Group Travel Planner for Quarterly Friend Trips

We’re looking for a detail-oriented, creative travel planner to help us organize quarterly “friend” trips — 3–5 day getaways for a group of 6–10 adults (mostly couples) to reconnect, relax, and explore new places together. We’d love your help with everything from finding the right destination to securing a great house and lining up optional activities. We’re hoping to build a long-term relationship with someone who can help us coordinate one trip every 3 months — ideally starting with a mid-September getaway and planning the next four (a full year) in advance. Here’s what we’re looking for: Trip Overview: • Frequency: Once every 3 months • Duration: 3–5 days (typically over a long weekend) • Group Size: 6–10 people (mostly couples) • Destinations: Fun, easy-to-access spots around North America (U.S., Canada, Mexico) • Accommodations: Large homes, villas, or cabins where everyone can stay together — ideally with en suite bathrooms for most or all bedrooms • Activities: 1–2 optional/planned activities depending on location and season (think boat rental, wine tasting, hike with a guide, etc.) • Flexibility: All bookings should be cancellable with 60–90 days’ notice in case we can’t align the group We’d love your help with: • Researching and proposing 2–3 destination/home options for each trip • Identifying great houses that meet our needs (location, space, amenities, cancellation policy) • Suggesting 1–2 optional local activities or experiences we can book • Coordinating bookings (or handing off to us with links/instructions to finalize) • Maintaining a simple tracker for planning and future trips If you have experience planning small group travel, sourcing unique stays, or organizing retreats, we’d love to hear from you. Bonus if you’re familiar with platforms like Airbnb, Vrbo, Plum Guide, boutique travel agencies, or are a travel agent yourself. Apply tot his job Apply To this Job