Onward Deals | Travelzoo

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TOP 20 - Sells out quickly! $1199 ~~$2072~~ Luxe Sicily trip for 2: cooking class, meals & more

Tenute Baglio Passofondo • Italy

This 19th-century-farmhouse-turned-5-star hotel and winery is nestled among sun-drenched vineyards in the northwest of Sicily. There, ancient UNESCO sites and a unique culinary heritage offer plenty to delight the senses and inspire la dolce vita . Starting from $1199, 4-night stays for 2 guests come with a traditional Sicilian cooking class, two 3-course dinners and a guided tasting of the estate's wine. Daily breakfast is also covered. We checked and found this offer saves $659–$873 compared to regular prices for spring and early fall stays. Peak summer dates are also available.

April–October

TOP 20 - Sells out quickly!
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TOP 20 - Sells out quickly! $999 Italy for 9 nights: visit 4 cities incl. flights

Rome, Florence, Milan, Venice

Explore Italy's greatest cities for $999.

November 2026–January 2027; more dates from +$100

TOP 20 - Sells out quickly!
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Tripmasters

$1159 & up Rome, Florence & Venice: 7 nights incl. flights

Italy

This fully customizable deal includes hotels, taxes, and train travel throughout. See the gondolas in Venice, monuments of Rome and art in Florence.

Select dates March 2026–February 2027
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TOP 20 - Sells out quickly! $1499 ~~$3005~~ Tuscan retreat for 2 w/cooking class

Borgo Scopeto Wine & Country Relais • Italy

When you think of a Tuscan getaway, this is probably what you're picturing. Borgo Scopeto Wine and Country Relais is a secluded 14th-century estate surrounded by rolling green hills. This intimate retreat blends historic charm with modern conveniences, including two pools, a spa and tennis courts. Plan a trip this summer and save 48%–51% on 3-night (or longer) stays in an upgraded suite. Daily breakfast is included. The price covers 2 adults and you'll also score great culinary perks, like a cooking class, a three-course dinner and a welcome glass of wine.

July–August 2026

TOP 20 - Sells out quickly!
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The Flights Guru

$1899 Italy and Greece 9-night explorer w/airfare

Venice, Rome, Santorini, Athens

This itinerary combines big city adventures, cultural sights and fun in the sun in fall when crowds thin after the busy tourist season.

October; other dates higher
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TOP 20 - Sells out quickly! $899 Italy: 8 nights w/flights

Rome, Florence, Venice

Pack light for an Italy trip during the holiday season, you’ll need the extra room for gifts.

October 2026–January 2027; more dates from +$100

TOP 20 - Sells out quickly!
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Tripmasters

$2899 & up Upscale 8-night Italy vacation w/air

Florence, Siena, La Spezia

Explore the Tuscan countryside, Cinque Terre, Monteriggioni and more with the help of a private driver.

Select dates March 2026–February 2027
$2669 ~~$6039~~ Lake Como 5-star hotel w/dinner for 2, reg. $6039

Nuvole Garden Hotel • Brunate, Italy

High above Lake Como in the village of Brunate, Nuvole Garden Hotel offers a quiet vantage point over one of Italy’s most iconic landscapes. The historic villa recently reopened after a renovation, transforming it into a 5-star destination. As a notoriously pricey destination, deals in Lake Como are rare, especially for summer travel. But with this offer, Travelzoo members save 43%–57% on 4-night (or longer) stays for two guests. You’ll stay in an upgraded room with lake views, plus get a three-course dinner, spa access and more. Daily breakfast is also included.

Select dates, April 1–Dec. 27
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Tripmasters

$3559 & up Upscale Rome, Florence & Venice trip w/flights

Italy

This posh vacation visits three of Italy's most iconic and historic cities over 12 nights.

Select dates March 2026–February 2027
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Wingbuddy

$2298 & up See Italy by train: 10 nights w/flights

Italy

This package allows you to visit Venice, Florence and Rome at your own pace and includes flights, transfers, trains, hotels, breakfasts and more.

Select dates through November 2026
Book now at
The Flights Guru

$1499 Weeklong Rome, Florence, Venice vacation w/air

Italy

This itinerary balances tours of historic sights with plenty of free time to explore three of Italy's essential cities.

November; other dates higher
$1799 & up Europe: visit 3 countries in 9 nights w/flights

Paris, Dijon, Zurich, Lucerne, Milan, Florence, Rome

This European tour visits some of our favorite across-the-pond destinations (and then some).

October 2026–February 2027; other dates also on sale
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Travelodeal

$799 & up Ischia 5-night vacation w/flights & ferry

Italy

Revel on Ischia's stunning beaches and enjoy its thermal spas over 5 nights for under $800. Daily breakfast is included.

October; additional dates also on sale
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Exoticca

$1599 & up Rome, Florence & Venice: 6-night trip w/flights

Italy

This independent itinerary includes guided walking tours across three of Italy's most iconic cities.

Departures through December 2026
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Travelodeal

$999 & up Sicily road trip for a week (w/flights + car)

Italy

Sicily is known for its coastal views, rich culture and seaside charm. Experience it all with flights, hotel and car included.

March; other dates are also on sale
Book now at
Exodus Adventure Travels

$2505 & up Walk the Amalfi Coast this year: land only

Italy

This land-only trip spends a week on the Amalfi Coast, where you'll spend four days taking in the incredible views on guided walks.

June 2026; more dates available
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Travelodeal

$1199 & up Sorrento weeklong roadtrip w/flights & car

Italy

Sorrento's sea views, vibrant piazzas and cliffside beach clubs will be on full display. With your car, access to Capri and Amalfi Coast is a breeze.

April; other dates are also on sale
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Tripmasters

$1179 & up 9-night, 4-city Italy vacation incl. flights

Italy

This fully customizable deal includes hotels, taxes, and train travel throughout. See the gondolas in Venice, monuments of Rome and art in Florence.

Select dates March 2026–February 2027
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Travelodeal

$2099 & up Mediterranean cruise incl. Italy, France & Spain

Barcelona, Gibraltar, Marseille, Genoa, Florence, Rome

Enjoy an overnight stay in Barcelona, then sail out on the Sun Princess for nine nights in 2027. Port stops include Gibraltar, Marseille and more.

May; other dates are also on sale
$1199 & up Epic vacations around the world

Peru, Ireland, Italy, Portugal, South Africa, Japan and more

We sourced some of the most popular deals across four continents, which include guided tours, excursions, flights, transfers and more.

Departures available into 2027
Book now at
Travelodeal

$1299 & up Milan & Lake Garda trip w/flights and cruise

Italy

Northern Italy’s culture and lakeside beauty will be explored on this self-drive vacation. Flights, car, a scenic Sirmione cruise & more are included.

November; other dates are also on sale
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Globus

$5449 & up Explore Italy: 6-city tour from Rome

Florence, Venice, Assisi, Sorrento

This 12-night itinerary includes boat rides along Lake Maggiore and the Cinque Terre coastline.

April 2026
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Travelodeal

$1199 & up London, Milan & Paris vacation w/flights + hotels

Italy & France

Stay at well-reviewed hotels in each city and enjoy daily breakfast. Explore iconic landmarks and cultural highlights with transfers included.

November–December; other dates are also on sale
$1499 & up Europe for 12 nights: explore 3 cities w/flights

Rome, Zurich, Paris

With savings starting at $1180, these gems of Western Europe have never been more accessible.

October 2026–February 2027; other dates also on sale
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Indus Travels

$2899 & up Europe group tour: 5 countries in 12 nights w/air

Portugal, Spain, France, Switzerland, Italy

This group tour will take you across southwestern Europe, visiting multiple cities across five countries.

Options through January 2027
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Yes Getaways

$1049 A week in Sicily incl. flights & rental car

Italy

Head to Sicily this year for 7 nights of exploring at your own pace. Includes flights, accommodations and a rental car.

Best price February–March, November; more dates on sale
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Indus Travels

$2999 & up Italy by rail: 11 nights w/flights

Rome, Florence, La Spezia, Milan, Venice

Explore Italy by train as you visit five different cities with guided tours, wine tastings and more.

Options through January 2027
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Globus

Save $500 Italy 11-night guided tour this summer

Rome, Venice, Assisi, Capri

Visit the Leaning Tower, wander the streets of Venice and cruise around Capri all in one guided trip.

July 2026
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Road Scholar

$6499 & up Southern Italy small-ship getaway w/Newark air

Italy, Malta

Journey to southern Italy, Sicily and Malta via mega yacht with Road Scholar, an educational travel company for adults ages 50+.

August 2026
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Yes Getaways

$1199 & up Rome & Paris at your leisure

Italy, France

Spend 6 nights exploring these two iconic European capitals. Includes flights and accommodations.

February, November–December; more dates on sale
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Wingbuddy

$3498 & up Mediterranean escape: 2-week Italy & Greece w/air

Venice, Florence, Rome, Athens, Paros, Santorini

Explore Italy and Greece at your own pace with this trip including flights, trains, ferries, hotel transfers, hotel stays, breakfasts, taxes and fees.

Select dates through October 2025
$599 Italy vacation w/flights & car (SOLD OUT)

Lake Maggiore

TK TK

Limited availablity
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Wingbuddy

$1698 & up Venice, Florence & Rome: 7 nights w/air

Rome, Florence, Venice

See three of Italy's greatest cities, including hotels, trains, flights, transfers and breakfasts.

Select dates through October 2026
$3399 & up Europe 3-country guided tour: 2 weeks w/flights

Paris, Reims, Strasbourg, Colmar, Montreux, Zermatt, Milan, Venice, Florence, Rome

This European adventure packs in the very best of each country—all in one trip.

Select dates September-November; other dates on sale
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Wingbuddy

$2198 & up Paris & Rome: 8 nights w/flights & transfers

France & Italy

Explore two storied European capitals at leisure on this eight-night trip, including flights, transfers, centrally located hotels and daily breakfast.

Select dates through October 2026
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Globus

$4149 & up Rome to Palermo: 13-night trip incl. guide

Italy

Pair Southern Italy with Sicily on this one-of-a-kind vacation, including an expert guide and 4-star stays throughout.

November 2026
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Wingbuddy

$2998 & up Italy from North to South: 10-nt. tour w/flights

Rome. Florence, Venice, Sorrento

Enjoy this slice of Italy—packed full of architecture, history, cuisine and free time to explore. Plus, a skip-the-line pass to the ruins of Pompeii.

Select dates through to September 2026
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Yes Getaways

$1099 & up Visit ancient Athens & Rome this year

Italy, Greece

Spend 6 nights exploring the capitals of Greece and Italy. This trip covers flights, accommodations and transfers.

Best price November–December; more dates available
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Wingbuddy

$2198 & up Weeklong guided Italy trip w/flights

Rome, Venice, Florence

Explore Rome, Florence and Venice on this seven-night trip, including some meals and an experienced, English-speaking guide.

Select dates through March 2025
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Tripmasters

$1339 & up 8-nights in Paris, Venice & Rome with flights

France, Italy

From the romantic streets of Paris to the Venice canals, enjoy an unforgettable vacation across two countries.

Select dates March 2026–February 2027
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Tripmasters

$1689 & up Venice, Florence, Rome & Amalfi Coast trip w/air

Italy

This fully customizable deal includes hotels, taxes, and train travel throughout. See the gondolas in Venice, monuments of Rome and art in Florence.

Select dates March 2026–February 2027
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Tripmasters

$1039 & up 6-night Paris & Rome European escape w/air

France & Italy

Explore the Eiffel Tower one day and tour the Colosseum the next on this vacation, which includes flight between the two cities.

Select dates March 2026–February 2027
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Tripmasters

$1499 & up 9 nights in London, Paris & Rome w/air

United Kingdom, France, Italy

This multi-city vacation includes a high-speed train journey between London and Paris.

Select dates March 2026–February 2027
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Tripmasters

$1019 & up Rome to Athens: 6-night trip w/air

Italy, Greece

Enjoy the stunning architecture, history and culture of two iconic European cities.

Select dates March 2026–February 2027
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Tripmasters

$1029 & up Rome & Florence vacation w/flights

Italy

Explore the "Eternal City" before catching a train to Florence with this flexible package.

Select dates March 2026–February 2027
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Tripmasters

$1189 & up Barcelona & Rome: 9 night vacation incl. flights

Europe

We love that this package includes your hotel stays & taxes and is fully customizable.

Select dates March 2026–February 2027
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Tripmasters

$1379 & up France & Italy for 10 nights w/flights

Paris, Venice, Florence, Rome

Travel from the Eiffel Tower to the Colosseum in days, with intra-vacation flights included.

Select dates March 2026–February 2027
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Tripmasters

$1509 & up 9-night London, Paris & Rome vacation incl. air

Europe

See famous sites like Big Ben, the Eiffel Tower and the Colosseum on this fully customizable trip.

Select dates March 2026–February 2027
Book now at
Tripmasters

$1219 & up Rome, Cinque Terre, Florence & Venice trip w/air

Italy

This fully customizable deal includes hotels, taxes, and train travel throughout. See the gondolas in Venice, monuments of Rome and art in Florence.

Select dates March 2026–February 2027
Book now at
Tripmasters

$3449 & up Upcale Rome, Sorrento & Amalfi vacation w/air

Italy

Explore the Colosseum and cruise to the island of Capri on this weeklong getaway.

Select dates March 2026–February 2027
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Tripmasters

$1389 & up Best of Italy: 8-nights, 4-cities w/flights

Venice, Florence, Rome, Sorrento

See Venice, Florence, Rome and Sorrento on this customizable vacation across Italy.

Select dates March 2026–February 2027

TOP 20 - Sells out quickly! $1199 $2072 Luxe Sicily trip for 2: cooking class, meals & more

Tenute Baglio Passofondo • Italy

April–October

TOP 20 - Sells out quickly! $999 Italy for 9 nights: visit 4 cities incl. flights

Rome, Florence, Milan, Venice

November 2026–January 2027; more dates from +$100

Tripmasters

$1159 & up Rome, Florence & Venice: 7 nights incl. flights

Italy

Select dates March 2026–February 2027

TOP 20 - Sells out quickly! $1499 $3005 Tuscan retreat for 2 w/cooking class

Borgo Scopeto Wine & Country Relais • Italy

July–August 2026

The Flights Guru

$1899 Italy and Greece 9-night explorer w/airfare

Venice, Rome, Santorini, Athens

October; other dates higher

TOP 20 - Sells out quickly! $899 Italy: 8 nights w/flights

Rome, Florence, Venice

October 2026–January 2027; more dates from +$100

Tripmasters

$2899 & up Upscale 8-night Italy vacation w/air

Florence, Siena, La Spezia

Select dates March 2026–February 2027

$2669 $6039 Lake Como 5-star hotel w/dinner for 2, reg. $6039

Nuvole Garden Hotel • Brunate, Italy

Select dates, April 1–Dec. 27

Tripmasters

$3559 & up Upscale Rome, Florence & Venice trip w/flights

Italy

Select dates March 2026–February 2027

Wingbuddy

$2298 & up See Italy by train: 10 nights w/flights

Italy

Select dates through November 2026

The Flights Guru

$1499 Weeklong Rome, Florence, Venice vacation w/air

Italy

November; other dates higher

$1799 & up Europe: visit 3 countries in 9 nights w/flights

Paris, Dijon, Zurich, Lucerne, Milan, Florence, Rome

October 2026–February 2027; other dates also on sale

Travelodeal

$799 & up Ischia 5-night vacation w/flights & ferry

Italy

October; additional dates also on sale

Exoticca

$1599 & up Rome, Florence & Venice: 6-night trip w/flights

Italy

Departures through December 2026

Travelodeal

$999 & up Sicily road trip for a week (w/flights + car)

Italy

March; other dates are also on sale

Exodus Adventure Travels

$2505 & up Walk the Amalfi Coast this year: land only

Italy

June 2026; more dates available

Travelodeal

$1199 & up Sorrento weeklong roadtrip w/flights & car

Italy

April; other dates are also on sale

Tripmasters

$1179 & up 9-night, 4-city Italy vacation incl. flights

Italy

Select dates March 2026–February 2027

Travelodeal

$2099 & up Mediterranean cruise incl. Italy, France & Spain

Barcelona, Gibraltar, Marseille, Genoa, Florence, Rome

May; other dates are also on sale

$1199 & up Epic vacations around the world

Peru, Ireland, Italy, Portugal, South Africa, Japan and more

Departures available into 2027

Travelodeal

$1299 & up Milan & Lake Garda trip w/flights and cruise

Italy

November; other dates are also on sale

Globus

$5449 & up Explore Italy: 6-city tour from Rome

Florence, Venice, Assisi, Sorrento