Ann’s Tuscany Adventure

I’ve been to Tuscany before, but always with Florence as my home base. Doing day trips to Siena or Lucca, or heading out into the countryside for a day of winetasting before retreating back to the city. When the opportunity arose to spend a whole week in Tuscany, I jumped at it! 

The focus for this trip was romance travel (destination weddings and honeymoons). We had the opportunity to tour some gorgeous properties and meet some fantastic local business owners (florists, caterers, event planners, and photographers). And, of course, eat and drink some amazing local food and wine.

If you’ve ever dreamed of getting married in Tuscany, we can absolutely hook you up!

[Photo: The dining hall of Corte dei Papi villa in Cortona]

But I am really excited about Tuscany in general, and what a different experience it offers vacationers when compared to the big cities.  


We stayed at the Buccelletti Casali and Cantina, in Castiglion Fiorentina. It’s a charming property that has been in the Buccelletti family since 1625. They’ve been growing olives and making olive oil for generations, and they now make wine as well.

They have converted the old farm workers’ houses into clusters of villas and apartments. Plus, they’ve turned the olive oil mill into a stunning event space. It was the perfect home base for a week spent exploring the surrounding countryside.

[Photo: Buccelletti Casale and Cantina]

The accommodations themselves were the first big difference from previous trips to Italy. I was in a cute little house with two bedrooms and bathrooms, a living/dining area and small kitchen, and a private yard/garden.

We could prepare our own breakfasts of farm-fresh eggs, homemade bread, and locally produced yogurt, jams, honey, and fruit. We had bottles of wine and olive oil produced right there on site. And the cuisine could not have been more “farm to table”. So different from staying in a hotel! 

When you’re out in the country at an agriturismo like this, it does help to have a car, so that you can get out to the local shops and markets. But at the Buccelletti Casali, we had a basket of provisions (replenished mid-week) and it was more than enough for breakfasts and snacks.  

The Countryside

We were a group, with a very organized itinerary (and drivers/guides), but I would highly encourage clients to rent a car and enjoy a more independent stay in Tuscany. The roads are great, the traffic is light, and they drive on the right side of the road. It’s very manageable for American drivers.

[Photo Credit: MIP Studios via Shared Adventures – a road in Cortona]

While we were there, we had a busy itinerary filled with site inspections at hotels/inns/B&Bs, guided tours of Tuscan hill towns, tastings at local vineyards, and many lengthy multi-course meals with wine pairings. Brutal, I know.

We learned how cheese is made. We met mayors, hoteliers, restauranteurs, and the fascinating couple who purchased and renovated the villa featured in “Under the Tuscan Sun”.

[Photo: Ann & Kristy at Villa Laura]


Some of the highlights, for me, included: 

  • Cortona – a town of steep streets, gorgeous views, Etruscan history, and tempting shops.
  •  Pici – traditional hand-rolled Tuscan pasta, made from just the “poorest” of ingredients (flour and water).  
  • Podere il Casale – a pecorino cheese producer, organic farm, and farm-to-table restaurant outside of Pienza, where we enjoyed a fabulous meal completely sourced from right there onsite. (So delicious that I purchased and carried home their very heavy hardbound cookbook in the hopes of recreating that magic
  • Brunello di Montalcino wines – made with 100% Sangiovese, bold and fruity, one of the best Italian reds!

The Tuscany Takeaway

Tuscany is all about the slow food movement, slowing down to take it all in, and enjoying the views.

There’s no long list of “must-sees”. You can while away an afternoon (guilt-free) sitting by the pool sipping wine and snacking on prosciutto. Or riding an e-bike through the countryside. Or rolling up your sleeves for a cooking class.  

I realize now that I was doing it all wrong when I visited Tuscany as a quick side trip from Florence. Tuscany invites you to stop, linger, indulge, experience, and enjoy. And I can’t wait to come back and do it all again! 

[Photo: Villa Le Prata in Montalcino]

Villa Vacations

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When planning a vacation, the first thing that most people think about is the destination itself. Second only to that, the thing that really makes or breaks a getaway is the accommodations. It sets the tone for the whole trip. You want someplace that provides comfort, relaxation, and a sense of well-being — someplace you’ll enjoy coming back to at the end of a busy day, or relaxing and spending the whole day in. If privacy, space, and a home-like setting are on your wish list, a private villa might be the perfect option. And it’s not just for the rich and famous. Here’s what you need to know:

What is a villa?

an italian style villa against a blue sky and green lawn

When you think of a villa you probably imagine a grand house on a large estate nestled in the rolling hills of Tuscany. And while a villa certainly can mean this Italian “Under the Tuscan Sun” dream, villas have become much more flexible, diverse, and unique.

[Photo Credit: Shaun Gehring via Unsplash]

Initially, the term “villa” was used in ancient Rome to describe an upper-class country house. Someplace luxurious and sprawling where ancient Romans went to get away from it all. Since then the term villa has evolved, ranging from small farming compounds to magnificent mansions on private islands.

a cottage-like villa surrounded by the stunning mountain views

At its core, a villa is a detached house with plenty of space between you and your neighbors. It can range from a cozy and intimate 1-2 bedroom cottage to large estates that can accommodate 20 or more.

[Photo Credit: Pradidpong via Unsplash]

Why Should You Rent A Villa?

a sprawling villa framed by the pink and orange of a beautiful sunset
[Photo Credit: Fran Hogan via Unsplash]

Villas are available pretty much anywhere in the world — the Caribbean, Europe, the US, Mexico and more. They come in different shapes and sizes but they all offer privacy, comfort, and a sense of home. In the Caribbean, it’s very common for the villa to come with staff like cooks or housekeepers, but in other places around the world, it’s easy enough to add them on if you want to.

You can join everyone in the dining room for a delicious breakfast. Then head out to the back deck to enjoy a sun lounger and a good book by your private pool. After spending the morning snorkeling on the nearby beach and exploring the local side of town, you can enjoy a peaceful and relaxing afternoon without other people’s screaming children. You can listen to your friends laughing as they whip up margaritas in the kitchen and then join them for a snack without fear that your sun lounger will be poached by someone else. In the evening you can watch a stunning sunset streaking over the ocean from the deck, before heading into the huge living room to sit on the comfy sofas and play games with the whole group laughing late into the night.

a peaked roof villa in a desert landscape with large glass windows
[ Photo Credit: Nuzha Naashidh via Unsplash]
a pool and back deck surrounded by trees and greenery at a villa in bali
[Photo Credit: Nelbali Photography via Unsplash]

Top 5 Reasons to Rent a Villa

  1. Whatever you want to do, whenever you want to do it – A villa lets you be master of your own vacation schedule without any restraints

  2. Privacy & Seclusion – No stress from crowds or queues. A secluded villa allows you to unplug, unwind, and enjoy the company of your friends/family without the intrusion of other vacation goers.

  3. Hotel-like amenities all to yourself! – Many villas come with private pools, spas, and gyms! Everything you love about a hotel or resort, and it’s all yours.

  4. Space – Most hotel rooms have just enough space for two adults. Villas offer everyone a private room, plus comfortable living spaces to gather and enjoy being together without feeling on top of each other

  5. Price– Even the most upscale villas can be more cost-effective than renting multiple hotel rooms. Families, reunions, or even just a couple of couples- the price per person often works out to be equal to a nice hotel or resort.

Top Tips When Renting A Villa

a bright blue pool at the back of a large house in Panama
[Photo Credit: Fran Hogan via Unsplash]
  • Be sure you know what kind of vacation you want. If your idea of relaxing is curling up with a good book, make sure the villa has plenty of nooks where you can get some time to yourself! If you plan to do a lot of cooking, make sure the kitchen is big enough for everyone to roll up their sleeves and help out.
  • What are your staffing needs? Do you want to cook or would you rather have a personal chef? Do you want housekeeping every day? A butler? A bartender? A driver? The possibilities are endless!

  • Choose your group wisely – make sure your expectations are the same and you know that spending a week together under one roof is a good idea!
  • Always think about the specific bedding arrangements that you need, not just the number of bedrooms. Married couples don’t usually want twin beds, and no one wants to get stuck with the bunk bed room.
  • Be clear on location- How far out in the country will you be? Will you need a car to get into town? Is it actually on the beach or is there a road down to the sand?
  • See if the villa allows pets and children. Oftentimes villas can accommodate pets, letting you take your furry family member with you instead of paying for boarding.
  • Remember that many properties have one-week minimums and rent Saturday to Saturday.
  • Plan well in advance so that we can help you get the exact kind of villa you’re looking for with all the amenities you want!

Villas provide more than just a place to sleep while you’re on vacation. They provide a unique backdrop for your getaway, combining an exciting new setting with all the comforts of a home. And in the time of COVID, they provide a safety bubble where you can enjoy a vacation without the concern of being around large groups. No matter what your destination, there’s a perfect villa waiting for you! Let us know and we’ll help you find the perfect size, location, and price for your home away from home.

Caribbean Villas for the Holidays

Haven’t made your plans for the December holidays yet?

Thinking about running away with friends and family to sit on a beach in the Caribbean this year?

It’s not too late! 


Normally, by this time of year, you’d be hard-pressed to find availability for Caribbean villas over the holidays, and any that were still available would be requiring a two-week minimum stay. But not this year.

I’ve been receiving promotional emails from several of my villa vendors touting last-minute availability (and decent pricing) for 3-, 4- and 5-bedroom villas in Turks and Caicos, Barbados, Jamaica, Grand Cayman, and the USVI.

Caribbean villa

Just imagine…your own private beachfront hideaway, surrounded by your closest friends/family, with staff (if you want it) to do the cooking and cleaning. That sounds like a holiday to me!

If you’re interested, don’t delay. Give me a call today.

You provided excellent guidance for us. I appreciated that you really had us think about what was most important to us when we were selecting the right cruise – and not to totally focus on what other people had to say. THANK YOU for helping to make this a memorable trip for our family! It really was a trip of a lifetime!

Clare and Mark (family cruise to Alaska)

The level of service we experienced was out of this world (and we did NOT make it easy on Ann). We weren’t quite sure where we wanted to go, when we would be able to go, or what “vibe” we were going for. After asking us some key questions (what we liked, didn’t like, why, etc.) Ann helped us narrow down our trip details and planned the honeymoon of our dreams. She helped book some of our excursions, answered some emergency questions while abroad and was always available/willing to help. I think it’s safe to say we won’t be using anyone else for future travel planning – Ann is a rockstar!

Carli (Italy and Spain)