We’re doing something BIG — and we want you there with us.

Shutter and Compass is thrilled to announce our First Annual Group Trip — and this one’s for the books. We’re heading to the stunning Sandals Montego Bay in Jamaica, May 2026, for a sun-soaked, soul-filling experience that blends luxury, purpose, and unforgettable connection.

While you’re welcome to extend your stay on either side of the trip, the official group dates are April 30–May 7, 2026— and trust us, you’ll want to be there for every second.

Why Montego Bay? Why Now?

Photography: Kristen Alfred
Travel with Kristen

Because she goes anyway.
Whether she’s juggling a million tasks, feeling overdue for joy, or unsure of what comes next — she chooses the adventure, the escape, the connection. That’s what this trip is about. A chance to say yes to yourself while making a difference in the lives of others.

This trip is more than beautiful beaches and butler service (although, yes, there will be that — it’s Sandals after all). It’s about joining with like-minded women — travel lovers, dreamers, givers, storytellers — to celebrate everything Shutter and Compass stands for.

And we’re not going alone.

We’ve teamed up with the incredible Kristen Faye Alfred of @travel.with.kristen, a Sandals and Beaches travel advisor who knows these resorts inside and out. Kristen invited us to be part of something special — and you’re invited too.

Here’s What Makes This Trip Extra Meaningful

✨ The Jill Stewart 5K

This optional charity 5K is a highlight of Sandals Foundation’s philanthropic calendar. Named in honor of a beloved Sandals Resorts team member who lost her battle with breast cancer, the Jill Stewart 5K brings together Sandals guests, staff, and locals for a walk/run benefiting the Sandals Foundation’s work in health, education, and community development. You can run, walk, or cheer from the sidelines — all in the spirit of giving back.

📚 Reading Road Trip

Another optional excursion with big impact: the Reading Road Trip gives guests a chance to visit local schools and spend meaningful time reading with children in nearby communities. It’s a beautiful way to connect with Jamaica beyond the resort and to share your love of storytelling and learning.

Let’s also add: this part of our trip is something we are both looking SO FORWARD to! In an upcoming Shutter and Compass podcast episode, you’ll hear more, but let’s just say this combines Shelby’s long time desire to do mission work with travel to help those in need. While this is obviously not a “mission” trip, we are very excited to connect with the local community and share love in a meaningful way, while having the option to go back to the resort for our food and comforts we are accustomed to. We promise a funny story goes with this, so be sure to stay connected for more background!!

✏️ School Supplies Drive

Shutter and Compass will be bringing much-needed school supplies for the children of Montego Bay and surrounding areas — and we need your help! Whether you join the trip or support from home, we’re accepting donations of:

Notebooks
Crayons, markers & pencils
Backpacks
Art supplies
Flash cards & learning tools

Or you can contribute to our fundraising goal to help us purchase in bulk and transport supplies directly. Stay tuned for our upcoming donation drive — and if you're a teacher, mom, or office supply enthusiast, start setting things aside now!

What’s Included with a Sandals Group Stay?

Sandals resorts are all-inclusive — and we mean ALL inclusive:

✅ Unlimited gourmet dining at multiple restaurants
✅ Premium drinks (yes, even top-shelf cocktails 🍹)
✅ Beautiful beachfront accommodations
✅ Watersports, snorkeling, and SCUBA for certified divers
✅ Entertainment, themed nights & live music
✅ Airport transfers and all tips/taxes
✅ Group perks like room upgrades, spa discounts, and exclusive group activities (based on group size)

And for our Shutter and Compass group? We’ll also have:

🦩 Welcome meet-up & farewell dinner
🦩 Curated excursions and photo ops
🦩 Optional sessions on content creation & travel planning
🦩 And yes… time to just be — in a hammock, by the pool, with your favorite book or podcast (don’t forget your sun hat and packing cubes — you know we’ve got you covered in our blog shop 😉).

Let’s Travel With Purpose — Together

This is our first-ever Shutter and Compass Group Trip — and we couldn’t be more excited to partner with Kristen, celebrate service and sisterhood, and build a travel community that gives back.

Come solo (well, Sandals books rooms for two, so this may be the best time to invite someone along, even your husband!).
Or, bring your sister. Grab your best friend. We’re sure you’re overdue to hang out, are we right?!!

Just don’t wait too long — rooms are limited and this will sell out.

To join us, inquire today through Instagram @travel.with.kristen or drop us a DM at @shutterandcompass.
We’ll make sure you get all the details and pricing options based on your room type and length of stay.

We can’t wait to see you in Jamaica.
Because wherever she goes — she goes anyway.

P.S. Want to support the school supplies drive or sponsor a suitcase of donations? Stay tuned — we’ll be sharing all the details soon, including Amazon wish lists, collection events, and how to help even if you’re not traveling with us this time.

She Goes Anyway: Join Us for the First Annual Shutter & Compass Group Trip to Sandals Montego Bay