How to Plan Your European Trip in Nine Easy Steps

Nine steps? Don’t let the number worry you. Each step in the Europe travel planning process flows naturally into the next, and several steps overlap.

Work on creating an itinerary for a perfect European trip with the same spirit of adventure and curiosity you will bring to the trip itself.

Over the years, I’ve developed a trip planning system that I return to again and again.

Your first thing to do (even before Step 1!) is to decide which countries you want to visit.

Changing your mind is never off the table, but once you have some idea about where you want to go, you’re ready to get cracking with creating your itinerary.

Ready? Let’s plan!

Step 1: Determine Your Time and Travel Budget

How much time and money do you have for the trip you want to take? Calculate total travel expenses of about €135-225 per person per day to travel in Europe, not including airfare and transportation costs.

I provide a general cost breakdown below. These costs presume you’re on the go most days. If you home-base in a destination for a week or more, your per-day costs will be lower, depending on your transportation needs and the price of your accommodation.

Accommodation Costs

Budget about €150-300 per night for 2 people. I wish it was less (it used to be!) but it’s not anymore, especially in western Europe.

Within this budget, your accommodation costs will likely vary widely, depending on where you’re staying and how much comfort you want to pay for. Count on closer to €400-400 per night in cities or for resort properties and €90-110 per night in the countryside for small guest houses.

Apartments are a bargain if you’re traveling with three or more people. For two people, apartments work out to about the same price as hotels. However, you get much more room, you can cook some of your meals (thereby saving on restaurants), and you get the experience of living like a local.

Putting together portable fan, apartment in Lisbon, Portugal.
Gregg puts together his portable fan in our two-floor apartment in Lisbon, Portugal.

For advice about choosing accommodations, read Six Tips for Making Awesome Accommodation Choices in Europe.

Food Costs

Budget at least €45 per person per day. Again, this amount can vary a great deal. Save money by renting apartments and cooking some of your meals. We generally spend about €60 per person per day for three meals when we’re on the road because we eat in restaurants more often than we do when we’re home-basing and eating in.

Sightseeing Costs

This cost varies from place to place. In big cities, budget at least €45 per person per day for museums. If the city has a lot of interesting museums and other sights, you’ll spend more. When you’re staying put and enjoying the scenery, you’ll spend less.

One way to save money is to buy a museum pass, city pass, or a combination. Most major European cities have several options to choose from. Match the time you have available with what you want to see and then determine if you’ll get your money’s worth out of any of the passes on offer.

Total Basic Costs

At about €270 per day for two people traveling together, a one-month trip to Europe costs close to €8,500, not including airfare and other transportation costs. But let’s be real. You’ll likely pay closer to €13,000 for your trip once the smoke clears.

Traveling is not cheap these days.

On the up side, traveling in eastern Europe is less expensive than in western Europe, and country stays will cost less than city stays. Tweak your destinations according to your budget.  

Other ways to cut costs include staying in budget hotels, rarely eating out, and doing a walking or biking holiday instead of renting a car and taking trains.

Transportation Costs

I don’t include transportation costs in my estimated per-person-per-day calculation because these costs vary so much depending on your transportation needs.

Following are guidelines about transportation costs depending on the type of transportation you choose.

Car Rental & Gas

Renting a car makes sense for two or more people traveling together. I estimate about €90/day for car rental and another €45/day for gas when you’re on the road doing long point-to-point drives.

On extended driving trips across Europe, gas costs skyrocket, so make sure to factor estimated costs into your budget. Also factor in costs for toll routes that can range from €10-50 per day, depending on where you’re driving and for how long.

Gas costs vary across the continent but figure on spending about €1.70/liter, on average.

Rail Pass

Rail passes might make sense if you’re planning to travel long distances across several European countries; for example, from Stockholm to Rome. Pass costs vary depending upon the number of days you travel within a given period, the class of travel you choose, and even your age.

High-speed trains in Europe make rail travel a pleasure.
High-speed trains in Europe make rail travel a pleasure.

For example, a Eurail Global pass good for five travel days in one month in a 2nd class train car will cost a 60+ traveler $383 USD. Note I quoted this price in dollars because you must purchase your pass before you arrive in Europe. Find out more on the Eurail website.

Before you purchase a pass, check the countries included and calculate costs.

Use the Rail Europe site to check costs for individual trips and then compare the total to the price of the pass. Bear in mind that pass holders are often required to purchase seat reservations separately.

Sometimes (actually, very often), flying between destinations is faster and less expensive, although your carbon footprint is greater.

Flight Costs

I use Cheapo Air to check flights and to purchase my airline tickets. Their prices often beat those of their competitors.

Departing from the west coast of Canada, we can count on a flight to Europe costing around $1,500 CAD for an open-jaw ticket. On top of the basic cost, we pay for extra baggage if we’re taking an exhibition of Gregg’s paintings to Europe, and we always splash out for extra leg room.

Comfort over cost is my motto! (within reason, of course).

Vacation Packages

Research vacation packages available through companies such as Expedia and Flight Center. You may save money by bundling your airfare, car rental, and accommodation costs.

Vacation packages are a good option when you’re going to one or two destinations for a relatively short time (for example, a two-week vacation in Italy).

Step 2: Select Your Travel Mode

You have two choices—escorted tour or independent travel. If you choose independent travel, consider purchasing the occasional day tour. You can relax and enjoy the attractions without the headaches of navigating.

I have traveled on guided tours and independently, and both methods have benefits and drawbacks.

The remaining steps relate primarily to independent travel.

Step 3: Set Up Your Itinerary

Once you’ve determined how much time and budget you have and you’ve chosen to travel independently, the real fun begins!

Launch Microsoft Excel, Google Sheets on your Google drive, or the spreadsheet app of your choice and set up your itinerary.

In the first column, enter the start date for the trip and then add each date of the trip’s duration on subsequent lines.

TIP: Set the format for each date so that the day of the week (Monday, Tuesday) is displayed to help you when you start filling in information about events, transportation connections, and day tours. Travel on Sundays can be limiting if you’re planning to use public transit, or you may discover that the museum you want to see is closed on the day you’ve allocated to visit.

Add headings for Destination, Transportation, Activity/Event, Accommodation, and Cost.

The start and end dates may shift when you start looking into flight options, but your goal at this point is to create a ‘big picture’ view of the trip.

Enter as many costs as possible as you create your itinerary. Set up the spreadsheet to calculate totals. I often add columns for costs incurred each day; for example, Accommodation Cost, Transportation Cost, Event Tickets, etc.

Step 4: Choose Your Destinations

For me, this step is the most challenging and the most satisfying of the planning process. How to figure out where to go and what to see?

Head first to the library or go online to find guidebooks about the destinations you’re considering. Also explore the posts and pages on the Artsy Traveler website and search for destination ideas on the Web.

Enter search terms such as “what to see in London” or “itineraries for Scandinavia” and then start surfing. Over the course of several days, a picture starts to emerge of the main sights and points of interest in an area.

Start filling in the itinerary spreadsheet with your preferred destinations. This phase of trip planning is a lot of fun because you’re discovering new ideas and letting your imagination run free.

For Gregg and me, part of the decision about where to travel is made for us because Gregg is exhibiting his artwork (see My Story) in a particular location. We plan the trip around the exhibition location and dates.

Step 5: Find Events, Exhibitions & Tours

Once you know where you want to go, search for information about what’s on. This step puts the ‘artsy’ into artsy traveling.

For example, on a trip to England, I wanted to see a play at Stratford-upon-Avon. When I check the Royal Shakespeare Company website, I discover that I can’t see the play I want to see on the date I’ve allocated for Stratford.

Back to the drawing board! I rejig my itinerary until finally I can see everything I want to see and catch a performance of Richard III!

Find out what’s happening in the locations you’re visiting using search terms such as “concerts in Vienna”, “what’s happening in Amsterdam,” “exhibitions in Paris”, etc.

Also visit the websites for specific institutions, such as the Uffizi, the Louvre, or the Rijksmuseum. To find concerts, check the websites of concert venues, such as the Royal Albert Hall, the Berlin Philharmonic, and so on.

Musée D'Orsay in Paris
What’s on at the Musée D’Orsay while you’re in Paris? Check the website!

If you’re visiting London, check the theater listings and choose the plays and musicals you want to see. By the way, theater in London is both fantastic and a bargain, especially compared to New York.

Every time I visit London, I set aside time to attend as many performances as my schedule will allow. I can often get good deals by going to the theater the day before the performance to see what seats are available.

Step 6: Calculate Transportation Needs

Flights

Your first job, presuming you’re traveling to Europe from elsewhere, is to determine which city you’ll land in and which you’ll leave from.

I’m a big fan of the open-jaw itinerary – that is, flying into one city and flying home from another city.

You save travel time between cities and cover more ground. We generally fly into Amsterdam and then fly home from somewhere in the south, such as Nice or Portugal. The cost of open-jaw tickets is surprisingly reasonable, often not much more than the cost of a regular return ticket.

SkyScanner offers a wide range of open-jaw flights and cheap flights. Booking an open-jaw flight is easy. Just click the Multi-City option when you enter your departure cities.

Once you’ve chosen your arrival and departure cities, you need to determine how you plan to get around.

Car Rental

If you plan to drive in Europe, your selection of an open-jaw flight will depend on whether you’re able to purchase an open-jaw car rental.

You’ll pay a premium to drop off the car in a different location from where you picked it up. Do the math to determine if the extra cost is worth it, considering the gas and accommodation costs required to drive back to where you picked up the car. We usually find that the one-way stipend is much less than the cost of taking an additional few days to drive back to our starting point.

If you’ve planned your itinerary as a circle tour, you’ll pick up and drop off your car in the same location, thereby saving money.

To help you plan your car rental needs, check the car rental sites like Europcar and AutoEurope.

Rail Travel

Your best resources for train travel are the Rail Europe and UK Rail websites. Enter your start and end cities to find out schedules, durations, and costs. Note that these sites only allow you to view tickets within a six-month time frame, so if you’re doing your planning in January for travel in August, enter dates in May or June to get some rough data to work with as you build your itinerary.

The big decision when it comes to training it around Europe is whether to buy a pass or pay for point-to-point tickets. Which choice is better depends on how far you plan to travel and for what duration. If you plan to travel from Paris to Berlin to Rome to Madrid in a one-month period, a train pass likely makes sense.

As mentioned above, Eurail passes must be purchased before you leave for Europe. Find out more on the Eurail website.

If you’re home-basing in Siena and planning to use busses and local trains to explore the area, you don’t need a train pass.

Make use of the trip planners on the train websites to calculate costs for point-to-point tickets, then compare them to the cost of a rail pass.

For a great analysis of rail passes vs point-to-point tickets, check out this article by Rick Steves.

Ferries

Check ferry fares and times if your itinerary takes you over the water, for example, from Italy to Greece. Confirm when and from where the ferries sail and enter the options into your itinerary.

Ferries in Norway

Day Tours

Check guidebooks and the Web for information about day tours in the destinations you’re visiting. When I travel solo, I usually travel by public transport which means touring the countryside can be challenging. My solution is to train it to a central location and then purchase a day tour that takes me into the countryside. I always opt for small group tours and have yet to be disappointed.

You’ll want to ensure that the day tour you’ve chosen is available on the day you want. If not, keep revising your itinerary!

This process is not done in a day, that’s for sure. 

Step 7: Revise and Replace

How long you spend on Step 7 depends on the information you discovered during Steps 5 and 6. I’ve been known to spend a few weeks jigging and rejigging an itinerary until finally I’m satisfied that I’m seeing the maximum number of concerts, theater performances, art exhibitions, etc., and visiting as many places as I comfortably can in the time available.

Err on the side of spending more time in a destination rather than less. Avoid creating an itinerary that has you on the move every day. That pace gets extremely tiring after just a few days.

Plan to spend at least two nights in a destination – preferably three – to settle in and really get to know the area. And make sure you build in time for relaxing. When I’m in a bit city, I often return to my hotel in the afternoon for a restorative nap.

Step 8: Book Accommodations

Once I’ve more or less set my itinerary, I’m ready to start checking and booking accommodations. I never consider my itinerary completely set until I’m home from my trip! I frequently change the itinerary during a trip after learning about new exhibitions and events or meeting new people.

Use a booking agency, such as booking.com, to find and book your accommodations and select the Free Cancellation option. You can always return to the site closer to your trip time and change the booking to the cheaper ‘no cancellation’ option. Your goal at this stage is to secure places to lay your head. Hotels and apartments book up fast in Europe.



Booking.com

Over the months leading up to a trip, I book and unbook accommodation until I’m sure I’m getting the best pillow bangs for my euros.

Step 9: Book Transportation

If your transportation options don’t allow free cancelations, you’ll need to wait until you’re 100% sure of your dates before booking.

However, typically, the sooner you book your flights, the better the deals, so don’t wait too long. You can also save on car rentals by booking early. Some car rental companies allow you to cancel your reservation right up to the day before.

We had to do this in Spain once. We were scheduled to pick up our car at the crack of dawn in Madrid and drive for six hours to Cordoba. Unfortunately, both of us had come down with nasty colds, and the thought of driving for that long was not a pleasant one.

I was able to cancel our car reservation without penalty hours before we were to pick up the car, and then purchase train tickets that whisked us south. The other people on the train may not have appreciated the hacking and coughing, but at least we could doze off before arriving in Cordoba.

You can purchase train passes at any time prior to your departure. However, you can only buy point-to-point tickets within three to six months of your travel date.

Complete Your Itinerary

In the weeks before your trip, fine-tune your itinerary so it becomes your personal guidebook as you travel around Europe. Enter every possible detail, including contact information for all your hotels, information about your car rental and train trips, performance times for events, etc.

Format the itinerary so it’s easy to read and then print a few copies.

Print? Yes. Print!

You never know when you’ll hop into a taxi to be taken to your hotel only to find your phone has died. If your driver doesn’t speak English, you can pull out your paper itinerary, point to the address and, voilà! You’re on your way.

By the time I return from a European trip, my paper itinerary is in tatters. Now, that’s a trip well taken.

Happy planning and happy travels!

Woman sitting on a balcony overlooking an Italian city - example of hotel accommodations in Italy

Recommended Places to Stay in Italy That Will Make Great Memories

I’ve had great luck finding marvelous places to stay in Italy. Hotel proprietors are friendly, and these days almost all of them speak English.

In this post, I provide general tips about accommodations in Italy and list hotels I recommend.

Choosing a Room

To Book or Not to Book?

I book almost all the hotels on my itinerary before I leave home so I know I’ll have places to stay in every location. While traveling, I sometimes change bookings to follow a new route or in response to hearing about a cool location I hadn’t known about.

TIP: Stay flexible when you travel. You never know when you might meet someone who recommends a festival or event or exhibition. More than once, I’ve altered an itinerary to attend a special exhibition or visit a new attraction.

Choose a hotel booking site that allows you to book and then cancel hotel reservations as your itinerary changes. Most sites offer you a no-cancellation option at a lower price. I never choose the no-cancellation price unless I’m 100% sure I’ll be staying at the hotel. For example, I’ll select the no-cancellation price for hotels I’m staying at in the cities I fly into and depart from because I know those locations won’t change.

But overall, stay flexible. I’ve learned from experience that sticking to a rigid itinerary with no-cancellation accommodations can end up costing you more money than you save.

Breakfasts – Prima Colazione

Breakfasts in Italy usually consist of scrumptious pastries, fresh fruit, dry cereal, cold meats and cheeses, and coffee. I only eat the hotel breakfast if it’s included in the room rate or if I didn’t get a chance to buy food before checking in.

Buffet breakfast at an Italian hotel
Buffet breakfast at an Italian hotel

If hotel breakfasts cost extra (and the cost can be exorbitant), I buy yogurt and fruit at a local grocery store and then go to a bar or café for my morning cappuccino.

Location

In Italy in particular, I only stay in the center of a town or city if I’m not driving. As I’ve mentioned elsewhere, driving into medieval hill towns can be a nightmare, and driving into cities like Rome is definitely not recommended!

A great advantage of traveling in Italy by public transit is that you can choose to stay in picturesque and historic town centers (centros). Grab a taxi from the train station and let your driver negotiate the tiny cobbled alleyways while you enjoy watching the passing throngs and imagining yourself back in the Middle Ages.

Tips for Drivers in Italy

When driving in Italy, I book places on the outskirts of the town or city and then take trams or taxis into the centro for sightseeing. In rural areas, like Tuscany and Umbria, I always book places located in the gorgeous countryside so I can take walks and, if it’s hot, enjoy a dip in the pool.

When selecting a hotel outside a city, I usually opt for a modern business hotel that includes free parking. Chains such as NH, Blu, and Best Western are generally reliable.

TIP: For a taste of la dolce vita, consider booking an agriturismo property for a week or more in a rural area. Attached to a working farm or vineyard, these properties provide you with opportunities to meet local families and to sample local food.

Star Rating

Over the years, I’ve stayed in many clean and well-run budget hotels in Italy, but these days I favor three- or four-star properties because I appreciate amenities such as elevators, air conditioning, parking, bathtubs, and in-room WIFI.

I also like larger rooms. Check the square meterage of the room. Anything under 15 square meters will be small, with a child-size shower stall and barely enough room to wedge your suitcase against the wall.

Reviews – Should You Care?

Yes, I pay attention to reviews. If a property’s aggregate review is under 8.0 out of a possible 10, I usually pass. Sometimes the difference between a property with a 9.6 review and one with an 8.2 review is only a few euros, and yet the quality of the higher-rated property makes the extra money worth spending.

You have to take reviews with a grain of salt, however. Just because a property has a score of 9.8 doesn’t meant it’s five-star luxury. Check the star rating, remember that a 9.8 score for a two-star hotel is not the same as a 9.8 for a four-star, and proceed accordingly.

TIP: Read reviews on a few sites, such as booking.com and TripAdvisor. I take my time when booking accommodations in Italy and elsewhere to make sure I’m getting the best value for my travel dollar.

Accommodation Options by Region

To help you plan your Italy getaway, here are my recommendations. For each destination, I describe properties I’ve stayed in along and suggest alternate properties that look good.

You can click the link to the hotel to make a reservation with booking.com.

Northern Italy

Turin

The Parco Hotel Sassi, located 4 kilometers from Turin, worked well for us when we were driving from France to Italy. We checked the pictures of the hotel and noted it was surrounded by the greenery of the Po Natural Park. When booking hotels on the outskirts of a town, make sure you don’t end up in a dreary suburb. Parco Hotel Sassi is situated in an attractive area outside of Turin.

We appreciated the large rooms, beautiful grounds, and proximity to a family restaurant that served one of the best meals we’ve had in Italy. We left the car in the free car park and hopped the tram to get into Turin.

On another trip to Turin, we stayed in an apartment in the heart of the city. This was a great choice because we were staying in Turin for ten days and wanted to be able to walk everywhere. We parked our car in an underground lot nearby.

Called the Casa Vittoria, the two-0bedroom, well-appointed apartment was great value and in an excellent location for exploring lovely Turin.

Milan

I can’t recommend the nondescript 3-star hotel we stayed in while visiting Milan a few years ago. It was located near the train station and was a bit on the dark and small side. I don’t recommend getting places too close to the train station in big cities. In my experience, such hotels tend to be rather soul-less!

I’ve provided two options located in the lively center of Milan for travelers who are not traveling by car (take a taxi from the train station). If you are traveling by car, check the maps and select a hotel located near the main highway of your route into the city. Note that Milan is not as crazy to drive in as, say, Rome. However, it is a big city, and, as a rule, steering clear of big cities is the less stressful option. After all, you’re on vacation!

I once stayed in a teeny tiny room in a business hotel near Malpensa airport, but I can’t recommend it unless you have an early flight to catch.

In central Milan, Antica Locanda Dei Mercanti looks like an excellent, relatively high-end choice located close to the Sforza Castle and featuring terraces and views. The reviews are excellent, and the rooms appear quite spacious. The hotel includes an airport shuttle, but parking is €38 a day so probably not the best choice for drivers.

Also in central Milan, Hotel Gran Duca Di York is a three-star hotel in an excellent location near the Duomo. Ratings are good, although room sizes are not specified for all room types, and some look small. However, the price is reasonable, considering it’s Milan..

Have a look at the map below for additional accommodation options in Milan.



Booking.com

Bolzano

The Hotel Magdalener-Hof, high on a hill above Bolzano, was a perfect stop for us when we were en route to Venice after crossing into Italy through the Brenner Pass from Austria. We had a dip in the pool overlooking the view and then caught the local bus into Bolzano to wander its colorful streets before enjoying dinner at a restaurant on the town square. At the end of the evening, we grabbed a taxi back to the hotel for about €5–much easier and less stressful than driving into town and looking for parking.

Dolomites

We drove up into the Dolomites to the picturesque Alpine village of Seis and stayed in the Parc Hotel Florian. The view from our balcony of needle-sharp Mount Schlern looming above the village was fabulous–exactly the view of the Dolomites I’d hoped for. The hotel included a hearty dinner, which was great because restaurant options in the area were limited. The hotel makes a good home base if you plan to spend a few days in the area and take lifts up to the Alpe di Siusi to go hiking.

Venice and Ravenna

Venice

If you have the time, rent an apartment in Venice and stay for a week. Live like a local, not that you’ll see many locals these days. Venetians are moving out of the city at an alarming rate. But at least you’ll experience shopping in tiny local grocery stores and get to know your way around a neighborhood.

If you’re staying in Venice for two or three days, consider the Dorsoduro district across the Grand Canal from the Piazza San Marco. I recommend you avoid the area immediately adjacent to Piazza San Marco. Hotels there can be expensive, and the tiny streets in the area are wall-to-wall tourists during the day.

Here are suggestions for hotels that we have stayed in–one in the Dorsoduro and one near the Rialto Bridge.

Hotel Canaletto: We stayed there a few years ago and loved it. The rooms were small, but that’s par for the course in Venice. The location, just 200 meters from Rialto Bridge, was fantastic as was its situation on a charming side canal.

Hotel Messner is a more modest option, located in the Dorsoduro neighborhood close to the Peggy Guggenheim Museum. It was quiet, and the area was peaceful and uncrowded, particularly at night.

For other options in Venice, check the map below. Resist the temptation to stay on the mainland. The savings will be minimal once you take into account train fares and your time. Stay in the middle of Venice and enjoy this unique city.



Booking.com

Ravenna

We were driving when we visited Ravenna, so we stayed at the Grand Hotel Mattei, about a ten-minute taxi ride from the center of Ravenna. The hotel was large and modern and included free parking–a perfect choice! When we’re driving in Italy, convenience usually wins out over charm.

The map below shows more options in and around Ravenna.



Booking.com

Tuscany

We’ve stayed in marvelous hotels and bed-and-breakfasts in Tuscany–some in the countryside and some in the towns. You’ll find amazing villa properties in Tuscany and pay equally amazing prices. Most of my suggestions are in the modest €80-150 per night range.

Florence

One of the best weeks I spent in Florence was at a rented house high above the city, near Fiesole. While swimming in the pool, we could see the Duomo shimmering in the distance. If you have the time and a car, consider renting a house a few kilometers outside Florence. You can then drive to one of the parking lots on the perimeter of the city and catch a bus into the centro.

Here are two suggestions for hotels I’ve stayed at in central Florence.

Hotel Pitti Palace at Ponte Vecchio is a great choice because it’s across the Ponte Vecchio in the atmospheric and marginally less crowded San Giovanni district. I stayed there on a solo trip to Florence and was especially taken by the views from the rooftop bar. Highly recommended.

View from the rooftop bar at the Hotel Pitti Palace in Florence
View from the rooftop bar at the Hotel Pitti Palace in Florence

The Hotel Alba Palace is an elegant property in a good location near Santa Maria Novella Basilica.

If you’re driving, you do not want to drive into central Florence. Instead, find a place on the outskirts and take a bus. Here are two places we’ve stayed in that I recommend.

The Hotel Ungherese is a two-star, budget option that includes a statue-filled garden, views over Florence, spacious rooms, and easy parking. It’s a good bargain and not far from Florence on the local bus. The Hilton Garden Hotel Florence Novoli is a four-star, reasonably-priced property a 15-minute bus ride from the center of Florence. The hotel is slick and modern and lacking in charm. However, it’s easy to find, and parking is underground and secure.

For other accommodation options in Florence, check the map below.



Booking.com

San Gimignano

I heartily recommend three places outside the walls of San Gimignano that I’ve stayed in over the years. My favorite is the Hotel Pescille which I’ve stayed in at least four times since we discovered it back in 1999!

Hotel Pescille: This three-star establishment has a killer view over the valley to the towers of San Gimignano. I keep returning to the Hotel Pescille for its simple but comfortable rooms, its fabulous location in the Tuscan countryside, and the rustic furnishings. The walls in the common areas are decorated with farm implements, and ceramic pumpkins adorn niches and stairwells. The Hotel Pescille is located about a five-minute drive south of San Gimignano.

On our most recent trip, we took several walks near the hotel to admire the view. Here’s a shot of San Gimignano from a vantage point close to the Hotel Pescille. Look at those clouds!

San Gimignano, Tuscany, Italy
I give you San Gimignano!

Relais Cappuccina: On the north side of San Gimignano, the Relais Cappuccina affords a different–and equally stunning–panoramic view of San Gimignano than that of the Hotel Pescille. The pool at this hotel is lovely, thanks to its situation overlooking San Gimignano. Our room was spacious and bright and included a terrace.

Relais Cappuccina with San Gimignano in the distance
The swimming pool at the Relais Cappuccina with San Gimignano in the distance

Villa Ducci: I stayed here on my own while researching my novel, The Towers of Tuscany, and loved it. The staff were friendly and helpful. They even allowed me to view the cellar with its 14th-century foundations that later played a role in the novel. The Villa Ducci, like the Relais Cappuccina, is located on the north side of San Gimignano. Here’s a sunrise view of the town I snapped one morning.

Sunrise over San Gimignano seen from my balcony at the Villa Ducci

The map below shows more options for staying in or near San Gimignano. If you’re traveling without a car, consider one of the hotels in the center of the town so you can enjoy moonlit strolls around the medieval streets before turning in.



Booking.com

Siena

Palazzo Masi: This small bed-and-breakfast in the center of Siena is steps from the Campo and located in a building that dates from the 14th century. I stayed here while researching The Towers of Tuscany. It’s a great choice if you’re not driving in Siena.

Athena Hotel: This is a wonderful choice if you’re driving because it’s located just inside the city walls and easily accessible. The rooms are large and the views over the countryside spectacular. We’ll stay there again, for sure.

Check the map for more accommodation options in Siena. If you’re driving, choose properties at or near the city walls rather than in the center of the city where access is tight and parking at a premium.



Booking.com

Tarquinia

Casale Dinelli: This is a lovely agriturismo property near Tarquinia, consisting of two small guest cottages set in beautiful grounds that included vegetable gardens we were welcome to raid.

Charming cottage accommodations at the Casale Dinelli
Charming cottage accommodations at the Casale Dinelli
Breakfast food supplied; strawberries fresh from the garden
Breakfast food supplied; strawberries fresh from the garden

Umbria

We stayed for ten days in Umbria in an amazing apartment attached to the gallery where Gregg had an exhibition. Located outside the lovely little town of Gualdo Tadino, the place made a wonderful home base for exploring the principal towns of Umbria.

Because we chose a homestay for our Umbria visit in 2018, most of my recommendations for these towns are based on user reviews rather than personal experience. We did, however, stay in the Hotel Valentino in Orvieto the first time we visited Umbria.

Assisi

The Vico del Poeta looks like an excellent, medieval bed-and- breakfast in Assisi. Reviews are good, and free parking is included (always a bonus!).

Grand Hotel Assisi: I like the look of this place–panoramic views, a swimming pool, and a reasonable price.

Orvieto

Hotel Valentino is situated in the centro storico (the historical center) of Orvieto but is accessible by car. We loved being in the middle of the medieval action here–able to stroll the cobbled streets after all the crowds were gone. The hotel itself is old and rather dark but comfortable and clean. A solid choice.

Hotel Palazzo Piccolomini has great ratings and looks pretty posh but with a reasonable price.

Agriturismo Podere Pescara is located in the countryside near Orvieto. The surroundings look amazing! Very Tuscan.

Perugia

Sangallo Palace includes balconies, views, and what looks to be a lovely ambiance near Perugia.

Marche

I have to put in a plug for the Hotel Emilia, high on a cliff overlooking the Adriatic Sea on the east coast of Italy. If you drive east through Umbria, you’ll likely end up in the Marche, the biggest city being Ancona on the coast. Once a bit off the tourist track, the region is getting more popular and for good reason.

The Hotel Emilia is wonderful; stunning views and fabulous modern sculptures and paintings decorate the grounds and public rooms. We stayed for two nights, relaxing in the gardens overlooking the misty view of the legend-shrouded Adriatic, taking long walks along the cliff top, and enjoying a beachside dinner in the village of Portonovo a few minutes’ drive down the hill. We were there in May, which is still the off-season. I gather that in the summer, the beach is mobbed!

View from the grounds of the Hotel Emilia
On the sandy beach at Portonovo, Italy
On the sandy beach at Portonovo
View over Portonovo from the Hotel Emilia
View over Portonovo from the Hotel Emilia

Rome

We tend to favor apartments when staying in Rome. Our favorite location is in the tiny streets leading into the Piazza Navona. One year we had an apartment that included a rooftop terrace! Hotels are plentiful but not budget-friendly in Rome. Here are two hotels and one apartment I’ve stayed in that I recommend.

Deko Rome is a small bed-and-breakfast located close to the Borghese Gardens in a lovely residential area of Rome. I stayed there when I traveled to Rome on my own and found it comfortable and budget-friendly.

Hotel Paba is a small, two-star hotel that occupies the second floor of a residential building conveniently located on the Via Cavour, not far from the Colosseum. In fact, you can see the Colosseum from the street. The decor is old-fashioned and cosy and the price reasonable, considering the central location.

Viam 16B Suites is probably my very favorite suite hotel I’ve stayed in anywhere in Europe. It’s stylish, includes a private terrace, and is located in a great area of Rome – close to the Piazza Popolo and the Spanish Steps.

Check the map for more accommodation options in Rome. I suggest the area around the Piazza Navona or the less touristy Trastevere.



Booking.com

Campania

Naples

We stayed in the Hotel Paradiso. Located on Posillipo Hill, the hotel has a commanding view across the Bay of Naples to Mount Vesuvius. Relax on the terrace and enjoy! The hotel is comfortable and reasonably priced.

Sorrento

The Hotel Eden has a central location in Sorrento, with rooms on the upper floors overlooking the stunning view of the Bay of Naples. Lush gardens and a pool provide a welcome oasis. This is a good choice for Sorrento, although not budget-friendly.

Positano

We didn’t stay in Positano, so my recommendations are based on what I think looks good. Prices are high in this holiday mecca, so if Positano is above your price range, consider staying longer in Sorrento and taking a day tour down the Amalfi coast.

In Positano, the über posh Sirenuse Hotel is über expensive, but if you’re budget runs to it – wowee! Scenes from Only You were filmed there.

A more budget-friendly option is the Villa Antonietta that still has sea views but is much more modestly appointed.

Paestum

The Hotel Savoy, steps from the beach near Paestum is an awesome place to stay. It’s super luxurious and yet surprisingly affordable.

Tours & Tickets in Italy

Here are some options to explore through GetYourGuide and Tiqets.com, both companies I’ve booked with several times, and had good experiences.

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Share Your Best Picks in Italy

Do you have accommodation recommendations to share? Please let me know in the Comments section. I’m always on the lookout for new places to stay in Italy. I’m always on the lookout for new places to stay in Italy.

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