Custom Italy Vacations

What You Can Expect

When you work with Italy Beyond the Obvious to create an Italy custom vacation, “custom” is exactly what you get! We have never created the exact same itinerary twice.



After creating a detailed itinerary, we’ll recommend and book accommodations you’ll love that are available for your dates, meet your preferences, and are within your budget.

Tours & Logistics

Tours & Logistics

We book private guides, small group tours, skip-the-line tickets and concert tickets. We supply hiking maps and city maps. We book drivers, trains or rental cars for a smooth trip.

Food & Wine

Food & Wine

We recommend and book restaurants, cafes, trattorias, gelaterias, wine tastings and tours, and local farm experiences. We’ll even give you a checklist of local foods to try.

Our Italy Travel Services

We offer three levels of Italy trip planning services;
Gold, Platinum, and Diamond.


Our Gold Italy travel planning service is for the traveler looking for a service that covers the essentials.

Pricing and more →


Our Platinum Italy travel planning service is for the traveler looking for VIP level tours and treatment.

Pricing and more →


Our Diamond Italy travel planning service is for groups of 6 or more looking for either level of serivce.

Pricing and more →

Comparison Table of Italy Trip
Planning Services and Fees

Consultation of overall flow, where to go, what to seeiTailored recommendations for you and your travel partners based on your interests.
Unlimited Travel AdviceiAdvice on logistics and getting from A to B; guide books, phrase books, travel insurance, cell phones and technology, packing tips, driving in Italy, and anything else you can think of.
Hotel AdviceiHotel, B&B, farmhouse, apartment or villa recommendations that work within your budget and are available for your specific dates. We don't work with a limited portfolio of accommodation, rather we find the best fit for you.
Restaurant AdviceiRecommendations for Trattorias, Osterias, restaurants, cafes, gelaterias that fit your style and budget and work logistically for your itinerary.
Activities Advice (tours, wineries, hiking, biking, shopping)iSpecific recommendations for guides, tours, classes, and other activities based on your interests.
Advice for Internal Transfers (limos, rental cars, trains, boats)iDetailed information about the best way, and all the options, for getting from A to B within Italy.
Hotel BookingsiWe'll book your hotel, farmhouse, B&B, apartment, villa, or other accommodation.
Restaurant BookingsiWe'll make restaurant reservations for you so that you only need to show up, sit down, and enjoy your meal.
1 Per Day2 Per Day2 Per Day
Activity BookingsiWe'll book and confirm tour guides, classes, museum tickets and anything else that should be booked ahead of time.
Half DaysFull DaysFull Days
Bookings for Internal Transfers (limos, rental cars, trains, boats)iWe'll reserve your rental car, book your airport transfer, buy your train tickets ahead of time, make sure you have up to date boat schedules, and give you tips on how to get a taxi.
Written itinerary (pdf and app versions)
Number of TravelersUp To 6Up To 6Up To 25
VIP Tours 
Maps (daily maps, hiking maps, road atlas) 
Historical Information 
Multiple daily itinerariesiWe'll put together a rainy day itinerary if you'd like, or a separate itinerary for others in your party.
24/7 Concierge Support 
Cost$225/day$350/dayContact Us
Ready To Move To The Next Step?
How we create your Italy Custom Vacation: our 5-step process

How we create your Italy Custom Vacation: our 5-step process

We have a proven 5-step process that we use, over and over, to create highly personalized Italy itineraries. 

About Our 5-Step Process

5 reasons an Italy Custom Vacation is the right fit for you

Below I’ve started with the most common reasons that a custom vacation may be the right approach for you. Then read about the five-step process we use, over and over, to create highly personalized Italy itineraries.

1. You’re just not a “tour” person

I hear this all the time. There are lots of types of Italy tours: large bus tours, small bus tours, private tours, small group tours with no bus… the list goes on. At Italy Beyond the Obvious, we create your Italy custom vacation, starting from scratch. There are no templates. You can decide what you’d like to do, and what you’d like to skip, and we’ll make it happen.

2. There are specific things you want to see

Sometimes, that’s Rome, Florence, and Venice. Other times, it’s an off the beaten track itinerary. You may know where you want to go, but not how long to spend in each place, or the best way to get from A to B. Tell us what you want to see, give us a budget if you have one, let us know how many days you have, and we’ll do the rest.

3. You just don’t have time to create this trip

We work with lots of people who are well-traveled and have put together their own trips in the past. The amount of information online about Italy is overwhelming. You know how to research, plan, and book, but you don’t have the time to do it.

4. Your group or family has specific needs

Maybe you’re traveling with a two-year-old and not sure how to make the trip toddler-friendly. Or maybe one of the travelers has severe food allergies. Or you have a group with diverse interests that you’re not sure how to incorporate into one trip. Aunt Sally wants to go to the beach, while Dad wants to hike but also not miss main sights. The kids want to go up the Leaning Tower of Pisa and eat gelato.

5. It’s your dream trip and you want it to be perfect

Maybe you’ve been dreaming about an Italy trip for a long time. You’ve seen photos in magazines, and you want to have an amazing trip and fall in love with Italy. But you aren’t sure where to start, how much time you really need, or even how much it will cost. You don’t want to travel with strangers, and all the tours you read about sound great. Or, maybe you don’t want to be the one responsible for making sure everyone else’s dream trip is perfect.

Ready to Move to the Next Step?

Client Testimonials

"We had a wonderful trip! We did so many amazing things and experienced many wonderful places yet never felt like..."

"We thank you so much for all you gave us, guided us to, arranged for, and detailed for us. Not..."

"We are in love with Venice and the Dolomites. The ski adventure was amazing and beyond anything we could have..."

"Absolutely everything that you planned went off without a hitch. Every tour, every restaurant, every train and activity came through..."

"Thank you again from all three of us for your help in planning such a delightful trip. I know that..."

"Madeline carefully planned a fabulous, personalized 19 day itinerary (Lake Garda, Dolomites, N/S Tuscany, Rome) that enabled us to be..."

Read More Client Testimonials

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Italy Advice & Tips In Your Inbox

Italy Advice & Tips In Your Inbox

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The Travel Expert Network

Check out the Travel Expert Network where you’ll find Certified Travel Experts™ ready to plan custom bucket trips for you all over the world!

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Office Locations

San Francisco
+1 773 621-3024
Contact San Francisco

+39 320 028 6827
Contact Milan

+39 331 222 2349
Contact Rome

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