Plan Your Wedding Weekend Itinerary & Checklist
Planning a destination wedding weekend? Let’s break down the ultimate step-by-step guide to help you create an unforgettable multi-day celebration. From choosing the perfect wedding venue to tackling logistics like budgeting and guest accommodations, this guide has everything you need to make your dream wedding a reality, without the stress.
Why Plan a Weekend Wedding?
Weddings are no longer just a one-day thing, especially if you’re going destination! A wedding weekend itinerary means more time to celebrate, more memories with your people, and way less stress trying to cram everything into a few hours. Whether you're saying "I do" at an elegant European-style wedding venue in Florida or a beach wedding venue in the beautiful Island of Puerto Rico , giving yourself a whole weekend makes the entire experience feel like a luxurious getaway instead of a giant blur.
Decide on a Budget
Before you start pinning a million ideas and falling in love with every couture dress, let’s talk money. Destination wedding costs can add up fast, depending on where you go, how many guests you bring, and how extra you want to get. Whether you're considering destination wedding packages or planning everything yourself, be real about what you (and your guests) can swing. And don’t forget the little things; favors for destination weddings, travel costs, and who’s covering what (destination weddings who pays for what is a whole convo in itself!)
Pick the Perfect Wedding Destination
Alright, now for the fun part… where in the world are you getting married?! If you're going for a destination wedding weekend, you need a spot that’s not just gorgeous (duh), but also has plenty to do so your guests are entertained from the welcome party to the farewell brunch. The goal? Keep the wedding magic going for more than just one day. Whether you’re dreaming of Caribbean beaches, European romance, or iconic U.S. hotspots, these locations are perfect for a wedding weekend that’s equal parts fun, romantic, and unforgettable.
Caribbean
Puerto Rico
Puerto Rico is the ultimate vibe for a wedding weekend! Think tropical paradise meets rich history. Your guests can wander through Old San Juan, sip piña coladas at the birthplace of the drink (yes, really!), and dance to live salsa in the streets. Bonus: No passports needed if you’re coming from the U.S.!
Dominican Republic
If you want the ease of an all-inclusive resort with the beauty of turquoise waters and white sand beaches, Punta Cana is your spot. Say “I do” with your toes in the sand, then keep the party going with a catamaran cruise, waterfall hikes, or even a cigar-rolling class for your guests. No one’s going to be bored, trust me.
Cancún, Mexico
Cancún is the queen of destination weddings, and for good reason. Luxurious resorts? Check. Insane beach views? Check. Endless activities? Check. Spend the weekend snorkeling in cenotes, exploring ancient Mayan ruins, or just lounging by the pool with unlimited margaritas. Your wedding weekend will feel like a full-on vacation.
Europe
Italy
Italy = pure romance. Whether you’re sipping wine in Tuscany, cruising the canals in Venice, or saying your vows on the cliffs of Amalfi, every backdrop looks straight out of a movie. Plan a pasta-making class or a vineyard tour for your guests so they can soak in the Italian magic while you soak up the newlywed bliss.
Paris, France
Getting married in Paris? Talk about main character energy. Picture saying your vows with the Eiffel Tower twinkling behind you, followed by a croissant-filled brunch, museum-hopping, and a sunset cruise on the Seine River. It’s the perfect mix of romance and iconic city vibes.
Greece
If white-washed buildings, crystal blue waters, and Greek island sunsets sound like a dream, then Santorini is calling your name. Spend the weekend island-hopping, sipping ouzo, and indulging in the freshest Mediterranean food your guests will ever eat. It’s the kind of wedding weekend people will talk about forever.
United States
New York
For the couple that wants that big city energy, a New York wedding is a total flex. Say “I do” in Central Park, party in a chic Manhattan loft, and treat your guests to Broadway shows, rooftop cocktails, and late-night pizza runs. Your wedding will basically feel like the plot of a rom-com (in the best way possible).
Miami, Florida
Miami is for the couple that wants beachfront elegance meets vibrant nightlife. Exchange vows at the Biltmore Hotel or a glam waterfront venue, then spend the weekend sipping mojitos in Little Havana, lounging at South Beach, and dancing till sunrise at one of Miami’s famous clubs. It’s a full-on experience, not just a wedding.
Pro Tip: If the Miami vibe is for you, check out my Top 25 Luxury Wedding Venues in Miami blog for all the hot places to get hitched. Trust me, you will not be disappointed.
California
Whether it’s a Napa Valley vineyard, a Malibu beach estate, or an epic Palm Springs resort, California has something for every kind of couple. Picture a wedding weekend filled with wine tastings, scenic hikes, and chic outdoor dinners under twinkling string lights. It’s giving effortless luxury.
Your Destination Wedding Weekend Planning Timeline: What to Do & When to Do It
Now that you’ve locked in the perfect location, it’s time to get into planning mode. Destination weddings take a little more coordination than local ones, so having a solid timeline will make all the difference. From booking flights and hiring vendors to sending invitations and organizing guest accommodations, here's a stress-free breakdown of when to handle everything, so you can actually enjoy the journey to your big day!
12+ Months Before: Dream and Scheme
Set Your Budget: Figure out what you can spend and maybe look into financing options.
Choose a Destination: Think about the vibe you want and any legal stuff for getting married there.
Hire a Wedding Planner: Especially if you're eyeing a spot where you don't speak the language.
Research Venues and Accommodations: Popular places book up fast, so start early!
9-12 Months Before: Lock It Down
Visit Your Destination (If Possible): Seeing it in person can make a huge difference.
Book Your Venue and Hotels: Make sure there's a range of options for your guests.
Send Save-the-Dates: Give everyone plenty of time to plan.
Start Shopping for Attire: Consider the destination's climate when picking your outfit.
6-9 Months Before: Details, Details
Choose an Officiant: Whether it's a local or someone special to you.
Book Vendors: Think photographers, caterers, florists, etc.
Plan Group Activities: Make the weekend memorable with fun events.
Set Up a Wedding Website: Keep everyone in the loop with all the deets.
3-6 Months Before: Final Touches
Send Formal Invitations: Include all the important info and an RSVP deadline.
Confirm Travel Arrangements: Make sure you and your guests are all set.
Plan the Ceremony and Reception Details: Think about music, readings, and décor.
Arrange Legal Requirements: Ensure all your paperwork is in order for the marriage to be official.
1-3 Months Before: Almost There
Finalize Guest Count: Let your venue and caterer know the numbers.
Confirm All Bookings: Double-check with vendors and venues.
Have a Hair and Makeup Trial: Make sure you're happy with your look.
Prepare Welcome Bags: A little something for your guests upon arrival.
2-4 Weeks Before: The Final Countdown
Pack for Your Trip: Don't forget the rings and important documents (like passports if needed)!
Confirm Arrival Times: Touch base with vendors and the wedding party.
Break In Your Shoes: Avoid any wedding day blisters.
Relax and Enjoy: Take some time for self-care before the big day.
Your Wedding Weekend Itinerary
Your planning isn’t done just yet! You have your dream destination and your 12 month checklist but how about the details of your actual wedding weekend? I’ve got you covered there! Here’s a quick three-day itinerary for each location so you-and your guests can have an epic celebration from start to finish.
Puerto Rico
Day 1: Welcome guests with a beachfront cocktail hour in Old San Juan, followed by a lively welcome dinner with local Puerto Rican cuisine and live salsa music.
Day 2: Spend the morning exploring El Yunque Rainforest, then unwind on Flamenco Beach before a sunset rehearsal dinner with ocean views.
Day 3: Exchange vows at a historic fort or beachside resort, then dance the night away with a live plena band.
Pro Tip: Book a group kayak tour to the bioluminescent bay for a magical post-wedding experience!
Dominican Republic
Day 1: Greet guests with tropical drinks at the resort, then enjoy a relaxed beachfront bonfire with Dominican music.
Day 2: Take a catamaran excursion to Saona Island, then host a seaside rehearsal dinner with fresh seafood and cocktails.
Day 3: Have a stunning beach ceremony at sunset, followed by a reception featuring bachata dancing and premium Dominican rum.
Pro Tip: Plan a waterfall excursion for adventurous guests who want to explore beyond the beach.
Cancún, Mexico
Day 1: Kick off the wedding weekend with a tequila tasting and welcome dinner at a rooftop venue with ocean views.
Day 2: Explore ancient Mayan ruins in Tulum, then relax at a cenote before a beachfront rehearsal dinner.
Day 3: Say "I do" on a white-sand beach, then celebrate with a lively reception featuring a mariachi band and mezcal bar.
Pro Tip: Organize a post-wedding brunch with authentic Mexican chilaquiles and fresh tropical juices.
Italy (Amalfi Coast)
Day 1: Host a welcome happy hour at a cliffside terrace, sipping Limoncello as the sun sets.
Day 2: Take a private boat tour along the Amalfi Coast before a candlelit rehearsal dinner at a local trattoria.
Day 3: Have a romantic villa or seaside ceremony, followed by an Italian feast with fresh pasta and endless Prosecco.
Pro Tip: Plan a group wine tasting in Ravello for a relaxed post-wedding experience.
Paris, France
Day 1: Welcome guests with a champagne toast at a rooftop bar overlooking the Eiffel Tower.
Day 2: Organize a Seine River cruise and let guests explore iconic landmarks before a cozy rehearsal dinner at a Parisian bistro.
Day 3: Tie the knot in a historic chapel or garden, then indulge in a reception filled with French pastries and jazz music.
Pro Tip: Treat guests to a private macaron-making class as a fun farewell activity.
Greece (Santorini)
Day 1: Kick off your wedding weekend with a sunset welcome party featuring local Greek wine and mezze platters.
Day 2: Take guests on a catamaran tour around the caldera, then enjoy a scenic rehearsal dinner in Oia.
Day 3: Say "I do" overlooking the Aegean Sea, then dance under the stars with a traditional Greek band.
Pro Tip: Arrange for post-wedding donkey rides through the village for a fun and unique touch.
New York City
Day 1: Welcome guests with rooftop cocktails, then head to a Broadway show or chic dinner in SoHo.
Day 2: Plan a private sightseeing tour, then host a glamorous rehearsal dinner in a stylish Manhattan loft.
Day 3: Get married in Central Park or a rooftop venue, then party the night away at a swanky NYC lounge.
Pro Tip: Surprise guests with a late-night food truck serving NYC-style pizza or hot dogs.
Miami, Florida
Day 1: Greet guests with mojitos and Cuban bites at a South Beach welcome party.
Day 2: Enjoy a boat day on Biscayne Bay before a rehearsal dinner at a trendy Wynwood restaurant.
Day 3: Exchange vows at a chic waterfront venue, then keep the energy high with a salsa-filled reception.
Pro Tip: Treat guests to a farewell brunch with Cuban coffee and pastelitos.
California (Napa/Malibu/Palm Springs)
Day 1: Welcome guests with a vineyard wine tasting in Napa, a beachfront bonfire in Malibu, or a retro pool party in Palm Springs.
Day 2: Plan an outdoor adventure like a scenic hike or wine tour, then host a relaxed rehearsal dinner.
Day 3: Have a dreamy outdoor ceremony, then celebrate with a farm-to-table feast and dancing under twinkling lights.
Pro Tip: Surprise guests with customized wine bottles as wedding favors!
Wedding Insurance & Local Laws: What You Need to Know (Without the Boring Stuff)
Wedding Insurance: The Ultimate Backup Plan
Okay, picture this: You've planned every little detail of your dream destination wedding, but then — BAM — unexpected weather crashes the party, or a vendor totally flakes. Nightmare, right? That’s where wedding insurance comes in. It’s basically your safety net for when things go not-so-according-to-plan. Whether it’s lost deposits, delayed flights, or a rogue tropical storm (ugh), insurance keeps your big day from turning into a budgeting disaster. Definitely worth looking into, especially if your wedding is happening in a far-off, dreamy-but-unpredictable location.
Don't Let Local Marriage Laws Surprise You
So, fun fact: Not every country lets you just show up and say I do. Some require you to be there for a certain number of days beforehand, others need specific documents (sometimes in a different language, because why not make things more complicated?). The last thing you want is to realize your marriage isn't legally recognized once you’re back home. Major yikes. A little research upfront (or hiring a local planner who knows the ropes) can save you a ton of stress later.
Wedding Weekend Packages: Should You Go All-Inclusive or DIY?
The Perks of an All-Inclusive Package
If planning every tiny detail makes you want to scream into a pillow, an all-inclusive package might be your new best friend. Resorts and venues often bundle the big stuff like venue, catering, décor, even a photographer, so you don’t have to juggle a million vendors. It’s a total lifesaver if you want to keep things simple and stress-free (aka, actually enjoy your wedding instead of playing event planner). Plus, these packages can be a sneaky way to save $$$.
When to Fly in Your Dream Team
Now, if there’s one thing worth splurging on, it’s your photographer. Sure, the resort might offer one, but if you’ve been stalking a specific photographer’s Instagram for months (or years, no judgment), it’s totally worth bringing them along. Your wedding photos are the only thing (besides the ring and maybe a dress) that’ll last forever, so make sure you’re obsessed with who’s behind the camera.
Capturing Every Moment: Why Your Destination Wedding Weekend Package Matters
Wedding Weekend Multi-Day Coverage = No Missed Moments
Your wedding isn’t just one day, it’s an entire experience. From the welcome party to the teary farewell brunch, you’ll want every little moment captured. That’s where a destination wedding photographer who gets it comes in. They know how to tell the full story of your wedding, not just the ceremony. And let’s be real, those candid, in-the-moment shots are the ones you’ll love the most.
Stunning Scenery, Meet Stunning Photos
A photographer who specializes in destination weddings isn’t just there to snap pics, they know exactly how to work with the location to make your photos next level. Whether it’s golden hour on a beach or a dramatic clifftop shot, they know how to use the scenery to make your wedding look like it belongs in a magazine.
At the end of the day, your wedding is your adventure. Whatever your choice is, going full all-inclusive, DIYing your dream team, or eloping in the middle of nowhere, make sure your choices feel right for you. And most importantly? Have fun with it. Because that’s what you’ll remember the most.
Destination Wedding FAQs: Everything You Need to Know!
Q: Are destination weddings worth it?
A: 1000% YES. If the idea of saying "I do" somewhere breathtaking while turning your wedding into a full-on experience sounds like your vibe, then a destination wedding is totally worth it. You get a built-in honeymoon, quality time with your favorite people, and photos that look straight out of a magazine.
Q: But wait... are destination weddings selfish?
A: Nope! Your wedding is about you, but being thoughtful about your guests is a nice touch. Give plenty of notice, pick a location that’s easy-ish to get to (hi, Miami beach weddings), and share a range of lodging options to fit different budgets. If they can’t make it, they’ll celebrate you from afar!
Q: How much does a destination wedding even cost?
A: That depends on the location, guest count, and how extra you want to be. You can totally pull off a dreamy destination wedding for under $10K with a small guest list, or go full luxury mode at a European-style venue in Florida (Biltmore Miami, anyone?).
Q: How do I even start planning a destination wedding?
A: Step one: don’t panic. Step two: figure out your budget, dream location, and guest list. Once you’ve got that down, lock in your photographer, venue, and key vendors. Check out local marriage laws, send those invites early, and plan a fun weekend itinerary to keep the party going. (This blog is basically your go-to brides guide, so you’re in the right place!)
Q: Should I book an all-inclusive wedding package?
A: If you want a no-stress wedding, YES. Resorts in Cancún, Punta Cana, and even Coconut Grove Miami offer packages that cover everything, venue, catering, décor, and sometimes even your photographer. But if you’re a details girlie with a specific vision, booking vendors separately might be the move.
Q: Who pays for what in a destination wedding?
A: Typically, you and your partner cover the wedding events (venue, food, etc.), and guests pay for their flights and hotel. If you want to help, consider booking a block of rooms at a discount or covering a fun welcome dinner or farewell brunch.
Q: Where are the best places to get married?
A: It depends on the vibe you’re going for! Dreaming of a European romance? Italy, France, and Greece are chefs kiss. Want beachy and beautiful? Mexico, the Dominican Republic, and yes, Miami, have stunning venues. Looking for something different? Napa Valley, NYC, and Palm Springs bring the drama in all the best ways.
Q: When should I book my photographer?
A: ASAP, bestie! The top destination wedding photographers book up FAST, especially if you want that high-fashion, editorial look. If possible, go for multi-day coverage so they can capture everything, welcome party, beach hangs, farewell brunch, all of it.
Q: Should I bring my own photographer or use the resort one?
A: If gorgeous, cinematic wedding photography is a priority (and it should be), bring your own. Resort photographers tend to have a generic, cookie-cutter style. But a photographer you love? They’ll capture your day exactly how you imagined, no awkward poses, just pure magic.
Q: What do I wear to a destination wedding?
A: Match the vibe! Beach wedding? Light, flowy fabrics (you do not want to sweat through a heavy gown). European villa? Go elegant. Chic city wedding? A sleek, modern dress will turn heads. If you’re outdoors, a second, more dance-friendly look for the reception is always a good call.
Q: Pros and cons of a destination wedding?
A: Pros: Iconic locations, multi-day celebrations, built-in honeymoon, and a more intimate guest list. Cons: Travel logistics, legal paperwork, and some guests might not be able to make it (but honestly, that might just help trim the list).
Q: How do I get the best couples photos?
A: Book a photographer who gets editorial wedding photography and knows how to direct you without making you feel awkward. Need inspo? Look up couples photography ideas, couple photo pose ideas, or even couple photoshoot poses for that Pinterest-worthy magic.
That’s a wrap, babe! Hopefully, this FAQ clears up all your burning questions. At the end of the day, trust your gut, book vendors you actually vibe with, and focus on what makes you and your partner happiest. Your dream wedding weekend is about to be everything.
