Romantic 14-Day Honeymoon Itinerary: Boston to Italy and Greece

Day 1: Arrival in Rome

Boston, USA

8:00 AM

Departure

Begin your dreamy honeymoon by departing from Boston's Logan Airport, excited for the adventures ahead.
Flight to Rome
USD500, 7 hours

4:00 PM

Arrive in Rome

Arrive at Fiumicino Airport in Rome, filled with anticipation for the stunning Italian scenery and culture.
Transportation to hotel
EUR75, 1 hour

6:00 PM

Dinner at Da Enzo al 29

Savor traditional Roman dishes like pasta all’amatriciana at this charming trattoria to kickstart your culinary experience.
Short taxi ride
EUR50, 30 minutes
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Day 2: Explore Rome

Rome, Italy

8:00 AM

Breakfast at Antico Caffè Santamaria

Enjoy a typical Italian breakfast of cappuccino and cornetto to fuel your day of exploration.
Walking distance from the hotel
EUR10, 1 hour

9:00 AM

Visit the Colosseum

Step into history as you explore the majestic Colosseum and learn about its fascinating past.
Take Metro B from Termini to Colosseo
EUR25, 2 hours

12:00 PM

Lunch at Trattoria Da Francesco

Indulge in wood-fired pizza and local wines for an authentic Roman lunch experience.
Walk from the Colosseum
EUR30, 1.5 hours

2:00 PM

Stroll through Vatican City

Marvel at St. Peter's Basilica and the Vatican Museums, soaking in the rich art and history.
Walk or take a taxi
EUR20, 3 hours

6:00 PM

Dinner at Osteria Bonelli

Enjoy a romantic dinner featuring local pasta dishes and delicious wines, ending your day in style.
Taxi back to the hotel
EUR30, 30 minutes
View Hotel Availability

Day 3: Travel to Positano

Positano, Italy

8:00 AM

Breakfast at Hotel

Have a leisurely breakfast at your hotel before checking out and heading to Positano.
Breakfast in hotel
EUR0, 1 hour

9:30 AM

Train to Naples

Take a scenic train ride to Naples, admiring the shift from urban to coastal landscapes.
Walk to Termini Station
EUR20, 1 hour

11:00 AM

Ferry to Positano

Travel from Naples to Positano via ferry, with breathtaking views of the Amalfi Coast along the way.
Ferry terminal in Naples
EUR40, 1 hour

1:00 PM

Check-in at Hotel Le Sirenuse

Settle into your luxurious hotel and enjoy stunning views of the coastline and charming Positano.
Walking distance from the ferry
EUR500, 1 hour

2:30 PM

Lunch at Chez Black

Dine on seafood pasta within view of the ocean, feeling the coastal breeze and vibrant atmosphere.
Short walk from hotel
EUR60, 1.5 hours

4:00 PM

Relax on the Beach

Spend the afternoon soaking up the sun and enjoying the beautiful beach in Positano.
Walk to the beach
EUR0, 3 hours

7:00 PM

Dinner at Ristorante Max

Enjoy a candlelit dinner at this romantic eatery, famous for its fresh seafood and local ingredients.
Walking distance from the beach
EUR100, 2 hours
View Hotel Availability

Day 4: Day Trip to Capri

Capri, Italy

7:00 AM

Breakfast at Hotel

Start your day with a delightful breakfast overlooking the sea before heading out.
Breakfast in hotel
EUR0, 1 hour

8:30 AM

Ferry to Capri

Take a morning ferry to Capri, a stunning island known for its cliffs and azure waters.
Walking to the ferry dock
EUR40, 1 hour

9:30 AM

Visit the Blue Grotto

Take a small boat tour to the mesmerizing Blue Grotto, where sunlight reflects off the water.
Small boat tour
EUR35, 1.5 hours

11:00 AM

Explore Capri Town

Stroll the charming streets of Capri Town, visiting boutiques and enjoying the views.
Walking around the island
EUR0, 2 hours

1:00 PM

Lunch at Da Paolino

Dine under the lemon trees at this famous restaurant, indulging in fresh local seafood.
Walk from Capri Town
EUR70, 2 hours

3:00 PM

Chairlift to Monte Solaro

Ride the chairlift to Monte Solaro and take in breathtaking panoramic views of the island.
Walking distance to the chairlift
EUR15, 1.5 hours

5:00 PM

Ferry Back to Positano

Return to Positano for a relaxing evening after a day full of adventure.
Ferry dock
EUR40, 1 hour

7:00 PM

Dinner at Hostaria da Antonio

Reflect on your day while savoring Italian comfort food at this cozy eatery.
Walking distance from your hotel
EUR50, 2 hours
View Hotel Availability

Day 5: Explore Amalfi

Amalfi, Italy

8:00 AM

Breakfast at Hotel

Fuel up for a day of exploration with a delicious breakfast at your hotel.
Breakfast in hotel
EUR0, 1 hour

9:30 AM

Ferry to Amalfi

Savor the stunning views as you take a ferry to Amalfi to discover its historic charm.
Ferry dock
EUR25, 30 minutes

10:00 AM

Visit the Amalfi Cathedral

Marvel at the stunning architecture and rich history of the iconic Amalfi Cathedral.
Walking distance from ferry
EUR3, 1 hour

11:30 AM

Explore Amalfi's Paper Museum

Learn about the traditional paper-making techniques that Amalfi is famous for.
Short walk from the cathedral
EUR5, 1 hour

1:00 PM

Lunch at Pizzeria Da Michele

Enjoy some of the best pizza in Amalfi with local toppings and fresh ingredients.
Walk along the coast
EUR40, 1.5 hours

2:30 PM

Relax at Amalfi Beach

Spend your afternoon lounging on the beach, soaking in the sun and stunning scenery.
Walk to the beach
EUR0, 3 hours

5:30 PM

Ferry Back to Positano

Enjoy the scenic ferry ride back to Positano in the early evening.
Ferry dock
EUR25, 30 minutes

7:00 PM

Dinner at Il Capitano

Unwind after the day's adventures with a romantic dinner filled with local dishes and wines.
Short walk from hotel
EUR80, 2 hours
View Hotel Availability

Day 6: Travel to Puglia

Puglia, Italy

8:00 AM

Breakfast at Hotel

Enjoy one last breakfast overlooking Positano before departing for Puglia.
Breakfast in hotel
EUR0, 1 hour

9:30 AM

Ferry to Sorrento

Take the ferry from Positano to Sorrento as you head to your next destination.
Ferry dock
EUR30, 30 minutes

10:00 AM

Train to Bari

Catch a train from Sorrento to Bari, witnessing the lush landscapes of Italy's countryside.
Train station in Sorrento
EUR35, 2.5 hours

1:00 PM

Check-in at Hotel in Alberobello

Arrive at your charming hotel in Alberobello, known for its beautiful trulli houses.
Walking distance from train station
EUR100, 1 hour

2:30 PM

Lunch at Trattoria Terra Madre

Try local Pugliese cuisine at this delightful restaurant celebrated for its homemade pasta.
Short walk from hotel
EUR40, 1.5 hours

4:00 PM

Explore Alberobello's Trulli

Wander the picturesque streets, admiring the unique trulli architecture and taking stunning photos.
Walking distance from restaurant
EUR0, 2 hours

6:30 PM

Dinner at Il Ristorante della Pizzeria Mastro Ciccio

Relish a delightful dinner featuring local specialties in a cozy setting.
Short taxi ride
EUR50, 1.5 hours
View Hotel Availability

Day 7: Discover Puglia

Puglia, Italy

8:00 AM

Breakfast at Hotel

Enjoy a hearty breakfast at your hotel, preparing for a full day of exploration.
Breakfast in hotel
EUR0, 1 hour

9:30 AM

Visit the Castellana Caves

Take a guided tour of the stunning Castellana Caves and admire its remarkable formations.
Drive to the caverns
EUR20, 2 hours

12:00 PM

Lunch at La Locanda di Federico

Enjoy a traditional meal with local flavors, before continuing your adventure.
Off the main road
EUR40, 1.5 hours

1:30 PM

Visit Matera

Discover the UNESCO World Heritage site with its stunning ancient cave dwellings and historic charm.
Drive to Matera
EUR5, 1 hour

4:30 PM

Explore the Sassi di Matera

Stroll the picturesque streets of Sassi, soaking up the history and local culture.
Walking tour
EUR0, 2 hours

6:30 PM

Dinner at Ristorante Il Terrazzino

Enjoy a romantic dinner with a view in Matera, serving authentic regional dishes.
Near the caves
EUR70, 2 hours
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Day 8: Return to Rome

Rome, Italy

8:00 AM

Breakfast at Hotel

Savor your final breakfast in Puglia before heading back to Rome.
Breakfast in hotel
EUR0, 1 hour

10:00 AM

Train to Rome

Take a scenic train back to Rome, reflecting on your Puglian adventures.
Train station in Alberobello
EUR30, 3.5 hours

2:00 PM

Check-in at Hotel

Arrive in Rome and settle into your hotel, recharging for the next leg of your journey.
Walking distance from Termini
EUR150, 1 hour

3:30 PM

Lunch at Il Margutta RistorArte

Dive into delicious vegetarian cuisine that emphasizes fresh Italian ingredients.
Walk from the hotel
EUR40, 1.5 hours

5:00 PM

Visit the Spanish Steps

Enjoy some leisure time at the famous Spanish Steps, perfect for people-watching.
Walking to the steps
EUR0, 1 hour

6:30 PM

Dinner at La Pergola

Treat yourselves to an unforgettable dining experience at Rome's only three-star Michelin restaurant.
Grab a taxi
EUR300, 2 hours
View Hotel Availability

Day 9: Fly to Mykonos

Mykonos, Greece

8:00 AM

Breakfast at Hotel

Enjoy breakfast at the hotel before checking out and heading to the airport.
Breakfast in hotel
EUR0, 1 hour

9:30 AM

Flight to Mykonos

Board your flight from Rome to Mykonos, ready for sun-soaked fun on the island.
Transportation to the airport
EUR40, 1 hour

11:30 AM

Check-in at Hotel

Arrive and settle into your hotel in Mykonos, feeling the island's vibrant energy.
Walking distance from the airport
EUR100, 1 hour

1:00 PM

Lunch at Kiki's Tavern

Savor local Mediterranean cuisine at this enchanting beach tavern.
Short drive to Kiki's
EUR40, 2 hours

3:00 PM

Beach Day at Agios Sostis

Spend a relaxing afternoon at Agios Sostis beach, away from the crowds.
Short drive from lunch
EUR0, 3 hours

6:00 PM

Dinner at Niko's Taverna

Indulge in authentic Greek dishes while enjoying the vibrant atmosphere of Mykonos.
Taxi to town
EUR60, 2 hours
View Hotel Availability

Day 10: Explore Mykonos

Mykonos, Greece

8:00 AM

Breakfast at Hotel

Fuel up for the day at your hotel, prepping for more island adventures.
Breakfast in hotel
EUR0, 1 hour

9:00 AM

Visit Mykonos Town

Wander the charming streets of Mykonos Town, exploring local shops and culture.
Walking from the hotel
EUR0, 3 hours

12:00 PM

Lunch at Jimmy's

Dig into delicious gyros and savor the lively atmosphere at this iconic spot.
Walking distance
EUR30, 1.5 hours

2:00 PM

Visit Delos

Take a small boat to the sacred island of Delos, rich in mythology and archaeological wonder.
Take boat from Mykonos
EUR25, 3 hours

5:00 PM

Return to Mykonos

Return to Mykonos after a day filled with history and exploration.
Boat to Mykonos
EUR25, 1 hour

6:30 PM

Dinner at Kadena

Enjoy fresh seafood and Mediterranean flavors while watching the sunset.
Short drive from the dock
EUR70, 2 hours
View Hotel Availability

Day 11: Travel to Santorini

Santorini, Greece

8:00 AM

Breakfast at Hotel

Start your day with breakfast, gearing up for travel to Santorini.
Breakfast in hotel
EUR0, 1 hour

10:00 AM

Ferry to Santorini

Take a scenic ferry to Santorini, watching the stunning Aegean landscapes unfold.
From Mykonos harbor
EUR50, 2 hours

12:00 PM

Check-in at Hotel

Arrive in Santorini and check into your beautiful hotel overlooking the caldera.
Near the ferry port
EUR150, 1 hour

1:30 PM

Lunch at Lucky’s Souvlakis

Satisfy your hunger with mouthwatering souvlakis from this beloved local eatery.
Short walk from your hotel
EUR20, 1 hour

3:00 PM

Visit Oia

Explore the picturesque village of Oia, famous for its stunning sunset views.
Drive or take a local bus
EUR10, 3 hours

6:00 PM

Dinner in Oia

Have dinner at a cliff-side restaurant, enjoying gourmet Greek cuisine with an unbeatable view.
Walking distance in Oia
EUR80, 2 hours
View Hotel Availability

Day 12: Explore Santorini

Santorini, Greece

8:00 AM

Breakfast at Hotel

Begin your day with breakfast at your hotel, overlooking the magnificent caldera.
Breakfast in hotel
EUR0, 1 hour

9:30 AM

Visit Akrotiri

Explore the ancient ruins of Akrotiri, a Minoan settlement preserved in volcanic ash.
Car rental or taxi
EUR10, 2.5 hours

12:00 PM

Lunch at To Perasma

Feast on traditional Greek dishes in a cozy restaurant with local flair.
Driving or taxi
EUR40, 1.5 hours

1:30 PM

Relax at Red Beach

Enjoy the unique landscape of Red Beach and take a refreshing dip in the Aegean Sea.
Short drive from the restaurant
EUR0, 2.5 hours

4:00 PM

Wine Tasting at Santo Wines

Partake in a wine-tasting experience at this renowned vineyard, savoring local varieties.
Taxi or drive
EUR50, 2 hours

6:30 PM

Dinner at 1800 in Oia

Enjoy your last evening in Santorini with a romantic dinner and panoramic views.
Taxi to Oia
EUR80, 2 hours
View Hotel Availability

Day 13: Relax and Unwind

Santorini, Greece

8:00 AM

Breakfast at Hotel

Have a leisurely breakfast, taking in the final views of your beautiful surroundings.
Breakfast in hotel
EUR0, 1 hour

10:00 AM

Spa Day at Hotel

Indulge in a couple's spa treatment to rejuvenate before your journey back home.
At the hotel
EUR120, 2 hours

1:00 PM

Lunch at Ammoudi Fish Tavern

Savor fresh seafood by the water at this lovely beachside tavern.
Short drive to Ammoudi
EUR50, 2 hours

3:00 PM

Relax by the Pool

Spend the afternoon lounging by the hotel pool, soaking in the last rays of sun.
Poolside at the hotel
EUR0, 4 hours

7:00 PM

Final Dinner at Aressana

Celebrate your last night with a romantic dinner, enjoying Greek flair and celebrating love.
Reservations recommended
EUR80, 2 hours
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Day 14: Departure

Santorini, Greece

8:00 AM

Breakfast at Hotel

Enjoy your last breakfast in Santorini while taking in the views for one last time.
Breakfast in hotel
EUR0, 1 hour

10:00 AM

Check-out from Hotel

Check out and say goodbye to Santorini, ready to return home.
Check-out process
EUR0, 1 hour

11:30 AM

Flight Back to Boston

Board your flight, reflecting on the many unforgettable memories from your honeymoon.
Transportation to the airport
EUR40, 30 minutes
View Hotel Availability