Let Italy Beyond the Obvious create a fantastic Italy itinerary for your family or small group. You’ll get excellent recommendations, and everything will be booked and double checked so that every traveler in your group enjoys a dream trip to Italy! We’ve got decades of experience creating wonderful Italy itineraries and working as an Italy trip advisor.

Italy trip advisor

1. Italy Itinerary Initial Consultation

Contact Madeline directly at madeline@italybeyondtheobvious.com or call +1 773 621 3024 to start discussing your Italy trip. We’ll start discussing your dream trip: when you’re going, the interests of your family or group, your travel pace, any existing commitments or pre-existing constraints. We’ll brainstorm Italy itineraries you’ll love, and work together to finalize the perfect vacation for your family or friends!


2. Planning and Booking of your Italy itinerary

Italy Beyond the Obvious will propose an Italy itinerary or two that you’ll love, and we’ll be your Italy trip advisor all along the way. We’ll make changes or adjustments until you are ecstatic about your trip. We’ll then do the bookings for you: the details will be arranged, transfers finalized and final hotel choices discussed, booked, and confirmed. If you’d like a more flexible itinerary, we’ll give you recommendations with contact information, opening hours, and prices so that you can make last minute decisions based on how you’re feeling that day.


3. Written Italy Itinerary

During your trip, you’ll use your Italy Beyond the Obvious written itinerary, which includes day-by-day details of activities, and suggestions for other things you may enjoy should you have more time or energy. It contains contact information for all hotels, tours or guides, opening hours and entrance fees for attractions, and train or boat schedules where relevant. In summary, it’s your complete peace of mind.


4. Italy On Trip Support

We’ll continue to work as your trip advisor or personal concierge during your trip, you can call or email for help. Italy Beyond the Obvious is happy to sort out misunderstandings, negotiate on your behalf where possible, or just converse in Italian where needed. Note: this service is included in Platinum Italy Trip Planning, but for Gold Italy Trip Planning or Coaching services, it is an additional per-day charge.


Italy Itinerary Design Services: Details


Italy Beyond the Obvious dream vacation planning





Consultation of overall flow, where to go, what to see

Unlimited travel advice




Activities e.g. guides, beaches, wineries, hiking, biking, shopping

Internal transfers e.g. limos, rental cars, trains, boats





Activities e.g. guides, beaches, wineries, hiking, biking, shopping

Internal transfers e.g. limos, rental cars, trains, boats

Written itinerary (pdf and app versions)

Maps: daily maps, hiking maps, city maps, road atlas where needed

Multiple daily itineraries

Detailed historical information on specific sights

On trip support


Fees [Note: Fees are based on up to 6 travellers. For larger groups, contact us.]

$750 flat fee

$225/trip day

$350 - $500/day

For an example of a written Platinum itinerary, check out the sample itinerary.

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