What to Consider Before Finalizing a Date for Your Cape Cod Destination Wedding

Wedding Video Advice

Posted by:

Cindy Caughey

Avoid planning headaches and find out what you need to know about picking a date for your destination wedding on Cape Cod.


When planning a Cape Cod destination wedding, there are a few things you need to consider when picking a date. Because we’re a popular summer destination, it can be a little more complicated to plan a wedding due to local events and vacation patterns.

We thought it’d be best to hear it from an expert. So we asked Jessica Hennessey of Jessica Hennessey Weddings (Emmy award-winning wedding planner for Cape Cod, Boston, and across New England) for her take on picking the perfect date for your Cape Cod wedding.

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

Bridesmaids overlooking Nantucket Sound

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 roadblock 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 for your guests, it will likely not run on time.

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

Delicate wedding dress hanging on window

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 a little vacation if they are going to be traveling anyhow. And it gives you the weekend to relax and celebrate with them instead of cramming it all in!

Glass of champagne with bridesmaids on the beach on Cape Cod

When should you start planning wedding on Cape Cod

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!

And if you’re thinking about getting a wedding video

Do you know that we create authentic stories for best friends in love specifically for Cape Cod and the Islands? It’s true! Take a look around. If you’re getting a good feeling about all that, fill out the form on our Contact Page, introduce yourself, and tell me about your wedding!


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Drawing from our experience as a graphic designer (Cindy) and journalist (Sean), we see stories differently. Our films reflect honesty, strength of character, and real moments, all in a way that's natural and comfortable. 

Whether our films help you to find the light within or provide a story of your day, we feel this is our opportunity to help your legacy live on throughout time. 

My husband and business partner, Sean, and I have spent past 16 years living out our dream on Cape Cod as wedding cinematographers. We believe that every story is unique, and we help even the most camera-shy couples feel free to be themselves in front of the cameras.