14-Day Italy and Greece Journey: Rome, Florence, Tuscany, Athens & Santorini Highlights

Day 1: Arrival & Rome Highlights

Rome, Italy on June 20, 2025

9:00am

Colosseum Visit

Kick off your trip with a visit to the iconic Colosseum, the ancient Roman amphitheater known for gladiatorial battles. Booking tickets online ahead is recommended to skip long lines.
EUR16, 2h0m

12:00pm

Lunch at Ristorante Aroma

Savor authentic Roman dishes with a spectacular view of the Colosseum, blending excellent cuisine and ambiance.
EUR40, 1h30m

2:00pm

Roman Forum & Palatine Hill

Explore Rome's ancient city center ruins illustrating the heart of Roman civilization, including temples, marketplaces, and imperial palaces.
EUR16 (combined ticket included), 2h0m

5:00pm

Check-in at Hotel De Russie

Relax in this iconic luxury hotel situated close to Piazza del Popolo blending historic charm with elegance.
EUR450/night, N/A

7:30pm

Dinner at Trattoria Da Enzo al 29

Experience traditional Roman cuisine in the lively Trastevere neighborhood, renowned for its cozy vibe and classic dishes.
EUR30, 1h30m
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Day 2: Vatican & Rome Sights

Rome, Italy on June 21, 2025

8:00am

Breakfast at Bar Fondi

Enjoy freshly brewed coffee and buttery cornetti to start your day near the Vatican.
EUR7, 0h30m

9:00am

Vatican Museums & Sistine Chapel

Marvel at world-famous art collections including Michelangelo's magnificent ceiling in the Sistine Chapel. Pre-book tickets to avoid waiting.
EUR25, 3h0m

1:00pm

Lunch at Pizzarium

Indulge in delicious Roman-style pizza al taglio crafted with fresh, local toppings by renowned pizzaiolo Gabriele Bonci.
EUR15, 1h0m

2:30pm

St. Peter's Basilica & Dome Climb

Explore the grandeur of St. Peter’s Basilica and climb the dome for breathtaking views of Rome’s skyline.
EUR10 (dome climb), 2h0m

6:00pm

Evening Walk - Piazza Navona & Pantheon

Enjoy a sunset stroll around beautiful piazzas adorned with fountains, street artists, and historic architecture.
Free, 1h30m

8:00pm

Dinner at Osteria della Suburra

Delight in authentic Roman specialties in a friendly atmosphere near the ancient city center.
EUR35, 1h30m
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Day 3: Rome Leisure & Secrets

Rome, Italy on June 22, 2025

8:00am

Breakfast at Pastificio Guerra

Grab a quick and affordable pastry or fresh pasta takeaway near Spanish Steps.
EUR5, 0h30m

9:00am

Visit Borghese Gallery and Gardens

Explore exquisite Renaissance art and sculptures, then relax in the lush surrounding gardens. Advance booking required for the gallery.
EUR20, 3h0m

1:00pm

Lunch at Osteria del Pegno

Enjoy classic Roman dishes in a charming setting within walking distance of Piazza Navona.
EUR30, 1h0m

2:30pm

Explore Trastevere Neighborhood

Wander the cobbled streets of this lively bohemian area known for artisan shops, historic churches, and vibrant atmosphere.
Free, 2h30m

5:30pm

Relax at Gianicolo Hill

Ascend this hilltop park for panoramic views of Rome and to watch the traditional cannon firing at noon (or just relax in the park).
Free, 1h0m

8:00pm

Dinner at Glass Hostaria

Dine at this Michelin-starred restaurant in Trastevere with inventive Italian dishes and extensive wine list.
EUR70, 1h45m
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Day 4: Travel to Florence

Florence, Italy on June 23, 2025

7:00am

Train Rome to Florence

Catch an early high-speed train (~1.5 hours) to Florence, the cradle of Renaissance art and culture.
EUR50, 1h30m

9:00am

Breakfast at Ditta Artigianale

Enjoy artisan coffee and pastries at this popular café near Santa Maria Novella station.
EUR12, 0h45m

10:00am

Duomo Complex and Baptistery

Visit Florence’s stunning cathedral with its terracotta dome and ornate baptistery, including a climb up the dome for views.
EUR20 (complex ticket), 2h0m

1:00pm

Lunch at Trattoria Mario

Sample hearty Tuscan favorites such as ribollita and bistecca alla Fiorentina in a lively, authentic setting.
EUR25, 1h0m

2:30pm

Uffizi Gallery

Explore masterpieces by Botticelli, Leonardo da Vinci, and Michelangelo in this world-class art museum. Advance tickets strongly recommended.
EUR20, 2h0m

5:00pm

Check-in Hotel Brunelleschi

Settle into this boutique hotel housed in a historic medieval tower in Florence’s center.
EUR300/night, N/A

7:30pm

Dinner at La Giostra

Enjoy delicious Tuscan fare with romantic ambiance and family recipes passed down through generations.
EUR45, 1h30m
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Day 5: Tuscany Countryside & Chianti

Tuscany, Italy on June 24, 2025

8:00am

Breakfast at hotel

Start your day with a fresh and hearty breakfast at your hotel before a day in the countryside.
Included, 0h30m

9:00am

Full-day Chianti Wine Tour

Join a guided tour visiting elegant wineries, tasting award-winning wines and olive oils, and exploring medieval villages like Greve and Castellina.
EUR120, 7h0m

5:30pm

Return to Florence & relax

Head back to Florence after a fulfilling day of wine and countryside scenery.
Included, N/A

8:00pm

Dinner at Enoteca Pinchiorri

Treat yourself to Michelin 3-star dining with inventive Tuscan and international cuisine and an extensive wine cellar.
EUR150, 2h0m
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Day 6: Leisure Day in Florence

Florence, Italy on June 25, 2025

8:30am

Breakfast at Caffè Gilli

Enjoy a traditional Italian breakfast in one of Florence’s most historic cafés in Piazza della Repubblica.
EUR12, 0h45m

9:30am

Boboli Gardens & Pitti Palace

Visit the grand Medici Palace and stroll through its expansive Renaissance gardens filled with sculptures and fountains.
EUR16, 3h0m

1:00pm

Lunch at Mercato Centrale

Sample a range of Tuscan and Italian delicacies in this vibrant indoor market perfect for casual dining.
EUR20, 1h0m

2:30pm

Leather Shopping & Artisan Workshops

Explore Florence’s famed artisan leather shops and crafts in the Oltrarno district.
Free to browse, 2h30m

6:00pm

Sunset at Piazzale Michelangelo

Enjoy breathtaking panoramic views over Florence from this iconic viewpoint.
Free, 1h0m

8:00pm

Dinner at Trattoria 4 Leoni

Dine in a rustic and friendly environment serving classics like wild boar pasta near Santa Croce.
EUR35, 1h30m
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Day 7: Fly to Athens

Athens, Greece on June 26, 2025

7:00am

Flight Florence to Athens

Depart early on a direct flight (~2.5 hours) to Athens for the Greek segment of your adventure.
EUR90, 2h30m

10:30am

Check-in Electra Metropolis Hotel

Stay centrally located with excellent amenities and easy access to Athens’ historic sites.
EUR250/night, N/A

12:00pm

Lunch at Ta Karamanlidika Tou Fani

Enjoy traditional Greek tastes through delectable cured meats, cheese, and meze in a welcoming tavern.
EUR20, 1h0m

1:30pm

Acropolis Museum

Discover the extensive collection of artifacts from Acropolis, housed in a breathtaking modern building overlooking ancient ruins.
EUR10, 2h0m

4:00pm

Acropolis Hill Visit

Ascend the Parthenon hill to witness historic temples and stunning panoramic views of Athens, best in late afternoon when light is soft.
EUR20, 1h30m

7:00pm

Dinner at Strofi

Dine on Greek classics coupled with spectacular nighttime views of the illuminated Acropolis from Strofi’s rooftop terrace.
EUR35, 1h30m
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Day 8: Athens Cultural Gems

Athens, Greece on June 27, 2025

8:00am

Breakfast at Mokka Specialty Coffee

Start your day with premium Greek coffee and fresh pastries in central Athens.
EUR8, 0h30m

9:00am

Ancient Agora & Temple of Hephaestus

Explore the ancient marketplace and well-preserved classical temple reflecting daily life in Athens' golden age.
EUR8, 2h0m

12:00pm

Lunch at Taverna Klimataria

Experience lively Greek tavern dining with traditional dishes and local music in a charming setting.
EUR20, 1h0m

1:30pm

National Archaeological Museum

Visit Greece’s largest museum showcasing ancient art and artifacts from Mycenaean to Roman periods.
EUR10, 2h0m

4:00pm

Stroll through Plaka District

Enjoy wandering narrow streets dotted with shops, cafes, and neoclassical houses.
Free, 1h30m

7:00pm

Dinner at To Kafeneio

Taste homemade Greek food in a cozy tavern in Plaka with authentic atmosphere.
EUR25, 1h30m
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Day 9: Athens Adventure Day

Athens, Greece on June 28, 2025

8:00am

Breakfast at Hotel

Enjoy a relaxed breakfast at your hotel in preparation for your day.
Included, 1h0m

9:30am

Day trip to Cape Sounion and Temple of Poseidon

Take a scenic half-day tour to Cape Sounion to see ancient Greek ruins perched dramatically by the sea, ideal for captivating views and photos.
EUR50, 5h0m

3:00pm

Return & Coffee Break at Little Kook

Enjoy themed décor and delicious coffee with dessert back in central Athens in this whimsical café.
EUR15, 1h0m

4:30pm

Free time or shopping

Stroll Ermou Street for shopping or relax at a nearby café before dinner.
Free, 2h0m

7:00pm

Dinner at Varoulko Seaside

Celebrate with an exquisite Michelin-starred seafood dinner overlooking Piraeus marina.
EUR80, 2h0m
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Day 10: Fly to Santorini

Santorini, Greece on June 29, 2025

7:00am

Flight Athens to Santorini

Take an early morning flight (~45 minutes) to mystical Santorini island, famous for its stunning caldera views.
EUR70, 0h45m

8:30am

Check-in at Canaves Oia Hotel

Stay in a luxurious cliffside resort offering breathtaking views of the caldera and Aegean Sea.
EUR400/night, N/A

9:30am

Breakfast at Passaggio

Start your Santorini experience with a fresh and beautifully served breakfast near Oia’s center.
EUR20, 1h0m

11:00am

Explore Oia Village

Wander the iconic whitewashed streets, boutique shops, and charming churches famous worldwide for their beauty.
Free, 2h0m

1:00pm

Lunch at Ammoudi Fish Tavern

Dine on freshly caught seafood right on the water’s edge in picturesque Ammoudi Bay below Oia.
EUR35, 1h30m

3:00pm

Relax at Red Beach

Visit volcanic red sand beach perfect for sunbathing and swimming in crystal-clear waters.
Free, 2h0m

6:00pm

Sunset Dinner at Sunset Ammoudi

Reserve dinner here for a spectacular view of the sun setting over the Aegean with fine dining nearby.
EUR50, 2h0m
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Day 11: Santorini Volcano Tour

Santorini, Greece on June 30, 2025

8:00am

Breakfast at hotel

Enjoy a leisurely breakfast at your hotel with stunning views of the caldera.
Included, 1h0m

9:30am

Santorini Volcano & Hot Springs Boat Tour

Embark on a half-day boat tour to explore the volcanic islands, hiking the active volcano and relaxing in the warm hot springs.
EUR60, 4h30m

2:30pm

Lunch at Metaxi Mas

This hidden taverna offers authentic Cretan and Santorinian dishes in a warm, off-the-beaten-path setting.
EUR30, 1h0m

4:00pm

Visit Ancient Thera

Discover this dramatic archaeological site atop Mesa Vouno mountain with incredible views down to Kamari Beach.
EUR6, 1h30m

7:00pm

Dinner at Argo Restaurant

Feast on modern Greek and Mediterranean dishes with fresh local produce and stunning caldera backdrop in Fira.
EUR40, 1h30m
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Day 12: Santorini Wine & Villages

Santorini, Greece on July 1, 2025

8:00am

Breakfast at hotel

Enjoy a relaxing breakfast with views of the sea and caldera.
Included, 1h0m

9:30am

Santorini Wine Tasting Tour

Spend your morning visiting top wineries like Santo Wines for tasting worlds-renowned volcanic wines and touring vineyards.
EUR50, 4h0m

2:00pm

Lunch at Roka

Dine on creative Mediterranean cuisine in a charming atmosphere in Imerovigli.
EUR40, 1h30m

4:00pm

Explore Imerovigli Village

Wander through this quaint village known as the 'Balcony to the Aegean' with spectacular views and quiet charm.
Free, 1h30m

7:30pm

Dinner at Franco's Bar

Enjoy a casual yet elegant dinner with panoramic caldera views and a chilled ambiance.
EUR45, 2h0m
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Day 13: Relax & Explore Santorini

Santorini, Greece on July 2, 2025

9:00am

Breakfast at Pelican Kipos

Enjoy a lush garden setting for a relaxed breakfast in Fira town.
EUR20, 1h0m

10:30am

Hike from Fira to Oia

Embark on the famous 6-mile cliffside hike offering stunning views and photo opportunities between Santorini’s two main towns.
Free, 3h0m

2:00pm

Lunch at Pelekanos

Enjoy traditional Greek dishes with a stunning caldera view perfect for fueling after your hike.
EUR30, 1h30m

4:00pm

Relax at your hotel or local café

Take time to unwind or explore local artisanal shops and galleries at a leisurely pace.
Free, 2h0m

7:30pm

Farewell Dinner at LAUDA Restaurant

Conclude your trip with imaginative cuisine and fine wine in a modern Santorini restaurant known for quality and ambiance.
EUR60, 2h0m
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Day 14: Return to Athens

Athens, Greece on July 3, 2025

9:00am

Flight Santorini to Athens

Take a morning flight back to Athens in time for a final afternoon enjoying the city or catching connections home.
EUR70, 0h45m

10:00am

Check-in Electra Metropolis Hotel or luggage storage

Store luggage or rest briefly at your hotel before heading out for any last sightseeing or shopping.
EUR250/night or luggage storage EUR10, N/A

12:00pm

Lunch at Kuzina

Enjoy contemporary Greek cuisine on a terrace with views of the Ancient Agora, a favorite spot for locals and visitors alike.
EUR25, 1h0m

2:00pm

Last-minute shopping or visit Benaki Museum

Explore some final Athenian culture or pick up souvenirs from nearby shopping streets before heading to the airport.
Museum EUR12 / Shopping Free, 2h0m

5:00pm

Airport transfer and depart

Arrange transport to Athens International Airport for your flight home, reflecting on a remarkable journey.
Taxi EUR40, N/A
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