Ahhh Boston. Probably one of my favorite cities to date. So much history. So much to see and do. I could go back dozens of times and never get tired of it.
For this post I’m going to break it down by accommodations, transportation, and activities. This is just a general overview. Not too much detail. If you would like more details, feel free to contact me! I keep all of my receipts for travel, so I can get you a pretty good cost estimate if needed. This is based on my few short trips to Boston. So, feel free to add your opinions and suggestions in the comments!
Staying in a hotel in Boston can get expensive, especially going during the summer months (peak season). Usually I stay on the outskirts of town in Burlington, Woburn, etc. Rooms are more affordable, but you are still close enough for public transportation and the city amenities. Plus, most hotels in larger cities don't offer free parking. Staying just outside the city can save you upwards of $20 a day just in parking.
I've stayed at both the Boston Marriott Burlington and the Hyatt House (which has a kickin' omelette station!). Both hotels booked for just under $100 when I checked the prices last (Oct 17, 2020).
The average hotel in the outskirts is going to cost about $150-$200 a night during those peak months, but you can usually find a good deal. Most rooms sleep 4 people. So, if you split it up, it’s not bad at all. If you have any special discounts (ADA, AAA, Senior, Military, etc.) now would be the time to use them. I always recommend finding a hotel that has breakfast. Food can get a little pricey and breakfast is the easiest one to save on!
AirBnB has become one of my favorite tools in recent months. You can find some AMAZING places at decent prices. It sometimes comes out cheaper than hotels and gives you a more local experience. A quick search delivered me with a studio apartment in Beacon Hill for $155. My only advice is to really pay attention to the service fees when booking AirBnB or VRBO. Those can really jack up the prices. For example, the same studio apartment after taxes and fees is $241 per night.
NEVER book the first great deal you see. Research is your best friend and shopping around is in your wallet’s best interest.
Boston has great public transit. At least in my experience. They offer commuter lines, subways, buses and ferries. All of which are affordable and cover a rather vast area around Boston. I usually stay in Burlington. Close to the hotel, we had easy access to the commuter rail and a bus station. Both of these take you right into the city. I prefer commuter rails for time purposes, but the buses were alright too.
The closest rail station was Anderson/Woburn. They have parking on-site which costs between $4-7. No too shabby considering you’ll pay well above that in the city. A round trip commuter ticket costs $13.50. However, if you happen to be traveling on the weekend, they offer a ‘Weekend Pass’ for just $10. That gives you unlimited rides on the commuter rails. All commuter trains end at North Station. From there you can catch the Green Line (GL) or the Orange Line (OL).
Once you get into the city, you can basically walk to most of the major sites. Everything is rather close together. We walked basically everywhere and it was only about 3-miles and minimum hills. If you insist on using public transit, it is relatively simple and cheap! They have 1-day passes for just $12. That is all the riding your heart desires on subway lines, buses, and Zone 1A of commuter rails.
Boston has SO MUCH HISTORY. I’m a bit of a nerd in that sense, so I was in heaven! Of course, the Freedom Trail is a must-see. It covers a large majority of the famous sites in Boston and gives a good overview of the city in general. It will cover places like the site of the Boston Massacre, Granary Cemetery, Paul Revere’s House and the USS Constitution.
Tours are going to cost you anywhere from $15 to $40. I don’t recommend them. They are often crowded, rushed and overrated. I downloaded the ‘GPSmycity’ app on my phone. It’s totally FREE! Even with the limited free features, I was able to pick the sites I wanted to see and plot them out in a walking trail. It also provides you with information about each site and a few tips when you get there. Well worth it! I saved money on a tour and was able to take my time in seeing exactly what I wanted.
Another must-see in my opinion is Beacon Hill. It is seriously the cutest neighborhood ever. Very Greenwich Village, but EVEN BETTER. If you’re not one for architecture, you could probably skip this one, but I recommend it!
While in Beacon Hill, go to Acorn Street. It is something straight out of a movie. All y'all trying to get a kicking Instagram shot, this is a MUST! Do keep in mind that this is a private street for the folks who live there. We were able to take a few pictures no problem, but just be respectful and courteous. Don’t overstay your welcome!
There are countless sites to visit, so you won’t have a problem filling up your schedule. If you’re a sports fan, head to Fenway park to catch a game. Scholars can visit Harvard. Plymouth Rock is just south of the city. My spooky friends can visit Salem which is just north of the city. I mean the list is endless really. It all depends on what your interests are.