There’s something magical about traveling with friends, family, or colleagues. Group travel brings people together in ways few experiences can, creating lifelong memories from exploring new destinations together. Whether it’s laughing over a shared adventure, bonding over dinner, or just spending quality time away from the hustle and bustle of everyday life, group travel is an amazing way to strengthen connections. But anyone who has tried to plan a trip for a group knows that it’s not always easy!

Coordinating dates, managing preferences, handling logistics, and making sure everyone is happy can quickly turn what should be an exciting trip into a stressful one. That’s where we come in. At Rosedale Travel, we specialize in planning group travel and have experience organizing trips up to about 60 people.

Why Choose Rosedale Travel for Group Trips?

We Take the Stress Out of Planning: Rosedale Travel can handle the intricate details of your group trip, from securing rooms and locking in pricing to possibly landing you some perks—like room upgrades and exclusive amenities—after booking a certain number of rooms. Plus, we often have flexible options that don’t require minimums if that better suits your group’s needs.

Payment and Guest Management: Coordinating payments from a large group can be a headache. We manage deposits, final payments, and all communications for your group, so you don’t have to worry about chasing anyone down. We can even help arrange transfers, activities, and special experiences tailored to your group’s interests.

Here are some of the types of group travel we’ve planned:

1. Milestone Birthdays

Celebrate in style! Whether it’s a 30th birthday or 60th, these milestone moments deserve a trip to remember. Think all-inclusive resorts in sunny locations or adults-only cruises like Virgin Voyages, where you can relax, party, and let someone else do all the work.

2. Family Reunions

Reconnecting with extended family is such a joy (mostly), and a trip gives everyone the perfect chance to come together. We can help find destinations with activities for all generations—from grandparents to grandkids—while also building in some downtime for the parents. A cruise with Royal Caribbean or Disney offers something for everyone and makes managing a large family much easier. Or let’s find a large upscale villa with chef services and have a more homey feel.

3. Executive Retreats

Taking your executive team out of the office and into a new environment can be the perfect way to focus on the future. From golf, tennis, or pickleball resorts to luxurious European castles, or even salmon fishing in Alaska, we can curate the ideal retreat for your team. If you’re looking to relax and recharge, we can arrange a stay at a world-class wellness spa to focus on health, wellness, and creativity.

4. Affinity Groups

Whether you’re organizing an alumni reunion, a trip for your adult sports team, or a getaway for the parents of a school group, Rosedale Travel can design a trip that reflects your group’s shared interests. Whether the trip aligns with your organization’s mission or is just a fun escape, we’ll make sure every detail is tailored to your group’s vision.

Let’s Plan Your Group Trip!

At Rosedale Travel, we love hearing about the special moments and milestones that bring people together, and we would be thrilled to help make your group travel dreams come true. Whether it’s a milestone birthday, a family reunion, or an executive retreat, our team is ready to guide you through the planning process from start to finish.

There’s no obligation—just reach out, and let’s chat about your group’s needs. We’d love to hear from you!