Trip Planning Video Call
Ask a Local:

Siena Trip Planning Video Call

30-90 minutes English
5 (62)
100% Personalized

Discover serene gardens, tucked-away teahouses, and quiet alleyways with a local host who crafts the perfect day just for you

How It Works

Step by step of our video calls

1

Tell us what you're looking for

After booking, fill out a quick personalization form to let your host know your interests, style, and needs.

2

Hop on your video call

Get live, tailored recommendations and ask your burning questions directly to your host.

3

Receive your customized plan

Your host will send a summary of your conversation, with links, tips, and local suggestions, so you can travel confidently

Why Video Call With a Local Before Your Trip?

Fully Personalized Advice

Get recommendations crafted exclusively for your tastes, interests, and plans—no generic tips.

Maximize Every Moment

Quickly pinpoint must-dos and safely skip overrated spots. Don’t waste precious vacation time.

Travel Stress-Free

Sort out neighborhoods, transport, local etiquette, and logistics upfront. Arrive confident and prepared.

Authentic Insider Knowledge

Unlock hidden gems and unique local insights you won’t find in guidebooks or online forums.

Easy & Convenient

Plan comfortably from home, at a time that suits you. Ask your questions, get answers immediately.

Why guests love exploring with us

G
Gregory 17 December 2025

Filippo was professional, knowledgeable, and attentive to us. He was engaging and easy to be around

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H
Helen 1 November 2025

Great!!

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C
Christoph 22 October 2025

Thanks to Filippo for that great day in your city.

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C
Christoph 22 October 2025

Our guide Filippo did lead us to parts of the city, where we would have not gone on our own. He also explained allot about the inhabitants of Siena and their very interesting habits. The tour was perfectly timed and we did see very interesting spots of the city. At the end of the tour he led us to his famous restaurant, where we hat a great lunch. Thanks to Filippo for that great day in your city.

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C
Cynthia 14 October 2025

Lillo was very informative and helpful. He spoke excellent English and gave us a good sense of Siena.

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J
John 13 October 2025

Filippo was a great tour guide. He was very knowledgeable of the culture and history of Siena.

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M
Michael 8 October 2025

Francesco was an excellent to a guide , very personable and informative! His explanations of sites and cultural meanings, made us want to extend our visit in Siena.

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L
Layne 6 October 2025

A private tour specialized to our interests and be an amazing local guide. We would not have learned to much about the city without Francesco as our guide. It was wonderful.

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FAQs

Your questions, answered

What is the Trip Planning Video Call?

It’s a one-on-one session with a local host who knows the city inside out. It’s a chance to get personalized advice, ask questions, and start shaping your trip before you arrive.

How does the session work?

The session takes place on Zoom in a relaxed, conversational format. You’ll receive your link and all the details you need via email beforehand, so you can simply join and connect with your host.

Who will I be speaking with during the call?

You’ll be matched with a local host who fits your travel style and interests. They’ll bring their personal knowledge, tips, and recommendations to help shape your trip.

What makes City Unscripted different from other travel planning services?

Everything we do is personal. Instead of fixed itineraries or generic advice, your host tailors suggestions around you—your interests, pace, and what you want to get out of your trip.

How does personalization work?

After booking, you’ll receive a short questionnaire where you can share your interests, travel style, and any must-see spots. Based on that, we’ll match you with a local host who’ll reach out to plan your personalized itinerary.

What if I don’t know what I want to explore yet?

That’s absolutely fine! Your host will help you figure it out during the call, suggesting ideas and options based on what you enjoy.

Can I request specific places, interests, or experiences?

Yes! You can share any must-see places, interests, or ideas in advance or during the call, and your host will help you build a plan around them.

Is this suitable for first-time visitors or returning travelers?

It’s ideal for both. If it’s your first time, your host can help you understand the city, plan your days, and avoid common pitfalls. If you’ve been before, they’ll go deeper—helping you discover new areas, refine your plans, or experience the city from a more local perspective.

Is the call scheduled in my time zone or the host’s?

The call is scheduled in your time zone, so you can choose a time that works best for you.

How long is the session?

You can choose between 30, 60, or 90 minutes, depending on how much you’d like to cover. Most guests opt for 60-90 minutes to have enough time for a relaxed, in-depth conversation with their host.

When will I receive the Zoom link?

You’ll receive your Zoom link as soon as you’ve been matched with a host, along with all the details you need to join your session.

Can I join the call from my phone or tablet?

Yes, you can join from your phone, tablet, laptop, or desktop—whatever is most convenient for you.

Can I reschedule or cancel my session? What is the policy?

Yes, you can reschedule or cancel your session up to 24 hours in advance, just get in touch with us at info@cityunscripted.com.

What should I do if I have technical issues joining the call?

If you run into any issues, try reconnecting or switching devices. If you’re still having trouble, contact us at info@cityunscripted.com and we’ll help you get back on track as quickly as possible.

Can I follow up with additional questions after the session?

If you have a few follow-up questions, feel free to reach out at info@cityunscripted.com—we’ll do our best to assist.

Can I book an in-person experience with the same host after my call?

Yes! If your host is available, we’ll do our best to match you with them for a private experience.

City Unscripted

One chat. A better trip.

Whether you’re a planner or a wanderer, your local host can help you feel confident, prepared, and ready to discover more. Start Booking with us