Budget Friendly Trip to Boston in the Fall
This post contains references to products from one or more of our advertisers. We may receive compensation when you click on links to those products. Terms apply to the offers listed on this page. For an explanation of our Advertising Policy, visit this page.
My dad, Buddy, AKA “Grandpa Points” has a love for travel as fierce as mine, yet our travel patterns are distinctly different. He and my mom are now in their mid-60’s, are (mostly) retired, and are ticking off “bucket list” destinations quicker than they ever thought possible thanks to miles, points, and travel deals. They have an intense love of this country, of its National Parks and treasures, and have no problem with a clean budget hotel room and an economy seat as long as it gets them where they want to be. A photographer by trade, his adventures are usually captured not just in his mind, but in his camera. He shares his thoughts and travels here from time to time, and I’m excited to share another one of their adventures. Listen my children and you shall hear the whys and the wherefores of Boston this year.
We have always planned on a comprehensive fall visit to the northeast once my wife retired from her career as an educator. I think such a trip is in all teachers’ DNA. We wanted to experience the area’s rich history, unique character and color. The trip was, and is, tentatively set for October of 2016, but something happened this past summer that gave us an unexpected preview of what is to come. An appetizer, a shrimp cocktail, of sorts. That something was a Jet Blue airfare sale into Boston Logan called “The Blue Barrel Special”. This sale, which Jet Blue occasionally seems to promote, offered the price of a ticket at the price of a barrel of oil. On the day of the sale, the price quoted for oil was $108 a barrel and consequently the round trip airfare was priced at $108. United matched the fares out of Houston, and we subsequently booked United as their flight times and departure airport fit our needs better. We actually ended up with $102 fares thanks to the Veteran’s Advantage 5% discount on United flights. Thank you Jet Blue for the sale. We hope to fly with you some time in the near future.
This is a great example of putting into practice the Mommy Points advice of “acting quickly” when you stumble across very discounted airfare.
So, for the past few months, we would occasionally say to each other, “We’re going to Boston!” It was like we couldn’t believe we were going. The trip wasn’t planned or expected. It was just an offer we could not refuse. And neither could our youngest daughter or my wife’s sister, as they both also came along. We only had general objectives. Nothing absolute, nothing specific. It felt like an impromptu trip that we would just fill in the blanks as we went along.
It didn’t take long once we got to Boston to realize that Bostonians are a proud bunch. They like their city, their heritages and their sport teams. We also quickly realized they talk differently than we do in Texas. For example, a ballpark in Boston is a bahpahk. In Texas it is a bawlparrk. In Boston a harbor sounds like hahbuh, in Texas, its horrberr. Here, we really do not have soda or soda pop. We have Coke. And up there, it seems as though there is Dunkin Donut around each corner and down here we definitely have two Mexican Food restaurants on each block. All of these regional and cultural distinctions are really fun to explore and encounter. They just make life and travel even more interesting, y’all.
One of the first things we did was to take The Trolley Car Tour of Boston. We figured it would give us a good feel of the city with some history and anecdotes added in. We ended up having the ultimate driver/guide. His name was CrackerJack. Apparently, he is the head guy in this tour company and his uncle owned the Red Sox and he was the bat boy and he played catch with Yastrzemski and Mickey Mantle and his daughter goes to Harvard and he seemed to know everybody and everything in and about Boston. And he was funny. And it was a delightful tour. This was the perfect introduction to our Boston experience. It provided us an outline and a direction for the balance of our trip. As an added bonus, our trolley car tour purchase included a relaxing, pleasant and informative 45 minute Harbor Cruise.
After docking, our party of four split into two groups. One group went to Faneuil (rhymes with Daniel) Hall, and my youngest daughter and myself went to a tour of Fenway Park. Faneuil Hall was built as an assembly hall and marketplace and was an important site for discussions leading up to our independence from Britain. Today, it is a national landmark and sits next to a thriving and very popular indoor and outdoor mall.
Fenway Park is a monument of a different sort. To many Bostonians, it is almost like a religious holy ground, a spiritual experience. It is the home of The Red Sox and to both their well known travails (see The Curse of The Bambino) and to their World Series Championships. It was a fascinating tour that took you from the bowels of the stadium to the visitors clubhouse to the press box and also to the top of the left field wall, The Green Monster. It was a very thorough, detailed and unhurried tour. It began in what might be the world’s largest team memorabilia shop and ended in a well done museum. I did not feel the urge to genuflect or look for holy water on the tour, but it was a grand experience that I would unhesitatingly do again.
Our second day was devoted to traveling west of Boston in a rented car to visit the historic towns of Lexington and Concord and to sample the legendary fall foliage. We were not to be disappointed. It was compelling being where the decisions were rendered and the battles were waged that would ultimately lead to our United States of America. We walked across the Lexington Battle Green on a beautifully clear and cool morning. The peacefulness of our visit must have been in stark contrast to the anxiety and uncertainty felt by the colonial militia gathered there awaiting the marching British forces in the spring of 1775. What might not have been accomplished there was certainly achieved later at The Old North Bridge in Concord where the Minutemen won their first victory on the road to independence. Both these towns are steeped in history and their storied names and events read like an encyclopedia.
I was impressed and surprised at the small areas in which skirmishes were fought and the relatively few people that were actually involved in them. Some of the important battle sites were not much bigger than those where we waged neighborhood dirt clod or sweet gum ball fights in when I was young. It seems in retrospect that our history and its unfolding was very tenuous and fragile and dependent on so few doing so much. My thoughts went to the current movie, AMERICA, whose premise seems to be a hypothetical look at how history would be different had we lost the War of Independence.
From the battlefield we took a left into the literary field. We revisited Alcott, Emerson, Hawthorne and Thoreau. All of these giants have left footprints and fingerprints, words and deeds all over this part of rural Massachusetts. We did not expect to see Walden Pond, but there it was. It was much larger than I had imagined. I had pictured a pond that one could possibly throw a rock across. I had pictured wrong, this was a small lake. A picturesque lake, with a beach and with swimmers.
These four American writers are all buried on the same rolling hillside in the nearby hauntingly beautiful Sleepy Hollow Cemetery.
Human impact was the keynote of this day but the beauty of the countryside accented by the brilliantly colored trees provided an inspiring and appropriate background. The foliage was not at its peak, but it was magnificent.
We were then joined by Mommy Points and Little C for the remainder of our visit to Boston that was mostly dedicated to exploring, following, and experiencing The Freedom Trail. This red brick line winds 2.5 miles from Boston Commons to The U.S.S. Constitution (Old Ironsides).
In between are 14 other historical landmarks that helped define our nation’s history. Some of our favorites, in addition to the aforementioned Boston Commons and Old Ironsides, were the Granary Burial Ground, the Old South Meeting Hall and State House, Faneuil Hall, Paul Revere’s House and the Old North Church.
The walks to these sites often weaved through three century old quaint ethnic neighborhoods that lined both sides of narrow brick and cobblestone streets. History was everywhere. We were fortunate to get to board and tour Old Ironsides while it was still moored in the harbor. It will soon be dry docked for about three years for repairs and restoration. The ship was elegant in design and impressive as a powerful and swift warship that retired with a perfect won, loss record. This is a “must see” (free) exhibit.
Boston Commons is a large park that offers recreation, serenity, beauty and inspiration. It is home to the famous Swan Boats, Make Way For The Ducklings statues, and to one of the most artistically classic carousels I have ever seen.
We took advantage of the parks playground for Little C to climb and slide and run and imagine in. We also utilized the park setting for some family photos, as a meeting place, and as a landmark and reference point.
On our last evening we all dined at America’s oldest restaurant, ye olde Union Oyster House. The price of the food was moderate but the laughs, smiles and delicious fare were, as they say, priceless.
We had great weather during our four day early October stay. Boston and its surrounds are richly significant and educationally enlightening. And speaking of education, Boston is the home of 400,000 college and university students attending its dozens and dozens of institutions of higher and highest learning. I feel my I.Q. must have surely been elevated strictly through some osmotic assimilation. I was impressed that the names and events that rolled off my American History teacher’s tongue were in such evidence here. An example would be the plaque across the street from our hotel (Hyatt Regency Boston for 15,000 Gold Passport points per night) that depicted the site of Alexander Graham Bell’s first successful complete telephone transmission. You know A.G. Bell, the patron saint of the Apple iPhone and Samsung Galaxy crowd, which includes just about everybody on the planet. It happened first right there across from our hotel. Who would have known?
We are all glad that we got this unexpected Boston experience. The cool and refreshing fall breezes gently blew the dust off the covers of our mental history books and brought to life what had previously only been black and white facts and figures.
Thank you Boston, you are indeed Boston Strong. We look forward to our return, be it one if by land, two if by sea or three if by air….
Welcome to The Points Guy!
WELCOME OFFER: 80,000 Points
TPG'S BONUS VALUATION*: $1,650
CARD HIGHLIGHTS: 2X points on all travel and dining, points transferrable to over a dozen travel partners
*Bonus value is an estimated value calculated by TPG and not the card issuer. View our latest valuations here.
- Earn 80,000 bonus points after you spend $4,000 on purchases in the first 3 months from account opening. That's $1,000 when you redeem through Chase Ultimate Rewards®. Plus earn up to $50 in statement credits towards grocery store purchases within your first year of account opening.
- Earn 2X points on dining including eligible delivery services, takeout and dining out and travel. Plus, earn 1 point per dollar spent on all other purchases.
- Get 25% more value when you redeem for airfare, hotels, car rentals and cruises through Chase Ultimate Rewards®. For example, 80,000 points are worth $1,000 toward travel.
- With Pay Yourself Back℠, your points are worth 25% more during the current offer when you redeem them for statement credits against existing purchases in select, rotating categories.
- Get unlimited deliveries with a $0 delivery fee and reduced service fees on eligible orders over $12 for a minimum of one year with DashPass, DoorDash's subscription service. Activate by 12/31/21.
- Count on Trip Cancellation/Interruption Insurance, Auto Rental Collision Damage Waiver, Lost Luggage Insurance and more.
- Get up to $60 back on an eligible Peloton Digital or All-Access Membership through 12/31/2021, and get full access to their workout library through the Peloton app, including cardio, running, strength, yoga, and more. Take classes using a phone, tablet, or TV. No fitness equipment is required.