Tuscany Biking & Cycling Tours

start planning your trip with a local travel specialist
How kimkim works  
Our local travel specialists have been recommended by

Travelers love kimkim

- ., traveled to in

Italy Travel Insights

Friends cycling along the famous L'Eroica
Map of Cycle the Eroica Among Tuscany's Famous Vineyards - 7 Days
Cycle the Eroica Among Tuscany's Famous Vineyards - 7 Days

Get ready, cyclists: this one's for you! The Eroica is a world-renowned vintage bike race, held annually in the hilly, vineyard-dotted region of Chianti in Tuscany. With a week to spare, you can follow the route of this legendary race, experiencing the "strade bianche" (unpaved white roads) that take you through the heart of this magnificent countryside. Between epic rides, you'll spend your free time strolling through hilltop medieval villages, sampling the local wines, and relaxing at peaceful agriturismos.

Discovering the Italian Highlights: Rome, Florence, Venice - 8 Days
Map of Discover Italy's Highlights: Rome, Florence, Venice - 8 Days
Discover Italy's Highlights: Rome, Florence, Venice - 8 Days

Discover the sights and delights of Italy on this week-long highlights tour. Visit Rome, the Eternal City, Florence the Renaissance Jewel and Venice one of the world's most romantic cities. Then head to the Tuscan countryside to taste its tradition, culture and famous Italian food and wine.

Views of Syracuse
Map of Sicilian Bike Tour - 7 Days
Sicilian Bike Tour - 7 Days

Sicily is a captivating destination, with scenic beauty, historic sites, and culinary delights. This 7-day itinerary is for the active traveler looking to experience the best of the island while cycling and walking.

Tre Cime di Lavaredo
Map of Dolomites High Traverse - 10 Days
Dolomites High Traverse - 10 Days

Traverse the northern Dolomites starting at the Tre Cime di Lavaredo, three of the range's most famous peaks, and make your way to the Grupo Latemar near Bolzano. You'll hike through a number of national parks, crossing desert rocklands, forests, and green pastures as you travel the cultural and historic border between Europe's southern Latin and northern Germanic regions.

Bicycles are a great way to get around Florence and the surrounding region
Map of Cycling Tuscany: Florence to Siena - 5 Days
Cycling Tuscany: Florence to Siena - 5 Days

Take a quick spin through the birthplace of the Italian Renaissance with this five-day Tuscan cycling tour. This challenging bike route will take you through the medieval villages and cypress-spotted hills of the Tuscan wine region . Go from Florence to Siena as you take in the region's food, historic castles, and sun-kissed landscapes, accompanied, of course, by a good glass or two.

A cyclist in the narrow streets of Puglia
Map of Cycling In Southern Italy - 8 Days
Cycling In Southern Italy - 8 Days

Soak up the sunshine and go off the beaten track on this 8-day cycling expedition around Puglia in the heel of Italy's boot. You'll bike to lesser-known towns and villages on this moderate-level ride, pedaling through lush inland plateaux and down the coastline on mostly flat terrain. Enjoy southeastern Italy's historic sites, flavorful food, and natural beauty on this active tour.

See more travel articles about Italy
How it works
Chat with specialist icon Step 1
Tell us what kind of trip you want
Complete our quick travel quiz
Chat icons Step 2
Chat with a local travel specialist
Work out the details together
Credit card icon Step 3
Securely book your trip
100% satisfaction guaranteed

Meet our Local Travel Specialists

Experienced travel agents with a passion for Italy
Travel specialist Eirini Daouka
active 11 hours ago

Eirini Daouka

I was born in Thessaloniki, Greece's second largest and —to my belief— most vibrant city, and a gastronomic paradise. I always loved being a traveler of my own birthplace, collecting all the city...

read more...
Travel specialist Melanie Rapuano
active 12 mins ago

Melanie Rapuano

My name is Melanie and I'm a Travel Specialist based here in Italy! I'm half Italian and half British and I come from a city just off the Amalfi Coast! I've always loved creating travel plans for...

read more...
Travel specialist Rita Pagano
active 1 min ago

Rita Pagano

"Travel as much as you can, as far as you can, for as long as you can. Life is not meant to be lived in one place." This is my motto. I’m from Italy, specifically Naples (yes, the birthplace of...

read more...
Travel specialist Chris Gravas
active 15 hours ago

Chris Gravas

My name is Chris and I have a passion for authentic experiences, cultural awakenings, and nature explorations. As a partner of a local boutique travel agency, I take every chance to explore Greece...

read more...
See all Italy travel agents

Trip Reviews for Italy

The latest reviews by travelers who booked their trip on kimkim

The whole KimKim team was amazing, very knowl...
Italy | May 2 - May 15, 2025

A
Alex H.
Dallas, TX | Reviewed on May 16, 2025
The whole KimKim team was amazing, very knowledgeable about the area and set up wonderful excursions and experiences as well as great tips for down time. We did have one encounter where on of the vendors no showed but KimKim rallied and found us another similar experience in no time. Overall I am very happy with my experience with KimKim and will definitely use them again for future trips. Read more

The whole KimKim team was amazing, very knowledgeable about the area and set up wonderful excursions and experiences as well as great tips for down time. We did have one encounter where on of the vendors no showed but KimKim rallied and found us another similar experience in no time. Overall I am very happy with my experience with KimKim and will definitely use them again for future trips.

Hotel Reviews
Hotel Orto de' Medici
Florence

Great room, beautiful garden, great breakfast

Authenticity & Character
Location
Very centrally located in Florence, only 15 mins from Duomo
Staff
Cleanliness & Comfort
Relais Della Rovere
Colle di Val d'Elsa

Great hotel restaurant and beautiful ground, only real issue we had was the lack of air conditioning on a night- rooms got rather hot.

Authenticity & Character
Location
Staff
Cleanliness & Comfort
Una Villa - Amalfi Boutique B&B
Amalfi

Amazing staff who made our honeymoon so special. We have nothing but positive things to say about our time at Una Villa

Authenticity & Character
Location
Staff
Cleanliness & Comfort
Ca' dei Proverbi Suites
Venice
Authenticity & Character
Location
Staff
Cleanliness & Comfort
Activity Reviews
Boat tour to Li Galli islands and Capri from Amalfi
Boat tour to Li Galli islands and Capri from Amalfi
Italy

What was originally supposed to be a boat day with opportunity to swim just turned into a ferry ride to Capri. The boat never stopped in any of the swimming areas that were advertised and no one else on the boat had planned to swim. Felt like a missed opportunity on an otherwise good day.

Quality of Experience
Guides, Drivers and Staff
Transport
Venice Gondola Ride with Prosecco
Venice Gondola Ride with Prosecco
Venice

Loved our gondolier, he was so nice and welcoming as well as knowledgeable about the area and architecture

Quality of Experience
Guides, Drivers and Staff
Transport
Hand-made Pasta & Typical Dessert Cooking Class
Hand-made Pasta & Typical Dessert Cooking Class
Florence

We were originally supposed to have a private market tour and cooking class but when our original vendor cancelled. Kim Kim found us a group class in very short time. Overall an enjoyable experience and the chef, Frederico, was an absolute delight.

Quality of Experience
Food
Guides, Drivers and Staff
Transport
A Guided Hiking Adventure in the Heart of Chianti
A Guided Hiking Adventure in the Heart of Chianti
Italy

Our guide was wonderful and so friendly. She certainly put us through our paces over a 4.5 mile hike through all different types of terrain and landscape. We really enjoyed this whole experience and loved the passion and knowledge that our guide had for all things nature.

Quality of Experience
Guides, Drivers and Staff
Winery visits with Driver at disposal in Tuscany
Winery visits with Driver at disposal in Tuscany
Chianti

We had a wonderful time visiting wineries. All the staff were extremely knowledgeable and helpful. We also had a driver for the day and he was very courteous and cordial. Overall a great experience

Quality of Experience
Food
Guides, Drivers and Staff
I’m
Transport
Local specialist: Eirini Daouka
Read all Italy reviews

Italy Trip of a Lifetime
Italy | May 1 - May 11, 2025

Braden
Braden S.
Sioux Falls, SD | Reviewed on May 13, 2025
Everything went so smoothly between transports, tours, and hotels. The accommodations were beyond our expectations. All of the tours were amazing. Having a private guide for those tours made it so much better as well as skipping the long lines. Very happy with location and quality of hotels. Eirini did a great job. Always responsive and created a itinerary perfect for our liking. All of the guides and transport drivers were friendly and great. Will recommend to friends for future... Read more

Everything went so smoothly between transports, tours, and hotels. The accommodations were beyond our expectations. All of the tours were amazing. Having a private guide for those tours made it so much better as well as skipping the long lines. Very happy with location and quality of hotels. Eirini did a great job. Always responsive and created a itinerary perfect for our liking. All of the guides and transport drivers were friendly and great. Will recommend to friends for future vacations.
Being able to see 4 different Italian cities all were unique and different in their owns ways made this trip always exciting with never knowing what the next location would entail.

Local specialist: Eirini Daouka
Eirini
Eirini Daouka
Local specialist in Greece | Replied on May 14, 2025

Dear Braden, Thank you so much for your lovely words. It’s a great pleasure to hear that the trip exceeded your expectations and that each destination brought a new and exciting experience. We’re so glad you were able to enjoy the diversity of our beloved Italy in such a smooth and comfortable way.
We also truly appreciate your kind recognition of our guides and drivers, we’re proud to collaborate with them.
Looking forward to helping you or your friends plan another unforgettable adventure in the future.
Arrivederci!

Read all Italy reviews

Gentleman's Trip to Italy
Italy | Apr 17 - Apr 26, 2025

S
STEVE T.
Canada | Reviewed on May 13, 2025
My brothers and I had a amazing trip to Italy, beautiful Italy with its historical sites, amazing food, and incredible coastal and mountain views. The tour guides were very knowlegeable and were very interesting. The drivers and boat captain were very professional and always on time. The hotels that were selected met our needs and were clean and were located strategically so our tours were close by. Irene (KimKim) did an amazing job of planning our trip, tickets were purchased ahead of... Read more

My brothers and I had a amazing trip to Italy, beautiful Italy with its historical sites, amazing food, and incredible coastal and mountain views. The tour guides were very knowlegeable and were very interesting. The drivers and boat captain were very professional and always on time. The hotels that were selected met our needs and were clean and were located strategically so our tours were close by.

Irene (KimKim) did an amazing job of planning our trip, tickets were purchased ahead of time so we could skip the line. Tour guides and drivers were all on time and pleasant to deal with. The hotels chosen were perfect for our needs. Overall I would give it a 9.5 out of 10.

Hotel Reviews
Hotel Modigliani
Roma
Authenticity & Character
Location
Staff
Cleanliness & Comfort
Hotel Pupetto Positano
Positano SA

Great location on the water but a lot of stairs if you want to go up to the road. However, nice easy path to get to Positano.

Authenticity & Character
Location
Staff
Cleanliness & Comfort
Palazzo Guardati Hotel Sorrento
Sorrento

great location right in the middle of Sorreto

Authenticity & Character
Location
Staff
Cleanliness & Comfort
Hilton Rome Airport Hotel
Fiumicino

Nice hotel but they were supposed to just hold our credit card but they actually charged it and we had to wait 2 weeks to see it get off our pending charge.

Authenticity & Character
Location
Staff
staff charged our credit card but was just supposed to hold it.
Cleanliness & Comfort
Activity Reviews
Aperitivo & Stroll around Sorrento
Aperitivo & Stroll around Sorrento
Sorrento

This was probably our best memory of our trip. Sorrento is such a beautiful small town on the coast. The shopping was really nice cheap and good stuff. The tour guide was very knowlegeable and interesting.

Quality of Experience
Guides, Drivers and Staff
professional, knowlegable, spoke very good english
Transport
Local transfer in Amalfi Coast
Italy
Quality of Experience
Guides, Drivers and Staff
Transport
Useful Information
Italy
Quality of Experience
Guides, Drivers and Staff
Transport
Express Colosseum Tour
Express Colosseum Tour
Rome
Quality of Experience
Guides, Drivers and Staff
Transport
Trastevere Afternoon Food Tour & Wine Experience
Trastevere Afternoon Food Tour & Wine Experience
Rome

Food and drinks were amazing. Tour guide too.

Quality of Experience
Food
Guides, Drivers and Staff
Transport
Vatican Guided Tour
Vatican Guided Tour
Rome

Tour guide very knowlegeable and spoke very good English

Quality of Experience
Guides, Drivers and Staff
Transport
Evening Drinks & Golf Cart Tour
Evening Drinks & Golf Cart Tour
Rome

This was our first day/night in Italy and it gave us a good sample of Rome has to offer. Tour guide gave us some good restaurant recommendations. He was amazing.

Quality of Experience
Guides, Drivers and Staff
Transport
Amalfi Coast Boat Tour From Sorrento
Amalfi Coast Boat Tour From Sorrento
Sorrento

Beautiful boat tour along the coast. It was a beautiful day weather wise. The captain was professional and knowledeable.

Quality of Experience
Guides, Drivers and Staff
Transport
Private Pompeii Tour
Private Pompeii Tour
Pompeii

Tour guide was very interesting telling us all about Pompeii and the history. One of our favorite stops.

Quality of Experience
Guides, Drivers and Staff
Transport
Local specialist: Irene Lappa
Read all Italy reviews
See more trip reviews by kimkim travelers

Why travelers love kimkim

Custom trips for independent travelers who are too busy to plan
Customize your trip with the help of a local travel specialist

Kimkim has handpicked the world’s top local travel specialists so you will have peace of mind and an unforgettable trip that meets your exact requirements.

Authentic travel experiences

Kimkim’s local specialists ensure that you will have the best experience based on up-to-date local insights. On top of that, the vast majority of your money will go straight to support and grow local economies.

Secure & easy booking

Once you are happy with the trip, you can easily book via kimkim’s secure payment platform.

Local support during your trip

You can always reach your local specialist with a quick message or call in case you hit a snag during your trip, or simply want some great local recommendations.