Top 10 Questions to Ask Before Booking with a Travel Planner
Travel planning today offers more options than ever, but with so many choices comes complexity. For those looking to take the stress and guesswork out of their journey, hiring a travel planner can be an invaluable decision. But not all travel planners are the same. To ensure you’re getting the personalized, thoughtful, and high-quality service you deserve, it’s important to ask the right questions before making your decision.
At Perennial Escapes Travel, we believe in transparency, connection, and crafting meaningful, healing travel experiences. Whether you’re planning a romantic trip to Paris, a rejuvenating escape to Costa Rica, or a family journey through Ireland, your travel planner should feel like a trusted partner.
Here are the top 10 questions to ask before booking with a travel planner, and why they matter.
1. What Destinations Do You Specialize In?
Not every travel planner knows every destination in depth. Look for someone who focuses on a select group of locations they truly understand. At Perennial Escapes Travel, we specialize in customized trips to Portugal, Spain, New York City, Paris, Costa Rica, and Ireland. Our deep knowledge of each place allows us to offer truly tailored experiences instead of generic itineraries.
Asking this question helps ensure the planner can provide meaningful suggestions based on lived or first-hand experience.
2. How Do You Personalize Each Itinerary?
A truly custom itinerary should reflect your interests, values, travel style, and goals for the trip. Some planners may offer only templated packages with small adjustments. Be sure to ask how deeply the planner tailors the experience to you.
At Perennial Escapes, we start by understanding who you are and why you’re traveling. Whether you seek wellness, romance, discovery, or emotional renewal, we design every aspect of your journey around your story.
3. What Services Are Included in Your Planning Fee?
Travel planners offer different packages. Some may charge per hour, others per trip, and some bundle services like itinerary design, accommodation booking, and tour arrangements. Ask for a clear breakdown so you understand exactly what you’re paying for.
We provide full-service itinerary creation, including accommodations, transportation coordination, curated activities, dining recommendations, and local support.
4. Can You Accommodate Special Interests or Needs?
Whether you’re traveling with dietary restrictions, accessibility considerations, or a desire for a slower-paced trip, your travel planner should be prepared to accommodate these needs with care.
Our team frequently works with couples, families, and senior travelers. We ensure every itinerary is built with the right pace, access, and comfort level for your group.
5. Do You Work with Trusted Local Partners?
A well-connected travel planner will have reliable relationships with local guides, hotels, and experience providers. This ensures smoother communication, higher quality services, and better value.
At Perennial Escapes, we work with carefully vetted partners in each of our destinations. From private drivers in Lisbon to expert guides in Galway, we ensure you’re in good hands throughout your journey.
6. How Do You Handle Unexpected Issues During Travel?
Things can go wrong while traveling, from flight delays to last-minute changes. You’ll want to know who to contact and how your planner will support you if the unexpected happens.
We provide on-trip support to all our clients, so you’re never alone. Whether you need help rebooking an excursion or just want a last-minute dinner recommendation, we’re just a message away.
7. Can You Help Me Travel with Purpose or Intention?
If you are someone who values personal growth, emotional healing, or cultural immersion, find a planner who understands how to create travel with depth.
At Perennial Escapes, our specialty is meaningful, healing-centered travel. We believe every journey can offer clarity, joy, and reconnection. Our itineraries are designed to support not only exploration but restoration.
8. What Kind of Accommodations Do You Recommend?
Ask whether the planner books large chain hotels, boutique stays, family-run inns, or luxury resorts. Their answer will reflect their approach to authenticity and comfort.
We prioritize boutique hotels, charming guesthouses, and unique stays that align with your style. Whether you’re looking for an eco-lodge in Monteverde, a heritage stay in Porto, or a stylish flat in Paris, we match you with accommodations that enhance your experience.
9. How Far in Advance Should I Start Planning?
Some destinations and experiences book up months in advance. A good travel planner will guide you on ideal timelines and help you avoid the stress of last-minute arrangements.
We recommend reaching out at least 3 to 6 months before your travel dates. This gives us the time to design something thoughtful and secure the best possible accommodations and experiences.
10. Why Should I Choose You Over Booking It All Myself?
This is one of the most important questions you can ask. A great travel planner should be able to articulate the value they provide beyond convenience.
Our clients choose Perennial Escapes Travel because we offer more than logistics. We offer peace of mind, expert insight, emotional support, and personalized care that turns travel into transformation. Our curated destinations are not just beautiful, they are soulful, safe, and ideal for those seeking deeper, more enriching experiences.
Your Journey Deserves More Than a Template
Choosing the right travel planner can set the tone for your entire trip. By asking the right questions up front, you’ll find a partner who not only understands your logistics but also your emotions, priorities, and travel dreams.
At Perennial Escapes Travel, we’re here to guide you through every step of the journey with insight, empathy, and unmatched attention to detail. Contact Perennial Escapes Travel today and discover how thoughtful planning can turn your next trip into something deeply meaningful.