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

Viewed by 91 travelers

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
Find Hotels in Boston

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
Find Hotels in Rome

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
Find Hotels in Positano

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
Find Hotels in Capri

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
Find Hotels in Amalfi

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
Find Hotels in Puglia

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
Find Hotels in Puglia

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
Find Hotels in Rome

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
Find Hotels in Mykonos

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
Find Hotels in Mykonos

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
Find Hotels in Santorini

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
Find Hotels in Santorini

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
Find Hotels in Santorini

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
Find Hotels in Santorini
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