1. Wondering if your wedding is even going to be legal.
Marriage laws vary from country to country (and even different U.S. states) so do your homework! Find out who is an acceptable officiant (friends ordained on the Internet don't always count), if there is a residency or blood test requirement, and what the marriage license process is. You may find that you need to have a small courthouse ceremony at home first and make your destination wedding mostly symbolic.
2. Booking a hair and makeup person from a distance.
We know you looked into the cost of flying your trusted hair stylist to Mexico. But since that likely won't be possible, consult your stylist at home first -- he or she may have a stylist friend at your destination -- and read reviews for any vendors you have to book long-distance. Then schedule hair and makeup trials for the day after you arrive at your destination.
3. Assembling and shipping the welcome bags for your guests.
Yes, they look adorable and guests love them but they still might cost a fortune to ship and could get caught up in customs. We suggest asking your bridal party and families to each pack a few welcome bags in their checked luggage (or to pack the supplies so you can assemble them on-site).
4. All the "no" RSVPs you'll receive.
Sure, you knew not everyone could afford to make the trip, but it's still a bummer when people officially decline. Try to remember that it has nothing to do with how much they love you and is mostly about their personal budgets and paid time off.
5. Finding the perfect hotel block for your guests.
If you're trying to find the best group accommodations, we're making it way easier to book your hotel room block. It's a fast, free, and simple way to cross that item off your checklist. You’re welcome.
6. Not having your pick of vendors.
If you opt for the more convenient all-in-one wedding package at your resort, you may not be able to get that gorgeous bouquet or super unique wedding cake you want. If you have your heart set on a certain look for your wedding, it might be best to hire a wedding planner who has experience at your destination venue and who can find the best vendors to bring your vision to life.
7. Not seeing your venue in person before the big day.
If you are planning long distance, you may have to book your venue without seeing it first, which can be stressful. We suggest going beyond the photos on the venue’s website; search for it by name on Lover.ly or do a Google search for "Wedding photography blog [destination name]" to find photos of other weddings at your venue. Seeing more photos of the venue in use will give you a better sense of the lighting, layout and any quirks about the space.
Packing for any trip is bad enough; packing your wedding dress, shoes, and accessories is definitely the worst. Start as early as possible and making extremely detailed packing lists. To avoid the "I thought you were bringing the wedding rings" moment, list everything you and your partner need to bring, who is responsible for packing it, and what suitcase or bag it will be packed in.
9. Making sure friends and family members all make it to the destination OK.
From people who wait until the last minute to book flights to sudden storms wreaking havoc on travel plans, getting everyone to the destination can be super stressful. Our advice? Request that VIPs book by a certain date (say, four weeks before the wedding), create a spreadsheet with everyone's flights and cell phone numbers, and cross your fingers that travel conditions are good.
10. The number of people who complain that you're having a destination wedding.
It's an invitation, not a summons! If people don't want to make the trip, they shouldn't make the trip. As long as you aren't making them feel guilty for not attending (you aren't, right?), they shouldn't make you feel guilty for planning a destination wedding.
Taken from: http://www.huffingtonpost.com/2014/08/16/destination-wedding-probl_n_5568510.html?utm_hp_ref=planning-101