5 Essential Tips to Start Planning Your Long Term Travel Adventure

If you’ve been dreaming of finally taking off on a long-term travel adventure, or you are working up the courage to take your first solo trip, here are 5 essential tips you need to hear to get started !

You will have plenty of things to do once you’ve decided to take the leap. But often the hardest part is making the decision to leave. I’ve uprooted my life more than once to set out on long-term travel adventure. Trust me, if I can do it, so can you.


Starting to travel long-term requires more than just logistics—it demands a deep well of motivation and the courage to break free from the norm. It begins with visualizing the life you want and understanding that the world has endless opportunities waiting for you. You’ll need the determination to step out of your comfort zone, embracing the unknown as a pathway to personal growth. Overcoming fear and doubt is key, and it helps to connect with like-minded travelerswho have made it happen, drawing inspiration from their stories. Long-term travel isn’t just a getaway, it’s a lifestyle choice that offers freedom, discovery, and fulfillment. If you need an extra push or inspiration, visit my YouTube channel, Alcohol & Airplanes, where we share real-life experiences, tips, and motivational content to help you make long-term travel a reality!

Without further ado, here are the FIRST five things you’re going to need to do to motivate your travel dreams.

  1. GET OVER YOURSELF.
    Yes, that’s write. Time to get out your own way. If you want to be one of those people you see on instagram, living your dreams in front of beautiful and historical landscapes… you’re going to have to get over yourself! What that really means is, you need to get over your self-doubt. Get over your imposter syndrome, your prejudices and most importantly.. get over your fears. Trust me when I tell you, the only difference between you and the people living your travel dreams is they decided to go for it. What’s stopping you? Stop listening to the voices in your head that tell you it ‘could never be you’.. YES IT CAN!

2. Be Realistic About Your Goals and Current Situation
Assessing your current situation is the first step toward making your travel dreams a reality. If you can afford to drop everything and book a ticket today—awesome! But before you head to the airport, there are a few practical steps you need to take. Start by double-checking your finances to ensure you’re ready for the cost of flights, accommodations, and daily expenses. Make sure your passport is up to date, and research any visa requirements for your destination. You’ll also need to sort out any responsibilities back home, like work obligations, bills, and housing arrangements. Whether you’re planning a long-term trip or a short escape, being realistic about what you need to do before you board the plane is key.

3. Is Solo Travel for you?
I highly recommend every young woman travel solo at least once, but it’s important to recognize that solo travel may not be for everyone. Ask yourself if you have someone to travel with who shares your timeline and travel style. It’s crucial to consider if your companion’s goals align with yours before making plans. However, don’t let fear hold you back from considering solo travel if that’s what you truly want. Think about whether traveling alone fits your personality and desires—there’s no wrong answer. And remember, not having a travel partner is no reason to postpone the trip you’ve been dreaming of. Solo travel can be empowering and life-changing, offering a chance to grow and explore on your own terms. 


4. Be Unrealistic
Yes, I said it—traveling will literally open up the world for you. Don’t sell yourself short when it comes to your travel dreams. Dream big, write down your craziest travel goals, and put them out into the universe. There’s no pressure to achieve them all, but allow yourself to believe that you can experience whatever you set your sights on—if you give yourself the chance. Be realistic about what you can achieve based on your current situation, but don’t let that stop you from pursuing your biggest adventures. If you say you want an adventure, let yourself have one. 

5. Start Making Your Lists!
Okay- you’ve convinced yourself you can do this, now it’s really time to start planning and organizing. Start by making your lists! First things first, address any major responsibilities, like your lease, pets, and insurance ( don’t forget to check your passport!) . Then, create an estimated timeline and budget to understand the costs involved. Make a list of things you need to buy, such as travel gear and essentials, and start drafting your packing list. If you need suggestions for must- have packing items, I’ve made a list of my favorites essentials for you here. These steps are just the beginning, but they’re crucial to getting organized. Write everything down or type it up so you can visualize what it takes to make your trip happen. Lists are incredibly helpful for staying on track, so organize yourself in a way that works best for you. This includes making to-do lists, tracking financial obligations, and outlining packing essentials.

What advice would you give to someone who wants to travel long-term? Comment below and don’t forget to subscribe to Alcohol & Airplanes for more travel tips and inspiration!

10 Essential Items for Long-Term Travel Every Backpacker Needs

From galavanting from city to city in Europe to living out of a car in the Outback of Australia, I’ve spent a good amount of my young life perfecting the art of long-term backpack travel. While  yes- less is more when you’re responsible for lugging your belongings everywhere – it’s important to be strategic about the things you’re bringing with you. 

Here is a list of my 10 essential no-brainer items I can’t live without while traveling long-term.

Disclaimer:
There are affiliate links which I may receive a small amount of commission if you were to purchase. Thank you for your support !

  1. Osprey Fair point 40L Backpack

This is a tried and true backpacking classic. It’s light, durable and in the 40L version.. carry-on friendly! This was the backpack I used while spending a few months hopping around Europe in the Summer of 2016. One of the best features is the integrated rain cover ! Impromptu rain will not be a concern with the quick access on the bottom. It’s zippers also allow you to thread a small lock through them for extra peace of mind when you have to leave your bag.

Another thing I love about the Osprey Fairpoint is the suitcase style zipper. You can open it up from the sides or top without having to unload the whole bag . While I was traveling in Australia I opted for another , slightly larger Osprey top-loader bag. It might have been a little bigger but it definitely wasn’t more convenient to load up.

When you’re constantly packing and unpacking, being able to shove your stuff in quickly will make all the different. Especially, when you got in from your night out an hour before, haven’t packed and need to catch a bus after check out. 

There is hundreds, if not thousands of backpacks to choose from. And it’s really a personal preference. Personally, I’ve had two Osprey bags and feel the quality and convenience features are well worth the price. 

2. Quick dry towel 

 If there is one thing you will not regret buying- it’s a quick dry towel. You can’t afford the space in your bag for a regular beach towel, and you’re not going to want to stick a musty, damp towel in with the rest of your stuff. Trust me. If there’s any no-brainer items you need to take my advice on- it’s this one. I prefer one that comes with it’s own bag to store it in, just in case it hasn’t completely dried yet. 

These towels come in a multiple of sizes, I recommend going to the biggest one you can find. It won’t take up much space and will be the closest to a regular beach size. You want to be able to wrap it around your whole body so you’re no exposing anything after a shower! 

If you can spare the space, it’s great to have a couple of sizes of these so you can use one as a face cloth or substitute loofah! 

3.  Small Foldable Tote Bag.

A foldable tote bag will be an excellent, inexpensive purchase for your travel needs. You’ll be able to fold it up so you don’t even notice it in your bag. This will come in handy for so many things, like carrying your souvenirs and groceries after a day of exploring. No need to bring a separate beach bag on your trip either. You can fold this one up and forget about it until you need it. Get one that is durable and able to fold into a space package. You will no regret it.  I always keep mine with me in my day bag just in case I buy something while out and about. 

4. Packing cubes.

 If you’re backpacking and not using compressing packing cubes, I honestly don’t understand you. There is no better organizational tool for you to have in your pack. There is a reason everyone recommends using them. There are a variety of sizes and colors to choose from. Just make sure you’re getting ones with an extra zipper to compress the cube even more. Space and compatibility is key when backpacking. It’s great to be able to just grab the cube you keep your pajamas when you’re in a dark hostel room, instead of rummaging through all your stuff. Packing cubes will also help you from leaving anything behind. 

PRO TIP : Keep the space things in the space cubes every time your packing up. It takes out the guesswork of where your things are and you’ll be able to pack up without struggling to figure out the best way to configure everything in your pack. 

5. International travel adaptor.

Don’t forget this one! Different countries have different style of power plugs. You could be up schitts creek if you arrive to a new country without considering this. I prefer an all-in-one international adaptor with additional USB plugs. You’ll probably have a bunch of things to charge, and you won’t be unlimited plugs available in your hostels and homestay. You can buy individual adaptors just for Europe for example, but buying on with multiple country set-up will save you from storing a few. 

6.Power Charging Bank with Built-In Cords. 

 Don’t underestimate the amount of things you will need to charge!! Tablet, phone, AirPods, camera, go pro … you name it. Having an extra charging bank will be a life saver if you aren’t in a place with a plug or you’re on the go without your international adaptor. Getting a charging bank with built in cords saves your from having to bring a thousand different cords with you on the road as well . 

7. Hanging Toiletry Bag 

 Being able to hang your toiletry bag will be a game changer! More often than not, there will not be a place to store your bag in the bathroom while you’re bathing or getting ready. A durable, hanging toiletry bag is the perfect system for on-the-go living. You can hang it from a door or on your dorm room bed, anywhere that works. This way, you don’t have to put anything on the ground, you never know the style of shower you’ll be faced with and you won’t want to pack a soaking wet bag in your pack!  I love this one I’ve linked because it has an extra pocket you can store your jewelry in.

PRO TIP:  You can also use it as a makeshift vanity while you’re getting ready if you prop a  small mirror up on it while it’s hanging!

8. Go Pro Camera

There’s been more than one time in my travel career I’ve been cursed with a broken phone. It is SO disappointing not being able to capture your memories if you only rely on your phone for photos. For this reason, I recommend a GO-PRO camera. I’m a huge fan of the Go Pro and will probably always travel with on. They are tiny and incredibly durable. Unless you are a photographer or photos are super important, you probably don’t want to be lugging around a delicate, expensive camera everywhere you go. That’s not to say you shouldn’t bring a good camera with you- this is your trip! Live the life you want. I recommend the Go Pro because you’ll be able to take photos and videos with out being afraid to break it. It’s waterproof and there are TONS of accessories to help you get all the amazing shots from your trip. Remember, durability is your friend when traveling long-term!

9. Waterproof Poncho or Foldable Light Jacket

The layers you decide to pack should be determined by the climate you’re headed to. Spending your time in tropical climates during the summer? You probably don’t need to bring a jacket for warmth. In this case, layers will be your friend. But- don’t for get about rain ! In places like Southeast Asia the rain can break you. Having a durable poncho is not something you will regret. You will be able to buy the cheap plastic ponchos in most places, but if it’s particaurly rainy where you’re traveling, you’re not going to want to buy a new one every day. A durable poncho can be packed in your day bag for when you need it. This one also can be turned into a little tent for shade in a pinch! We love items with multiple uses!

A poncho is not going to cut it in all climates. For my year in Australia, I had no clue where I might end up or in which climates. For this trip, I packed a compressible light jacket that was rain proof and super warm! I could fold it up small to fit in my bag for the summer months.  When it started to get colder I was so happy I’d been carrying it with me. 

10. Dry bag Day Pack 

Of course, you’re going to need another backpack other than your main pack. This will be great for day trips or to keep your valuables close to you while traveling. I love the idea of making this bag a Dry Bag. If you don’t know what a dry bag is; it’s a bag that can be sealed to be completely waterproof. Meaning you can take anything you want in your bag without worry if it’s going to get wet. Want to bring your camera to the trek to the waterfall but concerned you might get it wet? Dry bag. On a live aboard scuba adventure? Dry bag. Stuck in the rain all the time- Dry. Bag. 

Like I said, durability is your friend. And there’s nothing worse than realizing the change of clothes you brought got soaked at the beach. 



I hope this list is helpful for you when you start packing for your adventure. By no means is this comprehensive and everybody will have different preferences. These are just ten items I feel I couldn’t live without on my travels or ones I wish I had when I got to my destination.

What are your must-have travel items for long-term travel? Let me know in the comments below !

Six years later and now I’m exploring my thirties.

It’s been nearly six years since I dusted off the old keyboard and logged into this blog and while a lot has changed for me, there’s still a lot of similarities between the 24 year old setting off to Australia, and the 31 year old who moved to Texas in August of 2020. 

I blame Covid for my state-side existence. Here I am, my backpack is  gathering dust in my closet, my new passport has almost no stamp stamps, and I didn’t make it to 7 continents before I was thirty (okay 5 isn’t bad, but still). It’s not all so terrible, I moved across country, made some good friends and I’ve been working my ass off trying to advance my career. The problem is, I’ve found myself struggling in this life that I didn’t want to have in the first place. 

As I reread my posts from a younger-Dana, I’m terrified that I’ve let her down. I’m proud of what I’ve accomplished in the last four years don’t get me wrong. But it doesn’t change the ache inside my soul that just won’t sit still in one place for long. I guess it wasn’t Massachusetts, or Australia that kept me wanting to move, maybe it’s me. And the question remains the same as it was in 2018, how can I travel as much as I want, while being able to support myself? Well, it appears being able to support myself won out in this conundrum as of today. 

My need to travel is a feeling that’s hard for me to explain to others. I don’t just want to travel the World occasionally when it’s convenient around work. I have no other interest really, there is nothing my soul aches for other than the unknown. If it weren’t for my cat and my bills, I would have dropped everything once again after I was fired in May, to pick back up where I left off in 2018. 

I can’t let the former versions of myself down though. I’m not that girl, I’m the one who took off with a one-way ticket, a backpack and a dream. Now, I have to remind myself to be brave like she was.  The problem here is, my delusions and dreams don’t pay my bills and they certainly don’t pay for plane tickets and hotel rooms. 

I’m angry that I’m in a similar spot as when I wrote my last blog post. I have moved states, built restaurants, gotten my master’s degree and I’m still looking for the way out of the matrix. I’ve lost my job twice this year( tune into my podcast HEARD, for that story). The first time, I panicked, got the first job that came my way. The second time, I’m doing the opposite of panic job searching… I know it’s not my smartest move but I can’t bear to put myself back into the cycle of working hard to excel someone else’s success without any benefit to me and my goals. 

Maybe this time, I’ll learn. Maybe this time, I’ll make it. Maybe delusional is exactly how I need to be right now. 

The Aussie Chronicles: First Stop, Opera House.

After figuring out where I’d be staying for the next few days it was finally time to start exploring the new planet I had arrived on. I’d come to Australia without much of a concrete plan and the week I spent in Sydney would be the perfect amount of time to figure out my next few moves. It’s a big city. But also one with great public transportation. Luckily, my hostel was in a convenient location for all the Sydney must see’s.

Obviously, it was time to take a selfie with the Sydney Opera House. I boarded the train at Central Station and took it a few stops to Circular Quays Station. Seeing places in real life that you’ve seen thousands of times in picture is always a strange feeling. I’d made it. The Sydney Opera House is right in front of you once you’ve left the Circular Quay station. I walked around the boardwalk to get the perfect shot. It was cloudy but I didn’t care. After a significant amount of Opera House selfies I wandered to find the Sydney Harbor Bridge Walk. A free alternative to climbing up the bridge. I would suggest doing that if you have a disposable income but it wasn’t in my budget. Half way through the bridge there are also slightly higher point where you can pay 5/10 AUD to get a little bit higher of a view. I kept on walking. The Harbor Bridge is long and provides beautiful views of North Sydney and Sydney Proper. Before I walked on the Bridge I saw Luna Park, a small amusement park and another quintessential Sydney photo-op.

While on my way to the Bridge Walk entrance I found myself in a market on The Rocks. I love useless little souvenirs. I take mental notes of the boomerangs,kangaroo stuffed animals, and crocodile fashion I’ll buy when I’ve got less months ahead of me.

The entrance to Luna Park is a large face, with an open mouth. Although it’s your typical amusement park it offers great views of the Sydney Harbor Bridge and the city’s skyline. I wandered around North Sydney a bit more, hung out in the park under the bridge and made my way back over the Bridge Walk again.

On my way to The Royal Botanical Garden’s I stopped off a convince store to get myself some TimTam’s. I’d heard that Tim Tam’s are better than Oreo’s. At first, that idea was a hard no for me. However… considering I’ve already purchased another box, I’d say they’ve grown on me.

The Royal Botanical Garden’s are lovely. But at this point in my day my feet just hurt. I sat in the herb garden and read for a bit, mustering up more energy. Eventually I made may way to Mrs. Macquarie’s Chair, the only view point where you can get both the Sydney Opera House and the Harbor Bridge in one picture. It was nearly sunset when I’d arrived and the view lived up to my expectations.

The rest of my time in Sydney was spent meeting friends at the hostel and becoming as caffeinated as humanly possible, mooching off free wifi offered by most cafe’s. On my last night I’d gotten in touch with my Australian friend Johanna, who I’d met in Barcelona the summer before. Jo and I were quick friends and reunited in Paris as well. So Sydney was our third city together and it was great to get some Australian insight about the adventure ahead of me. She recommended we meet at the Opera Bar, an unpretentious bar that looks out of the Opera House and Sydney Harbor Bridge. I would highly recommend going for at least one drink there if you find yourself in Sydney. It offers unbeatable views, great food and live music.

By the time I’d met Jo I had a plan all set up for probably the next couple months. I’d heard how great Workaway’s are for travelers looking for unique experiences and free accomdation. So I’d spent most of my time in those cafe’s reaching out to potential Workaway hosts. One of which was Peter, owner of a 42 foot catamaran looking for a crew to sail with him to The Kimberlies in the Northern Territory. My next couple months in Australia fell together pretty quickly. I Skyped with Peter, and booked my ticket to Darwin. A four hour plane ride to the North. The next morning, I’d heard back from another Workaway host I’d reached out to. This one, a cattle and horse farm four hours north of Sydney (with motorbikes!).

So as it turns out, losing my first reservations in Sydney enabled me to pack up and leave for Darwin on a whim. Which brings me to the outdoor living space in my hostel in Darwin, where I’m writing this now.  While Darwin doesn’t have much going on as far as cities go, it’s going to be a jumping off point for what I think is going to be an incredible adventure ahead of me. Stay Tuned.

Irish Adventures. Great Music, People and Whiskey.

For me, it was a no brainer. My family’s heritage is Irish, The US city I’m from boasts Irish culture and I’ve met enough Irish people to know that I just had to go there. I was not disappointed. In fact, I look back on my time in Ireland as one of the best parts of my trip. What you’ll lose in nice weather, you gain in spirit. And I’m not just talking about the whiskey (which is great too…). I fell so in love with Ireland I even contemplated a second stop before I headed back home. Ireland is an amazing, small country that I urge you to explore if you find yourself in Europe.

As I mentioned, before I’d actually set foot in the country I’d had the pleasure to meet loads of Irish expats living in France. I loved them. I mean LOVED. So not only was I lucky enough that I got an introduction of their sense of humor and inevitable antics, I also got some insider tips before I headed to the country myself. In my experience, the people of Ireland are loud, welcoming, friendly and a breed all of their own. Get a bunch of Irish people in a room ( most likely with alcohol) and they’re singing folks songs, banging on tables, having the greatest random Tuesday you’ve ever seen.

The green hills are rolling and filled with livestock, The Cliffs of Moher are breathtaking, (to put it lightly), but if you’re in Ireland and haven’t been to the pubs… you’re not doing it right. From my experience,you’ll walk into a larger-than-expected dark building with grand wooden features. Some pubs are even converted churches with stained glass windows, which is impressive and something that I’d personally never seen. ( I mean, if anyone were going to convert churches to pubs, it would be the Irish).  But the best part of these pubs is not the Guinness or the grandeur, it’s the live music. I’m pretty sure every pub I went in had live music at least once a night. I’m talking, big bands, multiple instruments (instruments I’ve never even seen), incredible, live music. I am always a lover of this so to me, Ireland’s musical interludes was something I fell in love with. What was striking was how causal it all seemed. The locals weren’t surprised to see a 10 person band just hanging out at a table simultaneously playing and drinking… but I was !

On my first night in Dublin and Ireland in general, me and a friend I’d just met wandered into the nearest pub, finding it to be packed with people singing, dancing laughing.They were listening to a great cover of one of my favorite songs that reminded me of my time in France the summer before.It was really one of those, ‘ I’m traveling! I’m really doing this!’ moments. It was a feeling I’ll never forget and one that I continue to chase.So put on your dancing shoes, shoot your whiskey back and enjoy witnessing real Irish culture, you won’t have to try too hard.

The best tip I got about Ireland was simple. Go to Galway. I’m passing this advice on to you. Of course you want to go to Dublin, but I’m telling you, go to Galway. You know it’s a good time when you meet three Irish dudes who just came for a fun weekend getaway. It’s not a built up tourist destination it’s real and it’s amazing. To be honest, I’m even having trouble writing this because none of the words I’m coming up with truly capture what an awesome destination Galway is. You’ll just have to go yourself and let me know what you think! Galway is a quaint colorful city on the west side of the country. A perfect location for seeing places like the Cliffs of Moher and Connemara. While I was there I stayed at Galway City Hostel and it was fantastic. The entire time there I felt like I was part of a family. The facilities had everything I needed and as a solo traveler I easily made friends because of the hostel’s social atmosphere. I will a hundred precent be back to Ireland in my lifetime.

 

 

How to Travel Boston like a Local

Boston Massachusetts is my hometown. If you haven’t thought about traveling to New England, it should be on your list and Boston should be your first stop. I’m proud to be a “Mass-hole” as we’re called and I’m sure anyone else from the area would say the same.

Boston doesn’t care what you think. We not trying to be New York, LA, or Miami. Boston is a small city that packs a punch. Because of that, as a traveler you can see and do a lot in a short amount of time. I’ve been spending my days bartending giving advice to tourists, so I’m passing that advice on to you, my friends!
Let’s start with getting around..  It’s called the “T” or the train. For better or worse, the different colored lines of the MBTA travel from under ground to street level. Be sure to grab a CharlieCard. As I write this, a one way fare is $2.25 with a Charlie Card and $2.75 without. The MBTA could use some TLC but it’s reasonably reliable and will get you to where you want to be.

As a mentioned, Boston is a small city. Which means most of the T Stops are actually walking distance from one another. If it’s a nice day, walk! Boston is historical and really beautiful. If you see a red line painted on the ground- follow it. You’re on the Freedom Trail, which is the walking route you can walk for free or take a tour of. It will take you to all the best historical sites of the American Revolution.

The only thing we could be more proud of than our city’s past, is our current Sports teams. Bostonians have been fortunate enough to have several celebratory championship parades within recent years. Boston is affectionately known to those who live there as “ Title Town” and on that note let’s make one thing clear. Nobody wants to hear you talk shit about Tom Brady. Your point is moot, and people will get angry.  The Red Sox-Yankee rivalry still exists but I think only for the sake of tradition at this point. In my lifetime, I’ve seen the transition from chants of “ Yankees Suck” to “ F**k Goddell”. Haha..yeah…we’re a colorful bunch.

If you travel like I do and you’re in Boston, you’ll quickly realize our annoyingly strict liquor laws. We’re not kidding when we say, Boston does not have happy hours and pouring doubles is technically illegal. Despite this, drinking remains a huge part of Boston culture. Since I’ve spent my time deeply connected with Boston’s restaurant industry culture, I’d like to consider myself as an expert in this category.  With out further adieu, here are the bars to be at.

Nothing I love more than Brunch.. if you fall into this category you should check out The Friendly Toast in Back Bay. Sit at the bar and tell them Dana sent you. Nobody is doing the brunch and full bar thing better in town….

But now that I’ve shamelessly plugged a previous employer.. Also check out Daryl’s in the South End for some real good southern cooking accompanied by AMAZING live jazz/ funk/ soul music. Totally worth it.

Dive Bars, you say?
Corner Pub, Biddy Early’s, Bukowskis, Durty Nelly’s
The Silhouette, Model, The Avenue

Good Grub, Low key atmosphere?

Deep Ellum/ Lone Star, LuLu’s Allston,  De Lux, Lincoln, Boston Burger Company, Naco Taco, BatteryPark, CitySide

Irish

Boston has a large “we’re wicked Irish culture”. There are plenty of Irish pubs. Off the top of my head, Mcgreevy’s, LIR, Bell in Hand, The Burren, JJ Foley’s, The Black Rose 

College Bars with possible sticky dance floors
Scholars, Tavern in the Square Allston ( affectionally referred to as TITS), The Greatest Bar, Coogins, Patrons, The Tam. This category really isn’t my cup of tea, but to each their own.

Oh you Fancy, huh?

Tavern Road, Top of the Hub (on top of the Prudential Center) , Strega, Deuxrue, Tamezcal, The Daily Catch,

In general, you should wander around the North end for Italian food, wine and dessert. It’s super quaint and lively all year round. Do not drive in the area unless you want to have a panic attack before your cannoli.

The quintessential tourist traps that you should probably at least check of briefly :

Faneuil Hall / Quincy Market- There will be street performers and stores you’ve seen 100 times. But Quincy Market is an indoor food mecca. You will be overwhelmed by the choices- I always suggest going through the whole thing once before purchasing anything.

Duck Tours-  OKAY! Duck Tours will definitely mark you as a tourist however, they are super informative and really fun. Plus, you drive right into the Charles river from the Street. The Duck Boats are retired war vessels.

The Boston Commons/ The Fens/ The Esplanade –  These are all beautiful parks and areas to walk around. You will see beautiful gardens, great skylines and who doesn’t love a nice afternoon walk. Granted, you probably will want to do as little walking as possible if for some crazy reason you WANTED to come to Boston in the winter.

Boylston St & Newbury St-  Great shopping and restaurants, big Brownstones and the rich people who can afford to live in the area walking their cute dogs. This is the Copley Square area of Boston and where the Boston Marathon Finish Line is every April.

Cambridge- Technically speaking, Cambridge is a different city than Boston and it definitely has it’s own thing going on. Ever heard of Harvard, or MIT? Cambridge is eclectic and after living there myself for two years.. I am willing to bet on your visit you will be amazed by the people and things you see on the street. If you spend enough time there you will understand what it means when someone says “ only in Cambridge”. It’s worth checking out the Harvard Square and Central Square areas.

Good things To Know

  • For anyone making the move to Boston…NEVER drive a large Uhaul or anything like it on Storrow Dr (low bridges) .
  • Pack for multiple types of weather especially if it’s spring or fall. It’s completely normal to have a 30 degree Monday and a 75 degree Tuesday (that’s Fahrenheit folks). The saying of the New England climate goes, “if you don’t like the weather, wait a minute”. As for summer and winter, expect humid heat and freezing snow,respectively.
  • We don’t say hi to strangers passing on the street
  • There is absolutely no rhythm or reason for the street layout. Massachusetts residents are commonly known for aggressive driving and from a local, driving around Boston is a challenge. If you’re not comfortable driving, I’d save the rental car for when you want to head to the Cape.

Like I said, Boston is my hometown and I could talk all day about it,so I’d love to give you more insight. Any travelers have other favorite spots? Let me know!