Cool Destinations
Top Tuscany activities
Top Tuscany landmarks
Beyond Tuscany
Tuscany trip ideas
  • Tours by category
  • Tours by accessibility
  • Tours by feature
  • Tours by the numbers
  • Top Tuscany landmark tours
  • Tours in nearby places
  • Explore Italy tours
  • Tuscany travel guides
  • Tuscany travel calendar
Language $Currency
Login / Sign up
Bookings
Bookings
Cool Rewards Rewards
$0.00
Cool Rewards Rewards
$0.00
Wishlists
Wishlists
Profile
Help Center
Language
Log out
Start your search
Change your search
Place or activity
Select Dates

Top Tuscany Romantic Tours

24 Results
Sort by:
Featured
Filter
Languages Clear
Time of Day Clear
20
14
14
Duration Clear
1
18
9
0
0
Price Clear
$0 $500+
Rating Clear
20
21
21
Specials Clear
17
1
0
15
3
Features Clear
6
4
14
1
8
0
Accessibility Clear
0
7
22
Families Clear
5
6
2

Tuscany Tours

Attractions

Guides

Calendar

Experience the Magic of Tuscany from a Hot Air Balloon

Enjoy breathtaking views over the beautiful Tuscan countryside on a 1-hour hot air balloon flight departing from the area of San Casciano in Val di …More

Florence, Italy
4.9 (170)

Experience the Magic of Tuscany from a Hot Air Balloon

Enjoy breathtaking views over the beautiful Tuscan countryside on a 1-hour hot air balloon flight departing from the area of San Casciano in Val di...

3 hours • Free Cancellation
4.9 (170)
from
$346
Hot Air Balloon Ride over Chianti Hills

Just 20 minutes from Florence, Chianti reveals itself as the heart of historic Tuscany. You’ve likely tasted its world-renowned wine, but have you ever breathed …More

Florence, Italy
5.0 (193)

Hot Air Balloon Ride over Chianti Hills

Just 20 minutes from Florence, Chianti reveals itself as the heart of historic Tuscany. You’ve likely tasted its world-renowned wine, but have you ever breathed...

3 hours • Free Cancellation
5.0 (193)
from
$312
Photo Shoot in Florence with a Professional Photographer

Experience Florence and get some of the best vacation photos you'll ever see with a professional private photo shoot. Spend time with your own private …More

Florence, Italy
5.0 (25)

Photo Shoot in Florence with a Professional Photographer

Experience Florence and get some of the best vacation photos you'll ever see with a professional private photo shoot. Spend time with your own private...

90 to 240 minutes • Free Cancellation
5.0 (25)
from
$521
Siena & San Gimignano: Exclusive Tuscany Day Trip from Florence

Have you been dreaming of Tuscany? Then this tour is for you. Wake up in Florence, where your private driver will meet you at your …More

Florence, Italy
5.0 (33)

Siena & San Gimignano: Exclusive Tuscany Day Trip from Florence

Have you been dreaming of Tuscany? Then this tour is for you. Wake up in Florence, where your private driver will meet you at your...

8 hours • Hotel pickup offered • Free Cancellation
5.0 (33)
from
$461
Hot Air Balloon ride in the Chianti Valley Tuscany

See for miles over the beautiful Tuscan countryside on a 1-hour hot air balloon flight, taking place from the village of San Casciano in Val …More

Florence, Italy
4.9 (69)

Hot Air Balloon ride in the Chianti Valley Tuscany

See for miles over the beautiful Tuscan countryside on a 1-hour hot air balloon flight, taking place from the village of San Casciano in Val...

3 hours • Free Cancellation
4.9 (69)
from
$312
From San Gimignano: Tuscany Wine tour by Tuk Tuk with Lunch

What a better gift for your lover or best friend than visit Tuscany on board of a convertible Tuk Tuk for 2 to explore the …More

San Gimignano, Italy
4.8 (19)

From San Gimignano: Tuscany Wine tour by Tuk Tuk with Lunch

What a better gift for your lover or best friend than visit Tuscany on board of a convertible Tuk Tuk for 2 to explore the...

4 hours • Free Cancellation
4.8 (19)
from
$174
Hot Air Balloon Ride over Florence

Florence, is known worldwide as the birthplace of Reinassance. By over flying the city of Florence, you cane se the magnificent architecture from up above, …More

Florence, Italy
4.9 (46)

Hot Air Balloon Ride over Florence

Florence, is known worldwide as the birthplace of Reinassance. By over flying the city of Florence, you cane se the magnificent architecture from up above,...

3 hours • Free Cancellation
4.9 (46)
from
$576
Wine Tasting of Brunello with Tuscan Cold Cuts and Cheese

Enjoy an exclusive one-hour wine tasting experience featuring warm homemade bread and exquisite Tuscan olive oil. Take a leisurely stroll through the vineyard before indulging …More

Likely to Sell Out
Likely to Sell Out
Chianti, Italy
5.0 (6)

Wine Tasting of Brunello with Tuscan Cold Cuts and Cheese

Enjoy an exclusive one-hour wine tasting experience featuring warm homemade bread and exquisite Tuscan olive oil. Take a leisurely stroll through the vineyard before indulging...

1 hour 30 minutes • Free Cancellation
5.0 (6)
from
$45
Hot-Air Balloon Flight over Florence

A Hot-Air Balloon flight above Florence is a poetic and fascinating experience, a unique and suggestive way to admire the fruits of the Renaissance from …More

Florence, Italy
5.0 (59)

Hot-Air Balloon Flight over Florence

A Hot-Air Balloon flight above Florence is a poetic and fascinating experience, a unique and suggestive way to admire the fruits of the Renaissance from...

2 to 3 hours • Free Cancellation
5.0 (59)
from
$462
Private Hot Air Balloon Flight in Tuscany

Just 30 minutes from Florence, Chianti reveals itself as the heart of historic Tuscany. You’ve likely tasted its world-renowned wine, but have you ever breathed …More

Florence, Italy
5.0 (6)

Private Hot Air Balloon Flight in Tuscany

Just 30 minutes from Florence, Chianti reveals itself as the heart of historic Tuscany. You’ve likely tasted its world-renowned wine, but have you ever breathed...

3 hours • Free Cancellation
5.0 (6)
from
$347
Private Photo Shoot in Lucca

Explore Lucca with a professional photographer who can help you make the most of your time in the city. After a short consultation, visit Lucca’s …More

Lucca, Italy
5.0 (4)

Private Photo Shoot in Lucca

Explore Lucca with a professional photographer who can help you make the most of your time in the city. After a short consultation, visit Lucca’s...

1 hour 30 minutes
5.0 (4)
from
$52
From Florence to Portofino: Private Minivan Day Trip

Set off from Florence and reach Pisa in about an hour for a brief stop at Piazza dei Miracoli. Then continue toward the Ligurian coast, …More

Florence, Italy
5.0 (3)

From Florence to Portofino: Private Minivan Day Trip

Set off from Florence and reach Pisa in about an hour for a brief stop at Piazza dei Miracoli. Then continue toward the Ligurian coast,...

12 hours • Hotel pickup offered • Free Cancellation
5.0 (3)
from
$203
E-bike tour with Wine Tasting at Tenuta delle Ripalte

Bike tour of 2 hours, divided equally between bike ride and tasting. Departure at 16.00 and arrival in the cellar at 17.00 (a meeting time …More

Isola d'Elba, Italy
5.0 (3)

E-bike tour with Wine Tasting at Tenuta delle Ripalte

Bike tour of 2 hours, divided equally between bike ride and tasting. Departure at 16.00 and arrival in the cellar at 17.00 (a meeting time...

2 hours • Free Cancellation
5.0 (3)
from
$128
Private Photo Shoot in Siena

Capture your memories of Siena on camera with this private photo shoot in the heart of the city. The experience is led by a professional …More

Siena, Italy
5.0 (4)

Private Photo Shoot in Siena

Capture your memories of Siena on camera with this private photo shoot in the heart of the city. The experience is led by a professional...

1 hour 30 minutes
5.0 (4)
from
$406
Private Tuscany & San Gimignano by Exclusive Vintage Fiat 500

Experience a unique day tour through the Tuscan hills in a vintage Fiat 500. What sets this apart? We cruise fo real through the heart …More

Florence, Italy
5.0 (8)

Private Tuscany & San Gimignano by Exclusive Vintage Fiat 500

Experience a unique day tour through the Tuscan hills in a vintage Fiat 500. What sets this apart? We cruise fo real through the heart...

7 hours • Free Cancellation
5.0 (8)
from
$196
Sunrise Balloon Flight over Tuscany with Breakfast and Photos

Soar above Tuscany’s rolling vineyards and ancient villages in our exclusive hot air balloon adventure—the most photogenic flight in all of Tuscany. Whether you’re seeking …More

Florence, Italy
4.9 (9)

Sunrise Balloon Flight over Tuscany with Breakfast and Photos

Soar above Tuscany’s rolling vineyards and ancient villages in our exclusive hot air balloon adventure—the most photogenic flight in all of Tuscany. Whether you’re seeking...

3 hours • Free Cancellation
4.9 (9)
from
$312
Pisa Romantic Quest: Solve the Curse of Rosa

Pisa, 1501. Banished from your homeland, you and your twin sister Rosa were sent to this city of quiet beauty and hidden resistance. While you …More

Pisa, Italy
4.6 (7)

Pisa Romantic Quest: Solve the Curse of Rosa

Pisa, 1501. Banished from your homeland, you and your twin sister Rosa were sent to this city of quiet beauty and hidden resistance. While you...

35 to 65 minutes • Free Cancellation
4.6 (7)
from
$8
Sunset Magic E-bike Tour at Sunset in Capoliveri

Overall 2h bike tour: The departure time varies from 6:20 PM to 7:30 PM depending on the season. An experience full of 'Good Vibes'. The …More

Isola d'Elba, Italy
5.0 (3)

Sunset Magic E-bike Tour at Sunset in Capoliveri

Overall 2h bike tour: The departure time varies from 6:20 PM to 7:30 PM depending on the season. An experience full of 'Good Vibes'. The...

2 hours • Free Cancellation
5.0 (3)
from
$104
Siena E-Tuk Tuk panoramic Aperitivo with Local Snacks

Hop aboard our eco-friendly electric tuk tuk and embark on a panoramic journey around Siena. As you wind your way through the picturesque hills surrounding …More

Siena, Italy
5.0 (1)

Siena E-Tuk Tuk panoramic Aperitivo with Local Snacks

Hop aboard our eco-friendly electric tuk tuk and embark on a panoramic journey around Siena. As you wind your way through the picturesque hills surrounding...

2 hours
5.0 (1)
from
$151
1 Hour E-bike Sunset Tour in Lacona suitable for Families

Bike Tour of 1h. The departure time varies from 18.50 to 20.00 depending on the season. An Experience full of 'Good Vibes'. The energy of …More

Isola d'Elba, Italy
5.0 (1)

1 Hour E-bike Sunset Tour in Lacona suitable for Families

Bike Tour of 1h. The departure time varies from 18.50 to 20.00 depending on the season. An Experience full of 'Good Vibes'. The energy of...

1 hour • Free Cancellation
5.0 (1)
from
$104

Frequently Asked Questions

These answers are based on answers previously given to Cool Destinations customers' questions.

Recent tour reviews
Exceptional experience that we'd highly recommend
New York City
Hot-Air Balloon Flight over Florence
Olivia_M, Sep 2026
Exceptional experience that we'd highly recommend
I was put in contact with Ivan after booking through Cool Destinations & he was very informative & helpful prior to our holiday in Florence. Booked for two people & the experience was thoroughly enjoyed plus the bonus of a drone recording captured the flight perfectly. Ivan was so helpful in sending directions to departure sight & offered booking of transport if required due to our early morning slot. On the day Ivan was informative during the flight & made it interesting with his knowledge & humour! An amazing experience that we'd highly recommend to really enhance your visit to Florence. Once in a lifetime adventure well worth booking!
Read more
Bucket List experience without a doubt!!
New York City
Hot Air Balloon ride in the Chianti Valley Tuscany
Corinne_K, Sep 2026
Bucket List experience without a doubt!!
Experience of a lifetime! So very cool! Whole balloon team was amazing and our FEMALE pilot (sorry I forget her name) was incredible! She made it extra special with explaining how things work, pointing out sites on our hour-long journey, and answered questions with detail and enthusiasm. She really loves what she does and is extremely good at it. In fact, we learned she has the record of highest number of countries (125 so far) she has piloted in for a female pilot! Very impressive! This really is a bucket list experience and I highly recommend it as it is worth every penny! 🌸
Read more
The Hot-Air Balloon Ride over Florence was a dream!!
New York City
Hot-Air Balloon Flight over Florence
MerandaMalter, Sep 2026
The Hot-Air Balloon Ride over Florence was a dream!!
The hot-air balloon ride over Florence was an extremely amazing experience!! The pick up location was easy to find, the pilot was phenomenal and the view was breathtaking!! He even treated us to coffee and pastries afterwards. I would highly recommend this tour. It’s an experience of a lifetime!! Bucket list, check!!☑️
Read more
Incredible & once in a...
New York City
Hot Air Balloon Ride over Chianti Hills
Ariana_G, Sep 2026
Incredible & once in a...
Incredible & once in a lifetime experience! Everyone was super friendly and made the experience amazing!
Read more
We had the best time!...
New York City
Hot Air Balloon Ride over Chianti Hills
Delaney_H, Sep 2026
We had the best time!...
We had the best time! Francesco was a great pilot and guide. We chose the transportation option from our hotel and it helped immensely! It was a great sunrise and we landed to champagne and breakfast bites. The whole crew worked expertly. We would highly recommend this for anyone visiting Florence!
Read more
Great trip, tasty food & wine, lovely guide
New York City
From San Gimignano: Tuscany Wine tour by Tuk Tuk with Lunch
Helenabrookessmith, Sep 2026
Great trip, tasty food & wine, lovely guide
Alessandro is a super friendly and knowledgeable guide! He told us a lot about the local area and was a wonderful tour guide - thank you! Lunch was lovely, with three glasses of wine. The Tuktuk was really fun and we stopped to hear about some of the history.
Read more
Wonderful
New York City
Experience the Magic of Tuscany from a Hot Air Balloon
Chardae_R, Sep 2026
Wonderful
Such a fun and unique experience! Everyone was exceptional and kind. We loved getting to experience this.
Read more
Anniversary Flight
New York City
Experience the Magic of Tuscany from a Hot Air Balloon
D2903XJanthonym, Sep 2026
Anniversary Flight
The balloon experience was unforgettable. The crew and service was excellent. 10/10!
Read more
Worth Every Penny!!
New York City
Sunrise Balloon Flight over Tuscany with Breakfast and Photos
Ebony_A, Sep 2026
Worth Every Penny!!
This experience was worth every penny!! This bucket list item is BEST spent over the farmlands of the Italian countryside at sunrise - breathtaking in every way!! The team that handled our experience took lots of photos and videos, which they shared with us immediately, they were friendly and made the trip so much fun. 11/10 recommend!!
Read more
Amazing
New York City
Hot Air Balloon ride in the Chianti Valley Tuscany
E5601AOrachelm, Sep 2026
Amazing
Awesome experience! Crew was extremely professional! Would recommend!
Read more
Sunny tuktuk tour + wine experience
New York City
From San Gimignano: Tuscany Wine tour by Tuk Tuk with Lunch
Chelslolbrood, Sep 2026
Sunny tuktuk tour + wine experience
We had a wonderful trip, we learned about the vineyards, how Olive oil is made, what the difference between extra Olive oil and normal,... The guide also made some beautiful pics of us.The visit to the winery was also very nice and tasty to do. Definitely recommend it!
Read more
Beautiful balloon ride over florence and tuscan country side
New York City
Hot Air Balloon Ride over Florence
Davide_C, Sep 2026
Beautiful balloon ride over florence and tuscan country side
Fantastic experience! The organization and communication was impeccable. The balloon ride was breathtaking and the perfect length. Our aeronaut was skilled and safe. I cannot say enough good things about this experience!!! Definitely a highlight of our trip!
Read more
Exceptional
New York City
Hot Air Balloon Ride over Florence
Kristy_M, Aug 2026
Exceptional
Such an incredible experience very comfortable and welcoming Better than expected I would do it again
Read more
Off to the Races in Siena
New York City
Siena & San Gimignano: Exclusive Tuscany Day Trip from Florence
ankonag, Aug 2026
Off to the Races in Siena
Emanuela was excellent. She was kind and knowledgeable. We really enjoyed our laid back day seeing Siena, Tuscan countryside (with winery), and San Gimignano. The weekend we went was the horse race event and it was even more special to see the set-up and festivities for that tradition!
Read more
Amazing authentic experience!
New York City
Private Tuscany & San Gimignano by Exclusive Vintage Fiat 500
919harrietr, Jul 2026
Amazing authentic experience!
Incredible experience. Booked as part of our honeymoon adventures and Tuscany on Wheels was just the perfect authentic Italian experience. Alessandro was an incredible tour guide, full of knowledge, welcoming and a perfect guide. Highly recommend! Thank you! X
Read more
Tuscany
New York City
Siena & San Gimignano: Exclusive Tuscany Day Trip from Florence
133marcyh, Jun 2026
Tuscany
Driver spoke excellent English. He gave great advice on where to go in each stop. Very accommodating.
Read more
Tuscany Tours
Attractions
Guides
Calendar
View more