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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!