How might one pull that off in the coolest, most flexible way possible? Well, one way is to fly your own plane around everywhere.
For specificity, let's say you love boating around Nantucket on the weekends, but you got into the top English program at Yale. You want to have your cake and eat it too. The not-so-obvious solution is to buy a small airship and fly it to and from school as needed. How do you become a pilot and what are the costs?
You can obtain a Private Pilot license with 40 hours of instruction for $5,000 - $12,000. A flight instructor might cost $50-80 per hour to teach you, and each hour on a plane costs $100 (give or take) for small, old planes. There are other costs (like textbooks and logbooks that are minimal compared to these other costs). Therefore, if you are a sharp, hardworking student, you might get a license for just around $5,000. If it takes you longer, it may take over a year and cost more like $12,000.
You can do the training in under 2 months if you try hard. Try to log at least two hours of flight time each week because otherwise you forget your training each week and it will take you longer and cost you more. Because you can only begin training in clear, bright conditions, it can be much easier to learn to fly in places like Florida or California.
Alternatively, think about first obtaining just your Sport Pilot license which requires only 20 hours of flight time. This can halve your costs and training time. With your Sport license, the FAA lets you fly during clear, bright days with up to 1 other passenger at altitudes of up to 10,000 feet (basically the max altitudes of small planes). A Sport License has no requirements except that you must have a driver's license (and thus passed a rudimentary eye exam). You can always log the next 20 hours of training to obtain the Private Piot license so that you can fly at night with more people in more airspace later. The Private Pilot license has the extra requirements of accurate color vision and a full medical exam.
Then you can buy or rent a plane to fly between Nantucket and New Haven. Small planes cost about the same as expensive cars. You can buy a small, old cheap Cessna 150 for a round $20,000. They no longer produce these models, but they are reliable and common. The Cessna 172s are still in production and can be $40,000 used. These planes can achieve max speeds of ~150 miles per hour with ranges of over 800 miles. Other small ones that carry 1-4 passengers might go up to $80,000. Bigger or luxury planes can cost millions.
You can rent a plane cost effectively. Planes rent by the number of hours that you actually use them in flight. So, if you fly to Nantucket in the morning in 2 hours, go fishing all day, and then fly back at night then you only pay for 4 hours of flight time usage. The cheapest planes might cost only $80 per hour "wet" (with fuel included in the hours rate). More pricey small planes might be only $100-150 per hour wet. Even much larger planes that seat 10 or dozens might cost only $2000-$5000 per hour which is comparable to driving on a per person-mile basis. Note that you can rent a plane for multiple days, but most charge a minimum number of flight hours per day (like 4/day).
The advantages of your own plane include the flexibility of choosing your own schedule and the fact that you can fly into any airport you want. For small or secluded areas with infrequent travelers (like Nantucket and New Haven) this can save you a lot of time and car traffic congestion. Cities run small municipal airports for free just as they do roads for free.
Flying your own plane is a fun and safe (but expensive) way to travel or commute like a badass James Franco. It's not any more dangerous (it's safer with the right care, since a drunk driver won't hit you in the sky) than driving the same distance on a road trip.
I found it surprising how easy and attainable in price (though not cheap, unfortunately) it is to become a licensed pilot. It doesn't take millions to reach the heavens and fly like a bird, just a little saving up and a few weeks of training.