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Your Ultimate Guide to Planning a Dream Destination Wedding

Just imagine it: your friends and family are gathered together in a beautiful spot that belongs on a postcard. Everyone you love ooh's and ahh's over the sunset on the beach (or mountain or wherever else you picture) while sipping on piña coladas and watching you and your new husband dance the night away. Then, instead of leaving early for the honeymoon, you and your spouse stay and celebrate the honeymoon right where you are. 

Sounds like a perfect dream doesn't it? With a destination wedding, this can actually be a reality! Destination weddings are often overlooked or brushed aside based on budgets and stress, but they can be a lot easier than you think. Read on to see our helpful guide to navigating a destination wedding, including top spots and the best dresses!

Planning the Destination Wedding of Your Dreams

There's a lot to consider when it comes to choosing your wedding venue, whether it's a destination wedding or not. Before you choose, we complied a pros and cons list to help make your decision a little easier. 

Just so you know, this post contains affiliate links through Apple Vacations. Though we can receive commission, opinions are entirely our own. 

Pros & Cons of Choosing a Destination Wedding


* A romantic and unforgettable setting. Nothing says "love's eternal glory" more than saying your vows on the Rocky Mountains. Traveling to your wedding site will be an adventure you and your spouse will never forget, and will create so many special, amazing memories. Plus, your guests will never forget your wedding and their personal experiences surrounding it! (I mean who doesn't want an excuse to visit the Caribbean.) 

* It provides a unique setting and wedding. If you are hoping to have a wedding that celebrates you and your partner's personalities or unique relationship, a destination wedding is different from anything you could celebrate at home. You don't have to worry about having a "Pinterest" wedding like everyone else when yours occurs in such a unique location. 

All inclusive resorts. Need I say more? While you by no means have to celebrate your wedding out of the country or at a fancy resort, is there anything better than all you can eat food and drinks? For your wedding/honeymoon? 

  • * It's another way to trim that budget. Your largest wedding related cost will probably come from the food and drinks for your guests. With a destination wedding you'll have a smaller, more intimate guest list and as a result won't have to order as much food...and here enters the extra money you and your partner needed to go zip-lining. (It also provides you an excuse to not invite those people you were hoping would RSVP "no" anyways...)
  •  Destination weddings are romantic and unforgettable | Your Ultimate Guide to Planning a Destination Wedding | Kennedy Blue | Monica Lopez Photography

     Monica Lopez Photography


    * Travel expenses. While celebrating your love in Italy would be amazing, you also have to get there somehow. Plan to factor in plane tickets, hotels, food, souvenirs, passport fees (if you don't have one yet), and some possible additional luggage fees. Tip: if you choose to go abroad and want to save money, try and find a spot where the cost of living is lower or where your home currency will be worth more.  

    * You will have to plan your wedding remotely. Unless you have a large wedding budget, you probably won't get a chance to visit your venue before you arrive for the real deal. I'm personally a very visual person, so not being able to actually see where my decor will be placed and how the tables will be set up would kind of stress me out. (I think it would still be worth it though.) Thankfully, the internet has made this much easier because you can see other people's pictures and reviews online and can even video chat with your vendors.

    * It can be a lot of work. Suddenly, you also have to book plane tickets, rent a car, figure out how you will get your wedding dress on the plane, and more. That can be more of a headache than some people want. The nice think about destination weddings is that they can often be very simple. You don't have to worry about decor or a backdrop when you have the naturally beautiful venue to help you out. Tip: a lot of hotels or resorts may offer a destination wedding planner to help you out. Even if they don't, many are accustomed to weddings and are happy to help you plan and feel ready.    

    The Top 5 Best Destination Wedding Locations

    Punta Cana, Dominican Republic

    A cute and on-theme wedding invitation for a tropical destination wedding | Your Ultimate Guide to Planning a Destination Wedding | Kennedy Blue

    Apart from the clear blue water, sand beaches, and beautiful landscape, the Dominican Republic is also pretty affordable. And any resort you choose will offer all the friendly guidance and assistance you need. Added bonus: After the recent hurricane damage, the country will be really thankful for any tourist $$ that can help them rebuild.

    Vail, Colorado

    Celebrate your wedding at Vail, Colorado | Your Ultimate Guide to Planning Your Destination Wedding | Kennedy Blue

    Yes, Vail the world famous ski resort. You may expect to be tanning on the beach during your destination wedding, but they don't always have to be somewhere tropical (or abroad). Vail is an absolutely STUNNING location with picturesque mountains, a beautiful resort, more snow than you could hope for in the winter, but also flower-filled meadows in the summer. Your family won't have to worry about passports, and plane tickets can be relatively affordable. Did I mention that you can tie the knot on a literal mountain?!

    Apple Vacations offers a variety of deals to ski resorts across the U.S. Check out their selection of fabulous Vail deals here

    Outer Banks, North Carolina

    North Carolina is the perfect spot for a destination wedding | Your Ultimate Guide to Planning a Destination Wedding | Kennedy Blue | Tim Larsen Photography

    Tim Larsen Photography

    With its 130 miles of open beach, this region offers a picturesque location that might not be too far from home for you (but still feels like a vacation). The weather is best in the late spring, summer, or even at the start of fall. Of course, fall and winter will be most affordable for traveling, and the orange-y sunsets during those seasons will take your breath away.  

    You have the option of going with a tropical beach setting or a more rustic lighthouse backdrop – or both for different parts of the big celebration! Whichever route you choose, you can’t go wrong. Because even though it’s right here at home, it will feel like a scene out of a storybook.   


    Hawaii is a popular spot for destination weddings, for a very good reason. Absolutely gorgeous wherever you go, you will come out with some seriously stunning wedding pictures. Dry season runs from May through October, and after that, rainfall (if you get any at all) is short-lived and mild. Tourist season is winter to early spring, so even better if you can avoid that. Also a big bonus: there are endless options for fun things your guests can do, no matter what their ages and interests. I attended a destination wedding in Maui, Hawaii a few years ago and it is still the best wedding I have ever attended, hands down. The bride walked down the aisle (on the beach of course) to the song "Somewhere Over the Rainbow" played on a ukulele, everyone wore leis, and I kid you not there were sea turtles who came up on the beach shortly after the wedding ceremony. It was absolutely unforgettable, and so much fun. 

    Celebrate your wedding in Hawaii! | Your Ultimate Guide to Planning your Dream Destination Wedding | Kennedy Blue | Jim Kennedy Photographers

    Jim Kennedy Photographers

    The one downside of choosing Hawaii is that it can be expensive. Check out Apple Vacations' huge variety of Hawaiian resorts to find the best deal for you and your guests.

    Door County, Wisconsin

    Slate blue bridesmaid dresses look stunning for this outdoor wedding | Your Ultimate Guide to Planning your Dream Destination Wedding | Kennedy Blue | Bram Vandermark Photography

    Brad Vandermark Photography

    Besides the beautiful lakefront backdrop, this spot is convenient in so many ways. It’s a four-hour drive from Chicago, Illinois and Madison, Wisconsin. There are wineries and farms all around the area, making for the tastiest beverages and freshest meals of your own choice. This quaint little vacation spot, located between Green Bay and and Lake Michigan, has earned the title of the “Cape Cod of the Midwest.”

    Fall is gorgeous in Door County, although summer is usually the most popular time to wed here. If you choose to go the summer route, we recommend booking early. Winter is not ideal, as it often brings snow and icy roads. 

    What to Wear: Destination Wedding Dresses 

    Not shoes, for starters. I'm kidding, but hey isn't it awesome that at some destinations you totally don't have to?

    Choosing dresses for you and your bridesmaids will be vary based on your location. Consider temperature, if you expect the bottom of your dress to get dirty, and how you plan to transport your dress. If you are visiting during a rainy season, plan for that with umbrellas. Don't choose an extravagant ballgown wedding dress, because it will be harder to transport. Going somewhere warm? Elect for sleeveless or short bridesmaid dresses. You get the picture. And have fun with this! Find fun, short, floral dresses for your bridesmaids for your beach wedding or take pictures in flannels for your outdoor wedding in Wisconsin. The options are endless. 

    For your wedding dress, choosing something simple is usually best. Depending where you are, your dress could get dirty and plus, why go all out on an expensive dress when you could save the money for scuba diving? 

    Our two favorite Kennedy Blue destination-esque bridal gowns are Avery and Karlie. Simple but stunning, you will glow in these gowns. 

    Choose a simple bridal gown for your beautiful destination wedding | Your Ultimate Guide to Destination Weddings | Kennedy Blue

    Destination Bridesmaid Dresses 

    Bridesmaid dresses are totally dependent on your destination. While short dresses often come to mind, we've seen wedding parties in any and every style. My favorite is when brides have a lot of fun mixing and matching the 'maids dresses for a fun and unique look. While any Kennedy Blue dress is destination ready, here are my two favorite, Camilla featured in mint blue and Thea in navy blue. 

    Your bridesmaid dresses for your destination wedding can be anything from short to long to mix and match! | Your Ultimate Guide to Destination Weddings | Kennedy Blue

    Destination Guest Dresses

    Again, this choice is totally dependent on the wedding location. Destination weddings tend to be more casual and laid back, which also means guests' attire can also be more casual. If you have any questions about the dress code make sure to check with the bride and groom. Overall, choose something that's cute, comfortable, and will be appropriate for the weather/setting/theme. Tip: choose one of Kennedy Blue's short bridesmaid dresses to wear as a guest! One of the marketing ladies here wore Quinn to her cousin's wedding and it was adorable and nobody even guessed that it was a bridesmaid dress! If you don't want to go the short bridesmaid dress route, check out these super cute dresses from Etsy. These are both dresses you can definitely wear again, and totally fit the "wedding guest etiquette" guidelines. Wear the first dress to an outdoor wedding (I'm picturing a mountain or European wedding) and the second to pretty much any warm weather wedding.

    What should you wear when you're a wedding guest at a destination wedding? Wear this cute boho maxi dress! | Your Ultimate Guide to Planning a Dream Destination Wedding | Kennedy Blue

    Shop: silkandmore

    Wear this vintage floral dress when you're the guest at a destination wedding! | Your Ultimate Guide to Planning a Dream Destination Wedding | Kennedy Blue

    Shop: JasmineDresses

    Additional Planning Tips

    * If you have friends or family that live near the destination ask them to check out the venue, send you pictures, and coordinate with your planner if needed. 

    * After you choose your venue, ask if there's a wedding planner available to help you. 

    * Create a list of suggested activities or places to eat for your guests. You can coordinate to visit some places together, or it can serve as a way to keep them out of your hair. 

    * Also, create an itinerary for your guests. Make a run down of all the places they need to be and at what times (include addresses!) Add in contact information for who they can reach out to while you're there such as your maid of honor or groomsmen. 

    * Know which guests may need special care or accommodations, and make arrangements ahead of time. 

    * Delegate tasks. That's why you invited your family and friends along! Never feel bad about asking for help, and realize when to say no when you need to. 

    * Alert your credit card companies that you are leaving, where you will be, and how long you expect to be gone. I know this is weird advice, but you would hate to try and pay for your wedding food and get flagged for fraud! 

    * Most importantly, take a deep breath, smile, and have fun! You’re marrying your soulmate, in some gorgeous location, and what could be better than that? 

    Let's Chat

    After reading our guide to destination weddings, what do you think? Would you want to have a destination wedding for yourself? Did you see any locations you would love to try? Let us know in the comments below!

    Clearance Bridesmaid Dress sale!

    Ready to ship bridesmaid dresses from $19.95 to $69.99 — Available while supplies last.


    Leave a comment

    Brenna Baker
    October 22, 2017 21:02

    LOVE THIS! We are doing a destination wedding!

    Nicole Sauter
    October 21, 2017 20:23

    I’d love a destination wedding if the budget allowed!

    Brittany Cano
    October 20, 2017 10:45

    I wish my budget would allow for a destination wedding. Love all of these!

    October 19, 2017 15:21

    Love this! Thanks for the tips!

    October 16, 2017 17:50

    I love these tips! Will definitely consider a destination wedding now!

    October 15, 2017 12:13

    We are considering a destination wedding — though for us a big question is about the friends and family we want to celebrate with us that couldn’t come to a destination wedding. We still might consider it with a big reception party when we get back to include more of our loved ones though!

    October 14, 2017 21:29

    Yes, I definitely want a destination wedding!!!

    Leave a comment

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