Florida Man on the Run

Preparing for One Week in Boston

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Earlier this year I planned a massive two week trip along the Pacific Coast. It was a massive undertaking, especially for my first big road trip. My fall trip to Boston was a much less ambitious endeavor. Since I’ll be spending the whole week in a single city, the logistics are easier to work out. On the flip side, the city of Boston and its surrounding area is jam-packed with a huge amount to do. My road trip was focused on the daily drive and where to sleep, my trip to Boston will be focused what to see each day. For me planning all of it perfectly is a big part of the fun! With one week in Boston, its going to be a great adventure.

Travel and Accommodations in Boston

With one week in Boston, finding affordable accommodations is vital to making this trip not wildly expensive. There are a couple of approaches you can take when deciding where to stay. If you are for sure getting a car, finding a place a decent way out of town would be a good choice. You’ll be driving anyways and hotels are far cheaper outside the city center. However, parking is terrible in Downtown Boston and spending time in traffic won’t be the best use of that time. For me, I went with a tried and true approach from my stays in Los Angeles and San Francisco: Airbnb.

I’ve used Airbnb a couple of times and have always been pleased with it. For my big city stays, Airbnb has been far and away the cheaper option. While most of the hotels I had looked into in Boston proper were over $125 a night (before taxes) my entire week stay at my Airbnb in Jamaica Plains is only $490 (after taxes). That’s a saving of over $375 for one week in Boston. You really can’t beat that. In fact, that savings made it possible to rent a car and even pay for my attraction passes. If you’re comfortable with sharing spaces, Airbnb is the best option for an affordable stay in Boston. Make your first stay with Airbnb and you could get $40 off your first trip of $75 or more!

Since I’m not spending the entire week in Downtown Boston, I elected to rent a car. Public transportation is great for getting around Boston proper. The subway and bus lines run through the city, and there is even some commuter rail that runs much further afield. However, that doesn’t always provide the freedom you need on a trip of this length. I decided to get the car at the end of our second day in town and booking it downtown avoided the higher cost and fees of airport booking. It also allowed me to save a whole day of cost since I won’t use the car when we head downtown for the Freedom Trail. These are the small things you should keep in mind when planning, because it saved me over 80 bucks.

Best Attractions for One Week in Boston

Let’s get this out of the way at the start: There is a TON of places to see in Boston. When this trip was in its infancy, I had thought about splitting the week between Boston and New York. I quickly realized that would be a mistake. While you don’t have to spend one week in Boston, it seemed any less time would leave me disappointed. It also means that what you spend on attractions can add up extremely quickly. It is just me and my wife going, but paying two adult tickets into each place would blow our budget quick. There is a fantastic solution to this problem called the Go Boston Card.

The Go Boston Card, operated by Smart Destinations, is your ticket to almost 50 different attractions. They have a few different options, but the best deals are with the All-Inclusive Pass. This comes in variations from 1-day to 7-days, allowing you to visit an unlimited number of listed attractions over that consecutive span. I’m going with the 5-day option since I’ll spend one day in Cape Cod and won’t visit anything my first day. With the huge number of options, including ones outside Downtown Boston, you’ll be hard pressed to not get value from this card.

USS Constitution is just one of the many places to visit on the Freedom Trail

As for the places I’m lining up to visit, I decided to be ambitious. The Freedom Trail allows us to visit most of the historic sites in Downtown Boston in one day. From there we’ll be heading further afield to Concord, Salem, and Cape Cod. By grouping where we go by location each day, I’m limiting travel time between sites. My goal is to visit more than 30 sites in just one week, so planning is key. You can see a pretty solid list on my Facebook page. I also scored some sweet tickets to a Red Sox game at Fenway, something you simply can’t miss on a trip to Boston.

Stringing It All Together

The ultimate key to this trip is effective scheduling. Unlike having to map out how far I’d be going each day, I needed to layout what I’d be visiting instead. One week in Boston is almost a requirement to do the city justice. The first day in town is a travel day, so I settled on planning a small outing that night. Fortunately, the Red Sox are hosting the Orioles that night so that was a no brainer. Getting the game at Fenway done on Day One helped tremendously in freeing up the rest of the week.

Update: I got to touch the Green Monster!

From that point I settled on the most effective way to spend each day. With the Freedom Trail requiring some extensive walking, I decided that should be the first full day. Not only does it get the walking out of the way, but it puts us in Downtown Boston to pick up our car for the rest of the trip. Days Two and Three will explore away from Boston, putting that car to good use. Days Four through Six will be closer to Downtown, utilizing the final days of our Go Boston Card and catching anything we might have missed on Day Six. The final full day will be heading to Cape Cod for the sunrise. Saving Cape Cod for last means we won’t lose a day on our Go Boston Card.

All in all, the days will be packed but completely doable. Beyond attractions, I’ve also planned dinners and breakfasts as well. I’ll have a micro-blog on the vegan options around town at a later date. However, I will say that I’ve found Boston to be surprisingly vegan friendly.

Last Minute Thoughts

I spent less time planning this trip than my Pacific Coast Adventure. I think a lot of that was not having to find a place to stay each night. It also allowed me to really get a good feel for what is worth visiting in Boston. I encourage you to focus on what you want to see in Boston. I love history and so I’ve placed an emphasis on these types of places. You could easily decide you wanted a nature focus, and prioritize the parks, zoos, and tons of trails within a short drive of Boston. Boston truly has a little bit of everything for everyone, so take a chance and plan your visit.

Thank you for taking the time to read my thorough account of how I planned my one week in Boston. Please reach out to me if you have any questions at all because I’m happy to help you plan too! To catch more of my adventures in real time be sure to follow me on Instagram, Twitter, or Facebook!


Disclaimer: Links or advertisements on this page may pay a small commission if you use them to make a purchase. All of the products and links I promote here are for products I’ll be using on this trip because I’ll never actively promote a product I’m not planning on using or haven’t used. When you use my links, you help support my blog and future adventures so THANK YOU!

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