What to Pack for Your Boston Vacation

Packing advice for Boston visitors

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

Boston weather can be tricky - so here are packing tips about what to bring for your Boston vacation.

Top 10 tips for what to pack for Boston vacations

Tip 1:  Bring comfortable walking shoes 

Boston is a compact, walkable city . . . and that means you'll probably be doing some 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 close.  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 that requires 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.  Those with closed toes will give you protection from close encounters with uneven sidewalks or cobblestones (Keen is a brand that makes sturdy closed-toe sandals).

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

Boston weather can be unpredictable.  While temperature swings of 50° or more are not common, they can happen.  More likely are unseasonal events, such as a snowstorm in October or May, or a balmy 70° day in January or February.  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.

Tip 3:  Bring layers

As Tip 2 notes, Boston weather can be unpredictable and change rapidly.

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

In the winter, consider bringing long underwear no matter how dorky it seems. 

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, bring a warm coat, gloves, hat, scarf, and heavy socks. 

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

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 (lightweight "travel" umbrellas are fine) or be prepared to buy one if needed. 

You can usually find inexpensive umbrellas for sale at drugstores, small groceries, and "convenience" (meaning they sell all types of items) stores in all of Boston's neighborhoods.  I've recently bought 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 throw a pair of jogging shorts and a cotton t-shirt into 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, bring normal business clothes.  If you're coming for vacation, bring comfortable, casual clothing such as nice t-shirts and jeans. You'll generally see a lot of black here.

Tip 10:  What to pack for Boston nightlife

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, you can do emergency shopping at H&M (100 Newbury St in Back Bay, 350 Washington St in Downtown Crossing, Cambridgeside Galleria in Cambridge).  H&M features trendy styles and fairly cheap prices (usually $40 or less per item).

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, I see everything from very casual (jeans and t-shirts) to very dressy (semi-formal, jewels).  Black is always safe.

Tip 11:  Sports gear?

Do not bring or wear sports gear related to non-Boston teams.  We take Boston sports very seriously.  If you want to blend in, wear a Red Sox cap.

Tip 12:  Still not sure what to pack?

When in doubt, pack black.