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For the uninitiated, Boston, Massachusetts may not seem like a prime party spot.  However, if you have ever been to Boston then you know it is one of the country’s best places, not only for people who like to party, but for people seeking just about any type of experience.  The city is one of the nation’s hidden gems for tourism.  It has gorgeous sights to see, is full of history, has some of the nation’s best bars, and is known for its varied approach to culture.  Combine these together and Boston becomes a great place for a once-in-a-lifetime bachelorette party, whether you are traveling to Boston or a lifelong native.

Boston is popular with tourists, which means that it has a lot of tourist-friendly activities that are easily adapted to a bachelorette party vibe.  These activities happen day and night, and there is plenty to do year-round, even though Boston is known for its brutal winter weather.  Of course, summer is the best time to plan a Boston bachelorette; the mild temperatures and gorgeous summer weather make it a fantastic destination, especially for people looking to escape brutal weather in other parts of the country.

How to Get There

Boston is located in the northeast section of the United States.  While it is an easy road trip for folks in the rest of Massachusetts or nearby New Hampshire, Vermont, Connecticut, or Rhode Island, it is not generally a road trip destination for most of the rest of the U.S.   Fortunately, Boston has an international airport with flights from all over the country on several different airlines.


Boston’s Airport is General Edward Lawrence Logan Airport (airport code: BOS), which is usually referred to as Logan Airport.  The Airport code for Logan is BOS.  It is about 20 minutes by car and 45 minutes by subway from Logan to Downtown, where many people choose to stay for bachelorette parties.  If you are not renting a car, we suggest that you plan on booking a limo or van to take you from the airport to your hotel.  JB Livery offers limos and luxury vans for your convenience.  Boston has both Lyft and Uber, and we have a referral code that might make your first ride free!

Getting Around

Like most cities in the northeast, Boston has fantastic public transportation.  The Massachusetts Bay Transportation Authority operates subway lines, bus routes, commuter rail lines, and ferries in and around the Boston area.

If you have a big group and like the freedom of having your own car, you can always rent a car.  Enterprise has a rental at the airport, as do most of the other national car rental chains.  Car rentals might be a good idea for people who are not used to cities with great public transportation.

If you know that you will need to be somewhere at a specific time, you can also schedule car rides using a livery service like JB Livery or book a limo or party bus.

Looking for more party bus options?  Check out all available Boston Party Bus rental services.

Things to Do

Boston is chock full of tourist attractions and things to do.  A truly historic city, Boston played a pivotal role in the American Revolution.  With a city so rich in history, it should come as no surprise that some of the top hot spots in the city are historic attractions.  However, while the city may be rich in history, it boasts tons of modern day attractions, offering something to please every tourist.  In addition, because Boston experiences major seasonal changes, your to-do list might change significantly, depending on when you plan your visit.  Visitors to Boston in the winter are going to be confined to mostly indoor activities, while visitors to Boston in the spring, summer, and fall can find a wide variety of outdoor activities to occupy them.  However, while Boston may get insanely cold for people from warmer parts of the country, it is important to remember that the city absolutely does not shut down just because the weather gets chilly; there is plenty of fun to have in Boston year-round!

Daytime Activity Ideas

Daytime activity idea for Boston are extremely dependent upon the time of year for your visit.  While Boston has fabulous weather from late spring through early fall, if you plan any outdoor activities during Boston’s long winter, you will certainly want to bundle up!

Although not unique to the Boston area, a spa day is always a great activity for a bachelorette party.  We love the idea of a full-service spa like Bella Sante Day Spa.  Whether you want facials, massages, eyebrows, or other custom spa services, Bella Sante can meet your needs.

Visiting Boston in the wintertime?  Then you should plan on the ultimate girly-girl day: snowflake afternoon tea at the Langham Hotel.  This traditional British style tea is full of delicious favorites like scones with cream, but also has a decidedly winter-friendly twist.  We love the idea of juxtaposing this with a particularly raunchy night out on the town!

Bella Sante Day Spa

Pole dancing lessons remains a popular bachelorette activity.  We love the idea because it gives a sexy, naughty twist to a bachelorette party without getting dirty.  Gypsy Rose Exotic Fitness offers great pole dancing lessons and can customize a bachelorette party for you.  Why do we love them more than some other Boston area pole dancing places?  Because they have props to help you feel sexy and get in the right mind set.

Do you love to shop?  Then you will probably want to hit Bow Market in Somerville while you are in Boston.  This courtyard-centered shopping center reminds us a little of Jackson Square in New Orleans, because of the sheer variety of things you can find there.  This former warehouse now has over 30 different independent vendors offering food, arts, and retail shops.  There is even a comedy location.  You will find both permanent location and temporary booths, so the shopping experience is different every time you come.  It is a must-visit for anyone who considers herself a fashionista or a shopaholic! 

Boston’s Freedom Trail is probably the city’s most popular daytime tourist attraction.  Whether you follow it on your own or join up with a tour group, this 2.5-mile red brick trail winds through the city from Boston Common to Bunker Hill.  You can find great rates for guided tours on Groupon.

Are you hockey fans?  If you are in town during hockey season, then you can actually plan a super-inventive and super-cheap activity for your bachelorette fans.  You can head over to Warrior Ice Arena and watch the Boston Bruins practice.  You will be able to get up close to the ice and you may even be able to interact with some of the players.  In fact, while you are there, you might want to check out some of the activities that they have available, including ice skating lessons.  While certainly not a traditional bachelorette party activity, the hashtag writes itself: #BostonBruinsBacheloretteBabes.   

Are you already an ice-skating expert or feeling super-confident after your lessons at the Warrior Ice Arena? Then, in the winter time, head out for some ice skating on the Boston Common Frog Pond.  This iconic local attraction is known for its idyllic winter-wonderland style skating conditions in the icy cold months.  Heading to Boston when the weather is warmer?  The pond is still a great outdoor space at other times of the year.  Check out their calendar to see what is going on during your visit!

The wonderful weather makes Boston a great place for physical activities.  That is why you might want to consider a bike tour through the area; it is a great way to see the city, get some exercise, and enjoy gorgeous weather.

Boston is a sports town, known, not just for its great teams, but also for its over-the-top fans.  Head to Fenway Park to check out a Red Sox game or TD Garden to see the Celtics or the Bruins.  Just keep in mind that getting tickets can be a little bit tricky.  If you want to make a game part of your bachelorette party plans, then try to plan ahead as far as possible or be prepared to pay resellers higher prices for the tickets.

Bachelorette scavenger hunts are a ton of fun, and in a historic city like Boston, they can be really challenging.  While this Amazing Scavenger Hunt Adventure uses the whole city as a gameboard and takes about three hours to complete, you can also DIY a scavenger hunt or have one custom-created for your bachelorette.

The swan boats are one of the most famous Boston daytime activities.  A paddle boat decorated with a large swan, these inexpensive rides offer a tour of the Public Garden Lagoons.

Boston is not just located on a harbor, but probably on the most famous harbor in the entire United States.  So, get out and enjoy the water.  There are so many different marina areas where you can rent a boat for your group.  You can handle it yourself or hire a chartered boat, depending on your comfort level and the comfort level of all of the bachelorette party guests.  We especially recommend looking into sailing around Boston Harbor.  Plus, while you might think of this as a summertime activity, in Boston the water is calling year round; you can actually plan what is known as a Frostbite Sail. 

While other cities might be catching on, Boston seems to be on the forefront of a new trend: yoga at the brewery.  As the name suggests, this is yoga, performed at a brewery.  Each weekend, a new brewery hosts yoga.  Your admission usually includes at least one glass of the brewery’s custom brewed ale.  It is a great way to be healthy, but still have a great time.  And, as you might imagine, since it is mixing athleticism and alcohol, all skill levels are welcome! You can find an event on Eventbrite

People either tend to love heights or hate them.  If you fall into the love them camp, then you cannot miss seeing Boston from the top of the Prudential Building at the Skywalk Observatory.  This observatory offers stunning views of the entire city and, on a clear day, you can actually see up to 100 miles in each direction.  It also has an attached museum that gives you some of the best information on historical Boston. 

View all other Activities in Boston

Nightlife Activity Ideas

Perhaps because it has to provide entertainment for so many local colleges and universities, Boston has a thriving nightlife scene.  In addition to some great bars and dance clubs, Boston also has some unique entertainment options that truly cannot be found anywhere else.

If you are from the southwest part of the U.S., then you might be a little wary of heading to any activity labeled a donkey show.  However, The Donkey Show does not refer to any of the XXX shows you might see just south of the border, but instead to one of the most interesting and entertaining live theater shows you can see anywhere in the United States.  It is difficult to describe it to the uninitiated.  At its hearts, the show is a retelling of the Shakespearean classic A Midsummer Night’s Dream.  However, it also adds a dash of 70s disco, roller skating, and mirror balls.

Although not as well-known for comedy as New York or Chicago, Boston has a surprisingly vibrant stand-up comedy community.  Not sure what you want to see?  Well, if you are in town on a Friday night, head over to Laugh Boston and see their Dirty Disney show.

Heading out to the clubs?  Boston has some wonderful dance clubs, but if you are unfamiliar with Boston’s dance scene, you need to know that the bean town party scene starts earlier than it would in other locations and that the clubs really do shut down around 2 am.

You can also check out ImprovBoston, which as the name suggests, is an improv comedy troupe.  They have shows each weekend, but even more than the idea of attending a show, we love the idea of improv lessons as a unique bachelorette party idea.  They have a drop-in, 100% free intro-to-improv class every Saturday at 1pm. 

Venu Nightclub– Are you a fan of old-school hip-hop and a classic stylish lounge atmosphere?  Then Venu Nightclub is the place to be.  Just make sure and get to Venu early, because the lines get very long as the night goes on.

Venu Boston Nightclub

Estate Ultra Bar is extremely popular and is a great place to party.  You can choose the relative ease of bottle service or you can just flow through the club; it has plenty of bars so you will never be without a drink.  Need a temporary break from the chaos of the dance floor?  Retire to one of the lounges to get recharged.


Cheers- Probably Boston’s most famous bar, the real-life setting for the TV show Cheers was once known as the Bull & Finch pub.  It has since been renamed to Cheers and is a must-see for most pop culture buffs.  Because of its iconic status, we put it on the bar list, but we actually think visiting this bar is just as well suited for daytime as it is for nighttime.  A great place for pictures and to have a drink, it is not where you will be doing the bulk of your bachelorette partying.

We love a bar with a theme and Fat Baby bar in South Boston (Southie) is one of those.  They are well-known for the sushi and their drinks.  However, the gimmick that we love for bachelorette parties is that they serve giant cocktails that are designed to be shared.  We love the Chopsticks and Stones, a fruity concoction that packs one heck of a punch!

If you are going to visit any bars in Boston, you really need to stop by the Bell in Hand Tavern.  Is it a great bar?  Depends on your definition of great.  It is the oldest bar in America, which means they are doing something right.  Very much still a tavern, the Bell in Hand is known for two things- fantastic beer (or ale) and great tavern-style food.

We are not sure whether to put Branch Line in among the bars or in among the restaurants.  Yes, they offer some amazing food, but the reason that we include them in our bachelorette party list is that they turn their patio into a huge beer hall every Wednesday night.  We do mean every; they cover and heat the patio during the winter, so that the show goes on regardless of the weather.  We think the beer hall, though only available once a week, deserves to be on the list of best bars in Boston!

Bell in Hand Tavern

Faneuil Hall is not really a bar, but it does play host to some of the city’s favorite bars and smaller clubs.  This busy shopping district/ marketplace has a number of popular restaurants and drinking spots, making it a great place to have a few drinks.

Got some gamer girls in your group?  Then, you must put Versus on your list of places to see and visit.  This combination arcade, bar, and restaurant is a relative newcomer to the Boston scene, but is rapidly getting a reputation as one of the local favorites.  You will find yourself surrounded by all the best elements of 80’s pop culture, but with a modern twist.  Enjoy old-school video games in an atmosphere that reminds us a little of that huge adult arcade chain, but back before it became all about the profits.  You can even rent Versus for a private event.  

Visiting in the winter?  Consider hitting the Igloo Bar at the Envoy Hotel.  Year round the Envoy offers one of the city’s hottest rooftop bars.  In the winter, though, this bar gets extra extra, offering an igloo option.  The igloos are not actually crafted of snow and ice, but of colorful fabric igloos.  They fill up quickly, so you want to get there early. 

Male Reviews/ Male Strip Clubs

Boston is unusual for a smaller city, because it offers multiple male reviews for your bachelorette party entertainment.

Men in Motion is not Boston-based, but this traveling Magic Mike style male review frequently comes to the Boston area.

National chain Hunk-O-Mania, which is known for its high quality entertainers and its bachelorette party packages has a Boston location.  However, shows are only on Friday and Saturday nights, so plan your entertainment accordingly.

The Male Encounter is another male revue you can find in the Boston area.  This entertainment service offers public shows, but will also work with you to book private parties in a variety of venues.  It is a great in-between if you are not certain whether you would rather head out to a male revue or plan a private dancer for your party.  Their claim to fame is that Mr. Magic Mike, himself, Channing Tatum, got his start with their company back in the 90s, and they offer a Channing Tatum themed show for bachelorette and other private parties. 

Where to Eat

Boston may not be one of the country’s best known foodie cities, but it does have a great food scene.  A city on a harbor, you can expect to find very seafood-intensive menus and some of the country’s freshest catches.

Breakfast / Lunch / Brunch

While Juliet actually serves all meals, it is a great place for breakfast/brunch/lunch.  Our favorite brunch item is the Gruyere omelet.  While their food is amaze-balls, we actually put Juliet on this list because of its concept as a restaurant.  Have you ever been to a restaurant in the United States where tipping was prohibited, the staff all made a living wage, and the entire restaurant is housed in a room so that dining becomes an experience.  It is a great place for dinner, too, and the prix fixe dinner menu means you can pay for it ahead of time.

Looking for a classic pub or tavern feel for one of your meals?  Look no further than Beantown Pub, which bills itself as a pub with billiards.  You can get some Boston classics at this old-school restaurant, including Beantown Baked Beans and Baked Jumbo pretzels.  However, our favorite item on the menu is not exactly a classic; the tater kegs, which are like supersized and stuffed tator tots, are out-of-this-world delicious.  Surprisingly, this restaurant also offers some vegan options and several healthy dishes, so it is a great place to grab a meal if you have some group members who are trying to watch what they eat or have dietary restrictions.

Henrietta’s Table in Harvard Square has a well-established reputation as one of Boston’s best breakfast spots.  Everyone loves their waffles for a breakfast or brunch treat, but we are actually a fan of their lunches, especially the cornmeal-crusted monkfish sandwich.

Eventide Oyster Company opened up a location near Fenway Park.  If you have not heard of Eventide, please trust us when we tell you that this a very good thing.  Before they opened up this location, you had to drive two hours outside of the city to get the Boston area’s very best lobster roll.  Now, you can get one without leaving town.  What should you order there?  Clearly, the lobster roll.  It is served with brown butter on a soft roll and it is divine.  However, if you are not a fan of lobster, you will still find plenty of things to adore at this casual-dining establishment.  They are known for great quality oysters on the half shell and their creamsicle soft serve is one of our favorite desserts in the whole town!

Henrietta’s Table

Blunch is not quite a brunch place, and it is not exactly a lunch place, either.  Instead, think of a delicious breakfast in a sandwich.  It is a tasty place for breakfast or lunch, but, as the name implies, not exactly brunch.  The food is a bit more straightforward than you would expect at a brunch place and you are not encouraged to linger like you would at most brunches.  This is not a bad thing; the service is fast enough that you can have a great meal without spending hours there, and the food is absolutely delicious.  Our favorites?  We like the onion bagel with sausage, hot peppers, roasted red peppers, mozzarella, and a spicy aioli, but you can build your favorite.  Order one of their desserts, as well.  The best part?  Even if you have a drink or two and dessert, you will probably spend less than $20 on your whole meal!

Looking for an iconic Boston fine dining experience?  Then head to Parker’s Restaurant in the Omni Parker House Hotel.  One of the country’s most iconic restaurants, it is known for its outstanding whisky bar.  It also happens to be birthplace of the Boston Cream Pie, and you would be ridiculous to dine there and not try one.  We also highly recommend trying the French Onion Soup and the Lobster Grilled Cheese.  Just keep in mind that this is a fine dining establishment, which will enforce their dress code. 

Flour Bakery and Café is the place to go for a decadent breakfast experience, but it is also what we recommend if you want to have a delicious breakfast delivered to your door.  Their sweets are a very upscale take on the traditional breakfast pastry; think cinnamon cream brioche, sweet and savory scones, and hand shaped croissants.  Not in the mood for something sweet?  Try the mortadella sandwich.  This is a great place to go if you have any vegans or vegetarians in the group; they offer a good variety even for people with restricted diets.

Are we really going to send you to a food truck for a meal?  If that meal is the Double Awesome from Mei Mei’s food truck, we sure are.  The Double Awesome is a combination of eggs, cheddar, and green pesto served in scallion pancakes.  Not in the mood for a sandwich?  No problem.  This Asian-American locally sourced restaurant offers a little something for everyone.  Did we say restaurant?  We did.  While it may be known for its food truck, they also have a restaurant if you are feeling a little too bougie for food truck food!

Not exactly a bar, or at least not a bar serving alcohol, LA Burdick is one of the city’s most popular wintertime destinations.  People from around the Boston area flock here for some of the best hot cocoa you will ever drink.  That might not seem like a big draw if you are sitting in the warmth somewhere, but, trust us, if you are in Boston on a frigid winter day or even as the chillier temps hit in the evenings throughout spring and fall, a cup of hot chocolate may actually have a lot more appeal than a hot toddy! Not in the mood to drink your chocolate?  Then enjoy one of their specialty chocolates or pastries, instead. This is the perfect spot to hit if you have vegans in your group, as they offer fine, specialty chocolates that are vegan-friendly!


Bootleg Special is not your typical bachelorette dinner experience.  Instead of a complex menu in a fussy setting, it is a seafood boil in a rustic setting.  However, do not let this keep you away.  You get to custom build your boil, so you can get exactly what you want. We like shrimp and lobster with a moonshine sauce.

Bootleg Special

Craigie on Main offers one of Boston’s most sought-after dinners, but you can only get it at the bar.  It is called the Craigie on Main burger.  It is made from a combination of cuts of meat, like short rib, brisket, marrow, and suet.  It is served with Shelburne Cheddar, a milk bun, and steak fries.  It might be the best burger you will ever have.  However, they only make 18 each night, so if you want one, head over early for your dinner!

The Oceanaire Restaurant is one of our favorite seafood restaurants in a city full of great seafood restaurants.  Our favorite is the Seared New Bedford Sea Scallops.  Not a seafood fan?  No problem; you will also love the blue cheese crusted prime strip.

If you are a pizza fan, then you have probably already heard about Santarpio’s Pizza.  This casual no-frills eatery has a reputation for some of the best pizza on the East Coast.  While lots of places make that claim, this one actually has some pies that might be up to the boast.  They also serve something they call barbeque, which is not what people in other parts of the country might think of when they think of bbq, but is still damn delicious.  We love the zesty lamb sausage.

If you are a Boston native, then you have probably heard the buzz about Blossom Bar.  Although it is called a bar and has some amazing cocktails, both on and off the menu, its food is amazing. They offer Sichuan food updated for the modern palate.  We suggest the dan dan noodles.

No Name Seafood Restaurant is about as frilly as you would expect from its name. Do not let the lack of frills scare you away; this restaurant is one of the best seafood places in New England.  What to eat there?  Lobster, of course.  We also love the fried clams, and the Boston Cream Pie.

Do you have some serious meat lovers in your midst?  Then head over to Grill 23.  Order the 100-day aged prime ribeye.  Then thank us.  Want to get your meat on, but have some vegetarians or vegans in your midst?  You are in luck, because Grill 23 also has some awesome sides that you can put together for an amazing meatless meal, in addition to a menu that includes great raw and cooked seafood.  It is not what you think of when you think of bachelorette party dining, but it is absolutely fantastic!

Where to Stay

Boston has been a popular destination for travelers since before the United States became the United States.  It has some great places to stay, and plenty of variety, whether you are looking for a period B&B, a luxurious resort, or a home rental.

Hotels and Resorts

What do we love about staying in a hotel?  The maid service.  The concierge service.  The pampering.  If you are like us, and you like a little pampering, do not rule out the idea of a hotel for your bachelorette party accommodations.  While home rentals are becoming an increasingly popular way to travel, it is hard to deny the appeal of a great hotel.

The Revere Hotel in Boston Common has everything you could want in a Boston hotel: history, great rooms, and amazing customer service.  The rooms are large and well-appointed, and the location makes it easy to get to many Boston attractions.

The Godfrey Hotel Boston is an extremely upscale urban hotel in the heart of Boston.  It is so plush that Conde Nast named it one of the best new urban hotels of 2017.

Godfrey Hotel Boston

Boston is not really known for its resorts, though there are plenty of them nearby out in the cape area, which is the area of Massachusetts that extends, like a peninsula, into the water, and on islands like Martha’s Vineyard and Nantucket.  For a resort-like experience in the city, you can try the Westin Boston Waterfront.  This hotel, with its three restaurants, health club, and swimming pool has a resort-like feel, though it does not have a spa or golf club.

The Bostonian Boston is a four-star hotel with a five-star feel.  This hotel is located in the heart of the city and is within walking distance of most of the city’s big attractions, making it a great centralized location for any group of tourists.  We think it is especially perfect for bachelorette parties because the accommodations are luxurious and the rates are surprisingly affordable.  While much of a bachelorette party may be about constantly going and exploring, we love the quiet moments stolen with friends.  The Juliette balconies in many of this hotel’s rooms are a great place to pop open a bottle of wine, sit, relax, and chat with friends.

View all Hotels in Boston

Rental Houses

Boston is a very old city, at least by American standards, with a ton of history.  What this means is that it can be really cool to find a home to stay in while you are in Boston.  A home rental gives you a great common space for hanging out, tends to be less expensive, per person, than a hotel room, and gives you opportunities to save money by cooking meals at the house, and custom plan, like if you want to hire a dancer to come entertain your bachelorette party.  Fortunately, with services like AirBnB, VRBO, and Homeaway, finding a vacation rental is easier than ever.  Right now, you can even use our link to get $40.00 off your first AirBnB reservation.


This beachfront home has plenty of beds and even has its own bar.  Prior guests rave about its cleanliness, location, and the ease of the check-in process.

Beachfront Home

This Fenway Park area condo has nine beds, so it can accommodate even large groups.  The location makes it easy to get to many local attractions.

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Part of the appeal of going to Boston is the history, which is why we love this historic home.  Renovated with modern conveniences, it allows you to enjoy the history of the area without giving up anything you have come to expect from modern living!

This Victorian might be one of the most charming rentals in all of Boston.  It has gorgeous flower beds, a great outdoor space, and a beautiful spiral staircase, all lending it very period-appropriate charm!

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Are you a fan of the arts?  Then this Arthouse rental is just the thing for your bachelorette getaway.  The house is in a great location and full of amenities, but what makes it stand out from the crowd is its rotating collection of works by local artists.

Looking for beach access without losing convenient access to the city?  This beach access condo is located just 5 minutes from Blue Line Station, which can take you straight into the city.

Beach Access Condo

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book house rentals for bachelor / bachelorette party

When to Go

Best Time

The best time to visit Boston is late spring through early fall, like June through October.  The weather is amazing and the scenery is gorgeous during this time of year.  While high tourist season is summer, the fall in New England is amazingly gorgeous.  In fact, if you are headed to the Boston area in the fall, we strongly recommend extending your visit for a day or two and heading out to see the turning of the leaves in the nearby area.  It may seem like a very simple thing, and, if you are not from the New England area you cannot truly understand it, but the colors are so stunning that they should be on everybody’s bucket list.  

On a Budget

Catching Boston a little earlier in the spring is more affordable, and watching the emerging buds and the spring green of the season can be amazing.  However, the weather may be a little less reliable than in the summer.  That is no problem, just make sure and pack accordingly, not only with warm clothing, but also with rain gear.  

Worst Time

Boston’s winters are absolutely brutal.  If you are not used to the weather, just getting out in the cold to travel from place-to-place can be intimidating.  However, if the cold does not intimidate you, the city looks beautiful in the snow.  

Moreover, unlike some places where the city comes to a halt in cold weather, Boston just keeps chugging, pretty much regardless of weather.  Unless you are stuck in a literal blizzard, you will be able to find plenty to do in Boston, even on the coldest of winter days!

Current Weather


What Else

Big Events

If you have not heard of Boston’s famous St. Patrick’s Day Parade, where have you been hiding all your life?  The biggest and most iconic of all of the St. Patrick’s Day Parades, Boston says that everyone is Irish on St. Paddy’s day.  

While it may only appeal to real athletes, the Boston Marathon, which is held every April, is the nation’s oldest marathon.  How amazing to coordinate a bachelorette party around this iconic race if the bride is a marathon runner and can qualify. 

Just keep in mind that prices are going to be higher the weekend of the marathon, and, because of the race, there will be streets that are blocked and transportation around the city may be a little crazy.  This is especially true with recent security concerns.  That does not mean you should avoid the city on this weekend, even if you are not a runner, just that you should keep those things in mind when making your plans. 

Are music festivals your thing?  Then plan your Boston Bachelorette Party in May, to coincide with the Boston Calling music festival.  This three-day music festival is relatively new to the festival scene, having only started in 2013, but it is rapidly becoming one of the nation’s most anticipated music festivals.  Think big-name headliners, tons of smaller artists, and all-day/ all-night music.  One of the things we love about this festival is that you can actually pay for your festival passes over time, which lets you plan ahead and budget if you need to watch your pennies!

Of course, the biggest celebration in Boston is probably Harborfest, which is a multi-day July 4th celebration.  Just imagine spending the Fourth of July in the city where the American Revolution began?

What to Pack

Packing for Boston can be a little challenging, and what you pack really varies with the time of year.   Whenever you plan to visit, we highly suggest layers.  In the winter, layers are essential to keep you warm and allow you to be comfortable inside heated buildings.  In summer, the evenings and mornings can still get a little chilly, so you want some layers to make sure you are comfortable. 

Number one on our list for Boston is a cute, comfortable pair of shoes.  It is a walking city, and, while those stilettos may look cute, they probably are not practical.  We suggest something adorable, like these cute slip-on sports flats from Amazon:

Boston’s weather can be changeable and might get a little moist, so we think you will want to have an easily packable and portable rain jacket:

Because Boston can be wet, you will also want to pack an umbrella.  While you may be thinking compact and lightweight, the reality of the winds that come in to Boston means you actually need a sturdy umbrella:

You may not think of Boston as a sunny destination, but you may be doing activities on the water, which means you need to think in terms of protecting your skin and your eyes. 

A great non-greasy sunscreen can keep you from getting burned:

These affordable aviator sunglasses let you buy multiple pairs, which we always suggest if you are anything like us and always losing your sunglasses:

Sample Itinerary

We are such a fan of Boston’s big festivals that, to be honest, our sample itineraries would probably focus on St. Patrick’s Day or Fourth of July festivities.  If you plan on visiting during those times, the festivals are really going to dominate an entire day or more and your planning is going to be focused a lot on proximity to the event and transportation to and from the event.  Your weekend will look completely different from the itinerary that we have put together for a non-festival weekend. 

However, since not everyone can visit during those times, we put together an itinerary for a regular weekend in Boston.  Wake  up in your vacation rental and place your order from Flour.  By the time you are ready, you will have delicious breakfast at your home.  Head out for a tour of Boston’s Freedom Trail, and, once you have worked up an appetite, head to Henrietta’s Kitchen for a relaxing lunch.  Now that you are a little more familiar with Boston, spend the afternoon on a bachelorette scavenger hunt, then plan to feast on traditional New England seafood at No Name Seafood.  Make your plans early, so you can catch the early show at Hunk-O-Mania before heading over for an end-of-night drink at Bell in Hand. 

Bachelorette Party T-Shirts

Do you have to have matching t-shirts for a bachelorette party?  No.  However, they make really great, affordable favors. 

Is your group of girlfriends a little wild?  Then these funny bachelorette party t-shirts may be for you:

Because nobody chaperones the chaperone and brides can be a little boujee:

If your bride is a Harry Potter / Wizardry fan, we love these shirts:

These customized shirts are perfect for a bachelorette:

Custom Bachelorette Party T-Shirt







Travel Insurance

One thing we suggest for any trip is travel insurance.  Things happen.  Illness, bad weather, death in the family, or eek- a canceled wedding- can all derail a bachelorette party.  Getting travel insurance can protect your financial investment.  You may think that your trip is covered with your travel insurance offered by your credit card company.  It may be, but before you rely on your credit card company’s policy, make sure and check into what it covers.  Many credit card policies will cover cancellations for some reasons, but not for others.  You want to have comprehensive coverage that does not just kick in for natural disasters or major illnesses, but also if the wedding is canceled or you have a falling out with the bride.  Of course, we do not want these things to happen, but the only thing worse than a really bad thing happening is a really bad thing happening and you still being out the money!

Why Go

Boston is not usually the first thought people have when planning bachelorette parties.  That is a shame, because Boston might be one of the nation’s best party cities.  We highly suggest heading to Boston during those parties if you are one that wants to get a little wild, but it is also fantastic for people who enjoy beauty and history.  It is an all-season city, even if the winters are brutal, and it plays host to some of the nation’s most iconic events and festivals.  In addition, it is a great destination for the sports-loving bride, because it has almost all of the major sports leagues represented in its sports teams. 

Star Rating

Overall Rating: 3.5/5

While Boston is a great destination, it does not necessarily offer everything you could want for a bachelorette party.  That means that for some brides it is going to be a 2, while it will be a solid 5 stars for other brides.  As a result, we have to average out the star rating.  However, we do not want you to be discouraged by this number.  If you have a bride that loves Boston or has never been and has Boston on her bucket list, it can be a crazy-great destination.  It is also perfect for a road trip destination for people on the East Coast, providing a more casual vibe and often being far more affordable than the overplayed trip to New York City.  Just keep in mind that Boston is not everybody’s vibe, so you may have some lower participation from bachelorette party guests than you would in a more iconic bachelorette party destination location!   


Boston is one of those destinations that seems to surprise people.  When you think of Boston, you think of plenty of historical events and the role in played in the country’s history, but you do not necessarily think of it as a hard-partying city.  However, underneath that historical veneer lies a city with a ton of heart.  A lot more fun than you initially imagine, Boston can offer entertainment, history, and culture in many different ways.  It is also a surprisingly great foodie city, especially for seafood lovers.  However, because it is different than the traditional beachy or party-city bachelorette, make sure the bride is on-board for Boston before you start planning the bachelorette party!


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