What to consider when booking a date for your Cape Cod destination wedding

Picking a date can be super easy but when it comes to dates you prefer combined with sometimes having to work around other friends and family getting married around the same time, all while planning a Cape Cod destination wedding — picking a date can be a little more complicated due to local events and even vacation patterns.

We thought it’d be best to hear it from an expert so we asked our special guest, Jessica Hennessey of Jessica Hennessey Weddings, Emmy award winning wedding planner for Cape Cod, Boston and across the New England, to give us her take on navigating planning the perfect date for your Cape Cod wedding.

Jessica recommended four things to consider when picking a date for your Cape Cod destination wedding.

The most popular dates for weddings on Cape Cod

“Hot dates” are different from year to year, but I’d say the months that book up fastest on-Cape are June and September. July and August tend to be much hotter, and summer rentals and lodging are harder to get. I also work a lot of estate weddings and they do not rent out during that time.

Personally, I love end of May and June weddings. Celebrate at the beginning of the summer and relieve yourself of any planning duties, then celebrate your new marriage the rest of it!

Dates that come with unexpected challenges for a wedding

Definitely the Pan Mass Challenge in August, and any holiday weekends. Pan Mass really puts a big road block in place (no pun intended) for transportation on, off and around the Cape — which means your vendors may request extra nights stay and if you are providing transportation to your guests it will likely not run on time.

Holiday weekends are tough due to the surge in lodging costs and traffic as well. And most vendors will charge a “premium weekend fee” for those.

Dates to avoid when planning a wedding on Cape Cod

If you’re going to be (having your wedding) outside, I’d avoid anything outside of May-September. October can be very cold at night—so unless you have ample heaters it can be super uncomfortable for your guests.

Lesser-known dates that would make for an amazing wedding

Weekday weddings on the Cape are underrated! If most of your guests are traveling, there will likely be at least a 2-night minimum on accommodations. Sometimes up to a week minimum during peak season!

Don’t rule out a Thursday or a Monday wedding. Not only will you save on off-peak days, but most guests will welcome the chance to take an extra day or two and small little vacation if they are going to be traveling anyhow. And if gives you the weekend to actually relax and celebrate with them instead of cramming it all in!

Advice for planning a 2021 Wedding on Cape Cod

I think the biggest thing to think about is if they would like to plan a 2021 wedding, they should start much earlier than “usual” — I usually say 8-months is plenty but a year or more will be a larger guarantee they get the venue and vendors they’re hoping for.

Your Cape Cod destination wedding

To learn more about Jessica Hennessey and her planning services for your own Cape Cod destination wedding that’s coming up, check out her website or follow her on Insta!

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Why not take another minute or two to poke around our site and see what we’re all about. (Tl;dr: we create authentic wedding stories with integrity and sincerity, we’re super fun, and we love taking care of our clients.)

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If you’re looking for more wedding planning advice, you might want to check out these gems

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  How to Get the Best Experience When Hiring a Wedding Videographer
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  Bargain Wedding Video Prices—Let’s Talk About The Trade Offs
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  What to consider when booking a date for your Cape Cod destination wedding