San Filippo Vacations from $1,297

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Your San Filippo Vacation

With every last detail planned before you go, our San Filippo vacation packages mean you can concentrate on having a great time. Whether you base yourself in the neighborhood of Petrazzi, which is great for views, or somewhere else in town, this fun city offers plenty of discoveries. Eager to explore? Isole e Olena Winery, Castello di Monsanto and Casa Sola - Chianti Winery are just a few of the top places to visit during your trip to San Filippo. Whatever your travel plans or budget, organizing a tailored San Filippo vacation is a breeze with Expedia.

The Latest San Filippo vacation packages

Price found within the past 48 hours. Click for updated prices.
Tenuta di Artimino Member of Meliá Collection

Tenuta di Artimino Member of Meliá Collection

4 out of 5
Save 100% on your flight
Price was $1,973, price is now $1,297 per person
$1,297
per person
Oct 17 - Oct 24
found 1 day ago
Roundtrip flight included
New York (JFK) to Florence (FLR)
9.2/10 Wonderful! (129 reviews)
This is a lovely hotel. The rooms in the village are fresh and clean. The walk to the hotel was pleasant and looking at the views are stunning. The staff are all professional and curtious. A special thanks to Auri for always smiling. Most important question' would I recommend this hotel, Definitely !

Reviewed on Aug 21, 2025

L'Andana

L'Andana

5 out of 5
Save 100% on your flight
Price was $2,626, price is now $1,752 per person
$1,752
per person
Oct 24 - Oct 31
found 1 day ago
Roundtrip flight included
New York (JFK) to Florence (FLR)
9.4/10 Exceptional! (80 reviews)
What an amazing place I hope to get back here next year again everybody was super nice. Property was super nice. It is quite relaxing. Great food apparently a great wine as well but I don’t drink. I highly recommend anybody to go.

Reviewed on Jul 5, 2025

Monastero di Cortona Hotel & Spa

Monastero di Cortona Hotel & Spa

5 out of 5
Cortona Old Town
Save 100% on your flight
Price was $2,080, price is now $1,456 per person
$1,456
per person
Oct 24 - Oct 31
found 1 day ago
Roundtrip flight included
New York (JFK) to Florence (FLR)
10/10 Exceptional! (230 reviews)
Beautiful property, magical, great friendly staff, fantastic breakfast. Everything was perfect

Reviewed on Aug 7, 2025

The Club House

The Club House

5 out of 5
Save 100% on your flight
Price was $2,450, price is now $1,717 per person
$1,717
per person
Oct 24 - Oct 31
found 1 day ago
Roundtrip flight included
New York (JFK) to Florence (FLR)
10/10 Exceptional! (2 reviews)
Excellent overall. Amenities. Service. Food. Vibe. All top notch

Reviewed on Sep 2, 2025

Castello di Spaltenna- Small Luxury Hotels of the World

Castello di Spaltenna- Small Luxury Hotels of the World

5 out of 5
Save 100% on your flight
Price was $2,456, price is now $1,739 per person
$1,739
per person
Oct 24 - Oct 31
found 1 day ago
Roundtrip flight included
New York (JFK) to Florence (FLR)
9.6/10 Exceptional! (247 reviews)
This was the most authentic place I have ever seen really takes back but all the amenities by far the best place to stay in Tuscany IT Fantastic staff 5star

Reviewed on Aug 31, 2025

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Discover the most popular places to visit in San Filippo

Whenever you're in Tuscany, you must go to the countryside and visit the beautiful wineries. This one in particular has over 300 hectares of grapes, olive trees and beehives.

Fattoria di Montecchio

You can enjoy a tasting or tour at Fattoria di Montecchio during your travels to Tavarnelle Val di Pesa. Discover the beautiful countryside in this relaxing area, or enjoy its local tours.

Fattoria di Montecchio

Isole e Olena Winery

You can enjoy a tasting or tour at Isole e Olena Winery during your travels to Barberino Val d'Elsa. Discover the beautiful countryside in this quaint area, or enjoy its local tours.

Isole e Olena Winery

Casa Sola - Chianti Winery

You can enjoy a tasting or tour at Casa Sola - Chianti Winery during your travels to Cortine. Discover the beautiful countryside and wineries in this relaxing area.

Casa Sola - Chianti Winery

What to do in San Filippo

Having fun while tasting Chianti

Tuscany Wine Tour : 2 Wineries & San Gimignano from Florence

$222
per adult
100% of travellers recommend
Tuscany Wine Tour : 2 Wineries & San Gimignano from Florence
Siena, Cortona, Montepulciano & Val D'Orcia from Florence - Semi private tour

Siena, Cortona, Montepulciano & Val D'Orcia from Florence - Semi private tour

$234
per adult
Siena, Cortona, Montepulciano & Val D'Orcia from Florence - Semi private tour
Guided tour with wine tasting and local organic products

Guided tour with wine tasting and local organic products

$60
per adult
Guided tour with wine tasting and local organic products
See all activities in San Filippo

San Filippo Hotel Deals

The Social Hub Florence Lavagnini

The Social Hub Florence Lavagnini

4 out of 5
Viale Spartaco Lavagnini 70 72, Florence, FI
Fully refundable
$153 nightly
The price is $185 total per night from Sep 5 to Sep 6
$185 total
Sep 5 - Sep 6
Total with taxes and fees
The Social Hub Florence Lavagnini
Hotel Machiavelli Palace

Hotel Machiavelli Palace

3 out of 5
Via Nazionale 10, Florence, FI
Fully refundableReserve now, pay when you stay
$102 nightly
The price is $127 total per night from Sep 4 to Sep 5
$127 total
Sep 4 - Sep 5
Total with taxes and fees
Hotel Machiavelli Palace
Borghese Palace Art Hotel

Borghese Palace Art Hotel

4 out of 5
Via Ghibellina, 174r, Florence, FI
$172 nightly
The price is $205 total per night from Sep 7 to Sep 8
$205 total
Sep 7 - Sep 8
Total with taxes and fees
Borghese Palace Art Hotel
See all 13,700 properties in San Filippo
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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Frequently asked questions

How much does a San Filippo vacation package cost?
Offering great value package deals from $1,297 on Expedia, you'll be thrilled with how little a vacation to San Filippo costs! Expedia's packages mean less travel planning for you and greater savings.
What are the cheapest months to go to San Filippo?
You're likely to find reduced prices and greater availability in January, July and December. Check out our cheap San Filippo vacation packages and you could land some great off-season deals.
How many days is enough for San Filippo?
With a well-organized schedule, you can easily tick off the top San Filippo sights in a few days. But if you'd like to discover lesser-known spots or go on day trips, think about booking your San Filippo vacation for longer.
How to find the best San Filippo package deals?
Finding a cheap San Filippo package deal is a cinch with Expedia. After you've entered your trip dates and destination under our "Packages" tab, set your budget, add some filters and browse what's available. You can customize your search by "Area," "Amenities," "Property type" and more. Sort the results by "Price: low to high" to discover the most pocket-friendly San Filippo package deals. Want a simple trick to get even more savings? Be flexible with your departure dates and consider going away on a weekday, when prices are often lower.
Is it cheaper to book a San Filippo vacation as a package?
An Expedia vacation package could score you significant savings when compared to booking flights and stays individually. Better still, you can customize your San Filippo trip to fit your exact needs. Pick your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.
When to book a vacation package to San Filippo?
If you're planning a spur-of-the-moment San Filippo vacation, check out our last-minute deals that can be booked up to a week before you take off. Prefer not to wait until the last minute? You can land sensational deals on your flights and hotels by booking ahead.
Does Expedia offer Book Now, Pay Later San Filippo vacation packages?
Set off on your perfect trip to San Filippo with help from Expedia's Book Now, Pay Later vacations. No need to save up or wait for the next payday — we've partnered with online lender Affirm to give you flexibility and choice. Our vacation packages with payment plans let you split the cost across 3, 6 or 12 months. With no late payment fees or hidden charges, you can easily stay on budget and snap up travel deals while they last.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.