Wedding Weekend Planning Tips That Blend Adventure and Meaningful Time with Your People
What if your wedding wasn’t just a single day, but an entire weekend filled with presence, connection, and adventure with your favorite humans? More and more couples are moving away from traditional one-day weddings and choosing something that allows for more quality time with the people they love most.
If you’re craving both intentional time with your partner and a joyful celebration with your favorite people, a multi-day wedding weekend might be your perfect fit. Whether you want to hike at sunrise, throw a lake party, or end the night around a fire pit with your family and friends, a multi-day wedding lets you do it all, without feeling rushed or overwhelmed.
This guide on how to plan a wedding weekend is filled with practical tips and ideas that allow you to slow down, stretch the celebration, and be fully present in every moment.
The Benefits of a Multi-Day Wedding Celebration
There are so many beautiful reasons to plan a wedding weekend. Of course, more days mean more time to celebrate, but a multi-day wedding also allows for so much more!
- More time with your people. Instead of cramming hellos and hugs into one day, you get quality time with guests across several events.
- Space to be present. You and your partner can carve out intentional moments to connect, away from the crowd.
- A mix of adventure and ease. You don’t have to choose between a private sunrise hike and a backyard dance party. With a wedding weekend, you can have both.
- Less pressure, more fun. There’s room for spontaneity, rest, and real connection when you aren’t rushing from ceremony to speeches to cake cutting.
Not sure if planning a wedding weekend is right for you? Check out this guide on Elopements vs Intimate Weddings to explore some other options and find what feels right for you.
How to Plan a Wedding Weekend That Feels Like You
Choose Your Wedding Weekend Venue
The first step in how to plan a wedding weekend is to start with your location. Decide where you want your weekend to take place. Do you want to stay close to home, or are you envisioning a destination location?
If you’re dreaming up Catskills magic, I have a whole post dedicated to Catskills venues that would be amazing for your multi-day wedding!
Every couple’s version of a meaningful wedding weekend looks a little different, so start by imagining how you want the experience to feel. Do you picture slow mornings with coffee by the lake? A day of hiking and jumping into the water with your favorite people? A candlelit dinner under the stars?
When choosing your location, think about what kind of space can hold all of that. Look for venues that:
- Offer on-site lodging or are near cozy cabins or inns
- Are close to trails, lakes, or other activity-friendly areas
- Have room for both intimate, quiet moments and big, joyful gatherings
I’ve seen couples plan morning 5ks with their crew, lakeside parties, brewery dinners, and cozy firepit hangs, all in one weekend. The right location makes it easy to do the things you love with the people you love, without having to choose between adventure and tradition.
Decide on Your Budget
Budgeting for a multi-day wedding weekend isn’t just about assigning a dollar amount. It’s about making intentional decisions about the things that matter to you. With a celebration that stretches over two or three days, you have more space to invest in the experiences that matter most to you.
Start by identifying your top two or three priorities. Is it important to have a private chef dinner with your closest people? Photography coverage across the full weekend? Lodging that brings everyone together under one roof?
Once you’ve named what’s most important – whether that’s food and drink, guest accommodations, adventure excursions, or creating space for quiet connection – you can start building your budget around those values.
One of my favorite things about smaller, more personal weddings is the flexibility they offer. With fewer guests, you often have more room to splurge on what feels meaningful and DIY the rest. One of my past couples booked a stunning lakeside Airbnb, hired a chef for a cozy welcome dinner, and prioritized photography for the full weekend. Then they created their own bouquets with family, made their cake from scratch, and filled the rest of the weekend with moments that felt like them.
At the end of the day, your budget should reflect what matters to you, not anyone else’s checklist.
Hire Your Photographer, Planner, and Vendor Team
Once you’ve outlined your vision, decided on a location, and set your budget, the next step in how to plan a wedding weekend is building a team who can help bring it all to life.
When you’re planning a multi-day wedding, there are more moving parts: more moments to document, more logistics to manage, and more opportunities to be fully present with your people. That’s why choosing the right vendors (starting with your photographer and planner) makes such a difference.
Photography during a wedding weekend isn’t just about snapping a few pretty portraits, it’s about telling the full story. From cozy welcome dinners to carefree dance floor moments, I’m there to document it all so you can relive the entire experience, not just the ceremony. I also help with timeline flow, location scouting, and making sure each day feels intentional and smooth.
If your wedding weekend includes multiple setups (like a welcome dinner one night and a lakeside ceremony the next), consider hiring a planner to help with vendor coordination, transitions, and setup. Especially for rehearsal dinners, outdoor spaces, or anything that requires setup or coordination, having a planner means you get to spend your weekend soaking up the joy, not adjusting chairs or managing the catering team.
You may also need to coordinate with multiple vendors: caterers, rental companies, transportation, adventure guides, and more. The more organized events you have, the more energy and time each one will require, and the more helpful it is to have a planner facilitating the flow so you don’t have to.
Ultimately, if you want to intentionally choose presence and connection with the people you love, then surrounding yourself with an experienced vendor team is what will make that possible.
Book Your Accommodations
Where you stay sets the tone for your entire weekend, whether it’s cozying up in a rustic cabin or gathering around a fire pit at a lakeside Airbnb. When choosing lodging, consider things like comfort, connection, and ease. Look for accommodation options that…
- Keep your favorite people close (bonus points for group hangout spots!)
- Are within close proximity to your ceremony and activity locations
- Fit the vibe of your weekend, whether that’s relaxed and outdoorsy or elevated and modern
Some couples book one big house where everyone stays together. Others reserve a few smaller properties nearby to give guests flexibility while still keeping things convenient. Whatever you choose, your lodging is more than just a place to sleep. It can also be a part of your wedding weekend story, (think: coffee together in the mornings, stargazing at night, and spontaneous porch hangouts in between).
Plan Your Wedding Weekend Timeline
One of the biggest gifts of a wedding weekend is time to be fully present, connect with your favorite people, and create space for quiet, just-the-two-of-you moments amidst all the celebration. There are so many different ways your wedding weekend itinerary can look, but here is a starting point to inspire you. (And don’t worry, when we plan together, we’ll create a wedding weekend itinerary built around your energy, your priorities, and the kind of experience you want to have).
Day 1: Arrival & Welcome Gathering
Ease into the weekend with something low-key and welcoming. Maybe that’s a laid-back pizza night at your rental, a bonfire under the stars, or lawn games and craft beer at a nearby brewery. This time is all about setting the tone for the weekend ahead.
Day 2: Adventure & Connection Time
Make room for both connection and fun. This might look like a sunrise hike for just the two of you, followed by a mid-morning paddleboard session or picnic with your guests. Some couples plan a casual group 5K or rent bikes to explore the area. Whatever you choose, this is the day to blend adventure with downtime, and to soak in the beauty of where you are, with and without your people.
Day 3: Your Wedding Day
Whether your day is rooted in tradition or follows a unique, personalized rhythm, we’ll craft a timeline that gives you space to be present. You might start the morning slowly, exchanging letters or sharing coffee before getting ready. Then comes your ceremony, surrounded by loved ones or tucked away in an intimate setting, followed by a meal filled with meaningful conversations and a dance party that brings it all home.
Day 4: Post-Wedding Brunch & Farewell
Say your goodbyes without the rush. A cozy morning brunch or coffee hangout gives you one last chance to be with your people, reflect on the weekend, and wind down before heading into your next chapter.
For more wedding weekend itinerary tips and ideas, check out my planning guide below!
Wedding Weekend Planning Tip: Create Opportunities for Togetherness AND Downtime
Once you’ve mapped out the general flow of your weekend, take a moment to think about the feel of each day. Mix high-energy group activities (like a hike or lake day) with slower moments of rest. Encourage guests to explore local coffee shops or take midday naps. And carve out space for just the two of you, whether that’s a sunrise walk or a quiet dinner after everyone heads out.
Wedding Weekend Activities to Consider:
- Sunset hikes
- Private cliffside yoga class
- Stargazing or meteor shower viewing
- Lake swims or hot tub soaks
- Brewery or cidery visits
- Pizza-making nights or outdoor movie screenings
Inform Your Guests
With a multi-day celebration, there are more logistics to consider, so clear communication with your guests is everything. The more your guests know ahead of time, the more relaxed and present they’ll be throughout the weekend.
A wedding website is one of the easiest ways to keep everyone in the loop. Make sure to include:
- A detailed itinerary (including times + locations)
- What to bring (layers, hiking shoes, swimsuits, etc.)
- Transportation info (especially if you’re adventuring off-site or have limited parking)
- Lodging recommendations or group booking links
- RSVP or booking links for each day’s events
- Accessibility and Leave No Trace reminders
Think of your wedding website as a personal guidebook. Most of your people have likely never attended a wedding like this before, so helping them know what to expect will make them feel more at ease and help your weekend flow more smoothly.
Whether you’re envisioning a slow, intentional few days in the woods or a full-on adventure weekend with your favorite people, your wedding weekend should feel like you. If you’re not sure where to begin or how to plan a wedding weekend that brings all the moving pieces together, I’m here for you.
Reach out here to start your wedding weekend planning and design an experience filled with connection, joy, and a little bit of adventure.
