Notes on Travel Hacking Through Maine
We recently returned home from eight days spent traveling through Maine and Massachusetts (the reason for the missing posts from the last two weeks). We had not planned this trip until about three days before we left. Score one more for Financial Independence and the resulting lack of clients and/or bosses to respond to or seek approval from! Here are some notes describing our travels and the use of travel-hacking benefits.
First to Beantown, Then to Coastal Maine
The journey began with an early-am flight to Boston, where we spent a day dragging the troops to the historical highlights. I don’t think that they appreciated much of the rich historical tradition of this city, but they did enjoy the guy juggling torches while doing unicycle tricks in front of Faneuil Hall.
After about 24 hours in Beantown we left the frenetic city and—after a quick 20-minute jaunt through New Hampshire—easily moved into the rural beauty of coastal Maine. We spent two days in Ogunquit, a lovely beach village just an hour or so north of Boston. Here the Atlantic Ocean crashes against rocky coastline, and a natural sand beach is created along a barrier island.
We have done countless summer and spring vacations on the white sandy beaches in Florida, and I can state with emphasis that Maine is a different ballgame.
In Ogunquit a side-walk of sorts named “The Marginal Way” creates a lasting easement for the public to enjoy the stunning views of the jagged coastline along this stretch of southeast Maine. We probably could have spent another couple of days just sitting and looking at this.
But on to Portland
Next we moved on to Portland—by far the largest population center in Maine. Neither me nor Mrs. JF had ever been, and we had heard good things. I found the town to be quite interesting and enjoyable, if not a bit crunchy. (I wouldn’t mind being a bit more crunchy myself, but after 16 years as a corporate tax attorney, it just doesn’t come naturally.) The rest of the family would probably pass on this destination next time, but it had two significant perks luring us there on this trip: (1) we could stay the night for free using travel-hacked Starwood Preferred Guest points at the Westin, and (2) it’s a great beer-tourist town. (OK, so maybe this second perk was really only a benefit for me.)
Next stop: Boothbay Harbor (vis-a-vis Freeport)
We’ll get to Boothbay in just a minute, but as luck would have it, it’s almost impossible to get there from Portland without traveling right through Freeport—the home of LL Bean … and the Maine Beer Company. So while Mrs. JF and team waded through multi-colored kayaks and backpacks, I sampled world-class craft beer at this small-but-renowned craft brewery. There’s something about drinking beer that you can’t get in your home state at 11 am that tastes really really good.
We did eventually make it to Boothbay Harbor, and sat down for a lobster roll by the water at the local Lobster Shack. This blue-collar fishing village turned tourist destination has a lot of character and charm.
The Pinnacle of Our Journey: Bar Harbor and Acadia National Park
Just a three-hour drive north of Boothbay Harbor and across the fractured Maine coastline was our final stop: Bar Harbor and Acadia National Park. We would spend three full days here exploring the park by day and the village by night.
Reaping Some Travel Hacking Benefits
Although relatively new to the travel-hacking game, I have recently jumped in with both feet. Over the last five to six months I have accrued the bonuses from two Chase Sapphire Preferred Visa cards (me and Mrs. JF), two Barclays Arrival Plus Mastercards, and two Amex Starwood Preferred Guest cards. This effort provided us with the following card-bonus benefits:
Travel-Hacking Benefits
As seen above, the Chase Ultimate Rewards points covered the fare for all five of us to fly Southwest to Boston, with the exception of only about $90 for taxes and fees. The Barclays statement credit benefit covered $600 of hotel stays in small cities with no Starwood hotels, and the SPG points covered 100% of our hotel stays in Boston and Portland (except parking costs). That left us coming out of pocket for: (1) the balance of small-city inns and hotels; (2) rental car for eight days; and (3) food and miscellaneous expenses. (Bonus: if you have a fourth grader in the house—or maybe any small creature that can reasonably pass for a fourth grader—the National Park Service is currently offering a free one-year pass here. This saved us the $25 that we would have paid for a seven-day pass to Acadia National Park.) At the end of the day I estimate that we’ll have come out of pocket for about $2,400 for this trip that would have retailed for more than $5k (I haven’t closed the books for July yet and will update final figures when I do). The travel hacking generated about $2,500 of cash value on this trip alone as follows:
Note: We only had $600 of our $1,000 Barclays Arrival Plus benefit left because I’ve already used $400 to pay for airfare related to some future college-football tourism planned for September.
So all-in I’ve harvested about $3,000 worth of travel-hacking benefits so far this year, all for relatively minimal effort. Nothing more than putting our routine personal and business expenses on different credit cards. If you’re doing the math on the bonus spending for these cards, you’ve probably noticed that these six cards would require a total of approximately $22,000 of spend over the various bonus periods. Correct. We’ve had some technology outsourcing expenses in Mrs. JF’s business over this period that significantly jacked up our outflows and allowed me to rip through each of these cards pretty quickly. So in a more normal spending-pattern environment it would take a good deal longer to accrue the benefits for these various cards.
Looking for the Narrow Gate Instead of the Wide Path
Acadia National Park is located predominantly on Mt. Desert Island in the northeast part of Maine’s coastline. Bar Harbor is a small village located just outside the park on the northeast side of the island, and serves as a convenient and fun home-base for ventures into the park. The natural beauty of this area is like nothing I’ve seen before, so if you are a crunchy nature-loving type, Acadia should be on your short-list of destinations to see before you reach the ultimate FI (final independence).
Large chunks of the park—including many of the headline attractions—are made readily available to the public by the Park Loop Road that comfortably winds around the perimeter of the eastern side of Mt. Desert Island. Upon entering from Bar Harbor, the first “attraction” that a visitor encounters on Park Loop Road is Sand Beach: a stunning sandy beach area formed between two rocky cliffs with an island situated in between.
This was our very first stop upon entering the park on our first day, and because of the awesome physical beauty and the lure of the sandy beach there were murmurs among the troops of just sitting down and spending the whole day here. But I managed to resist the siren song of the lapping waves and the pressurized sun-screen bottles and forge on to the remainder of our day’s objectives.
Sand Beach is incredibly beautiful and worthy of some of your time during any visit to Acadia. But it’s also the shiny object at the start of the wide and well-trodden (and well-marked) path of Park Loop Road. Which means it’s crowded (at least for a destination where the intent is to soak in nature). Cars lined the street for a hundred yards leading up to the main parking area, which was slammed full and overflowing. The beauty of the environs was hard to appreciate through the throng. As a result of my contrarian streak that leads me to think that anything that everyone else is doing must not be the best option, we stopped, took a few pictures and appreciated the natural beauty … and then moved on and away from the masses.
After a little bit of way-finding with our GPS and old-school paper maps, we found ourselves here: Little Hunter’s Beach.
Little Hunter’s Beach is a small cove about a mile or two south of Sand Beach, in an area that is unmarked on Park Loop Road. We had to know that we were looking for it, and if we had blinked at the wrong moment we would have unwittingly passed it by. We saw a total of three people here during our two-hour stay. While roaming the cliffs that are lined with rocks and trees above the pebble beach I encountered an older gentleman studiously taking pictures. We chatted for a moment, and he told me that he had been to Acadia at least ten times in prior years, and this was the first time he had discovered this spot.
I saw an instructive analogy embedded in our experience here at Acadia. Sand Beach is like the world inhabited by the Working Joes: It’s the obvious choice. The first shiny object that presents itself on Park Loop Road to all the excited tourists entering the park for the first time. It’s also crowded, and hot and sweaty as you move among the herd and labor to stake out your own little 5×5 cubicle of sand. It’s not awful; you see some cool stuff, and hey, everyone else is here. Little Hunter’s Beach, on the other hand, is the destination sought out by the Joe Freedoms: more difficult to find, you can’t follow the crowd there, and if someone else doesn’t tip you off you may never even know that that it exists.
Once we found our way to Little Hunter’s Beach we had to work harder to get to its most spectacular views—an unmarked, narrow, and at times non-existent path provided the way. But we forged on, and were eventually granted the privilege of basking in its hidden spectacular beauty and wonder, and for the most part all to ourselves. All the Working Joes were still engaged in a scrum on Sand Beach vying for towel space.
Much like the journey to Little Hunter’s Beach, the trek to Financial Independence requires foresight, long-term thinking instead of short-term pleasure reaping, and a willingness to trust your instincts and keep moving even when the herd is sunning itself on the beach in apparent comfort. Think differently. Choose the narrow path rather than the wide gate. You can find a better result.
I really enjoyed this and the nice pictures. Going to places like this is what it’s really all about. I find it’s a good way to get away from everything, clear your head and regroup. I havent had to get into travel hacking yet, but I do similar things with other purchases by stacking offers and using a certain credit card etc. It all adds up. Might as well get something extra out of it if you are going to spend the money anyway. Loved the last picture and paragraph. It’s all very true and that mindset has worked the same for me also.
Hey Arrgo, good to hear from you. Yes, the travel-hacking game is all about maximizing the return that you get from your otherwise necessary spending. For years I’ve been using the 2% cash-back Fidelity Amex/Visa, which is a good card (zero effort; zero cost; 2% cash back on everything that goes straight into a Fidelity index fund). But with these bonus offers on these cards I’m getting an ROI more in the 15-16% on my spend. Just for a little extra effort. And from what I read about this topic, the real experts are getting a significantly higher ROI than that.
Thanks for the great photos. I’ve never been up and down the Maine coast before (only visited once on a trip to Sugarloaf). This despite two years living and working in Boston and another three years in law school. I’ve always felt like I needed to do this exact trip. Not sure when it’ll happen but this is inspiring all the same. Great work on the travel hacking. I use a combination of the same or similar cards for expenses that generate 3X points (usually airfare and dining) and then fall back on the USAA 2.5% cashback card for any other purchase.
Hey Biglaw. We first did this trip about 14 years ago (when I was a second-year associate I believe) and I’ve been itching to do it again ever since. What a great resource the Maine coast is for the folks in Boston and Mass. If I had gone there before law school I might have pursued interviews in Boston strictly for that reason!
Right, I use specialized cards to get higher rewards on things like groceries, travel, etc., and then fall back on the Fidelity card for everything else. I need to check out the USAA card–an extra .5% on all purchases would be nice–but I’m presuming you need to be USAA-member eligible.
Joe