THIS COULD BE YOUR ITALIAN VACTION
Welcome to your personalized trip itinerary!
Thank you so much for choosing Dream Trip Co to help plan your dream vacation. I truly appreciate the opportunity to be part of your travel experience, and I’m excited for everything you have ahead.
To make this page easier to use, you'll find quick-jump buttons below that allow you to instantly navigate to specific travel dates, excursions, train tickets, and other important sections of your itinerary.
Hotel names that are underlined contain a copy of the hotel reservation confirmation for easy reference. Train tickets and activity vouchers can be accessed by scrolling to their corresponding sections or by using the quick-jump buttons below. Simply click the appropriate button to download a copy of your tickets or confirmations.
If you have any questions at any time, I’m always here to help!
✈️ DAY 1 – WEDNESDAY, SEPTEMBER 15, 2027
Travel Day – Departure from USA
Flight: Delta Airlines
🔴 Booking Confirmation: TBD
🔴 Ticket Number: TBD
Departure:
Newark (EWR) → Munich (MUC)
🕒 8:30 PM Departure
Connection:
Munich (MUC) → Florence (FLR)
🕒 11:25 AM Departure
✈️ Overnight flight to Italy
DAY 2 – THURSDAY, SEPTEMBER 16, 2027
Arrival in Florence + Transfer to Sienna + Hotel Check-In
Arrival:
Amerigo Vespucci Airport Florence, Italy (FLR)
🕒 12:40 PM Arrival
🚗 Airport Transfer to Florence Train Station
🔴 Booking #: TBD
Pickup Details:
Driver will track your flight
Pickup begins approx. 60 minutes after landing (~1:40 PM)
Includes 45 minutes waiting time
📍 Meeting Point:
Arrival Hall – look for driver holding sign: “Cynthia Helfrich”
🚉 Train from Florence to Siena (Approx 1.5 Hours)
Train Number: TBD Seats: This regional train does not have assigned seating. You may sit in any available seat.
Departure Time: 2:45 PM
Arrival Time: ~4:15 PM
Transfer from Siena train station to hotel
🚶♀️Walking time: ~25 min
🚗 Uber / Taxi: 9 min Approx €10–€15 ← Recommend Uber / Taxi
🏨 Hotel Check-In – Siena
NH Siena 4 ★ Hotel
📍 Via La Lizza, 1, 53100 Siena SI, Italy
🔴 Confirmation #: TBD
Check-In Time:
From 3:00 PM
💡 Tip: You are arriving early, store luggage and explore nearby cafés.
First Dinner Recommendation:
🍷 Oro Di Siena
⭐ 4.7/5 Via Giuseppe Garibaldi, 61, 53100 Siena SI, Italy
Directions • 0577 282729
About a 5–10 minute walk from NH Siena.
Romantic atmosphere that's great for a couple.
Elevated Tuscan cuisine without being overly formal.
Excellent first-night "welcome to Tuscany" dinner.
🍷 DAY 3 – FRIDAY, SEPTEMBER 17, 2027
Brunello di Montalcino Wine Tour Day
🚶♀️ Getting to Your First Tour
🕒 Depart Hotel: NO LATER THAN 9:15 AM
Walk from NH Siena Hotel → Piazza San Domenico Piazza S. Domenico, 53100 Siena SI, Italy
⏱️ Estimated walking time: ~5 minutes
🍷 Small-Group Brunello di Montalcino Wine-Tasting Tour from Siena (Max Group 8)
🕒 Start Time: 9:30 AM
⏰ Arrive by: 9:25 AM
🔴 Booking Ref: TBD
📍 Meeting Point: In Piazza San Domenico, directly in front of the Basilica of San Domenico.
Your guide will be holding an orange umbrella
💡 This tour includes lunch and multiple tastings — come hungry and thirsty :)
🚶♀️ Return to Hotel
NH Siena (~5 minute walk from tour ending point)
➡️ Directions
🍕 DAY 4 – SATURDAY, SEPTEMBER 18, 2027
Ultimate Food Tour Day
🚶♀️ Getting to Your First Tour
🕒 Depart Hotel: NO LATER THAN 11:10 AM
Walk from NH Siena → Piazza Salimbeni, 4-3, 53100 Siena SI, Italy
⏱️ Estimated walk time: ~6 minutes
💡 Plan to leave by 11:10 AM to comfortably arrive and locate your guide without rushing.
🥐 Siena’s Ultimate Food Tour (Approx. 3 Hours)
🕒 Start Time: 11:30 AM
⏰ Arrive by: 11:16 AM
🔴 Booking Ref: TBD
📍 Meeting Point:
Piazza Salimbeni, 4-3, 53100 Siena SI, Italy
💡 This tour starts promptly — late arrivals cannot join, so timing here is important.
After your street food tour, check out some of what Siena is famous for.
Nice Afternoon Walk Loop
🚶 NH Siena Hotel
➡ Fortezza Medicea (5 min)
➡ Basilica of San Domenico (5 min)
➡ Piazza del Campo (10 min)
➡ Siena Cathedral (15 min)
➡ Gelato or wine stop
🚶♀️ Return to HotelNH Siena (~11 minute walk from Siena Cathedral)
🔥 This day is all about food and exploration — a true Siena highlight.
🏰 DAY 5 – SUNDAY, SEPTEMBER 19, 2027
Hidden Castles & Chianti Wine
🚶♀️ Getting to Your First Tour
🕒 Depart Hotel: NO LATER THAN 1:15 PM (Walking)
Walk from NH Siena → Siena FS 53100 Siena, Province of Siena, Italy
⏱️ Estimated walk time: ~23 minutes 🚗 Estimated Uber / Taxi: ~ 9 min Approx €10–€15 ← Recommended
💡 Plan to leave by 11:15 AM to comfortably arrive and locate your guide without rushing.
🏰 Hidden Castles & Chianti Wine Experience – (Approx 5 Hours)
🕒 Start Time: 2:00 PM
⏰ Arrive by: 1:45 AM
🔴 Booking Ref: TBD
📍 Meeting Point:
Siena FS 53100 Siena, Province of Siena, Italy
💡 Travel in an air-conditioned minivan for up to 8 people or a minibus for up to 30 people.
🍷 Tip: As your wine tour concludes, restaurants throughout Siena will be beginning dinner service.
🚶♀️ Return to Hotel
NH Siena
🍝 DAY 6 – SUNDAY, SEPTEMBER 20, 2027
Traditional Tuscan Cooking & Dining Experience
🚶♀️ Getting to Your First Tour
🕒 Depart Hotel: NO LATER THAN 11:45 AM (Walking)
Walk from NH Siena → Siena, Siena, Tuscany (held for privacy until booking)
⏱️ Estimated walk time: ~5 minutes
💡 Full address will be given once this is booked.
🍝 Cesarine: Typical Dining & Cooking Demo at Local's Home in Siena (Approx 2.5 Hours)
🕒 Start Time: 12:00 PM
⏰ Arrive by: 11:55 AM
🔴 Booking Ref: TBD
📍 Meeting Point:
Siena, Siena, Tuscany (held for privacy until booking)
💡 This will be in someone's home and would have a maximum group size of 10 people.
🧭 Spend the afternoon discovering Siena's hidden corners and historic landmarks.
🚶♀️ Return to Hotel
NH Siena
🍷 DAY 7 – MONDAY, SEPTEMBER 21, 2027
Best of Tuscany Wines & Montepulciano
🚶♀️ Getting to Your First Tour
🕒 Depart Hotel: NO LATER THAN 11:45 AM (Walking)
Walk from NH Siena → Piazzale Rosselli, 10, 53100 Siena SI, Italy
⏱️ Estimated walk time: ~23 minutes 🚗 Estimated Uber / Taxi: ~ 9 min Approx €10–€15 ← Recommended
🍷 From Siena Best of Tuscany Wines and Lunch in Montepulciano (Approx 9 Hours)
🕒 Start Time: 9:45 AM
⏰ Arrive by: 9:20 AM
🔴 Booking Ref: TBD
📍 Meeting Point:
Piazzale Rosselli, 10, 53100 Siena SI, Italy
💡 This tour/activity will have a maximum of 50 travelers
🚶♀️ Return to Hotel
NH Siena
✨ A wonderful day to enjoy authentic flavors, beautiful scenery, and a relaxed pace in Tuscany
🚤 DAY 8 – TUESDAY, SEPTEMBER 22, 2027
Train to Naples - Private Transfer to Sorrento - Food Tour
🚉 Train from Siena to Naples (Approx 5 Hours)
First Train Number: TBD Seats: This regional train does not have assigned seating. You may sit in any available seat.
Departure Time: 9:18 AM
Second Train Number: TBD
Connection Time: 11:14 AM 20 min connection time given Seats: TBD Arrival Time: ~2:30 PM
Private Transfer from Naples train station to hotel
🚗 Driving time: ~1.5 Hours Arrival Time Est.: ~4:15 PM
Booking Number: TBD
🏨 Hotel Check-In – Sorrento
Hotel Capri 4 ★ Hotel
📍 Corso Italia, 212, 80067 Sorrento NA, Italy
🔴 Confirmation #: TBD
Check-In Time:
From 2:00 PM
🚶♀️ Getting to Your First Tour
🕒 Depart Hotel: NO LATER THAN 4:45 AM (Walking)
Walk from Hotel Capri → Piazza Torquato Tasso, 80067 Sorrento NA, Italy
⏱️ Estimated walk time: ~6 min
🍷 Food Tour: 10+ Tastings from Gnocchi to Limoncello (Aprox 3 Hours)
🕒 Start Time: 5:00 PM
⏰ Arrive by: 4:55 AM
🔴 Booking Ref: TBD
📍 Meeting Point:
Piazza Torquato Tasso, 80067 Sorrento NA, Italy
💡 This tour/activity will have a maximum of 15 travelers
🚶♀️ Return to Hotel
Hotel Capri
✨ A relaxing and flavorful day that perfectly complements your time in Sorrento.
🚤 DAY 9 – WEDNESDAY, SEPTEMBER 23, 2027
Sorrento Farm & Food Experience
🚶♀️ Getting to Your First Tour
🕒 Depart Hotel: NO LATER THAN 11:45 AM (Walking)
Walk from Hotel Capri → Via Correale, 26, 80067 Sorrento NA, Italy
⏱️ Estimated walk time: ~6 min
🍷 Sorrento Farm and Food Experience including Olive Oil, Limoncello, Wine Tasting (Approx 4 Hours)
🕒 Start Time: 9:30 AM
⏰ Arrive by: 9:15 AM
🔴 Booking Ref: TBD
📍 Meeting Point:
Via Correale, 26, 80067 Sorrento NA, Italy
💡 This tour/activity will have a maximum of 25 travelers
🚶♀️ Return to Hotel
Hotel Capri
🚤 DAY 10 – THURSDAY, SEPTEMBER 24, 2027
Amalfi Coast Experience
🚶♀️ Getting to Your First Tour
🕒 Depart Hotel: NO LATER THAN 8:40 AM (Walking)
Walk from Hotel Capri → Hotel Antiche Mura Sorrento, Via Fuorimura, 7, 80067 Sorrento NA, Italy
⏱️ Estimated walk time: ~9 min
Full-Day Amalfi Coast Experience from Sorrento (Approx 9 Hours)
🕒 Start Time: 9:00 AM
⏰ Arrive by: 8:50 AM
🔴 Booking Ref: TBD
📍 Meeting Point:
Hotel Antiche Mura Sorrento, Via Fuorimura, 7, 80067 Sorrento NA, Italy
💡 This tour/activity will have a maximum of 21 travelers
🚶♀️ Return to Hotel
Hotel Capri
🚤 DAY 11 – FRIDAY, SEPTEMBER 25, 2027
Capri Island Experience
🚶♀️ Getting to Pickup Location
From: Hotel Capri
To: Sorrento Train Station (Circumvesuviana)
📍 Piazza Giovanni Battista de Curtis
⏱️ Walking time: less than 5 minutes
🕒 Leave Accommodation: 7:50 AM
💡 The pickup point is just outside the main entrance of the train station — very close and easy to find.
🚐 Shuttle Pickup for Boat Tour
🕒 Pickup Time: 7:55 AM
🔴 Booking Ref: TBD
📍 Exact Pickup Location: (MAP)
Outside the main entrance of Sorrento Train Station (PICTURE HERE)
Near the info point and train wagon
⚠️ Important:
Be ready and waiting a few minutes early
Do not be late — the shuttle will depart on time
🚤 Departure to Capri
🕒 Boat Departure: 9:15 AM
Proceed to boarding once dropped at the port
Your boarding pass will allow you to skip the line
🌊 What’s Included
Boat transfer to Capri
Guided boat tour around the island
Approximately 6 hours of free time on Capri
🌴 What to Do in Capri
You’ll have plenty of time to explore at your own pace.
🌊 Top Experiences
Blue Grotto (Grotta Azzurra) (optional)
Monte Solaro chairlift (Anacapri) for panoramic views
Scenic views of the Faraglioni rock formations
🛍️ Explore Capri Town
Walk through Piazza Umberto I (La Piazzetta)
Browse shops and boutiques
Stop for a drink or light lunch
🍝 Lunch Ideas
Da Paolino – famous lemon grove dining
Villa Verde – lively and popular
Ristorante Verginiello – relaxed with great views
💡 Keep your plans flexible — Capri is best enjoyed by wandering and discovering as you go.
⏱️ Return to Sorrento
Return boat departs in the afternoon
Shuttle transfer back included
Expected return: Late afternoon / early evening
🌙 Evening – Back in Sorrento
Enjoy a relaxed dinner
Take a final evening stroll through town
💡 A perfect way to end your time along the coast.
✨ A seamless, memorable day exploring one of Italy’s most iconic destinations.
🚤 DAY 12 – SATURDAY, SEPTEMBER 26, 2027
Cook Like a Local with a Stunning Sea View
🚶♀️ Getting to Your First Tour
🕒 Depart Hotel: NO LATER THAN 9:40 AM (Walking)
Walk from Hotel Capri → Parking Sorrento Via Correale, 25, 80067 Sorrento NA, Italy
⏱️ Estimated walk time: ~7 min
Full-Day Amalfi Coast Experience from Sorrento (Approx 9 Hours)
🕒 Start Time: 10:00 AM
⏰ Arrive by: 9:50 AM
🔴 Booking Ref: TBD
📍 Meeting Point:
Parking Sorrento Via Correale, 25, 80067 Sorrento NA, Italy
💡 This tour/activity will have a maximum of 24 travelers
🚶♀️ Return to Hotel
Hotel Capri
✈️ DAY 13 – SUNDAY, SEPTEMBER 27, 2027
Transfer to Naples + Stop in Pompeii
🚘 Private Transfer – Sorrento → Naples With Stop in Pompeii
🕒 Pickup Time: 10:30 AM
🔴 Booking Ref: TBD
📍 Pickup Location:
Hotel Capri – Lobby
👤 Driver Instructions:
Your driver will meet you in the lobby holding a sign with your name
💡 Enjoy one last scenic drive along the coast with a stop in Pompeii as you head back to Naples.
🏨 Arrival in Naples
Starhotels Terminus 4 ★ Hotel
📍 P.za Giuseppe Garibaldi, 91, 80142 Napoli NA, Italy
🔴 Confirmation #: TBD
🕒 Check-In:
From 3:00 PM
🧳 Afternoon – Free Time in Naples
After checking in, enjoy your final afternoon in Italy.
🛍️ Easy Ideas Nearby
Walk around Piazza Garibaldi area for shops and cafés
Take a short taxi to the historic center for last-minute exploring
Pick up souvenirs or enjoy one last espresso
🍕 Last Dinner in Italy
A few great options for your final night:
L’Antica Pizzeria da Michele – legendary Neapolitan pizza
Sorbillo – another top-rated pizza spot
Trattoria da Nennella – lively, authentic experience
🧳 Evening Tip
Pack and organize for your early departure the next morning
Set aside essentials (passport, documents, etc.)
✨ A relaxed final evening to reflect on an unforgettable Italian adventure.
✈️ DAY 14 – MONDAY, SEPTEMBER 28, 2026
Departure from Naples
🚕 Private Transfer – Hotel to Airport
🕒 Pickup Time: TBD
🔴 Booking #: TBD
📍 Pickup Location:
Starhotels Terminus (Front Entrance)
👤 Driver Instructions:
Driver will be waiting outside the hotel
Look for a sign with your name: “Cynthia Helfrich”
💡 Please be ready a few minutes early to ensure a smooth departure.
✈️ Flight Home
🕒 Flight Departure: TBD
📍 Naples International Airport (NAP)
🔴 Airline Confirmation: TBD
✈️ Flight Details
Airline TBD
Naples →
💡 Arrive at the airport with plenty of time for check-in, security, and boarding.
🧳 Important Departure Tips
Have your passport and travel documents easily accessible
Keep essentials in your carry-on
Confirm you have all personal belongings before leaving the hotel
✨ Thank you for allowing us to be part of your journey — we hope this trip to Italy is filled with unforgettable memories, incredible food, and experiences that last a lifetime.
Activity Tickets
Sept 21st Best of Tuscany Wines & Montepulciano
Sept 17th Brunello Di Montalcino Wine Tour Day
Sept 20th Traditional Tuscan Cooking & Dining Experience
Sept 19th Hidden Castles & Chianti Wine
Sept 18th Ultimate Food Tour Day
Sept 22nd Food Tour: 10+ Tastings
Sept 24th Amalfi Coast Experience
Sept 23rd Sorrento Farm & Food Experience
Sept 25th Capri Island Experience
Sept 26th Cook Like a Local with a Stunning Sea View
Hotel Confirmations
Sept 16th - Sept 22nd NH Siena
Sept 27th - Sept 28th B&B Hotel Napoli
Sept 22nd - Sept 27th Hotel Capri
Before Your Trip Preparation Worksheet
Getting ready for your adventure! A little preparation now helps ensure a smooth, stress-free vacation.
✅ Travel Documents
✔ Verify passports are not expired
✔ Passports should be valid for at least 6 months beyond your return date
✔ Bring a photo or printed copy of your passport (store separately from originals)
✔ Save digital copies of:
• Passport
• Flight details
• Hotel confirmations
💶 Money & Payments
✔ Notify your bank / credit card companies of international travel
✔ Bring a mix of Euros
✔ Smaller bills are strongly recommended
Many businesses prefer not to break large bills
✔ Useful for cash purchases:
• Gondola rides
• Small cafés / snacks
• Public restrooms
• Souvenirs
• Tips for guides / drivers
✔ Credit cards are widely accepted, but cash is still important
📱 Helpful Apps to Download
✔ Uber
Works in many larger cities
✔ ItTaxi
Official taxi app used in parts of Italy
✔ Google Translate
Great for menus, signs, conversations
✔ Google Maps
Download offline maps before departure:
How to Download Offline Maps:
Open Google Maps
Search “Italy” (or specific cities)
Tap your profile icon
Select Offline Maps
Tap Select Your Own Map
Download desired areas
✔ Rick Steves Audio Europe
Fantastic self-guided audio tours for landmarks and cities
✔ WhatsApp (Highly Recommended)
Most European hotels, drivers, and services use it
🧳 Packing Tips
✔ DO PACK
• Universal travel adapter (USB slots are very helpful)
• Comfortable walking shoes (critical!)
• Portable phone charger / battery pack
• Lightweight day bag / backpack
• Reusable water bottle
• Sunglasses / hat
• Any required medications
✔ DO NOT PACK
✘ Hair dryer
US hair dryers can be a fire hazard
Hotels will provide one
⚡ Electronics & Power
✔ Italy uses Type C / F plugs
✔ Voltage is 220V
✔ Most chargers (phones, laptops, tablets) work automatically
✔ You only need an adapter
💡 Helpful Travel Tips
✔ Smaller bills are preferred
✔ Many churches require modest attire:
• Covered shoulders
• No short shorts
✔ Expect walking. A lot of walking.
✔ Public restrooms often require small coins
✔ City taxes may be paid directly at hotels
✔ Emergency number in Italy: 112
✔ Pickpocket awareness:
• Use crossbody bags
• Avoid open backpacks in crowds
• Keep valuables secure
✔ Restaurants may include a small cover charge (“coperto”)
This is normal
🧾 Smart Extras (Often Forgotten)
✔ Luggage tags
✔ TSA-approved locks (optional)
✔ Backup credit card
✔ Small first aid items (blister pads = lifesaver)
✔ Travel laundry detergent sheets (optional but handy)
✔ Copies of itinerary & reservations
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