What is a Multi Day Wedding?
Think of it as breaking the mold. Instead of cramming everything into one day, a split wedding lets you divide your celebration into multiple parts. It gives you the chance to slow down, focus on what matters most, and make every moment count—just like Caitlin and Ryan did.
Caitlin and Ryan’s Perfectly Personalized Split Elopement/Wedding Day
When it comes to weddings, there’s no one-size-fits-all formula. Caitlin and Ryan proved this by designing a split elopement/wedding day that prioritized what mattered most to them and skipped the things they didn’t care about. The result? A celebration that was intimate, intentional, and completely their own.
Friday: An Intimate Elopement
Caitlin and Ryan started their wedding weekend with a private first look in the park, a moment filled with joy and anticipation. We then explored the garden together, capturing portraits of the two of them before their quiet, heartfelt ceremony at the Boston Public Garden. Surrounded by greenery and their immediate family, they exchanged vows in a way that felt deeply personal and stress-free.
They didn’t overcomplicate things—there were no florals, no aisle runners, no elaborate decor. It was just them, their love, and the beauty of the garden. After the ceremony, they headed to the Contessa wine room for an intimate dinner. The restaurant was meaningful to them, and the cozy setting made the evening feel even more special.
Saturday: The Big Celebration
The next day, Caitlin and Ryan threw a reception for over 100 of their favorite people at Neroli Ristorante. It was their chance to celebrate with extended family and friends, enjoy amazing food, and dance the night away. The energy was electric, and because they’d already had their private moments on Friday, they could fully embrace the party vibe on Saturday.
Why a Multi Day Wedding Worked for Them
Here’s the genius of a split elopement/wedding day: you get to prioritize what matters to you. Caitlin and Ryan didn’t feel pressured to follow traditions or accommodate everyone else’s expectations. Instead, they:
- Focused on meaningful moments rather than the usual wedding fluff.
- Spent money on experiences and locations that mattered to them, like reserving restaurants instead of random venues.
- Got to splurge on Caitlin’s multiple wedding dresses and Ryan’s fancy suit.
- Made photography a top priority. I was their only vendor aside from the florist and restaurant staff!
They went all out on the things that mattered and kept everything else minimal, creating a wedding that felt completely authentic to them!
How to Create a Multi-Day Wedding Weekend in Boston: More Ideas for an Unforgettable Celebration
If you’re inspired by Caitlin and Ryan’s split elopement/wedding day and want to create your own multi-day celebration in Boston, you’re in luck! Boston is filled with stunning locations, unique experiences, and exciting venues that make a weekend wedding unforgettable. Whether you want to keep things intimate or go all out, here are more ideas to design your dream multi-day wedding weekend!
Day 1: Intimate Elopement or Pre-Wedding Celebration
Boston Public Garden
Start your wedding weekend in the iconic Boston Public Garden, just like Caitlin and Ryan. You can say your vows surrounded by greenery, iconic swan boats, and flower-filled paths.
For an extra special touch, consider renting a swan boat for a post-ceremony ride—nothing says “romance” like floating through the park with your new spouse!
The Boston Harbor Islands
For an adventurous elopement, take a private boat to one of the Boston Harbor Islands. Imagine exchanging vows with the Boston skyline as your backdrop while on a secluded beach or at a historic lighthouse. The islands provide the perfect balance of natural beauty and privacy!
Private Dinner at a Historic Boston Restaurant
After your ceremony, head to a restaurant with history and character. Consider:
- Oleana: A Mediterranean-inspired restaurant in Cambridge, perfect for intimate dinners.
- No. 9 Park: Located right in the heart of Boston, this cozy spot offers delicious French dishes with views of the park! It’s a cute and romantic spot!
- The Contessa Wine Room: As Caitlin and Ryan did, this private wine room offers the ultimate intimate dining experience.
Day 2: The Big Celebration
Luxury Hotel Wedding Suite or Rooftop
Kick off Day 2 with a luxurious stay at one of Boston’s historic hotels, like The Fairmont Copley Plaza or The Ritz-Carlton, where you and your wedding party can get ready in style! For a rooftop reception with a stunning view, consider venues like The Envoy Hotel or Legal Harborside that will offer insane views of the Boston skyline. This would be perfect for a sunset reception!
Boston Museum of Fine Arts
For couples who love art and history, the Boston Museum of Fine Arts is a stunning venue for a wedding! Host your reception among the masterpieces or hold your ceremony in one of their gorgeous galleries. It’s a unique way to add culture and elegance to your wedding weekend.
Day 3: Post-Wedding Fun and Relaxation
Brunch at South End’s Flour Bakery
Start Day 3 with a relaxed brunch at Flour Bakery + Café in the South End. Enjoy mouth-watering pastries, quiches, and sandwiches with your closest family and friends. The bakery’s cozy atmosphere makes it a perfect place for a laid-back post-wedding gathering!
Private Tour of Fenway Park
If you’re a Red Sox fan, why not add a private tour of Fenway Park to your wedding weekend? Spend the day exploring the ballpark, taking photos on the field, and learning about its history. You can even catch a game if the timing is right!
Spa Day at the Mandarin Oriental
After the excitement of the wedding day, treat yourself to a relaxing spa day at the Mandarin Oriental. You can indulge in massages, facials, and enjoy the relaxing vibe! It’s the perfect way to unwind and reflect on your incredible weekend.
Sunset Cruise on the Boston Harbor
End your multi-day celebration with a romantic sunset cruise around the Boston Harbor. Enjoy the city skyline as the sun sets over the water! This is an intimate and stunning way to wrap up a weekend full of love and memories.
Additional Tips for Your Multi-Day Wedding Weekend
- Personalized Itinerary: Create a thoughtful weekend itinerary for your guests so they can enjoy the best of Boston. Include recommendations for restaurants, sightseeing, and activities. P.S.I love helping couples with this!
- Guest Experience: Consider offering a welcome bag with local treats (like Boston cream pies or Harvard Square chocolates) to get everyone excited about the wedding weekend.
- Group Activities: Plan group activities to bring everyone together—whether it’s a boat tour, a night out at the House of Blues, or a casual stroll through the North End (Boston’s historic Italian neighborhood).
Truly, Boston offers endless opportunities to craft a wedding weekend that’s as unique as you are!
Ready to Plan Your Own Unique Celebration?
Caitlin and Ryan’s story is proof that your wedding doesn’t have to look like anyone else’s. Whether you’re eloping in a garden or celebrating with a big reception, there’s a perfect venue, experience, or activity waiting for you. Ready to start planning your multi-day wedding? Let’s connect and make your Boston dream wedding come to life!
See more from this multi day wedding weekend in Boston on Pinterest!
Boston Wedding and Elopement Photographer | Paula Milena
Whether you’re drawn to the city’s urban charm, historic landmarks, or natural beauty, Boston is a wonderful place to elope. From choosing the perfect venue to navigating the logistics, this guide provides a starting point to help you craft a day that feels uniquely yours. Secure your date for your Boston Elopement today!
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