What to Pack for Your Boston Trip

10 Essential Tips & 3 Bonus Suggestions

What to pack for your trip to Boston - www.boston-discovery-guide.com
Need packing tips for your Boston trip?  Take a cue from these Boston visitors wearing layers
and comfortable shoes - great choices for the chilly October day when I took this photo
in Boston's Theatre District near the W Hotel

Do you have Boston travel plans and need to know what to pack? 

Boston weather can be tricky.

We have 4 distinct seasons ... kind of. 

Winter can continue into April.  December is occasionally balmy.

Weather conditions can change in a heartbeat.  "Unpredictable" should be your guiding principle, even when you check the forecast right before coming.

So with all that in mind, here are 10 essential tips about what to bring for your Boston vacation, plus 3 bonus tips about what to pack - and what to leave at home!


10 Packing Essentials for the Savvy Boston Traveler

Tip 1:  Bring comfortable walking shoes 

Boston is a compact, walkable city . . . and that means you'll probably be doing lots of walking.  Athletic shoes and the type of sturdy outdoor shoes that you can buy at REI or LL Bean work best when you travel to Boston. 

Ladies, don't try to walk around city neighborhoods in high heels, or anything similar.  Leave your Louboutins at home.

Cobblestones and brick sidewalks may look quaint and attractive, but they're ankle-breakers if you're wearing anything other than flat soles.  If you plan to attend an event requiring dressy shoes, do what Boston locals do - bring them in a bag and change when you arrive.

If you're coming in the winter, consider bringing boots. 

In warm weather, sandals are fine.  Sturdy styles with rubber soles and closed toes (such as Keen) will give you protection from close encounters with uneven sidewalks or cobblestones.  Flip-flops will not be the best choice for walking any distance.  Plus our streets are not exactly, um, clean.

Bringing comfortable shoes is my #1 tip! 

Tip 2:  Prepare for changeable Boston weather

Learn what Boston weather temperatures and conditions you can expect during your visit.  Then check the Boston weather forecast before you come to get a general idea about what to pack. 

In a nutshell:  our weather ranges from hot and steamy during the summer to frigid temperatures and piercing winds during the winter - and everything in between, including lots of bright, sunny, low humidity days year-round. 

Boston weather can be unpredictable.  Although temperature swings of 50° or more within a few hours are not common, they can happen - and usually do happen several times each year. 

More likely are unseasonal events, such as a snowstorm bringing a foot of snow in October or May, a balmy 70° day in January or February, or cold, damp weather until July 4th (I am not exaggerating).  And of course, the sun can shine brightly one moment and rain can pour down during the next moment.  Even after checking the weather forecast, you can't be sure what to expect.

A good thing to pack is a light weight canvas or cloth bag.  You can throw in an umbrella in summer or gloves, indoor shoes, and earmuffs during the winter - just in case. 

Tip 3:  Think layers

As Tip 2 notes, Boston weather can be unpredictable and change rapidly.  The best clothes to pack for Boston must provide flexibility.

So, the best strategy for what to pack for changeable weather is to think in layers.  Bring shirts, sweaters, vests, and jackets to layer according to how warm or cool you need to be.  Ideally, at least one of these layers should be waterproof.

In the winter, consider bringing long underwear, no matter how dorky it seems, especially if you plan to wear skinny jeans or leggings.  Trust me, you'll be happy to have a second layer.

In the summer, pare down as much as possible, and remember that loose clothing made from 100% cotton will feel much better than skin-tight nylon attire. 

Tip 4:  Prepare for winter weather

If you're coming to Boston in the winter and expect to be outside walking around for more than a few minutes, here's my winter clothing advice:  bring a warm coat, gloves, hat, scarf, and heavy socks. 

Pack sturdy, waterproof shoes or boots with heavy soles to insulate your feet from the cold pavement. 

In case you're thinking that "winter" ends sometime in February, be advised that March can also be cold, windy, and nasty, even though some days may be warm and balmy.  Sometimes April feels frigid.  You can probably get away with layers rather than a heavy coat - especially if one layer is Polartec.

But if you are coming in January or February, a puffer jacket or coat (those down-filled sleeping bag-like garments) can be your best friend.

Tip 5:  Prepare for rain

Rain can (and does) fall in Boston during every season throughout the year, although during winter months, precipitation may be in the form of snow or sleet rather than rain.  Either pack an umbrella or be prepared to buy one if needed.  Lightweight "travel" umbrellas are fine unless we have a nor'easter - but if that happens, you'll get wet whatever you carry.

You can usually find inexpensive umbrellas for sale at drugstores, small groceries, and "convenience" (meaning they sell all types of items) stores in all Boston neighborhoods.  I buy umbrellas in Chinatown for as little as $5, and about $10 in other neighborhoods.

Tip 6:  Do you need a swimsuit?

Yes, if your hotel has a pool or if you're planning a side trip to one of the Boston beaches or the Cape. 

Tip 7:   Consider athletic clothing

Most Boston hotels have nice fitness rooms. 

You also may want to enjoy a run along the Boston Esplanade or Harborwalk, especially if you're visiting during warmer months - so add workout clothe, such as a pair of jogging shorts, running shoes, and a cotton t-shirt to your bag.

Tip 8:  Prepare for sun

Bring sunglasses and sunblock, especially if a Boston cruise is part of your plans.  If you have room in your bag, consider bringing a sun visor or hat.

Tip 9:  How conservative?

Boston attire is generally fairly conservative.  If you're coming for business, want to blend in, and are wondering what to pack, bring normal business clothes in subdued, neutral colors (black, navy, tan, beige, taupe, gray).  If you're coming for vacation, bring comfortable, casual clothing such as nice t-shirts and well-fitting jeans (avoid baggy jeans, sweats, or shorts unless you're doing something athletic, such as sailing or jogging). 

You'll generally see a lot of black here.  It's the dominant color in many local closets, winter and summer.

Tip 10:  What to pack for Boston nightlife

Boston nightlife rocks, with plenty of dance clubs, places to hear live music, socialize, and relax.  Some clubs have strict rules forbidding jeans, athletic wear, t-shirts, and more.  Others are more casual.  Bars usually allow anything. 

If you're concerned that you haven't brought the right thing for clubbing, head over to H&M (100 Newbury St in Back Bay, 350 Washington St in Downtown Crossing, Cambridgeside Galleria in Cambridge) for emergency shopping.  H&M features trendy styles at cheap prices - usually $40 or less per item. 

Follow the general Boston rule - think black - but for a club, make it skimpy.

Most Boston restaurants are fairly casual.  You'll want to dress up for some of the fancier ones, such as Top of the Hub, even when there's no formal dress code.  Business casual or casual chic works well.  When in doubt, a jacket and/or tie is fine for men.  For women, anything black with a nice shawl works well.

As for theater and concerts, you'll see everything from very casual (jeans and t-shirts) to very dressy (semi-formal, jewels).  Black is always safe.

Be aware that on winter nights when snow is falling, most locals will look like they stepped out of an LL Bean catalog from a couple of decades ago, even at venues such as Symphony Hall.


3 Bonus Packing Tips

Bonus Tip 1:  Sports gear?

Do not bring or wear sports gear related to non-Boston teams. 

We take Boston sports very seriously here.  If you want to blend in, wear a Red Sox hat or a Bruins hoodie.  Wearing green in honor of the Celtics also works.  Ditto for styling your hair to look like Tom Brady's. 

Otherwise, just wear normal clothes. 

Leave stuff supporting non-Boston teams at home!  It will not be welcome here.  Seriously.

Bonus Tip 2:  Still not sure what to pack?

When in doubt, pack black. 

Bonus Tip 3:  Pack light

Sure, I know what you're thinking . . . every bit of advice you've ever read about what to pack for a trip offers this trite suggestion.  But if you're flying to Boston, packing light can save you money!

How?  Once you arrive at Logan Airport, you have basically 3 choices for getting to your hotel in Downtown Boston, Back Bay, or another part of central Boston:  you can take a cab (about $30-$40, depending on traffic), a water taxi ($12 each way, or $20 round trip), or the T, Boston's subway (about $2 each way).

So why does packing light matter? 

Although a cab will deliver you straight to your hotel door, taking a water taxi or the T means you'll need to get your luggage to your hotel.  Even though Boston is compact, you'll be much happier doing this if you have only one non-enormous bag - and make sure it has wheels!

Final tip:  A 4-wheel spinner bag will be your best bet for cobblestone surfaces.


More Planning Tips for Your Boston Trip

Cheap Flights to Boston Midtown Hotel - A Boston Bargain Hotel Top Boston Tourist Attractions


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