14-Day Scenic Journey from Boston to Ireland and Italy: Dublin, Rome, Naples, and Sicily

Day 1: Arrival and Exploration

Dublin, Ireland on June 1, 2025

10:00am

Breakfast at Queen of Tarts

Enjoy a traditional Irish breakfast with freshly baked pastries at this popular café located in central Dublin. Great start for your first day.
EUR15, 1h

11:30am

Trinity College & Book of Kells

Visit Ireland's oldest university and marvel at the beautifully illuminated manuscript Book of Kells. The historical and cultural significance makes it a must-see.
EUR14, 1h30m

1:30pm

Lunch at The Woollen Mills

Enjoy modern Irish cuisine with great views of the Ha'penny Bridge, offering seasonal local ingredients in a relaxed setting.
EUR25, 1h

3:00pm

Guinness Storehouse

Tour Dublin’s iconic Guinness brewery, enjoy interactive exhibits, and finish with a pint in the Gravity Bar overlooking the city.
EUR26, 2h

6:00pm

Dinner at Chapter One

Indulge in an upscale Irish dining experience here known for its Michelin-starred dishes and cozy atmosphere.
EUR70, 2h
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Day 2: Historic Dublin

Dublin, Ireland on June 2, 2025

8:30am

Breakfast at Bewley’s Grafton Street Cafe

Classic café experience with a range of pastries and coffee on the bustling Grafton Street.
EUR12, 1h

10:00am

Dublin Castle and Chester Beatty Library

Explore the impressive Dublin Castle complex and view unique manuscripts and art exhibitions at the adjacent Chester Beatty Library.
EUR12, 2h

12:30pm

Lunch at Fallon & Byrne

A food hall and restaurant offering fresh Irish and international dishes in a lively atmosphere.
EUR30, 1h

2:00pm

St. Patrick's Cathedral

Visit Ireland's largest cathedral with stunning Gothic architecture and rich history tied to St. Patrick himself.
EUR8, 1h

3:30pm

Phoenix Park and Dublin Zoo

Walk or rent a bike to explore one of Europe's largest urban parks and visit Dublin Zoo, ideal for outdoor lovers.
EUR22, 3h

7:00pm

Dinner at The Church

Dine in a beautifully converted church offering Irish dishes and vibrant nightlife afterward.
EUR40, 2h
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Day 3: Day Trip & Departure

Dublin, Ireland on June 3, 2025

7:30am

Breakfast at Brother Hubbard

Enjoy a cozy café known for rich coffee and hearty breakfasts.
EUR15, 1h

9:00am

Day Trip to Howth

Take a 30-minute DART train ride to the coastal village of Howth for scenic cliff walks, fresh seafood, and picturesque harbor views.
EUR8 round-trip, 5h

3:00pm

Return to Dublin and light snack

Stop by a local café such as Two Pups Coffee for a snack before heading to the airport.
EUR8, 30m

5:00pm

Flight from Dublin to Rome

Evening flight to Rome, arriving later in the evening for check-in and rest.
Varies, 2h45m
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Day 4: Ancient Rome

Rome, Italy on June 4, 2025

8:00am

Breakfast at Roscioli Caffè Pasticceria

Start the day with freshly baked Italian pastries and espresso in the heart of Rome.
EUR10, 1h

9:30am

Colosseum and Roman Forum

Explore Rome's iconic ancient amphitheater and surrounding ruins, gaining insights into gladiator battles and Roman life.
EUR18, 3h

1:00pm

Lunch at La Carbonara

Taste traditional Roman pasta dishes such as carbonara and amatriciana in this historic trattoria.
EUR25, 1h

2:30pm

Pantheon and Piazza Navona

Visit the remarkably preserved ancient Pantheon and enjoy the lively atmosphere at nearby Piazza Navona with its fountains and street artists.
Free, 2h

5:00pm

Trevi Fountain

Throw a coin and admire one of Rome's most famous fountains during sunset hours.
Free, 30m

7:00pm

Dinner at Trattoria da Enzo al 29

Cozy local eatery known for authentic Roman cuisine and excellent service.
EUR35, 2h
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Day 5: Vatican & Departure

Rome, Italy on June 5, 2025

7:30am

Breakfast at Caffè Greco

Experience Rome’s oldest coffee bar famous for its historic atmosphere and quality coffee.
EUR15, 1h

8:30am

Vatican Museums and Sistine Chapel

Skip-the-line tour of the Vatican Museums featuring masterpieces of Renaissance art and Michelangelo's Sistine Chapel ceiling.
EUR30, 3h

12:00pm

Lunch at Pizzarium Bonci

Famous for gourmet pizza al taglio, offering creative toppings in a casual setting near the Vatican.
EUR15, 1h

1:30pm

Travel to Naples by train

Afternoon train from Rome to Naples (approximately 1h10m). Check into your hotel and prepare to explore Naples over the next week.
EUR40, 1h10m

4:00pm

Evening stroll in Spaccanapoli

Walk through Naples' historic narrow street full of shops, churches, and street food vendors to soak up local atmosphere.
Free, 2h

7:00pm

Dinner at Pizzeria Sorbillo

Famous pizzeria known for some of the best traditional Neapolitan pizzas in the city.
EUR20, 1h30m
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Day 6: Naples Highlights

Naples, Italy on June 6, 2025

8:00am

Breakfast at Gran Caffè Gambrinus

Historic café serving espresso and pastries in downtown Naples.
EUR12, 1h

9:00am

Naples National Archaeological Museum

Home to an extensive collection of Roman and Greek antiquities including artifacts from Pompeii and Herculaneum.
EUR15, 2h

11:30am

Visit Castel dell'Ovo and waterfront

Explore the oldest standing fortification in Naples and enjoy panoramic views of the Bay of Naples.
Free, 1h

1:00pm

Lunch at Osteria Il Gobbetto

Traditional Naples cuisine in a friendly setting; excellent for fresh pasta and seafood.
EUR25, 1h

2:30pm

Explore underground Naples (Napoli Sotterranea)

Guided tour to discover ancient tunnels and cisterns beneath the city.
EUR15, 1h30m

5:00pm

Relax at Piazza del Plebiscito

Large open square perfect for people watching and visiting nearby landmarks like the Royal Palace.
Free, 1h

7:30pm

Dinner at Trattoria da Nennella

Lively trattoria beloved by locals for authentic Italian home cooking and fun atmosphere.
EUR20, 2h
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Day 7: Pompeii Day Trip

Naples, Italy on June 7, 2025

7:30am

Breakfast at hotel

Start early with a quick breakfast at your hotel to fuel up for the day.
Included, 30m

8:30am

Train to Pompeii

Catch the Circumvesuviana train to Pompeii for the day’s excursion (approx. 30 mins).
EUR4, 30m

9:15am

Pompeii Archaeological Site

Explore the vast ancient city preserved by volcanic ash, walking through ruins of homes, theaters, and baths.
EUR18, 4h

1:30pm

Lunch at Caupona Pompeii Restaurant

Roman-themed restaurant near the site serving traditional dishes to complement your historical day.
EUR25, 1h

3:00pm

Return to Naples

Travel back to your base in Naples for rest and evening plans.
Included in train fare, 30m

5:00pm

Coffee and dessert at Gay-Odin chocolate shop

Sample artisanal chocolates and relax before dinner.
EUR10, 1h

7:00pm

Dinner at La Cantina dei Lazzari

Hidden gem beloved by locals serving excellent seafood and regional specialities in cozy atmosphere.
EUR35, 2h
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Day 8: Capri Excursion

Naples, Italy on June 8, 2025

7:00am

Early Breakfast at hotel

Quick breakfast before heading out early to catch the ferry.
Included, 30m

8:00am

Ferry to Capri

Enjoy scenic 45-minute ferry ride across the bay to the beautiful island of Capri.
EUR20 round trip, 45m

9:00am

Blue Grotto Tour

Visit the famous sea cave illuminated by natural blue light; open from 9am to 5pm weather permitting.
EUR15, 1h

11:00am

Explore Capri Town and Gardens of Augustus

Wander charming streets and enjoy spectacular views of the Faraglioni rock formations from the gardens.
EUR1.50, 2h

1:00pm

Lunch at Ristorante Il Geranio

Elevated dining with panoramic views and delicious Mediterranean fare.
EUR40, 1.5h

3:00pm

Anacapri and Chairlift to Monte Solaro

Visit the quieter town of Anacapri and take the chairlift to the island’s highest point for breathtaking vistas.
EUR13, 2h

5:30pm

Return ferry to Naples

Scenic ferry trip back to the mainland for dinner and rest.
Included, 45m

7:30pm

Dinner at Tandem Ristorante Pizza & Cucina

Excellent handmade pastas and pizza in a friendly local spot.
EUR30, 2h
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Day 9: Relax and Local Life

Naples, Italy on June 9, 2025

8:00am

Breakfast at Bar Mexico

Popular cafè with fantastic espresso and pastries.
EUR8, 1h

9:30am

Visit Catacombs of San Gennaro

Underground early Christian burial sites offering insight into Naples’ early Christian history and art.
EUR8, 1.5h

11:30am

Stroll through Vomero District and Castel Sant’Elmo

Take funicular up to Vomero for superb views, then visit the medieval castle and surrounding gardens.
EUR5, 2h

1:30pm

Lunch at Pizzeria Starita

Another legendary Neapolitan pizza place known for quality and variety.
EUR20, 1h

3:00pm

Relax at Villa Comunale Park and Seafront

Enjoy a leisurely afternoon walking along the beautiful promenade and park by the sea.
Free, 2h

7:00pm

Dinner at Palazzo Petrucci

Michelin-starred restaurant offering refined dining with innovative dishes and sea views.
EUR85, 2h
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Day 10: Explore Amalfi Coast

Naples, Italy on June 10, 2025

7:00am

Breakfast at hotel

Early start with breakfast for your Amalfi Coast day adventure.
Included, 30m

8:00am

Bus or private tour to Amalfi Coast

Visit picturesque towns such as Amalfi, Positano, and Ravello along the coast; enjoy breathtaking views and unique shopping.
EUR25 for bus; varies for private tour, 8h

12:30pm

Lunch in Positano at Chez Black

Beachfront restaurant known for fresh seafood and great atmosphere.
EUR40, 1h30m

6:00pm

Return to Naples

Relax after the day’s coastal adventure.
Included in tour, 1.5h

7:30pm

Dinner nearby hotel

Choose a casual nearby trattoria or pizza place for a light dinner after a full day.
EUR20, 1h30m
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Day 11: Leisure & Markets

Naples, Italy on June 11, 2025

8:00am

Breakfast at Gran Caffè Gambrinus

Return to this iconic café for wonderful coffee and pastries.
EUR12, 1h

9:30am

Visit Mercato di Poggioreale

Explore Naples’ largest outdoor market for local goods, clothes, and souvenirs offering a very authentic experience.
Free, 2h

12:00pm

Lunch at Trattoria da Carmine

Known for amazing seafood pasta dishes in a friendly neighborhood setting.
EUR30, 1h

1:30pm

Naples Underground Cathedrals tour

Visit hidden underground religious sites and archaeological remains beneath Naples.
EUR15, 1h

3:00pm

Relax and shopping in Via Toledo

Stroll along one of Naples’ main shopping streets with cafes and boutiques.
Free, 2h

7:00pm

Dinner at Tandem Ristorante Pizza & Cucina

Enjoy another delicious meal of local Roman-style pasta and pizza favorites.
EUR30, 2h
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Day 12: Pack and Prepare

Naples, Italy on June 12, 2025

8:00am

Breakfast at hotel

Enjoy a relaxed breakfast before your transfer to the airport.
Included, 1h

10:00am

Free time for last-minute sightseeing or shopping

Optional visit to local sites or souvenirs shopping in areas like Via Chiaia.
Varies, 3h

1:00pm

Lunch at Pizzeria Di Matteo

Taste one last authentic Neapolitan pizza before your flight.
EUR15, 1h

3:00pm

Flight from Naples to Sicily

Fly to Sicily for a new chapter of your Italian adventure. Check into your accommodation and rest.
Varies, 1h15m
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Day 13: Discover Sicily - Palermo

Palermo, Sicily, Italy on June 13, 2025

8:30am

Breakfast at Antico Caffè Spinnato

Enjoy traditional Sicilian pastries and espresso in this historic café in Palermo.
EUR10, 1h

10:00am

Palermo Cathedral

Explore this impressive architectural landmark blending Arab, Norman, and Gothic styles.
EUR5, 1h

11:30am

Quattro Canti and Piazza Pretoria

Admire the ornate baroque squares and fountains in the historic heart of the city.
Free, 1h

1:00pm

Lunch at Antica Focacceria San Francesco

Famous for traditional Sicilian street foods like arancini and panelle.
EUR20, 1h

2:30pm

Palermo Markets - Ballarò or Vucciria

Experience the lively local markets with colorful stalls and bustling atmosphere.
Free, 2h

6:00pm

Relax at Foro Italico Park

Walk along the sea promenade and enjoy sunset views.
Free, 1h

7:30pm

Dinner at Osteria dei Vespri

Refined Sicilian dishes with local wine in an elegant setting.
EUR40, 2h
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Day 14: Agrigento and Valley of Temples

Agrigento, Sicily, Italy on June 14, 2025

7:00am

Early breakfast at hotel

Prepare for a full-day excursion west of Palermo.
Included, 30m

8:00am

Drive or tour to Valley of the Temples

Visit one of Sicily’s most extraordinary archaeological sites showcasing well-preserved ancient Greek temples.
EUR12, 4h

12:30pm

Lunch at nearby local trattoria

Enjoy Sicilian specialties with views of the archaeological park.
EUR25, 1h

2:00pm

Explore Agrigento town

Walk the historic streets, visiting churches and the old town atmosphere.
Free, 2h

5:00pm

Return to Palermo

Head back to your base for rest and dinner.
Varies, 2h

7:30pm

Dinner at Trattoria Ai Cascinari

Traditional home-style Sicilian food served in a cozy, welcoming spot.
EUR30, 2h
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Day 15: Taormina & Mount Etna

Taormina, Sicily, Italy on June 15, 2025

7:00am

Early breakfast at hotel

Eat light before traveling east toward Taormina.
Included, 30m

8:00am

Travel to Taormina

Drive or take train to Taormina (approx 3 hours).
EUR30, 3h

11:30am

Taormina Ancient Theatre

Discover this stunning Greco-Roman theatre with dramatic views over the sea and Mount Etna.
EUR10, 1h30m

1:00pm

Lunch at Trattoria da Nino

Popular restaurant offering classic Sicilian dishes with terrace views.
EUR30, 1h

2:30pm

Mount Etna Half-Day Tour

Join a guided tour to explore Europe’s most active volcano with hiking or jeep rides available (afternoon sessions).
EUR55, 4h

7:00pm

Return to Taormina and dinner at Bam Bar

Relax with Sicilian granita and light dinner at this famous bar after a day of adventure.
EUR20, 1h30m
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Day 16: Syracuse Visit

Syracuse, Sicily, Italy on June 16, 2025

7:30am

Breakfast at hotel

Prepare for a day trip to Syracuse.
Included, 30m

8:30am

Travel to Syracuse

Drive or train to Syracuse (about 1.5 - 2 hours).
EUR20, 2h

10:30am

Visit Neapolis Archaeological Park

Explore Greek theatre, Roman amphitheater, and Ear of Dionysius cave.
EUR10, 3h

2:00pm

Lunch at Ristorante Don Camillo

Elegant dining that features local Sicilian dishes in the heart of Ortigia island.
EUR35, 1.5h

3:30pm

Explore Ortigia Old Town

Walk through historic streets with beautiful baroque architecture, markets, and sea views.
Free, 2h

6:00pm

Return to Taormina

Travel back to your accommodation for rest and dinner.
Included, 2h

7:30pm

Dinner at Ristorante Al Duomo

Traditional Sicilian and Mediterranean cuisine set in a charming atmosphere.
EUR40, 2h
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Day 17: Relax & Coastal Walks

Sicily, Italy on June 17, 2025

8:30am

Breakfast at local café

Casual breakfast with Sicilian cannoli and espresso.
EUR10, 1h

10:00am

Relaxing day at Isola Bella Beach, Taormina

Enjoy swimming, sunbathing, and beautiful coastal scenery with easy hiking options nearby.
EUR5 for sunbed rental, 4h

2:00pm

Lunch at Beachside restaurant

Fresh seafood and Sicilian specialities served with sea views.
EUR30, 1.5h

4:00pm

Explore local artisan shops in Taormina

Browse handmade ceramics, crafts and souvenirs in charming shops.
Free, 2h

7:00pm

Dinner at Ristorante La Grotta Azzurra

Cozy restaurant known for fresh fish dishes and warm service.
EUR35, 2h
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Day 18: Catania and Local Culture

Catania, Sicily, Italy on June 18, 2025

8:00am

Breakfast at hotel

Start the day with a hearty hotel breakfast.
Included, 1h

9:00am

Travel to Catania

Short train or car ride from Taormina to Catania.
EUR10, 1h

10:00am

Piazza Duomo and Fish Market

Visit main square with elephant fountain and lively traditional fish market reflecting local culture.
Free, 1.5h

12:00pm

Lunch at Trattoria da Antonio

Enjoy typical Sicilian plates made from fresh local produce.
EUR25, 1h

1:30pm

Visit Monastery of San Nicolò l’Arena

Historic UNESCO site with stunning Baroque architecture and beautiful cloisters.
EUR8, 1h30m

3:30pm

Relax in Giardino Bellini Park

Large green park with fountains and walking paths to unwind.
Free, 1h

5:00pm

Return to Taormina

Travel back to Taormina for evening and dinner.
Included, 1h

7:00pm

Dinner at Osteria RossoDiVino

Cozy and welcoming restaurant serving innovative Sicilian dishes.
EUR40, 2h
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Day 19: Last Day in Sicily

Sicily, Italy on June 19, 2025

8:30am

Breakfast at hotel

Enjoy a slow morning breakfast as you prepare for departure.
Included, 1h

10:00am

Last local sightseeing or shopping

Spend remaining time shopping for souvenirs or enjoying leisurely walks in your base town.
Varies, 3h

1:00pm

Lunch at local favorite restaurant

Savour Sicilian flavors one final time with seasonal specialties.
EUR30, 1h30m

3:00pm

Flight from Sicily to Rome

Afternoon flight back to Rome for your final night before flying home.
Varies, 1h30m
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Day 20: Rome Farewell

Rome, Italy on June 20, 2025

8:00am

Breakfast at Sant’Eustachio Il Caffè

Enjoy Rome’s famous espresso and fresh pastries in the morning.
EUR12, 1h

9:30am

Visit Villa Borghese Gardens

Relax in Rome’s large public park with beautiful sculptures and lakes before your journey home.
Free, 2h

12:00pm

Lunch at Pizzeria La Montecarlo

Farewell meal with classic Roman pizza in a lively local spot.
EUR20, 1h

2:00pm

Relax and prepare for departure

Return to hotel or airport for your flight back to Boston.
N/A, Varies

5:00pm

Flight from Rome to Boston

Evening flight home with memories from an incredible journey.
Varies, 8h
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