Travel Planning

An Insider’s Italy trip is an experience most travelers find difficult, if not impossible, to organize independently. Even the traveler with unlimited time and planning resources is rarely able to replicate what we offer.

We are a boutique company that plans upscale travels exclusively to Italy. We offer a bounty of unique expertise based on the decades we have spent living in Rome and traveling throughout Italy.

“What makes a good first trip?” “What would you suggest for my fourth visit to Italy?” “What destinations are good for a winter itinerary ?” “What do you recommend for a family trip ?” “I’m on my honeymoon, where should we go ?” “Are hotels better for me or a villa ?” We answer all of these questions for you, and some that you may not even know to ask.

As noted in the Overview, please understand that our services are too much in request to offer partial planning.   That is to say, we are able to offer our travel planning services only to those for whom we also book, at minimum, accommodations.

Travel Planning with Insider’s Italy takes one of three routes:

SemplicitaCompleto and Ultimo (scroll through by clicking on numbers below). Note: If your web browser does not display the information below correctly, please click here to view an alternate version.

Accommodation Planning


Semplicita is meant for clients who want a thorough, thoughtful consultation on how to best organize their travels—choosing bases, specific hotels and inns—and want Accommodation bookings only. We personally make every hotel reservation for you at our favorite inns, hotels and country agriturismi (three, four and five star categories), and book by room number (almost always) directly with owners and managers.

Semplicita is ideal for last-minute travelers and for those who wish to fully coordinate all their own itineraries, touring and dining plans.

Semplicita includes full reviews of accommodations, and provides general information on routing from one hotel to the next, including driving or train access.

Semplicita comes in PDF format and is charged at our minimum fee of $1,000 (more for trips longer than 10 to 14 days or exceeding four bases). We typically have it out to you the day we receive payment.



Accommodation and Special Services Planning


Completo is intended for those who want more structure than Semplicita clients but wish still to undertake much of their day-to-day itinerary planning themselves.  Completo is Semplicita plus detailed restaurant suggestions and the coordination of our guides and docents, as well as our own drivers for airport transfers. We also coordinate car rentals, through the most efficient, least expensive car supplier in Italy. We will book our own drivers for car-and-driver wherever you would like to use them.

Everything we recommend is personally known to us. And we provide a page or two of detailed Insider's information on each base -- just enough to set you off on explorations of your own.

Typically, the fee for Completo is $2,500 (more for trips longer than 10 to 14 days or exceeding four bases). Completo comes in PDF form.



Premium Travel Planning


This is the service where we made our name and is our most popular service.  Ultimo is defined (Gourmet Magazine) as "remarkably detailed, with things I've never seen in any guidebook, the sort of advice you might get from a friend if the friend were very, very knowledgeable". See reviews of this service.

We start by sending you our Insider's Reading and Movie List, plus suggestions for self guided language courses. We have special Reading/Movie/Language suggestions for children too.

Ultimo offers everything you will find in Completo, but also includes an 80-150 page, detailed, personalized itinerary combining unusual historical background, a thorough report on special (usually off-the-beaten-track) sightseeing and  unique, informed tips on how to enjoy all locations most fully.

We offer our 16-page General Information, invaluable Italian travel advice, which you'll find nowhere else. We send the best maps made for Italy. We offer our Insider's Guide to the Italian Train, appropriate train schedules, and exceptionally detailed driving routes.

We offer our full Good Eating materials.  Every exciting food discovery we make is included in your  Plans. Our detailed reviews are for restaurants that are locally acclaimed. The focus is mostly on Slow Food. We include detailed information on wine producers, vineyards and tasting cellars, plus culinary destinations, such as Parmesan dairies, a wood-fired bakery in Puglia, an outstanding olive-oil producer, ice cream makers, pastry chefs. We offer our detailed Insider's Guide to the Italian Restaurant, Gelateria, Cafe/Bar and Regional Eating Guides for every region you visit.  Where advisable or you wish it, we will always make meal reservations —e.g. for special, small favorites, in Venice or in restaurants that we know will be full or for Sunday lunches.

Ultimo comes as a printed book (nicknamed by many "our Bible") that we typically send month or so before you depart.  Included is an "executive summary" for every day—though of course this one is not work-based, but filled with appointments with special docents, cooking classes, timed entry museum visits, trattoria meals!  We offer telephone consultation throughout the planning process and during your trip.

The sort of traveler who selects Ultimo is often one who longs to visit Italy in a special way, but has no time and/or no inclination to plan. With Ultimo, all you need do is purchase air tickets and have one relaxed conversation with us. We will plan it all : a remarkable, tailor-made experience that will include a rich array of special experiences. Each itinerary is highly customized to your interests, budget and needs.

The fee for Ultimo is typically $4,000 for 10 to 14 days of Planning.