I flew an unusual amount last year, and earned 6 upgrades on United international flights (economy to business class).

I also have banked a large number of Hilton points.

Would love to plan a vacation "of a lifetime" flying United business class with DH to some exotic Hilton location.

Has anyone planned such a trip + can make recommendations?

I've done something like this a number of times using United MP points and HHonors points, but I've always flown Star Alliance partners, rather than United to the final destination. Bali (our destination last year) or New Zealand (the year before) were amazing experiences for my wife and me, both in terms of getting there in business class and the quality of hotels at the destination.

I'm guessing that you have the GPUs for being a 1K? I've never been fortunate enough to hit that level. But, if I were in that situation, I'd target Eastern Asia. There are a lot of cities that United serves: Tokyo, Beijing, Bangkok, Singapore, Shanghai, and Hong Kong come to mind. Each has one or more highly regarded Hilton-family hotels. From personal experience, the Conrads in Tokyo and Singapore are among the nicest hotels at which I've ever stayed. Dubai is another intriguing possibility that I've thought about recently.

Yes, I have GPUs, so it needs to be United medal ... Thanks for your suggestion. (I had an unusual high volume of business travel last year!)

One note, just because United doesnt fly there doesnt mean it should be your final or only destination.

Also, agree that Conrad SIN is very nice. Once there, Thailand and Malaysia great beaches are only 60-90 minutes away(flight). Use UA to get there, then think about a quick jump via low cost carrier to final spot.

KL has a great Hilton(one of the best exec lounges in Asia) and great Doubletree(one of the best you will find).

Also, length of time(week, month ect) and what you like to do, as well as time of year.

My choice would be the Conrad Koh Samui. Can do UA metal to BKK. From there, it's an hour on Thai if you want to use miles or Bangkok Airways for better flight times.

Bali would be a similar situation. UA metal to SIN and then a short flight to DPS.

Awesome suggestions! Just Gold on Hilton honors, but really like the idea of combining a long haul business trip on United with a hop to a special destination. I think we are probably looking at a thurdsay - week - monday type of trip given pressures at work.

I do this about once a year. UA BF or GF to some Hilton. This year I am doing Singapore and Kuala Lumpur. I have done Berlin, Sydney and Melbourne, Tokyo and Osaka, Buenos Aires, and Hong Kong. I did Rome before the Cav changed. I have done others but the hotels at those locations were especially nice.

I heartily agree with the Koh Samui or Bali suggestions. We've been to the excellent Conrad Bali and will be going to the very nice looking Conrad Koh Samui later this month. Between the two, the CKS looks even nicer as a place to just get away and relax, as the rooms are all standalone hillside villas with their own decent-sized infinity pools. CB better if it's a priority for you to be able to walk to some other places to eat (which I understand you can't do from CKS) and if you want to take day trips (easily arranged with lots of reliable drivers there) to explore the beautiful island and culture of Bali, which retains more of its original identify than Koh Samui does. From what I can tell, I'd recommend CKS, but will have a firmer sense after actually visiting there.

If you do go to one place or the other, you could stop off in Bangkok or Singapore for a night or two, which would be fun. Make sure you leave lots of time for connections from UA to whichever airline you fly to the final destination (and vice versa), as you'll be on two different tickets.

As a HH Gold, you should free breakfasts for two included in both places.

One thing I'll emphasize is getting your UA tickets way in advance (which increases the chances of upgrades being available) and only doing so if the upgrades are available at time of ticketing. If you simply wait list for an upgrade you're very likely to be disappointed. To put it mildly, UA is not great on making international upgrades available, so starting to search ASAP and being flexible about your travel dates will be necessary.

It's also helpful is to book your hotel rooms way in advance, especially for the CKS as availability at normal award rates (as opposed to astronomical redemption rates) can start disappearing months in advance for that property.

Finally, be aware of what the climate is like in these places. For example, the US autumn is the rainy season for Koh Samui and our winter is the rainy season for Bali. You have a chance of some sun during those times, but also a chance of lots of rain. Here's a good site for checking out what precipitation and temperatures are like around the world at various times of year:

http://www.worldclimateguide.co.uk/

Happy trails!

How about IST? UA flies there from EWR and they have a fantastic new Doubletree right in the old town. I stayed there a couple of years ago when it first opened and it was fantastic. It's not a Conrad but it is nothing like a State-side Doubletree and Istanbul is a fantastic city. I don't consider Istanbul to be terribly exotic, but neither are Bali or Singapore.

Thanks, that is really helpful. I'm a totally newbie about these things, so this really makes a difference.

You're welcome!

Well, if you're a newbie another thing to know (that I hope you won't find too discouraging) is that to use your upgrades on UA you have to buy what's called a "W" fare, which is an economy fare that's definitely more expensive than the cheapest UA economy fares.

If you have enough miles to fly business class all the way as an award ticket you might want to consider that option (whether redeeming on UA or maybe on preferable partner airlines, such as NH), though of course that way you wouldn't get to use your upgrades.

By "exotic" you don't just mean beach locations (which some of us assume and which I'd recommend as an unusual trip) but other places, let folks here know and you might get some additional ideas. IST strikes me as good in that regard, but be aware that it is a huge, bustling city so it would be more of a cultural experience rather than a relaxing getaway.

Also, if by some chance you can't get upgrades to Bangkok or Singapore, a fallback might be Hong Kong. It's not as close to Bali or Koh Samui as the other two cities are, but you could still get decently regional flights and fares from there. Plus it's a great city for a stopover.

End of the day I'm not a big beach person, so this is intriguing. Can you spend a good week there? Good day trips?

I would not count on the upgrade voucher clearing. Just take a walk over to the UA forum to see how often the GPUs do not clear.
If this is a "lifetime" trip and you will be totally bummed out if you are not upgraded then you should rethink the trip
The only way to be sure you are sitting up front in UA is miles or paying for the flight. Unfortunately too many of us very frequently have sat in coach on an expensive coach fare (you need W or higher fare) with another unused GPU.
Sorry to be a downer (realist)

Award tickets in business are very reasonable on the saver rates 120k and 140k F.

Get rid of your upgrades on coupon connection, I mean trade them.... The dollars you would spend for coach W, go along way to people with alot of miles. Just a thought, but agree with others on using Up certs... Get the real deal on an award ticket if you can.

I think you could definitely spend a week in Istanbul/Turkey. There are many historical palaces and temples to visit from many of different eras and religions. Istanbul is also a great city for food, so you could eat your way around town for a week too. Bursa is a popular day trip from Istanbul and I'm pretty sure you could even do a day trip down to the Lone Pine Memorial in Gallipoli if that sort of thing interests you, although I think it'd be an exhausting day trip. Domestic flights are reasonably priced so if you have a day or two leftover from a GLON/AXON award you could check out Izmir on the Aegean Sea for something different. (They have a Hilton there)