The Multi-Day Wedding Weekend Itinerary, Done Right
PHOTO BY JUSTIN JUN LEE
Multi-day weddings have quickly caught on and even become the norm for many American couples. While many religions and cultures have long celebrated weddings over the course of several days, early Western wedding traditions were simpler: a simple church ceremony followed by cake and punch.
So, how’d weddings evolve into two- and three-day events (or longer)? We’d say it comes from couples’ desire to extend the time they’re able to spend with their guests. Weddings are one of the few moments in life where you’re able to celebrate a major milestone with nearly everyone you love, so why not include a few additional opportunities to spend time with them?
Multi-Day Wedding Itinerary Basics
We say this often around here: don’t make your wedding feel like a conference. When planning your multi-day celebration, you’ll want to ensure that guests are feeling welcomed and joyful rather than rushed from one mandatory activity to the next.
Turn meals into events. If your guests are traveling to your wedding weekend — even if you don’t consider it a destination wedding — one thing they’ll definitely be doing is looking for places to eat. Making meals celebratory is an easy way to get a high attendance rate: everyone wants to eat!
Plan to do nothing. Remember that your guests are either meeting each other for the first time or being reunited with one another. Create settings for unstructured chill time as well as activities, so guests are able to enjoy each others’ company in a relaxed setting.
Allow for free time. You may be hosting your multi-day wedding in the most exciting city or at the liveliest resort, but try not to overwhelm your guests with things to do. Keep in mind that while some will want to party all weekend, others may crave quiet time.
Communicate clearly. However you choose to communicate with your guests, whether it’s a printed booklet in each welcome bag or a “know-before-you-go” email, make sure guests have all the details needed to enjoy your multi-day celebration. Times, locations, dress codes, and transportation info are all key. An informed guest is a happy guest!
Now that we’ve laid out some guidelines, let’s look at a few curated examples of multi-day wedding itineraries.
PHOTO BY LORREN & BRAMAN
The Classic Three-Day Wedding Weekend Itinerary
Most couples are familiar with this format, and it's an ultra-popular choice because it works.
Day 1: Rehearsal Dinner & Welcome Party
Formal Dinner
Most traditionally, rehearsal dinners are attended by only the family and friends who participate in the ceremony. But you don’t have to be strict about this!Casual Drinks
Realizing that many guests arrive the night before the wedding, couples have begun to host more casual parties where everyone’s welcome. This is a good chance for your guests to get to know each other ahead of the wedding in a low-key setting.
Day 2: Wedding Ceremony & Reception
The main event. No explanation needed here!
Day 3: Farewell Brunch
Brunch Buffet
Hosting a buffet at the hotel where you’ve booked a room block is convenient and often comes with discounted rates. This tends to be a drop-in, optional event — there’s an understanding that guests may be traveling and/or recovering from partying the night before.
A Destination Wedding Weekend Itinerary
Considering hosting your wedding in a big city? Whether it’s your home or a place that holds memories for you, cities are perfectly suited for destination multi-day weddings. Let’s take it international, to San Miguel de Allende, Mexico: a vibrant and colorful city that’s rapidly gaining popularity as a wedding destination.
Day 1: ¡Bienvenidos a Mexico!
Hospitality Suite
Anticipate guest arrival the day before festivities begin, and welcome them with your own take on a hospitality suite. Offer drinks, snacks, and plenty of places to lounge after a day of international travel so guests can come and go as they please. This is also a chance to turn the traditional welcome bag into a shopping experience — let your guests pick up bags and choose from curated goodies to fill them with.
Day 2: Cultural Immersion
Cooking Classes, Walking Tours, & More
If you’re hosting your wedding at a resort like Rosewood San Miguel de Allende, you’ll find that they have several culture-specific activities to choose from. You can also provide a handpicked list of places to go and things to do in the city and encourage them to explore. Guests will appreciate a day to enjoy the destination!Welcome Dinner
After the rehearsal’s complete, host everyone for a lively, but relatively casual dinner (especially if your wedding reception will be more formal). Make the food and beverage local and lean into specialties of the region — San Miguel de Allende, for example, is one of the best regions for wine in Mexico.
Day 3: Wedding Day
Morning Yoga
Offer a quiet activity the morning of the wedding for guests who are looking for a calm start to the day.Wedding Ceremony & Reception
A late-night party is a must in Mexico.
Day 4: Relaxation Before Travel
Hospitality Suite, Part 2
Re-open the hospitality suite with brunch, lots of electrolytes (maybe even IVs), and parting gifts that fit easily into a suitcase. Encourage guests to drop by before checkout, but expect it to be a quiet day as guests leave for the airport throughout the day.
Resort Weekend Buyout Wedding
Imagine a multi-day wedding where every resort guest you see is a family member or friend. That’s the magic of a resort buyout! Here’s how we’d map out an itinerary for a multi-day wedding at a luxury resort like Half Moon in Jamaica.
Day 1: Welcome to Resort Life
Wedding Party Spa Day
Treat yourself and your wedding party to a relaxing afternoon at one of Jamaica’s best spas before everything kicks off. What better way to ease into paradise?Beachside Welcome Celebration
Once everyone’s arrived and settled in, invite them to join you at the beach for drinks and dinner by the Caribbean sea. This is a good opportunity to bring in as much local energy as you can: food, drinks, decor, and entertainment.
Day 2: Wedding Day
Pickleball Tournament
Half Moon is great for couples who enjoy a bit of sport with their leisure, with a world-class golf course, tennis and pickleball, horseback riding, and more available on property. Kick off the wedding morning with a low-stakes pickleball tournament to get loose before the ceremony in the evening.Wedding Ceremony & Reception
All outdoors to take advantage of the beautiful weather.
Day 3: Poolside
Pool Party
Spend the day recovering by the largest resort pool with brunch. Guests can come and go as they please, and even extend their stay if they’d like more time to experience everything the resort has to offer.
PHOTO BY LESLIE RODRIGUEZ
Choose Your Own Adventure
Whether your guests are traveling long or short distances, hosting a multi-day celebration is a thoughtful approach — creating an itinerary will give them options where they’d otherwise be researching things to do and places to go. Remember that they want to spend time with you!
Providing multiple opportunities to hang also relieves pressure you may feel to chat with every guest during the wedding reception (which is often a challenge, as you’ve likely heard from married friends). It’s all about creating those shared moments.
Ready to plan your multi-day wedding? Reach out to us and we’ll orchestrate the magic.