Wedding Weekend Itinerary: How to Plan a Destination Wedding Weekend for 100 Guests
If you’re dreaming of saying “I do” in a place that feels like an escape — whether it’s a sun-soaked coastal town, a cliffside villa, or a historic European estate — planning a destination wedding weekend is the perfect way to turn your celebration into a full experience for your guests. Your guide for how to plan a thoughtful wedding weekend itinerary is below.
But with so many moving parts, it can be hard to know where to start. Here’s a simple breakdown of how to plan a multi-day destination wedding for around 100 guests — complete with real examples and ideas to make each moment feel thoughtful, personal, and memorable.
Step 1: Choose Your Destination With Guest Experience in Mind
When planning a destination wedding, think beyond the wedding day itself. Choose a location that offers a natural sense of place and opportunities for connection — not just beautiful scenery.
For example:
- Santa Barbara, California offers ocean views, vineyards, and historic charm, all within a few miles.
- Savannah, Georgia gives guests walkable cobblestone streets, delicious southern fare, and live oaks draped in Spanish moss with exceptional hospitality.
- The Amalfi Coast, Italy is ideal for couples craving romance and adventure — pastel seaside villages, cliffside villas, and world-renowned cuisine make it a dream setting for both weddings and guest experiences.
When choosing your venue, consider on-site accommodations, nearby hotels, and transportation ease. Keeping your guests close together makes it easier to host multiple events throughout the weekend without logistical stress.
Step 2: Start the Celebration With a Welcome Cocktail Party
A welcome party is the best way to greet your guests and set the tone for your destination wedding weekend. It doesn’t have to be overly formal — think relaxed, social, and fun.
Timing: The evening before your wedding, typically 6–9 PM.
Ideas:
- Coastal vibe: Host a casual cocktail hour on a terrace overlooking the sea, with local seafood bites and live acoustic music.
- Garden chic: Set up bistro lights and serve signature drinks under the stars with lawn games and soft jazz.
- Amalfi-inspired: Welcome guests with Aperol spritzes, limoncello tastings, and an al fresco dinner featuring fresh pasta, citrus, and local wines as the sun sets over the Tyrrhenian Sea.
The welcome party helps break the ice so guests feel comfortable and connected by the time your wedding day arrives — which makes your photos (and overall experience) feel even more natural and joyful.
Step 3: Thoughtful Touches — Welcome Gifts for Your Guests
Destination weddings often mean your guests have traveled far to celebrate with you. Offering a welcome gift is a beautiful way to show appreciation and introduce them to your destination.
Many couples include these gifts in guests’ hotel rooms, have their wedding planner act as a concierge and greet every guest with a gift upon arrival, or deliver them during the welcome party. Items might reflect the region — like locally made olive oil, Italian chocolates, or a mini bottle of limoncello — alongside personal touches such as a handwritten note or itinerary for the weekend.
A well-curated welcome gift not only makes your guests feel appreciated but also sets the tone for the experience ahead. (Stay tuned for my upcoming post on exactly what to include in your destination wedding welcome gifts — I’ll be linking it here soon!)
Step 4: Craft an Effortless Wedding Day Timeline
When planning for 100 guests, prioritize flow and comfort. Build in generous transition times between events, especially if guests are unfamiliar with the area.
A well-paced Amalfi Coast wedding day might include:
- A late morning or early afternoon start for hair and makeup to allow for a leisurely morning.
- Pre-ceremony refreshments like lemonade or prosecco for guests arriving early.
- A golden hour ceremony followed by an outdoor dinner and dancing overlooking the sea.
If your venue offers stunning natural backdrops, keep your design minimal — let the setting do the storytelling.
Step 5: Plan a Low-Key Post-Wedding Hangout
The day after your wedding is your chance to relax and soak in the joy. A casual event — think poolside brunch or a seaside gathering — lets you reconnect with everyone before goodbyes begin.
Ideas:
- Pool Day Brunch: Reserve cabanas, serve mimosas and smoothies, and offer light bites like yogurt parfaits and avocado toast.
- Beach Club Day: On the Amalfi Coast, host a relaxed afternoon at a local lido with loungers, prosecco, and wood-fired pizzas.
- Farewell Coffee & Pastries: For a smaller crowd, invite guests for espresso and fresh cornetti before they depart.
Keeping it low-key ensures you can be present, laugh, and share stories from the night before — without the pressure of formal hosting.
Step 6: Build a Thoughtful Guest Itinerary
Once you’ve mapped out your events, create a simple itinerary to share with your guests. Include transportation details, dress codes, and a few free-time suggestions so guests can explore on their own.
For example, on the Amalfi Coast you might suggest:
- A morning boat ride to Capri
- Shopping in Positano’s boutiques
- A sunset aperitivo at a cliffside bar overlooking the sea
This helps guests feel taken care of and excited to immerse themselves in your destination.
A few final thoughts…
A destination wedding weekend on the Amalfi Coast, in Savannah, Santa Barbara, or wherever your heart takes you, is more than just a celebration — it’s an experience your guests will remember for years. When you weave in moments that encourage connection, relaxation, and joy, your wedding becomes a story everyone feels part of. See the photo for an example of an Amalfi Coast wedding weekend itinerary.
If you’re in the early stages of planning and wondering how to bring your weekend vision to life, I’d love to help you document it beautifully — from the welcome party to the final farewell.
