I find Cortona to be absolutely gorgeous. The views and the churches are outstanding. I’ve written about a few things I love about Cortona, but the food always stands out. The restaurants in Cortona are some of my favorites in Tuscany. And, the best way to maximize your culinary opportunities is by staying a few nights in Cortona.
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One of my favorite Tuscany hotels is the Monastero di Cortona Hotel and Spa. This boutique hotel in one of my favorite hill towns in Tuscany has drawn us back four times in a year. It’s one of my favorite hotels in Tuscany. It’s the perfect place to relax and enjoy all the delights of Tuscany.
Getting to Cortona, Italy
Cortona is the perfect gateway to Tuscany if you want to explore the smaller towns but not have to rent a car. It’s a little under 2 hours from Florence by train. There are several direct trains between Florence and Cortona throughout the day. If you opt for the train, you’ll want to think about packing light as you may have a fairly steep walk.
We always rent a car because we enjoy coupling our visits to Cortona with wineries and wine resorts that are off the beaten path in Tuscany and Umbria. The Monastero di Cortona has its own parking garage (by reservation). If you have to park in one of the additional parking lots in Tuscany, they will help you navigate that. The hotel provides point-by-point directions to navigate the narrow roads of Cortona, which you will want to save and/or print. Google maps will steer you wrong.
Why Do I Keep Booking the Monastero di Cortona?
There are a lot of reasons that I love the Monastero. Yes, it has a spa and I love a great hotel with a spa. The cavernous pool is stunning, and I’ve never had a bad massage here. This former monastery in Cortona provides a luxurious adults-only boutique hotel experience that is perfect for a romantic trip to Tuscany. It’s quiet, serene, and the views from some rooms are absolutely stunning. More than that, however, the Monastero di Cortona shines because of its staff.
From the moment we booked our first stay, they have reached out to help with anything we needed. Parking information and reservations. Spa reservations. Finding and scheduling a COVID test for re-entry into the United States (and making sure we got everything we needed – thanks Carolina!) Giving us recommendations on anything we wanted or needed. It’s important to read their emails and follow up, especially on reservations. The spa has limited reservations, and they want to try and accommodate you when possible. Similarly, Cortona restaurants will be full, especially on Sunday evenings.
The more you listen (and work with) the Monastero staff, the better your trip will be. They really take their commitment to providing a seamless luxury stay seriously. The Monastero staff anticipates every need and is ready to help. Beyond that, they follow up to make sure everything is perfect.
The only negative about the Monastero di Cortona Hotel and Spa is that it does close for part of winter. We’ve visited Cortona in spring, summer, and fall (twice). While I think it’s lovely all the time, fall is my favorite time to be there. I’d like to visit Cortona in winter, but it’s hard to want to stay anywhere besides the Monastero.
The Monastero di Cortona Hotel Members Club
There aren’t a lot of published deals for the Monastero di Cortona, but I joined the Monastero di Cortona Member’s Club before I booked our first stay. Not only do I save on our room rate, but they also offer a few extra benefits:
- Free Travel Insurance when booking non-refundable rates
- Free room upgrade at check-in (as available)
- Spa package included (worth 25-30 euro per person)
- Early check-in & Late check-out (as available)
- Breakfast à la carte included with room rate
Monastero di Cortona Hotel and Spa Rooms
We have stayed in a range of classic and superior rooms, though they offer larger rooms and suites, too. All of our rooms have been different, but they have all been very comfortable. I love the soft white hues. The mattress is one of the highest quality and the linens are so very soft. The rooms are understated, minimalist luxury and extremely comfortable. They have every modern amenity, from reading lamps to TV. However, the rooms are designed in a way to encourage relaxation.
I’m not going to provide extensive descriptions for each room we’ve stayed in, as they are all very similar. I will post pictures and room information, in the event that one is especially appealing to you. The sizes and shapes differ because of how the building lays out. They are all relaxing, luxurious, and very comfortable though. If a room with you a view is important to you, I would mention that to the hotel. Similarly, if you want a quiet room, there are some that face the interior courtyards. You could try to request those, too. The location of the Monastero di Cortona Hotel and Spa makes it so that all of its rooms are quiet, especially in the evening. We have been able to sleep with the windows open without any issues.
One of my favorite touches at luxury hotels is turndown service. I know it seems silly, but it just hits differently when you return from dinner to find soft lighting, slippers, and the bed waiting for you. The best extra from the Monastero turndown service is the chocolate truffle they leave on the pillow. It’s the thorough and thoughtful attention to details that take a hotel to the next level for me!
Room 203 (1st Stay)
Note: This is a corner room with absolutely gorgeous natural light. My favorite naps happen in this room when I could leave the windows open and enjoy the sounds of nature.
Room 205 (2nd Stay)
Note: This room has an excellent view of the Tuscan countryside, and it can be especially beautiful at sunset. It was one of the more cozy rooms that we’ve stayed in, but the view was so incredible that we didn’t want to leave. Buy a bottle of wine from Enoteca Molesini and take it back to enjoy the sunset over Cortona from your room.
Room 104 (3rd Stay)
Room 211 (4th Trip)
Note: This room was in a different part of the Monastero than we have previously stayed. It overlooked an interior courtyard, so it was really quiet! This room had much higher ceilings, which were absolutely lovely and made the room feel so much larger. The bathroom was smaller and difficult to photograph, as I didn’t bring my wide lens with me. Oops. Unlike the previous rooms, this room had a corner shower. I really liked it, but some people might find it small. I took these photos in the evening to show the difference that turndown service makes for the ambiance.
Breakfast at the Monastero di Cortona Hotel
Have you ever been to a hotel where it seemed as if everyone decided they needed breakfast at the exact same time, resulting in lines, nowhere to sit, and you left without breakfast or overly stressed? The Monastero staff has thought of the perfect solution for breakfast. When you check in, you’ll reserve a time for breakfast. These times are in hour blocks and you can visit at any time during that hour. This works really well as the hotel is often sold out.
Once you arrive, you are escorted to a table and you can order from a la carte selections, rather than line up for a buffet. (You are also able to reorder things you enjoy.) This allows everything to be fresh, and it’s beautifully presented. While we usually skip breakfast, the Monastero breakfast is one that I wouldn’t miss if I was hungry. If the weather is nice, I recommend enjoying a table in their courtyard.
Gli Affreschi Bar
In October 2022, the Monastero staff shared that they had a new mixologist on staff and encouraged us to check out the bar. Later that evening, while enjoying apertivo in the city center, we struck up a conversation with a few professors. They also raved about the mixologist and the classic cocktails at the Monastero di Cortona bar. So, instead of ordering dessert that evening, we headed back to our hotel for a nightcap.
I ordered an aviation and Tom ordered a hot chocolate, which was served with fresh biscotti. Both were exceptional, especially the hot chocolate, and we enjoyed the quiet ambiance of the bar, surrounded by 17th frescos. A few guests came in while we were there and chose to enjoy their drinks in the courtyard. The entire experience is very low-key. The Gli Affreschi bar is the perfect, quiet place to wind down for the evening.
The Monastero di Cortona Hotel Spa
One of the reasons that I love the Monastero is the spa. Similar to breakfast, the staff will contact you in advance about reserving two hour blocks for the spa. Time slots begin at 10:30am and end by 8:00pm. Only 6 guests are allowed in the spa at a time, which keeps it quiet and relaxing. The spa overs an indoor, heated vitality pool, a sauna, a hamman, and several areas for lounging. I have had the Mediterranean Massage a couple times, which is a lovely way to relieve the stress and strain of traveling. The massage therapist is very attentive, very kind, and very talented.
Beyond the spa facilities, there is also an outdoor plunge pool for guests to use. It is not heated, so it can be VERY cold at certain parts of the year. Outdoor pools are difficult to find in city center hotels in Tuscany, so it is a nice benefit.
A Few Tips for Visiting Cortona
- Cortona restaurants will fill up. Make your reservations in advance. If you arrive in Cortona without reservations, ask the front desk staff! They are happy to help and have some great recommendations. In fact, on our last trip, Iulia knew which restaurants we had visited. She made recommendations based on places that we hadn’t tried! (We were not disappointed with her recommendations either.)
- Make the trip up to the Basilica di Santa Margherita above Cortona. I think it’s one of the most beautiful churches in Tuscany. If you don’t want to walk it, you can book a bike tour around Cortona. Valentin is an excellent guide. The bikes are electric. You’ll see the Basilica di Santa Margherita and the more difficult to reach Convento delle Celle or the Hermitage Celle where St. Francis of Assisi stayed. (This is a nice complement to a trip to Assisi.) The grounds around this convent are especially beautiful and peaceful. We loved seeing different parts of Cortona that we would not have been able to reach easily on foot. Our tour ended with gelato at my favorite gelato in Cortona!
- Don’t feel like you need to over-schedule your time in Cortona. There are so many places where you can sit and watch the world go by, and it is so enjoyable. We’ve had apertivo on in the Piazza Signorelli where we were serenaded by area Philanthropic Societies. Enjoyed a picnic lunch at Piazza Garibaldi while overlooking the Tuscan countryside. And, enjoyed watching the sunset from our room with a bottle of wine. Part of the beauty of Cortona is that you can slow down while enjoying all the highlights of a perfect Tuscan hill town.
If you can’t book the Monastero di Cortona Hotel and Spa, I recommend Hotel Villa Marsili, also within the city center. It has a more traditional and regal feel than the Monastero, but the location is great. If you don’t mind being further out, I would consider il Falconiere, a Relais and Chateaux property that has been on my list for awhile, or Le Corte dei Papi or Cortona Resort and Spa, which are a bit further out in the countryside. Nothing beats the convenience factor of being in the city center while staying at the Monastero though. These properties would be a different vibe than the Monastero, but they would be a relaxing, luxurious experience, too.
Note: This post is not sponsored or posted in collaboration with the Monastero di Cortona Hotel and Spa. I just love this hotel, its staff, its location, and Cortona so much. I think you should consider adding it your trip to Tuscany!