FAQ

Yes. Here’s why:

We do not offer day-on / day-off planning services. We’ve been there and done that and it’s more work and is error-prone. If we are going to control the outcome, we need to control the process.

Also, when we plan “on your own” or beach days for people, there is still a lot of work involved. Let’s say you want to explore the Tuscan countryside. We’ll recommend which towns we think you might like, how long it will take you to get there, where you should park to avoid getting any fines or accidentally driving across the ZTL boundary. We’ll recommend museums, shops, bakeries and more, with opening hours so that you don’t show up to find things closed (very common in Italy). We’ll reserve a restaurant for you so that when you’ve walked and you want somewhere to sit down, you don’t end up in a tourist trap.

Same thing if you’re going to the beach. We can recommend which beach, tell you where to park, help you book a beach lounger (required at a lot of beaches in Italy) and make sure there are nearby services like showers, storage for valuables, a place to get lunch or a drink, etc.

Our travelers typically:

• Want to connect with the culture and feel like they have experienced the “real” Italy
• Want to see the main sights but avoid crowds if possible
• Value skip the line tickets and private guides
• Do not want group tours or bus tours
• Value our deep and broad Italy expertise and on-the-ground relationships
• Want a stress-free vacation
• Are overwhelmed with the options when they do online searches about what to see and do in Italy
• Have specific interests they’d like to incorporate into their trip, like soccer, archaeology, or doing a cooking class
• Often have requirements around – for example – traveling with a toddler or have a traveler with mobility issues
• Often have food requests like eating vegan, or severe allergies like celiac disease
• Are not budget travelers but want value for money (even when the Presidential suite with a private balcony over the Amalfi Coast is good value)
• Have often been to Italy decades ago as backpackers and now have the income to be more comfortable
• Are celebrating special occasions such as birthdays, anniversaries, graduations, or multi-generational trips
• Value our transparent pricing and custom planning

Our travelers are appreciative, decisive, and value our expertise.

Italy is a very cash-oriented society and you should always have cash in your wallet to cover small things like coffee, gelato, sandwiches and tips. In addition note that many taxi drivers, even though required by law to accept credit cards, often have “broken” credit card machines in their taxis so I always carry cash when I take taxis.

Keep in mind that while credit cards are widely accepted, American Express is not. Always carry a Visa or Mastercard as a backup if American Express is your preferred card.

It’s quite common for Italians to pass on the credit card charge to the consumer. So a price might be listed as 60 EUR, or 55 EUR if you pay cash. Or the reverse: it might be listed as 60 EUR but then when you go to pay, when you pull out a credit card, they tell you there’s an additional 4% fee for using a credit card.

Your travel app will include very detailed cash needed amounts while on your trip. You will know exactly how much cash you’ll need, by day, on your trip.

There are a few ways to get cash in Italy. You could use the ATMs in Italy to get Euros (this is what I do). You could get Euros before you leave home and bring them with you. You could bring your local currency to Italy and exchange it for Euros there.

As always, remember there are pickpockets in Italy. Do not store all your cash in your wallet – spread it out across a few places. When opening your wallet to pay for something, do not let the person behind you in line see all the cash you have.

Apple Pay, Google Pay, Venmo, and Zelle are not accepted in Italy.

The short answer is maybe, but it’s not guaranteed. If you’d like to do this, please let us know as soon as we start working together, because typically trip costs are quite spread out during the planning. We are not a tour operator, which means that we do not take your money and then pay the vendors. We use your credit card for all bookings.

Hotels: we book your hotel the way we’d book ours, by contacting the hotel and making a reservation. Hotels will hold the reservation with a credit card, with a cancellation policy. Typically the cancellation policy is between 30 days and 2 days (villas are different) however there is usually a pre-paid non-refundable rate. It varies by hotel but usually we can pre-pay hotels.

Activities: Because we work directly with many private guides, and we skip the middleman (who often provides the credit card machine), often you will be paying your private guides in cash at the time of service. No this doesn’t mean they are avoiding taxes. Yes there is still a cancellation penalty. If we book activities online, we can usually prepay those. When working with private guides, whether we can pre-pay depends on the guide.

Logistics: Airport drivers are typically paid with a credit card at the time of service and are hard to pre-pay. Rental cars can be prepaid but are still refundable until 72 hours prior to pick up. Train tickets can be purchased a few months in advance and can be prepaid. Private chefs and villas can be prepaid.

Tips: All tips should be paid in cash at the time of service.

The short answer is months. We build your trip the way we’d build ours, step by step. At each step, we will make recommendations, and ask you for feedback. There might be some back and forth with questions before you decide which hotel, activity, or restaurant you’d like us to book.

We start with the overall itinerary and make recommendations. Once you are happy with that, we move to hotels. For each destination, we will recommend a curated handful of hotels (or apartments, or B&Bs, or villas, or rustic farmhouses etc) that we think you’ll love. After your hotels are booked, we’ll move to activities. For each destination, we will make our best recommendations for activities based upon your interests, travel pace, budget, and more. After activities are booked, we’ll make sure logistics are smooth and stress-free. And then we’ll wrap up with pre-departure advice and restaurant recommendations and reservations. You’ll have all information at your fingertips in our app while you’re on the road. And, your trip planner will be available for any on-the-road support.

The timing depends on when you hire us and how long we have to plan your trip. We set your trip up in our backend planning system with a very detailed group of checklists and due dates. Every trip unfolds differently but here are the typical timelines for planning:

Overall itinerary: we create this together, 1-3 weeks after the contract is signed

Hotels / Accommodations: We send recommendations and then book, by destination, within 3-6 weeks after the contract is signed.

Activities: We send recommendations and then book, by destination, about 8-16 weeks after the agreement is signed. Note that sometimes we can recommend activities but we cannot book. For example, tickets to Rome’s Colosseum are available only 60 days in advance.

Logistics: We book these about 8-12 weeks before departure.

Restaurants: We book these a couple weeks ahead of time. If we try to book earlier than this, they will just tell us to call back. The exception is with Michelin-starred restaurants, which we can book early.

Final itinerary review call: A couple of weeks pre-departure, we will review all itinerary details over a zoom call. Then we will publish the app to you so you can review everything. Our restaurant recommendations are included in the app, and based on traveler feedback, we will make reservations, which will update live in the app as they are made.

No. The reason the Gold planning service has a lower fee is because we are skipping the first two steps of our 5 step planning process and diving right into activities. The Gold service does not include creating your overall itinerary and it does not include recommending or booking your accommodations. If you would like us to review your accommodations and / or suggest alternatives, you will need our Platinum planning service.

Yes! If you have Marriott points, Hilton points, AmEx points, Chase points or other, we can use those. In these cases, we will follow our standard hotel recommendations process, meaning that we will recommend hotels that are:

1 – Available for your specific dates, and are

2 – in excellent central locations, and are

3 – according to your preferences (suite, with balcony or view, bed configuration, etc), and are

4 – available with points.

After you’ve reviewed the options and have chosen the hotel, if we can book it, we’re happy to do that. However often our customers need to log in to a portal or call a special customer service number to make the booking. In these cases, they usually choose to make the booking themselves and then forward us the confirmation.

The short answer is probably, but let’s discuss.

It varies, but here’s a good place to start. The things to consider when thinking about costs are the accommodations, tours / activities, logistics, food, flights, and our planning fees.

Costs are based on 2024 prices and are for two people. Note that this is not a budget trip but it’s not the lap of luxury either.

Hotels: 300-500 USD per room per night. Note this is average across the trip. Venice and the Amalfi Coast are more expensive. A sea view room, a room with a balcony or a view, or a Suite are more expensive. Note that there are many less expensive hotels, Airbnbs, apartments, etc across Italy. However our travelers typically start with this budget and go up. This gets you a great 3 or 4 star hotel in an excellent central location, with breakfast and taxes included. Many hotels in Italy have moved from “high season / low season” pricing to dynamic pricing, which means that rates are based on demand, regardless of the season.

Tours & Activities: 400 USD per day. Note that this does not include VIP experiences. Note that this does not include activities with per-person costs such as cooking classes or vespa tours. Note that this does not include high end excursions such as a full day boat excursion off the Amalfi Coast or a balloon ride over Tuscany. This price reflects a half day private guided walking tour, and would include the cost of the guide, entry tickets, and a tip. You can have a fabulous trip with private guided half day tours on most days.

Logistics: 200 USD per day. This includes airport transfers, rental car costs, train tickets, and the occasional taxi. Note that this is average across the trip. Some days you’ll be on your own two feet with zero logistics costs, and some days you might have a 500 USD private transfer. If you are staying on the Amalfi Coast or doing a full day Tuscan wine tour, and need a private driver, you might spend 1,000 USD / day.

Food: 250 USD per day. Note that this assumes that breakfast is included with the hotel (most are). This assumes you’ll have a light lunch, like a salad at a café, or a quick sandwich. This assumes that you’ll sit down at a restaurant for dinner every night. You won’t be eating in Michelin-starred places, but you also won’t be going to the grocery store to grab a baguette and a hunk of cheese like you did in your backpacking days. This also allows a budget for coffee, gelato, and snacks.

Flights from the US are typically between about 800 USD and 1600 USD in economy class, depending on where you’re flying from and depending on the time of year. Economy Plus is more. Business is about double.

Planning fees: Our planning fees are either 250 USD / day or 375 USD / day, for up to 6 people. We always tell people that travel industry markups (inside those single-price packages) are about 20% – 25% so if our fees are in that range, that’s about right. If our fees are lower, you’re getting a deal. If our fees are more than that, it might not make sense to work with us. In the examples above, the trip costs add up to 1,150 USD per couple per day. If this couple hired us for Platinum travel planning at 375 USD / day, that works out to about 30% of trip costs. However, if two couples traveling together split the cost of trip planning fees, this is a good deal, compared to purchasing the exact same trip in a package deal.

Officially, we only do Italy. However, we can recommend other fee-for-service travel experts for other destinations.

Here’s where I am going to toot my own horn and talk about my amazing team. We are hard working, detail oriented, and will provide you excellent customer service. But anybody can say that. Here are nine specific reasons that separate Italy Beyond the Obvious from other travel consultants:

• We’ve actually lived in Italy. I lived in Italy for five years, and I have two Italy-based travel planners. We know how things work in Italy, including the little things, and how to navigate them. We know what can go wrong, and how to fix it. We have the answers to questions about Italy that you didn’t even know you should ask.

• I’ve worked as a tour guide in Italy, leading 25 people on 8 day biking and hiking tours. The benefits to you are that I know how to find great hiking and biking trails in Italy; I can recommend lots of great hotels and out of the way places and unique experiences; I have detailed knowledge of many Italian regions. And probably most importantly, I understand Italy’s “wow” factor and can ensure you have it on your trip.

• We speak fluent Italian. My Italy-based team consists of one Italian (who speaks fluent English) and one American who has lived in Italy for three decades. I speak fluent Italian and have taught Italian.

• I spent 8 years in corporate America. The benefits to you are that I am a process person, I can manage a project and a budget. Nobody can keep on top of every hotel and restaurant and guide in Italy, but our processes and methods mean I can make the best possible recommendations for your specific trip. We can ensure that each traveler has a personalized, high-quality and unique trip.

• We’ve traveled to lots of countries. We know what it’s like to feel like a foreigner in a foreign land. We have tips about travel insurance, luggage, cell phone usage, and language.

• We understand customer service. You get a North American level of customer service from us, as we act as the bridge between cultures. Customer service doesn’t mean quite the same thing in Italy.

• The Italy Beyond the Obvious team has six kids between us. We understand what it’s like to travel with a 4-month old, a two-year old, a six- year old, and teenagers, and will ensure that your trip is fun for the whole family.

• We’ve worked on the ground as local guides, which means we know how to choose good guides. We work with guides who are engaging, informative, and provide the context you need, whether that be good for the kids; a focus on Jewish history; or an emphasis on food.

• Because we are paid for our time and expertise, we can spend time on details like transportation, food, festivals, and overall flow and balance of your itinerary. Travel agents cannot earn commissions on any of these items so most cannot spend time on them. But these are details that will make your entire trip flow smoothly.

• We do not mark anything up or sell you a single price package. All your trip costs are transparent, because you don’t pay us anything except for consulting fees. We use your credit card to pay the vendors directly so you’ll see line item by line item, what each item costs you.

This Wall Street Journal article does a great job of outlining four reasons you should use a travel consultant:

When should you reach out to a travel agent?

• If you want someone to call when things go wrong: Nearly 70% of affluent consumers who use travel agents say what’s most important is that an agent protect them or help them when things go wrong with a trip, according to a study by Harrison Group and American Express Publishing. “Travel agents are a kind of insurance,” Taylor say. For many agents, this means being on call at all hours.

• If you’re pressed for time or just want to avoid hassles: About one in three travelers feels overwhelmed by the amount of travel information online, according to the American Express Spending & Savings Tracker, a survey that looks at Americans’ spending and saving habits. If you’re in this group, or simply don’t have time to deal with trip planning, travel agents can do it all for you. Tell them where you want to go and the types of things you like to do, and they can put together a list of options for you and book them, saving you time. Agents are particularly useful to travelers who plan to take complicated trips, or go to multiple destinations or with multiple generations, says Gonchar.

• If you want more of a local experience: Good travel consultants have relationships with locals in your destination, experts say, so they can do things like arrange for you to have dinner with a local family, recommend restaurants and pubs that residents like but tourists don’t tend to know about, or find a tiny B&B for you to stay at where you can get to know the owner.

• If you want a highly customized experience: More and more travelers are asking for one-of-a-kind trips specifically tailored to their likes, says Gonchar. A foodie might want something like a private cooking class in Italy, a meet-and-greet with a chef she’s been reading about and a table in the private wine room of a restaurant. While she might not have the connections to get this done herself, a travel agent with deep local knowledge might be able to make this happen for her, Gonchar says.

We should discuss this before we begin. Your Italy Beyond the Obvious itinerary will be very organized, with everything pre-booked and double checked. But you have to be able to execute it on your own when you get there.

You’ll know where to go, when, and how to get there, but you’ll still have to leave your hotel, on your own, in a foreign country with a foreign language and using foreign currency (and possibly in a jet-lagged fog). Your local guides, local drivers, hotel concierge, and our on-trip support can help a lot here, but if you haven’t spent time in foreign countries, all of this can still be overwhelming.

For travelers who have never been abroad, we only offer our Platinum travel planning service because it makes us too nervous if you don’t have on trip support.

Sure. Italy’s main sights are famous for good reason. Sometimes “beyond the obvious” means the way you travel, not what you see. So maybe you want to see the main sights with a 2 year old in tow, or maybe you want to avoid crowds as much as possible.

Sometimes. But more importantly, you can be assured that all recommendations are good value for the money. You get what you pay for, so I don’t necessarily recommend the least expensive option. We are very used to working within a budget. That said, Italy Beyond the Obvious is not typically for the budget traveler.

Return on your investment is in 2 parts:

Time saved during the planning process: To organize a trip to Italy with the level of organization and detail provided by Italy Beyond the Obvious, plan on spending about 8 hours per travel day if you are going to do it yourself. A 10-day trip would therefore take about 80 hours for an average person to plan (including internet and guidebook research, time spent on the phone to Italy, booking time, and double-checking everything). By contrast, plan on 2-3 hours spent via phone or email with Italy Beyond the Obvious. For a 10-day trip, that’s about 77 hours of time saved. How much is your time worth per hour?

Time used more efficiently on the trip: when a trip is well-organized ahead of time, you won’t waste time getting lost; showing up at the train station and realizing that train doesn’t run on Sundays; fixing errors due to the language barrier during the booking process; or waiting in line for 2 hours for a museum that could have been pre-booked. We estimate that travelers with organized pre-booked itineraries can accomplish 20% more in a day, and don’t forget: you accomplish more in a single day, at a lower stress level, for more enjoyment.

An Example:

Let’s say your 10-day trip to Italy works out to cost $600/day, including everything. Let’s say you have 12 hours per day of “out and about time”, to enjoy, explore, and relax. Each Italian vacation hour essentially costs $50. A 10-day vacation has 120 vacation hours. Therefore being able to do 20% more because of a well-planned vacation equals 24 hours during the vacation which are spent relaxing and enjoying Italy rather than spent problem-solving and stressed in a foreign country. To put a dollar value on it, those 24 hours x $50 per hour is $1200 worth of time that can be used to enjoy Italy instead of lost due to planning mistakes.

Put your own numbers in to the examples above in 1) and 2) (and take into account that part 2 can be multiplied by number of people traveling together) to calculate how much you will actually save by having Italy Beyond the Obvious plan your Italian vacation!

The short answer is: the business model. We charge consulting fees for our time and expertise, because we have deep Italy knowledge and can create your trip from the ground up. We do not sell other people’s packages – we book directly with local providers, cutting out any middlemen. We also do not mark anything up.

Travel agents receive commissions for booking hotels, cruises, flights, or tours for travelers from their portfolio and therefore they must spend their time booking things that give them commission.

It takes us about 5 hours of work to create one Platinum trip day, which means you are essentially hiring us as consultants at $75/hour for our time and expertise.

We spend a lot of time on things that do not offer commissions such as:

• Detailed recommendations for the best way of getting from A to B within Italy
• Specific shopping recommendations with maps for the most efficient shopping route in a city
• Recommendations and reservations for restaurants, cafes, gelaterias, and more
• Detailed driving routes with recommendations for parking, sights, and including detailed logistics
• Hiking route recommendations for people who can hike on their own but need to know the difficulty of hike, the distance, starting point, ending point, stops along the way.
• DIY recommendations so that you can explore on your own but not end up showing up with closed places, long lines etc.
• We can book Airbnb or VRBO, or use your Marriott rewards or credit card points

The Italy Beyond the Obvious team is available to you while you’re on the ground in Italy. We are available 24/7!

The on-trip support we provide includes behind-the-scenes reconfirming of all guides / activities and drivers the day or two before. People sometimes ask me: “what happens if a guide doesn’t show?”. That is not a thing here at Italy Beyond the Obvious.

In addition, we proactively check for strikes (trains, air traffic control, and more) that might affect your trip. If your trip is affected, we will be in touch with a plan. We also keep our eye on the weather. If your hiking, biking, or boat excursion needs to be cancelled or rescheduled due to weather, we will handle it.

In addition, we are available while you’re on the road. Note that on-trip support does not include on-the-fly trip planning, but you might have a quick question about an activity that is coming up or you might contact us about one of the examples below:

• Someone doesn’t feel well. Where’s the closest pharmacy or hospital? (We’ll also help translate)
• We’re tired. Please cancel tomorrow’s activity.
• We’re running late. Please let our guide / hotel / restaurant know.
• Please cancel/change our dinner reservation
• Someone is yelling at me in Italian. Please tell me what they are saying and yell back at them.
• The cigarette lighter on our rental car is broken so we can’t plug in our GPS. Please arrange for a new rental car and tell us when and where to do the exchange.
• We need to do laundry, what are nearby options?
• We are museumed out and would like to update tomorrow’s itinerary to include an outdoor activity instead.
• The forecast is for rain / heat tomorrow so we won’t be able to go hiking. Please suggest alternative activities.
• There’s a train strike tomorrow. What do we do?

Yes absolutely. Our Diamond Planning service is for groups of more than 6 people.

Absolutely. And, you should ask us for the cost breakdown, because the vast majority of the time, we can create the same trip for a lower cost. Online tours are sold at a package price, and when we break down the individual costs – even with our highest end Platinum level planning services – the total trip cost always comes out lower.

For trips in high season, the more notice we get the better. A year in advance is not too early to hire us! But for a low stress planning process, in high season, we need a minimum of 6 months.

The biggest factor here is whether we have the capacity. We hit capacity every single year. Because we offer a high-touch, white glove planning service, when we max out the hours of the team, we simply cannot take on any additional work. Often by January we are at capacity for June and September, for example. The best way to find out is to contact us and ask.

That said, if you have a flexible budget and a straightforward trip (Rome, Florence, Venice, Amalfi Coast for example) and you are traveling in shoulder season, we can usually fit you in!

We have a 5-step trip planning process that goes: Overall itinerary -> Accommodations -> Tours / Activities -> Logistics -> Food & Final details.

Our Platinum Planning Service includes all 5 steps of our planning process.

Gold Planning Service only steps 3, 4 and 5 of our process, meaning we start by recommending activities and go from there. This service is for travelers who have already booked accommodations. They need help with activities, restaurants, and want smooth and stress-free logistics.

Diamond Planning Service is for trips with more than 6 people.

ALL planning services include:

• Itinerary details in our travel app, with all information at your fingertips while you’re on the road
• 24/7 on-trip support from the Italy Beyond the Obvious team