Talking Your Way into the Best Views

(That monument below is where most people get a view of the city)

Some of the best views in the world are captured from inside the classy hotels and lavish apartment complexes that many of us will never have the opportunity to see. I don’t like that idea. I want to see how the other half lives and I don’t want to wait until I’m a stuffy-old man before I do so. Also, besides just the views, I have a secret obsession with architecture and the interior design of upscale hotels and condo high-rises (lofts especially).

The question is however, how can you catch a glimpse of beautiful city skylines, private beaches and incredible landscapes from these vantage points when you’re on a really tight budget?

Your typical options would include herding into the same tourist ‘look-out’ points to take the same over-viewed pictures and fight for a spot using those stupid metal binoculars that never really work. Sure, the vistas from these points are breathtaking, I mean they’re are popular for a reason. But as you know, this site isn’t about following the pack, it’s about getting off the backpacker trail and traveling deeper to explore and discover. With that being said… I came up with a plan.

Below I explain 3 highly-effective strategies to experience what wealthy jet-setters do, without spending a dollar. Hopefully, these guidelines will help you to get a 5-star view on a dorm-room budget.

I’ve been personally using these fun ploys for many years now and have successfully ‘toured’ hotels and condos way out of my price range in Chicago, San Diego, Los Angeles, Niagara Falls, Argentina, Colombia, Chile and Greece.

Strategy #1: Ninja-Style

I know this one seems simple there’s a lot more strategy to it than you think if you’re hitting the real high-end places. This one has the most risk and most opportunity. If you get caught (and can’t come up with a quick story that sticks) you’re usually kicked off the premises immediately. More importantly however, is that with this method you lack “key-viewpoint access” that normal guests will have or that a concierge would provide you.

Most high-end hotels these days have the key-activating elevators, so it’s tough to move around freely. For this I would try the ol’ piggy-back strategy and start walking to the elevators as you notice others making the move. Then, mess around to find your key (while on the “business call”) until they offer theirs up. The downside is that sometimes they only let you select one floor so you’re stuck. However, usually once you’re past the lobby the stairs open up. Check out the gym level first and then make your way to the roof for some great views. If there’s a bar or restaurant at the top you’re in the money. Just look at the menu for a minute and then ask to take some photos so you can show the “Mrs.” where you’ll be eating tonight.

Using this method, my sister and I once raided the fridge of an unlocked hotel kitchen in Chicago for some late-night chicken and yogurt. I also followed Ninja-Style in a different way, to spend a night sleeping under the stars, just footsteps from the Parthenon in Athens, Greece. Long story short, a friend and I didn’t have a place to stay on our first (very late ouzo filled) night in Athens so we snuck up to the Acropolis for some R&R. We woke up on this cement surface (see below) as the sun was rising over the city. *Both of these incidents happened when I was young and naive. I don’t condone this type of behavior… but man was it fun at the time.

PROS: The exclusive views that the typical tourist doesn’t get.

CONS: Lack of access and high risk of getting kicked off the property. This method never works in private condo/apartment complexes. That would be kind of creepy anyway.

(Our 5-star suite from under the Parthenon in Athens, Greece - That wet spot was my beer/pillow)

Strategy #2: Walk This Way

This is the walk-in method. There are 2 very important keys to this one. First, you need to look the part and ‘act as if’. If you walk in with your boys wearing t-shirts,  board shorts and flip-flops you’re not getting anywhere. Going alone is good but I’ve found that a guy-girl team is the best. Also, I would imagine a group of girls would do pretty well anywhere they went, but you still have to commit to the idea.

The second important factor is connecting with the right person. I would go to the front desk first and get some information on who to talk to from the receptionist. From there, if you play your cards right, they’ll put in a good word to the concierge or manager to show you around. From there you need to follow these steps:

1. Have a game plan: You are looking for a hotel for next weekend for your _______ (birthday, anniversery, witness protection, etc.) and you will be flying back to _______ (New York, London, Paris, Los Angeles) next week and want to make the most of your experience here in ________. Or if it’s a condo/apartment… you’re looking to finally buy that second home or decided to make the big life changing move because you fell in love with the ________ (polo, beaches, job, tractor-pulls) here.

Why are you taking pictures? To show your girlfriend/boyfriend/business partner who is arriving this afternoon/tomorrow morning.

2. Ask tons of questions: Once inside don’t blow your cover by acting amazed. Mention that things are nice but never get to excited. Ask very general questions about air circulation and ammedities rather than how many people can fit in the jaquzzi. If your “tour guide” thinks your faking the funk he or she won’t show you all the goodies or may even cut it short.

3. Have an exit strategy: If the hotel/apartment staff does their job well, the end of the tour will be their closing time. They might try to get you to sign something or schedule a reservation. Avoid this. Tell them you have to go back and talk to the other couple who are flying in that afternoon. Take their information, ask for prices (only at the very end) and then say goodbye (still in character).

With this plan I’ve gotten a grand tour of the famous Shutters Hotel in Santa Monica, watched a Padres game from the Omni Hotel in San Diego (see below), got a great view of the Obelisco in Buenos Aires, and most recently, a private beach bungalow tour at Arrecifes de los Naranjos in Tayrona National Park outside Santa Marta. All of these places also offered free refreshments while we were there… jackpot!

PROS: More legal than the first method, with less planning than the third.

CONS: They might say no or give you a limited tour. In which case you should have just done it solo. It’s harder to go back in once you’ve had the tour. Also, walk-ins could be difficult for touring condos and apartments if there’s only one person on duty. If that’s the case, just ask when you can come back.

Side note: The cool thing about California is that the ‘New Rich’ dress like beach bums and are often the young, Silica Valley types so its harder for hotel security to spot a fraud from a young millionaire.

(Checkout out the San Diego Padres game with a friend from atop the Omni Hotel in San Diego)

Strategy #3: Make the call Mr. Important

This is the ultimate coop. The best place to do this is in new developments, high-rises, office buildings and condos. Look for the giant signs outside that say “Now Available” and call the number. Before doing so however, do your research and think about ‘home buying questions’. How did you get so rich and what type of furniture are you going to have… is there enough room for a pool table?

Even better than calling yourself, have your “secretary” or “agent” make the call. From there, follow the same rules as above once you arrive on the property (have your story, ask lots of questions and have an exit strategy). Also, ask more about contact information and literature with #3.

Real Life Example: Last year around this time I was in Rosario, Argentina with a local friend and we wanted to get a view of the city from the look-out area in the monumento del bandera but it was under construction. As we started walking down towards the river we noticed a beautiful new high-rise, with a big sign that read “Now Available” (in spanish) and a phone number to call. We quickly devised a story that I was a baseball player from the States (White Sox of course) and he was my manager/translator. I had fallen in love with the city and was looking to buy a off-season home here pending my next contract (exit strategy).

He made the call to their offices and setup a meeting for the next day to see 3 different level condos.

The following day we arrived 10 minutes late, in-style and quickly asked to be shown around because we had to catch a flight back to the States that afternoon. With most of the staff watching on in amazement, the building manager escorted us to the top-floor penthouse (one floor above where Lionel Messi has his place) for the most amazing views of Rosario. Following the game plan we asked tons of stupid questions about plumbing, window-washing and dry cleaning services. I also took a ton of photos to “show my pregant (and still not convinced) wife back in Chicago”.

We collected an informational DVD and pricing packet and bid farewell to the staff after I shook some hands and kissed a baby or two. It was epic.

PROS: All-access and the best treatment.

CONS: It may take a few days/calls to schedule a meeting so it’s not as spontaneous as the first two options.

(My buddy "inspecting" the penthouse facilities while I sneak photos of the roof-top indoor pool)

Now, I know what you’re thinking…. “but Gareth, isn’t this lying?” To that I say on “the contrary my friends,” one day I’ll have the money to stay at these places for real and when I do I’ll remember the views and the service. I consider it scouting for my future life of wealth (very) well in advance. The point is, most people never think to ask to do or see things because they don’t think it’s possible without being rich. I’m not saying break the law or lead people on, I’m just saying have some fun, be spontanious and push the envelope a little bit sometimes. Live it up.

If you’re living near Chicago, Los Angeles or San Diego you should try these hotels:

Hotels near the Chicago Cultural Center

Hotels near the Los Angeles City Hall

Hotels near the San Diego Museum of Art

My name is Gareth Leonard, a Marketing Director turned World Traveler with a passion for slow, meaningful travel. I have been traveling the world full-time for the past 9+ years and document it all on Instagram and YouTube. Come join me!


  1. Definitely going to give some of these cons a go this summer! Maybe I’ll be lucky enough to do all three. Although at 19, I’m not sure how convincing I’d be for #3.. Maybe I’ll be the next teen pop artist

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