Frequently Asked Questions
Everything You Need to Know to Travel With Confidence
Caribbean Legacy Journeys
Service Fee: $750
Experience a bespoke Caribbean vacation meticulously crafted to reflect your family's travel style. With every detail taken care of, you’re free to arrive, connect, and celebrate—while we handle the coordination.
What’s Included:
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Fully customized 6–10 day itinerary tailored to your family’s interests
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Expertly curated activities and excursions for all ages
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Access to trusted local guides and unique experiences
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Generationally inclusive options (elders, kids, and everyone in-between)
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End-to-end booking management for lodging, transport, and experiences
Why It Matters:
This isn’t an off-the-shelf package. Each Legacy Journey is tailored to your family’s needs, ensuring a seamless, stress-free experience filled with unforgettable memories.
Please Note:
A signed service agreement and planning fee payment are required before bookings can begin.
Legacy Trip Vision Session
Service Fee: $125
Your travel dreams hold more possibilities than you realize. In this one-on-one session, we’ll work with you to shape your vision into a clear, actionable plan that reflects your style, preferences, and priorities.
What’s Included:
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A 90-minute video or phone consultation
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Review of your travel goals, preferences, and must-have experiences
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Recommendations for destinations and activities that fit your style and needs
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Ideas for accommodations, excursions, and dining
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Guidance for organizing multi-generational or group travel
Why This Matters:
Most travelers know they want “something special,” but struggle to bring the pieces together. This consultation turns your ideas into a clear plan, giving you direction before you commit time or money.
Please Note:
Trip Vision Consultations are for idea generation, destination recommendations, and general guidance only. No bookings or reservations will be made until a signed service agreement is in place and the applicable planning fee has been paid in full.
Legacy Trip Custom Itinerary
Service Fee: $250
For independent travelers who want the freedom to explore at their own pace—without sacrificing the insight and ease of a professionally crafted itinerary. Perfect if you prefer to skip group tours but still want expert guidance to make every day count.
What’s Included:
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A custom 3–5-day itinerary for your chosen destination
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Recommendations for local activities, attractions, dining, and hidden gems
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Vetted contacts for unique, authentic experiences
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Practical tips for navigating and making the most of your time
Why This Matters:
Without a plan, it’s easy to waste precious time figuring out what to do next. This service gives you the insider edge, so every day is mapped with intention while leaving room for spontaneous adventures.
Please Note:
Custom Discovery Planning services are for itinerary design only. No bookings or reservations will be made until a signed service agreement is in place and the applicable planning fee has been paid in full.
1. 💰 How do payments work for group trips?
We offer flexible group payment options. You can pay in full or use our installment plans with a secure payment link—perfect for splitting costs among multiple family members.
2. 🧳 Can you help with flights and airport transfers?
Yes! We can book flights, arrange airport pickups, and coordinate travel times for multiple family members—even if they’re flying from different cities.
3. 🏖️ Do you only plan Caribbean trips?
While the Caribbean is our specialty, we plan trips worldwide! Let us know your destination preferences, and we’ll tailor the perfect multigenerational escape.
4. 🧑🏽🦽 Can you accommodate special needs or mobility concerns?
Absolutely. We ensure hotels, activities, and transportation are accessible and comfortable for travelers of all abilities and ages.
5. 🎉 What types of group trips do you offer?
Milestone birthdays, family reunions, wellness retreats, cruises, and more! We’ll help you choose what fits your group’s vibe and needs.
6. 📆 How far in advance should we book?
Ideally, 6–9 months out for larger groups. But we can help on shorter timelines too—reach out to see what’s possible!
7. 🔐 Is my information secure?
Yes! We use secure platforms for payment and communications. Your privacy and protection are our priority.
8. Are service fees refundable?
No — all TravelwithKey service fees are non-refundable and non-transferable. They reflect the time, creativity, and communication that goes into crafting your personalized trip, even when parts of your journey are non-commissionable.
🧭 Still Have Questions
We’re here to help you every step of the way.
