nightlife--pretty much anything you might want to do on a vacation (and yet, if you are sunburned and jet lagged one afternoon, you could also just go to a movie or something). Plus two weeks will really make you feel like you got your money's worth. Not sure if $2,000 will cover you for all that, but depends on what your need is for cushy hotels.