It seems like when most people travel these days it’s to far away places and destinations.  With the onslaught of Facebook statuses and Instagram posts, it’s pretty easy to get sucked into the one upsmanship of bigger and better when it comes to travel.

I’m not saying that I’m any better, but sometimes we forget that there are some great travel destinations right here in the good ol’ US of A.  Boston isn’t necessarily an overlooked travel destination by any means for most people, but it is a place that my wife and I have both never had the pleasure of visiting.  In fact, the whole east coast is a little bit lacking on my list of places I’ve traveled to.

But the motivation for this trip came from the fact that my wife’s best friend and one of my very good friends both live in Boston (they also happen to be married) now and since they’re only going to be living there for two years, we thought it would be a great opportunity to visit and see a new city.

Many of you already know that I’m a huge enthusiast of traveling for free via miles and points so this trip was no different.  It also helps out a lot when you have friends that you can stay with in the city you plan on visiting.  We ended up staying 4 nights with our friends on an air mattress in their living room and they were very gracious hosts.

I’m usually comfortable crashing with friends for a night or two but 3-4nights is pushing it.  Luckily, these are two of our very best friends so I didn’t feel too bad.

So moral of the story is: try to stay with friends to cut the cost of your trip in half.

How To Fly To Boston For Free

In early 2015, I redeemed 270,000 Marriott/Ritz-Carlton points for an awesome travel package that netted me 7 nights at a Cat 1-5 Marriott hotel AND 120,000 Southwest points.  The latter was the real reason for the redemption though, since it also qualified me for the Southwest Companion pass which is far and away the best deal in all of travel.

I actually started planning for this trip about 5-6 months in advance but for some reason there were no flights on Southwest available from LAX to Boston the entire week we wanted to travel.

So I couldn’t use the Companion Pass on the outbound leg to Boston but I was able to book a flight on the way back using SW points and the CP.  I actually booked several on the way back since I wasn’t sure if we wanted to lay over one night in Boston after our trip to Ireland or fly back to LA the same day.

That’s another great thing about Southwest points.  Since there are no cancellation fees, I often book 2-3 flights at various times (and sometimes even to various airports ie. SFO/OAK) and cancel whichever ones I don’t use.

On the outbound leg, I ended up booking two first class award seats through American Airlines on US Airways (there was one stop in Philly).  Normally, I avoid domestic first/business class award tickets (Ex. of an exception: new trans-continental AA product on the A321) like the plague but since there were no economy AAdvantage awards available, the first class AAdvantage award was the same price as the economy Anytime award.

Flight to Boston

Our flight to Boston left out of LAX just after midnight on a Friday night.  As expected, the first class product was pretty crappy on an old 757 (I think).  Plus, it being a red-eye I wasn’t exactly chomping at the bit to take advantage of the free drinks.  We both ended up not getting much sleep and arrived in Philly somewhat dreary-eyed and sleep-deprived.

We stopped by the Admirals Club lounge in Philly and I tried to use my cancelled Aadvantage Executive Card to gain access.  A travel writer who shall remain nameless told me that this ‘trick’ would work but sadly it didn’t.  After a somewhat awkward exchange, I handed over a couple passes that were about to expire anyways.

The lounge wasn’t anything special but it was quiet, had good wi-fi, coffee and light breakfast items.  Again, it was too early for a drink so I wasn’t able to take advantage of the free alcohol.

Our flight to Boston was a lot better, it was an old Embraer single aisle but I slept from taxi right up until the time we pulled into the gate.  We were in ‘first class’ on this flight too and even though it wasn’t anything special, the seats were a lot more comfy than the last flight (or maybe we were just way more tired).

Once we got to Boston, I called an Uber and it was a short 15-20 minute ride to our friends’ place.

Day 1: Experiencing Boston For The First Time

Our friends lived in a nice area of Boston right off Westland Ave. near the Back Bay/Fenway area.  They had a pretty spacious 1 bedroom apartment on the fourth floor and a nice big living room that would be our home for the next few nights.

The weather upon arrival was chilly (50’s-60’s) but sunny.  One thing I learned while in Boston is that I have absolutely no idea how to dress for cold weather.  I found myself constantly being over-dressed or under-dressed and spent way too much time debating my outfits, only to sill be unprepared.

After we settled in, we rented bikes and headed over to the Cambridge side of town.  Boston has these cool hubway stations that allow you to rent bikes for up to 30 minutes at a time for only a few bucks per day.  It probably isn’t the most economical way to get around but it suited us well as tourists.

It was a cool experience to bike alongside the Charleston River and even though Boston is a pretty beautiful city, it’s no Harvard!  The Cambridge side of the river and namely Harvard boasted some spectacular sites and architecture.  Not a lot to do, but lots of cool stuff to look at.

We ended up eating at a famous local burger spot called Brantley’s burgers.  The burger I got was good but nothing to write home about.  I think you come to this place for the experience more than anything.  There was a short wait but you’re greeted by an old lady who must have some ties to ownership and everything is pretty old school.  They take your order at the door, cash only, super cramped little tables, etc.

Overall, it wasn’t the best meal I’ve ever had but the experience was worth it and I definitely recommend it if you’re in the area.  Afterwards, we got our first T experience and headed back home.  Having lived in SoCal for almost all of my life, I don’t know much about subways but man, the T seemed like a real piece of crap.  The cars were extremely old, made a ton of noise and just overall not the cleanest or best public transportation option I’ve ever seen.

At a couple bucks a ride, it’s not exactly cost-effective either.  We were traveling in a group of 4 so it likely would have been cheaper to call an Uber for almost any destination in Boston.  Once we got home, we took a well-deserved nap.

That night, we headed out for drinks and dinner at an Italian restaurant in North End.  Strangely enough, one of my very best friends from high school was actually in Boston for the weekend from New York.  She was running a 5k mud run on Sunday (which is pretty dumb in 50 degree weather) but we were able to meet up for a quick drink before dinner.

We ended up waiting 45 minutes for our table despite making a reservation, yikes!  The food was good though.

The highlight of the night had to be my first taste of a Boston Cannoli!  And no we didn’t go to Mike’s or any of the other famous places.  We actually went to a lesser known bakery called Bova’s and the cannolis were spectacular!  I ended up going back two more times, not kidding.

Day 2: Gloucester and Rockport

Day two was our big excursion day and our friends drove us out to Rockport/Gloucester to get some seafood and do some exploring.  Parking in Boston doesn’t seem like much of a hassle but in order to park on the street our friend did have to register their car in Mass and get a new driver’s license.

The drive out to Rockport was pretty quick and we got great weather too!  There wasn’t a whole lot to see but there were a few tourists out and about and Rockport did have a cute little main drag where all the shops were up and running in preparation for the summer high season.

Apparently, Gloucester is a big artist hangout since back in the 1800’s, artists from all over the world would come to paint the picturesque harbor scenes with tall-ships and wildlife.  Some of that spilled over into Rockport and the artist I talked to actually told me they have to rent their tiny shop year round.  In the summer, they sell a ton and in the winter, they close up shop and paint.  They were charging some pretty high prices yet only ‘scraping by’ so doesn’t seem like the best deal ever for building wealth but at least he gets to do what he loves.

There were a bunch of clam chowder places so we picked one randomly with a nice view and had a relaxing bowl of chowder and a beer.  The highlight meal of the trip was yet to come.

After Rockport, we headed up to the quarry which was one of my favorite sites of the trip.  It reminded me of the movie Breaking Away where all the local ‘Cutters’ hang out at the quarry, go swimming, drink booze and smoke cigarettes.  Unfortunately, this one was littered with no swimming signs, but they didn’t say anything about no selfies!

Our next stop on the tour was a local joint called The Causeway Restaurant.  This small, unassuming joint turned out to be my favorite meal in all of Boston.  We ordered a Lobster pie, which turned out to be a whole lobster baked in a casserole dish with butter and bread crumbs.  It was amazing.  That’s all that needs to be said.  If you’re in the area, go there and order it.  There is usually a short wait and one of the two waitresses is kind of a bitch but the lobster more than makes up for it.  They also had a seafood chowder that looked pretty to die for.

As soon as we got back, I actually had to rush over to a local meet-up I planned for some RSG readers.  This was something I sort of planned last minute and very casually but it was cool to meet a few readers in person.  4 people showed up which was on the low end of what I expected but I now have a very good plan of attack if/when I decide to do more local meet-ups.

Day 3: Go Sox!

Day 3 was all about the Boston Red Sox!  I’m not really a fan of the Red Sox or baseball in general anymore (I just don’t have the time to watch a 3 hour game although I do root for the Dodgers) but this day was a lot of fun.

We started off with a noon tour of Fenway park and it was pretty surreal to be walking around in the oldest ballpark in America.  They even let us go on the field and walk around in front of the Green Monster.

After a quick lunch, we did a tour of the Freedom trail.  Personally, there just wasn’t enough action on the tour for me although our tour guide was very enthusiastic and her outfit proved it.  If I had the option to redo it, I would do a self-guided tour of the freedom trail.  You’ll miss out on some of the history but it will also take about ¼ of the time.

That night was pretty much the highlight of our trip as we had tickets to the Red Sox vs. Blue Jays game.  We started off though at a place called Bleacher bar which is actually a bar in right centerfield of Fenway park.  We only waited a few minutes for a table then we sat down and ordered food.

It was pretty cool to hang out at the bar, there was a lot of good energy and just knowing that you were right on the other side of the Green Monster was a pretty cool feeling.  There is a garage door that they usually open that looks right onto the field but since it was raining, it was closed.  You could still see through the windows, but it wasn’t a direct line of sight like it normally is.

The game was actually delayed 30 mins at the start because of rain so we just hung out at the bar and were pretty drunk by the time we got to our seats.  It turned out to be a great game and probably the most fun I’ve had at a baseball game in a while.  The beers might have had something to do with that though.

The Sox ended up winning on a walk-off and like the end of a movie, it started raining after the final run was scored.  We ended up calling an Uber, making a quick pit stop at Bova’s for Cannolis and then retiring back to the apartment.

Day 4: Last Day in Boston

On our last day in Boston, we headed over to Jamaica Plains to tour the Sam Adams factory.  I’m a big fan of beer and even though I’ve brewed a few batches on my own the tour was still pretty interesting.  You also get a few glasses of fresh beer at the end so that doesn’t hurt.

Our flight to Ireland left that night left at 9 pm so we headed over to the airport at 7 ish and we were off!

Bonus – Day 5: One Night Layover in Boston (After Ireland)

Since I no longer have my day job, I decided that flying from Dublin all the way back to LAX in coach was a little too intense for me.  So after we got back in to Boston at 2 pm on Tuesday, we headed back to our friends’ place for one more night/day in Boston!

(It ended up being a really smart move since Ireland is only 5 hours ahead of Boston, we stayed up til around 10 pm and it was just like a really late night out if we would have been in Ireland.  No jetlag.)

That Tuesday was actually Cinco de Mayo so it was a great excuse to head out to the bars and keep the vacation going.  The weather also went from being cold to extremely nice out during the week we were gone.  I headed out in a t-shirt and jeans and we checked out a couple bars.

Boston isn’t exactly known for its Mexican food but we did grab a few Coronas and margaritas and one of the bars we stopped at had some free tacos.  The best part of the night for me though was heading over to Bova’s though for you guessed it, more cannolis!  I only hate half of one cannoli before I passed out when we got home but still totally worth it.

The next day, my wife and I were on our own before our 2 pm flight back to LA so we headed out to breakfast and stumbled upon an awesome place called Render’s Coffee.  They made a great cappuccino and some breakfast sandwiches that were excellent too.

It was pretty surreal walking around Boston in a t-shirt and jeans (I didn’t pack shorts) when the weather was so much colder the week before.  It also seemed like almost all of the trees were in full bloom because of the warmer weather.  It really was beautiful out with the Cherry Blossoms in full bloom and all sorts of other trees showing off their vibrant colors.

Living in Southern California definitely has its benefits with beautiful beach weather all year long but we don’t have anything like what we saw in Boston on this day.  I think the nice thing about having real seasons is that it really makes you appreciate nicer weather.  There are lots of days in LA when it’s gorgeous out but I just sit inside and work because pretty much every day is gorgeous!

We ended up taking a very nice walk along SW Corridor Park in The South End which may be my favorite area in Boston and then we went through Boston Common and then back along the river.

Our flight back to LAX was on Southwest and we actually made a stop in Baltimore, before our 5 hour flight to LA.  The one way ticket only cost 10,000 Southwest points and my wife was free as part of the companion pass.  It was the longest SW flight I’ve ever been on but I had my laptop, so after a couple movies, we were home!