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Small Group  |  Off the Beaten Path  | Authentic & Immersive

Small Group Tuscany Tours


5 - 7 total




2023: OCT 15 - 23



2024: OCT 13 - 21


take a TuscanY tour with
creative edge travel?

About Creative Edge Travel's Small Group Tours of Tuscany


For those who seek to live the culture instead of snapping pictures, this journey will satisfy daydreams of wandering untouched medieval villages, connecting with the land, and learning from locals along the way. This small group tour of Tuscany will have you hunting for truffles, helping with the olive harvest, & and experiencing a local chestnut festival, all while surrendering to the magic of the unexpected!



yourself in rural farm life, away from the crowds.



a fall chestnut festival with locally-produced food & crafts.



in the olive harvest and truffle hunting.


with locals and learn about history through their family stories.


mouth-watering recipes in a palazzo inhabited by the same family for 500 years.

Step into Italy as if you're a Local.


  • Who are these trips for?
    From solo travelers to groups of friends, our small groups of 7 travelers are made of all ages (above 18) and enjoy becoming a little community as we slurp through plates of pasta and laugh trying to pronounce Italian words. Our guests understand that travel in Italy can hold unexpected surprises and they’re up for going with the flow, trusting that we know the best place to be at any moment. They’re open-minded, love trying new things, and are accustomed to toeing the boundaries of their comfort zone for the rewarding experiences that lay just outside it. Our trips attract those who appreciate creativity and the arts, nature, meeting locals, and seeing things outside the guidebook that might not be luxurious but are authentic and genuine. All ages above 18 are welcome and we encourage the cross-generational exchange that occurs. A strong effort is made to make everyone feel part of the group no matter what age, sex, gender, sexual preference, or hair-do! Our off-the-beaten-path, immersive and laid-back travel style isn’t for everyone. If you're not sure let's chat about it!
  • How are Creative Edge Travel trips different from other tours?
    In comparing countless other trips, the #1 thing we have that others don't is our people-focused approach to bring you into the lives of locals. Imagine lingering over a homecooked meal in a local family's home with sweeping views and meaningful conversation about both the beauty and the challenges within their daily lives. We go beyond the typical tourist sites to create experiences around the passions of our local friends and add our own creative edge to assure it’s something meaningful and special. We don’t just plan trips, we design special moments around people. In addition, we lead a maximum of 6 trips per year. That means, for example, that a local who hosts a dinner during the trip does it only twice a year instead of twice a week like other tour companies. In this way, the experience remains coming from a place of passion and cultural exchange rather than simply a job. We also invite our local friends to join us here and there along the way so that travelers have an opportunity to interact with locals in a casual setting instead of always having them up on a pedestal.
  • What's included?
    Inclusions depend on your specific trip and you should check the trip details for an accurate listing. However, the following items are generally included with the cost of the trip: ​ -All accommodations incl all taxes & fees -Meals as listed in your trip documents, there will always be some meals not included (we believe scoping out your own hole-in-the-wall is part of the experience!) -Wine at included lunches and dinners -Arrival/Departure transportation & private driver for the duration of the trip -All activities, workshops, and visits -Tips for Guides and Drivers -24/7 Trip Leader -Professional Flight Booking Assistance -Carbon Footprint Offset -Pre-Trip Prep: Culture and language lessons (optional), arrival/departure advice, packing tips, and additional resources to fully connect with what you'll experience on the trip!
  • What's not included?
    Exclusions depend on your specific trip and you should check the trip details for an accurate listing. However, the following are generally not included with the cost of the trip. ​ ​Flights (We can help you find the best flights for your trip dates, free of charge!) Some meals (We believe scoping out your own hole-in-the-wall is part of the experience.) Incidental expenses (Air conditioning may cost extra but it is unlikely that it will be needed.) Mandatory travel insurance Optional guide, driver, and hotel gratuity
  • What are the accommodations like?
    The B&B's we partner with are comfortable but you shouldn’t expect the same standards you’re used to back home. For example, air conditioning is not standard in Italy and may be an extra charge. We look for accommodations that offer something special- an artistic flair, really unique history, family-feel, or a breathtaking setting, for example. ​ If you're traveling on your own, you'll have a single room to yourself (no sharing). If you're traveling with someone, you'll have a double bed to share. We’ve worked hard to pick unique accommodations that have a creative vibe and something special about them. We know you'll love them!
  • Where is the meeting point and how do I get there?
    Please check you trip specifics. Generally, we'll provide 2 - 3 transfers throughout the day from the airport to our first B&B and return you to the airport in the morning on the day of departure.
  • What is the cost of the trip?
    Please check your particular trip for pricing. ​ Prices are per person and in USD, unless expressed otherwise.
  • How much is needed to secure my spot?
    You don't need to pay the total cost of the trip up front. However, when you sign up for the trip, you have to pay a deposit to secure your spot. The remainder is due 60 days before trip start date and can be scheduled in 2 payments.
  • How do I register?
    To register for a trip, all you need to do is apply by filling out a simple form. We'll then have a chat so we can be sure the trip is a good fit for you and to answer any questions you may have. Once approved, we will send you the link where you can register and pay your deposit to secure your spot!
  • I have to cancel the trip. Will I get a refund?
    Our trips are carefully budgeted for 7 participants. This means we have to adhere to a strict Cancellation Policy in order to maintain cost effectiveness for everyone. However, we require you to purchase travel insurance in an effort to provide some protection from potential losses should you need to cancel*. COVID-19 Amendment If you or Creative Edge Travel cancel your trip due to COVID-19 travel restrictions in Italy or in your home country: *If you booked a custom trip, you can change trip dates within one year, permitted that the itinerary we've planned doesn't change. Otherwise additional planning fees will apply. ​ **If you booked a custom trip, the planning fee is non-refundable. If you cancel for any reason other than what is listed above, your cancellation will be subject to the full Terms & Conditions. Here's a synopsis: *If you booked a custom trip, you can change trip dates within one year, permitted that the itinerary we've planned doesn't change. Otherwise additional planning fees will apply.​ **There is a cancellation fee up to $300. If any non-refundable elements were booked for your trip, those amounts will be deducted from your refund. If you booked a custom trip or added an extension to a group trip, the Custom Trip Planning Fee is non-refundable. *It is up to you to make sure your travel insurance policy includes trip cancellation coverage. Click here for Travel Insurance info.
  • How much money do you suggest we bring for the things that aren't included?
    The amount of money you bring to cover expenses that aren't included in the cost of the trip is totally up to you. To give you an idea, a sandwich is about 3 - 6 euros while a plate of pasta is about 7 - 15 euros. If you add an appetizer, wine, and dessert, you're looking at 35 - 45 euros per person. Tipping is not mandatory nor expected in Italy.
  • Do you book flights?
    We have a flight expert who can search the best fare for you and book them, free of charge.
  • Do you sell travel insurance?
    We do not sell travel insurance. We recommend you contact our partners at VisitorsCoverage who will be happy to help you compare plans and find what you need. Please click here for our guidance on travel insurance!
  • Do I need a visa to visit Italy?
    The visa requirements for your trip vary depending on where you are from and where you are going. As a general rule most countries expect that you will have at least 6 months' validity on your passport but it's very important that you check before you travel. ​ U.S. citizens may enter Italy for up to 90 days for tourist purposes without a visa. Participants must have a passport valid for at least six months beyond date of departure from the Schengen area and at least two blank pages. You'll need to send us a scan of your passport 60 days before departure. Participants should check the Department of State website for up-to-date travel information and advisories.
  • I don't speak Italian, how can I connect with locals?"
    We do not require participants to be able to speak Italian as exchanges with locals often happen in more subtle ways than just verbally. However, before the trip, we will be sending you resources related to Italian language and culture to help you get the basics under your belt. You are not required to study Italian before your trip, but it will help you have a more meaningful experience. Our trip leader will be there 24/7 to communicate with locals, should you need it. In addition, most of our partners speak English!
  • Do you have suggested list of items for us to bring?
    What you should pack depends on the season and region you'll be visiting. Your trip leader will send you suggestions before your trip. You can check out our blog posts about packing: How to Pack for a Spring Trip to Tuscany How to Organize Your Suitcase for Stress-Free Travel
  • Can the itinerary change from what I've booked?
    Your itinerary is a base itinerary, which is subject to minor changes due to closure, festivals, weather, or unexpected events. Additionally, the itinerary is prepared well in advance, and at times there are unexpected closures for various reasons that require us to alter the plans. In the end, our goal is always to bring our guests unique experiences, and when substitutions happen, they are always wonderful!
  • How do your trips support positive change in the world?
    At Creative Edge Travel, we believe in the power of cultural experiences to transform lives. That's why we donate a portion of our proceeds to Global Glimpse. Global Glimpse is a non-profit organization that helps diverse high school students complete community projects in the developing world. Read about them here. ​ We also believe our impact on this earth should be light. At checkout, we offer the option to offset your carbon footprint through the Nature Conservancy's carbon offset program, helping fund forest conservation, improved forest management or reforestation projects that produce measurable climate benefits.



Slower-paced & stress-free travel

Unique experiences crafted directly with locals to highlight the authentic culture.

Exclusive group of just 7 like-minded travelers.

Plenty of free time to do your own thing.

Explore places that tourists have never heard of.

Thoughtfully crafted with extensive research in the area for genuine & meaningful connection with locals.


7 nights' accommodation in a private room (3 nights in Marradi, 4 nights in the countryside)

All breakfasts, 3 lunches and 6 dinners including wine, and 5 tastings/aperitivi

Carbon Footprint Offset: A donation will be made to fund projects that reduce carbon emissions and improve daily life in impoverished areas.

Transportation + Private Driver

Flight Expert to research and book flights

Arrival Transfer from center of Florence, Departure Transfer to Florence Airport

Trip Leader fluent in English and Italian

Tips for the driver & guides

Pre-Trip Prep: Cultural and Italian language guidance, packing tips, and additional resources to fully connect you with what you'll experience! Local recommendations in each location.

All Activities

Welcome Cocktail & Dinner

Olive Harvest

Truffle Hunting

Homemade Pizza Dinner

Cheese Farm Visit & Tasting

Visit Historic Palazzo dei Vicari

Winery Visit, Tasting, & Lunch

Visits to Lesser-Known Villages

Truffle Hunting

Homemade Truffle Lunch

Nature Walk

Private Palazzo Tour

Sunset Aperitivo

Cooking Class

Local Chestnut Festival

Free Time for Your Own Discoveries! 


  • Flights: We'll help you find the best flights for your dates, free of charge!

  • Some Meals: Meals not described in the itinerary. (We believe scoping out your own hole-in-the-wall is part of the experience and we leave room for that!) Our included meals are so abundant that guests usually stick to gelato or something light when a meal is not included.

  • Incidental Expenses

  • Mandatory Travel Insurance: Click here for more info and resources.

From $4,199 USD per person

Who Are Our Private and Small Group Tours of Tuscany for?

Active travelers who want to access authentic
Italy without the logistics.

Our travelers want to leave the crowded tourist paths behind, without spending weeks researching. They want to connect with locals, but don't have years to perfect a new language. And while they love back roads and hidden villages, they're not up for the hassle and risk of driving a rental.


Our travelers are warm. They’re curious. And they want to see Italy with open hearts, open minds, and without the growl of a giant tour bus announcing their arrival. They are immersion seekers who want to step into the everyday life of authentic Italy through small group tours of Tuscany and beyond!


Sound like you?

Our travelers are generally 35 - 55 years old but we also get adventurers into their 70's or 80's! We welcome everyone 18+!

Important Details for Your Tour of Tuscany
  • This Tuscany private tour involves walking on uneven ground for over an hour.

  • Please note that you'll need to carry your own luggage up and down stairs at hotels and across cobblestone.

  • The longest drive will be a little over 2 hours, with breaks.

  • Wifi is available in all locations but connection may be not be as strong as what you're used to.

  • Most dietary restrictions can be accommodated if you let us know well in advance.


October 13 - 21, 2024

Starting from $4,199 USD per person

Reviews from our small group tours and Tuscany private tours

At Creative Edge Travel, we believe every journey should be meaningful. It should teach you about the authentic local culture and a bit about yourself, too. That's why we push the boundaries of the typical Italian small group tours and add our own creative edge. We design our experiences with individual locals in off-the-beaten-path places to give you a culturally-immersive adventure.


Each activity is an opportunity to learn about both the beauty and the challenges of everyday life in Italy. Whether it's exploring a village with a local grandpa as he shares his stories growing up there, or learning traditional music and dance at a historic masseria, expect a deeper travel experience.

This also means that sometimes reasonable flexibility is required on your part. There's no science to getting a 90 year old Italian grandpa to show up on time, you just take what you get and roll with it! If you're the type of traveler who can stay flexible and relaxed knowing no matter WHAT you do, it's going to be awesome, then you're a great fit for this trip!


Experiences based on authentic connection with locals and their home.  

 Want more details? We love to talk about our trips!

Click below to schedule a call!

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