David Braddy

Trip Designer, Former Travel Agent

Book a 1:1 trip planning call with David for insider advice and personal recommendations and recieve a custom TripGuide following the call.

$60 for 30 min - saving hours of guesswork

Get To Know David Braddy

Hi, I’m David. I’ve been designing customized travel itineraries for individuals and small groups since 1984, with a lifelong passion for southern Europe. I specialize in creating journeys that are deeply personalized—whether that means finding a charming guesthouse tucked into a medieval village or a luxurious five-star retreat famous for its service and style.

Originally from the U.S., I now call Montefalco, Umbria home. After years of planning trips across Italy, Switzerland, Spain, and Great Britain, I decided to live full-time in the region I love most. I help travelers experience the real heartbeat of Italy—mountaintop towns, local vineyards, historic cities—and can also craft seamless adventures across Europe, blending iconic highlights with hidden gems. Whether you’re traveling solo, with family, or planning a special luxury escape, I’m here to design an experience that feels personal, meaningful, and unforgettable.

Specializations

Luxury Travel
Wine Experiences
Culinary Experiences
Walking
"Traveling changed my life—it brought me closer to people, places, and a way of living that I now call home."

Where David can help

📍 Italy

I live in Montefalco, Umbria, and have spent decades designing detailed itineraries through Rome, Florence, Venice, Lake Como, the Amalfi Coast, and the hill towns of Tuscany and Umbria. I know Italy’s rhythm intimately—from luxury hotels to hidden villages.

📍 Spain

I’ve traveled extensively through Madrid, Toledo, Salamanca, Barcelona, Seville, and Asturias, offering detailed knowledge of both major cities and quieter inland regions.

📍 Switzerland

A longtime favorite destination, I know Switzerland’s cities, hiking trails, and scenic routes well—especially Lucerne, where I’ve visited eight times in the past two years alone.

📍 England

Beyond London, I’m deeply familiar with Devon and Somerset, where I lived for extended periods. I know the local rail networks, festivals, small towns, and coastal hikes around Brixham and Castle Cary.

📍 Turkey

After a three-month stay in Istanbul, I have fresh, firsthand knowledge of the city’s diverse neighborhoods, hotel landscape, ferry routes, and private tour contacts.

📍 France

I’ve traveled extensively through Paris, Colmar, the Cote d’Azur (including Saint Paul de Vence, Nice, Cannes, and St. Tropez), and the Alsace wine region—helping travelers experience France beyond the obvious.

📍 The Netherlands

I’m highly familiar with Amsterdam, its neighborhoods, local dining, and boutique hotels.

Some happy campers

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What you get:

  • 25-min Zoom call with your expert
  • Personalized TripGuide with your recommendations, logistics info, and a day by day approach following the call
  • Custom Google map, curated by your expert

Note: your map and TripGuide are shareable so you can give to your travel companions

Send me a message

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Common Questions

How does Outdoorable work?
Outdoorable connects you with experienced outdoor pros through 1:1 video calls. Whether you’re deciding between destinations, need insider tips for a specific trail, or want advice tailored to your skill level, our experts are here to help. Simply browse expert profiles, book a call, and get the guidance you need to plan your next adventure with confidence.
What can I ask an Outdoorable expert?
Anything about your outdoor trip! Need advice on hiking routes, family-friendly trails, or navigating backcountry terrain? Want to know the best time to visit Patagonia or if a specific climb is doable for your skill level? Our experts are here to give personalized insights based on their firsthand experience.
How long are the calls?
Calls are 30 minutes, giving you plenty of time to ask questions, explore options, and get personalized advice. If you need more time, you can always book a follow-up session.
Can I choose which expert to talk to?
Yes! You can browse detailed expert profiles to find someone who matches your destination or activity needs. Whether it’s a hut-to-hut trek in the Alps or beginner-friendly kayaking in Croatia, you’ll find an expert who’s been there and done that.
What happens after I book a call?
Once you book a call, you’ll get a confirmation email with a link to share your questions or trip details in advance. This helps the expert prepare and ensures you get the most out of your session. You’ll also receive a link for the video call closer to the appointment.
How much does it cost?
A 30-minute call costs $60, with $45 going directly to the expert. We believe in fair pay for our pros who have invaluable expertise while keeping it affordable for adventurers.
What if I need to reschedule or cancel?
We get it—plans change. You can reschedule or cancel your call up to 24 hours before the scheduled time. Just head to your confirmation email for details on how to make changes.
What if I don’t find the call helpful?
We strive to connect you with the best experts and provide actionable advice. If you feel your call didn’t meet your expectations, let us know. We’ll work with you to make it right. All Pros can see your questions in advance, and they will let us know beforehand if they don’t think they are the best person to provide insight.
Can I share the call with someone else?
Yes! Whether you’re planning a trip with friends or family, feel free to include them in the call. Just make sure everyone’s ready to hop on when the session starts.
Do experts plan my trip for me or give me an itinerary?
No, Outdoorable is not a trip-planning service. Our experts provide personalized advice, answer questions, and guide you with insights to help you plan your trip. Think of it as having a knowledgeable friend with all the lowdown so you can plan your perfect trip.
How do you choose your experts?
Our experts are handpicked for their firsthand experience, regional knowledge, and ability to give actionable advice. Many are professional guides, trip designers, or seasoned adventurers with years of expertise. That means their jobs are to find the best places off the beaten path. Needless to say… you’re in good hands.
What kind of trips can Outdoorable help with?
Outdoorable is perfect for all types of nature-based adventures:
• Planning a big bucket-list adventure
• Deciding between destinations based on your outdoor skill level and interests
• Finding hidden trails, parks, routes
• Preparing for a solo trip, family outing, or group adventure