Just for fun I put a list together of my favorite 18 cities across the world. Carrie also approved the list, and I’m pretty sure it’s a factual order.

I’ll go into further detail about the top 5 cities, how to get there with miles (and how to get those miles for free) and how to stay there for free.

Here are the Best 18 cities in the world (that we’ve seen so far):

1. Vienna, Austria
2. Venice, Italy
3. Hong Kong
4. Sydney, Australia
5. Budapest, Hungary
6. London, UK
7. Seattle, USA
8. Tokyo, Japan
9. Bangkok, Thailand
10. San Francisco, USA
11. Edinburgh, UK
12. Rome, Italy
13. New York, USA
14. Singapore
15. Salzburg, Austria
16. Paris, France
17. Kuala Lumpur, Malaysia
18. Warsaw, Poland (Old Town Warsaw at least)

1) Vienna

The beauty of Vienna is in its incredibly clean and beautiful buildings and how incredibly pedestrian friendly the city is. Staying in the city center is magical as you’re surrounded by giant, grand, old imperial pieces of architecture. The buildings are huge and romantic like Paris, but instead of a 6 lane road splitting the sites, you have cobble-stone streets.

You may notice that Vienna is one of the few cities on this list that isn’t on the water’s edge in some way. It does have a river, but the city isn’t built around the river like Budapest or Salzburg. But by not having a river or highway cutting through the center, it’s incredibly pedestrian friendly, as I mentioned before.

Walking around at night, listening to street serenaders in their suits and the horses pulling carriages makes Vienna one of the most romantic cities to stroll through.

Let me say that Vienna is a little slower. So if you love action packed nights, then maybe this isn’t your top-pick city. But it’s so close to Budapest, Salzburg and Prague. The train to Budapest is about 2 hours, if I recall correctly.

Doing Vienna for free

Flights: See the post on Best Miles for Getting to Europe to see what miles to start collecting. But off the cuff, here are some great options.

• 40,000 roundtrip to Europe with AA off peak. Get AA miles from the AA credit cards or transfer from Starwood.
• US Airways has an off peak of 35,000 miles roundtrip and if you fly US Air you get a 5,000 point discount as a credit card holder.
• It’s 60,000 miles to Europe with United miles and you can get a stopover and two open-jaws, which you can earn from the United card and Chase Ultimate Rewards points (like the CSP or Ink Bold).

Hotels: There are a number of points options in Vienna. Here are a few downtown.

• IHG: There are a number of ways to get free nights with IHG. You can get IHG points from the credit card for instance. The credit card also gives a free night at any hotel, and only has a $49 annual fee. Another way to get a free night with IHG is with the IHG Best Rate Guarantee. And you can earn points super fast by reading Earning IHG Rewards Points on Steroids.

  – InterContinental Vienna is 35,000 points. But we got this hotel for free using the BRG.
  – Holiday Inn Vienna City for 25,000 points.

• Hilton: HHonors points which you can get from the Hilton credit cards, and the Hilton Reserve card gives two free weekend nights. You can also transfer from Amex points 1:1.5, but I don’t personally advise it.– Both the Hilton Vienna & Hilton Vienna Plaza go for 40,000 points or ~49 Euros + 16,000 points.
• Starwood: You can get SPG points from the SPG credit card.– Hotel Bristol is 12,000 points.
  – Le Meridien is 12,000 points.
  – Hotel Imperial is 20,000 points.
• Marriott: You can get Marriott points from the Marriott credit card. You also get a category 5 certificate every year you keep the card (that has an annual fee of $85).– Vienna Marriott is 35,000 points.
  – Ritz Carlton is 50,000 points.
  – Imperial Riding School Renaissance is 30,000 points.
  – Slightly away from downtown the Courtyard is a category 4 and the other Renaissance is a category 5, in case you’ve gotten certs from a Megabonus promotion.
• Club Carlson: You can get Club Carlson points from the Club Carlson credit card. Plus it gives you a free night per award stay of 2 nights or more.– Radisson Blu is 50,000 points and has an awesome location.
• Hyatt: The Hyatt credit card gives 2 free nights at any hotel. You can also transfer from Chase Ultimate Rewards, but I don’t personally advise it.– A Park Hyatt should be opening this summer. The Hyatt card gives two free nights at any hotel. Would love to try this hotel – they had me at “Park Hyatt”…

2) Venice

Again with getting away from the cars, Venice is the ultimate destination for a big city you can “get away” in. Take the bus or train across the bridge to this island city of canals and ancient architecture and then you can go to the center by boat or by foot.

On foot you pass over dozens of small bridges on streets designed for people. Not cars nor even mopeds can enter or cross these stoned bridges.

Doing Venice for free

Flights: See the Flights section under Vienna above for tips on getting to Europe with miles and how to earn those miles.

Hotels: Make sure you get a hotel on the island of Venice and not across the bridge in the dumpy looking Mestre.

• Hilton: You can use HHonors points which you can get from the Hilton credit cards, and the Hilton Reserve card gives two free weekend nights. You can also transfer from Amex points 1:1.5, but I don’t personally advise it.– Hilton Molino Stucky Venice is 50,000 points or 65 Euros + 20,000 points.
• Choice Hotels: You can get a free night with the Choice Best Rate Guarantee.– Comfort Hotel Diana can be BRGed.
• Starwood: You can get SPG points from the SPG credit card. Their hotels are beastly expensive in terms of points and cash. I wouldn’t recommend it. Although I did stay at the slightly cheaper Westin and sincerely regretted it.– The Gritti Palace is 30,000 to 35,000 points.
  – Hotel Danieli is 30,000 to 35,000 points.
  – Westin is 20,000 points but the rooms and service are crap, especially for the high price, in my opinion.

3) Hong Kong

Imagine the largest, tallest and most incredibly sprawled out skyline of modern skyscrapers across a number of tropical islands. From the top of the Hong Kong island you can look down on the 100 story skyscrapers, and across the waters to the other islands.

A city across beautiful tropical islands is unique on its own. But the sheer size of this city is mind blowing. Skyscrapers for as far as the eye can see. The combination of the two makes Hong Kong so unique. But what makes it even more unique is how this modern big city is still very Chinese. Markets with animal heads hanging and other typical Asian and even third-world nuances make it feel farflung.

Doing Hong Kong for free

Flights: See the Best Miles to East Asia Showdown for tips on getting to Asia with the fewest miles possible.

• 65,000 miles roundtrip with American Airline miles, which you can get from the AA credit cards and the SPG card.
• 60,000 miles roundtrip with US Airways, which you can get from US Airways credit card and SPG.

Hotels: There are so many hotels in Hong Kong that I’ll try to stick to “downtown” hotels.

• IHG: There are a number of ways to get free nights with IHG. You can get IHG points from the credit card. The credit card also gives a free night at any hotel, and only has a $49 annual fee.Another way to get a free night with IHG is with the IHG Best Rate Guarantee. And you can earn points super fast by reading Earning IHG Rewards Points on Steroids.

  – The Holiday Inn Golden Mile and Holiday Inn Causeway Bay are both 35,000 points.
  – The InterContinental Hong Kong is 45,000 points and one of my favorite hotels in the world.

• Hyatt: The Hyatt credit card gives 2 free nights at any hotel. You can also transfer from Chase Ultimate Rewards, but I don’t personally advise it.– Grand Hyatt Hong Kong can be had by your free night certs or 25,000 points.
  – Hyatt Regency Hong Kong, Tsim Sha Tsui can be had for 15,000 points. Or by using the Category 4 free night certificate given every year you keep the Hyatt card (for the $75 annual fee).
  – Hyatt Regency Hong Kong, Sha Tin can be had for 12,000 points.
• Marriott: You can get Marriott points from the Marriott credit card. You also get a category 5 certificate every year you keep the card (that has an annual fee of $85).– The Ritz Carlton Hong Kong is 70,000 points and the highest hotel in the world! Imagine swimming on the 118th floor and over looking Hong Kong.
  – JW Marriott is 40,000 points.
  – Courtyard Hong Kong is 25,000 points and a category 5 if you have a free night cert from the card or Megabonus promotions.
• Hilton: HHonors points which you can get from the Hilton credit cards, and the Hilton Reserve card gives two free weekend nights. You can also transfer from Amex points 1:1.5, but I don’t personally advise it.– Conrad Hong Kong is 80,000 to 95,000 points, but you can use your weekend certificates.
• Starwood: You can get SPG points from the SPG credit card.– Sheraton Hong Kong Hotel & Towers is 16,000 points.
  – W Hong Kong is 25,000 points.

4) Sydney

Sydney is hip, beautiful and has a ton going on! The harbor, the old European architecture, the late night downtown with locals dressed to the nine, and a ton of beautiful sites. You could spend more time exploring Sydney without getting bored than most cities I can think of.

Doing Sydney for free

Flights: There is a post on the Best Use of United Miles to Australia. In it I explain how you can add a trip to a Pacific island like Fiji to drop the roundtrip price from 80,000 miles to 70,000 miles. 

• 80,000 miles (or 70,000 miles when you also stop in Fiji) with United miles, which you can earn from the United card and Chase Ultimate Rewards points (like the CSP or Ink Bold).
• 75,000 miles with AA miles, which you can get from American Airlines credit cards and SPG.
• 80,000 miles with US Airways, which you can get from US Airways credit card and SPG.

Hotels:

• Hyatt: The Hyatt credit card gives 2 free nights at any hotel. You can also transfer from Chase Ultimate Rewards, but I don’t personally advise it.– Park Hyatt Sydney is 30,000 points or you can use one of the free nights from the credit card.
• Club Carlson: You can get Club Carlson points from the Club Carlson credit card. Plus it gives you a free night per award stay of 2 nights or more.– Radisson Blu Sydney is 50,000 points.
• Fairmont: The Fairmont credit card offers two free nights at any hotel.– Swissotel Sydney is available for using free night certs.
• Hilton: Use your HHonors points which you can get from the Hilton credit cards, and the Hilton Reserve card gives two free weekend nights. You can also transfer from Amex points 1:1.5, but I don’t personally advise it.– Hilton Sydney is 60,000 points or you can use a weekend night cert.
• IHG: There are a number of ways to get free nights with IHG. You can get IHG points from the credit card. The credit card also gives a free night at any hotel, and only has a $49 annual fee.Another way to get a free night with IHG is with the IHG Best Rate Guarantee. And you can earn points super fast by reading Earning IHG Rewards Points on Steroids.

  – InterContinental Sydney is 50,000 points.
  – Holiday Inn Potts Point-Sydney is 30,000 points.
  – Holiday Inn Darling Harbor and Holiday Inn Old Sydney are both 35,000 points.

• Marriott: You can get Marriott points from the Marriott credit card. You also get a category 5 certificate every year you keep the card (that has an annual fee of $85).– Sydney Harbour Marriott Hotel at Circular Quay is 35,000 points.
  – Pier One Sydney Harbour, Autograph Collection is 35,000 points.
  – Courtyard Sydney-North Ryde is a little away from downtown but is 20,000 points and a category 4, if you have category 4 or 5 certs.
• Starwood: You can get SPG points from the SPG credit card.– The Westin Sydney is 12,000 to 16,000 points.
  – Sheraton on the Park is 12,000 to 16,000 points.
  – Four Points, Darling Harbor is 12,000 to 16,000 points.

5) Budapest

So close to Vienna both in location and design, but this is hands down in my top 5. But it is distinctly different from Vienna in two ways – the river and the hill.

The river splits the two once two separate towns, Buda and Pest. On one side is the Royal Palace, on the other side the stunning baroque style parliament building. One side has many of the down town activities and the other side has an ancient castle. The river with its artistic architecture surrounding it makes this city the most picturesque.

But the Buda side is also distinct in that it is very hilly.  Meanwhile Pest is extremely flat. Thus, viewing this wonderful city (and snapping a photo) is a bit easier. In Vienna, you’re always looking up at the buildings and can therefore only see what’s in front of you. But from the top of Buda, you can see the entire city at once.

Doing Budapest for free

Flights: See the Flights section under Vienna above for tips on getting to Europe with miles and how to earn those miles.

Hotels: Actually, I wrote an entire post on the subject. Check out Doing Budapest For Free.

•  IHG: There are a number of ways to get free nights with IHG. You can get IHG points from the credit card. The credit card also gives a free night at any hotel, and only has a $49 annual fee.Another way to get a free night with IHG is with the IHG Best Rate Guarantee. And you can earn points super fast by reading Earning IHG Rewards Points on Steroids.

  – InterContinental Budapest is 35,000 points but we got it for free with a BRG.

• Club Carlson: You can get Club Carlson points from the Club Carlson credit card. Plus it gives you a free night per award stay of 2 nights or more.– Radison Blu Beke Budapest is only 9,000 points. Not real luxurious but it’s downtown and with the card you can get two nights for 9,000 points. A steal.

• Hilton: Use your HHonors points which you can get from the Hilton credit cards, and the Hilton Reserve card gives two free weekend nights. You can also transfer from Amex points 1:1.5, but I don’t personally advise it.– Hilton Budapest is only 30,000 points and overlooks the parliament building.
  – Hilton Budapest City is 40,000 points.
• Starwood: You can get SPG points from the SPG credit card.– Le Meridien Budapest is 10,000 points.
• Marriott: You can get Marriott points from the Marriott credit card. You also get a category 5 certificate every year you keep the card (that has an annual fee of $85).– Marriott Budapest is 30,000 points.
  – Courtyard Budapest is 15,000 points and a category 3 if you have free night certs.
  – Boscolo Budapest, Autograph Collection is 30,000 points.

Conclusion

These are 5 cities I would not get bored in, and wouldn’t mind spending a fair amount of time in. And obviously, the big cities are super easy to get to with miles.

Personally, I’m more of a nature person but these cities are beautiful and/or interesting. And you can always fly into Budapest and then head to the Alps (like Berchtesgaden). Make Hong Kong a stopover on the way to Bali or Phuket. Make Australia a stopover on the way to Fiji. Just because you’d rather be snorkeling or hiking doesn’t mean you won’t love these cities!

Ya know, this list could go on and on and on as there are thousands of hotels with most of these major chains, and there are plenty of cool cities in the world. But the concepts are the same.

Pick where you want to go. Check out United miles (via the United cards or Chase UR points), AA miles (via the AA cards or SPG) or US Airways (via the US Airways card or SPG), because these airlines don’t pass on fuel surcharges.

Then check out the hotels and figure out using the tips above what hotel strategy you’ll go with.

Then just go.