Santorini & Lake Como Signature Trip: Oia, Bellagio, Positano & Naples

Our Santorini & Lake Como Signature Trip is a 10-day journey through four unforgettable destinations — the cliffside caldera views of Santorini, the alpine elegance of Lake Como, the dramatic coastline of Positano, and the vibrant streets of Naples. This fully private, custom-curated itinerary blends Greek island romance, Italian lake-country charm, and Amalfi Coast beauty into one seamless luxury experience.

A Curated Luxury Journey Through Santorini & Italy

June 26 – July 5, 2027 · 10 Days / 9 Nights · 2 Travelers

Santorini blue-domed cathedral, Greece

From sunset views over the Santorini caldera and a stay in an iconic Oia cave-style suite, to lakeside mornings in Bellagio, the pastel cliffs of Positano, and a final taste of Naples before heading home — this journey is built for travelers who want it all: island romance, lake-country elegance, and Amalfi Coast beauty in one trip.

📅 10 Days / 9 Nights👥 Double Occupancy✈️ International Airfare Not Included🚐 All Transfers Included

✈️ Flights

Jun 29 · A3 137 · Santorini (JTR) → Athens (ATH) · 9:50am–10:35am
Jun 29 · A3 844 · Athens (ATH) → Milan Malpensa (MXP) · 12:15pm–1:55pm
Jul 2 · AZ 1487 · Milan Linate (LIN) → Naples (NAP) · 10:30am–11:55am
Regional flights between destinations included · round-trip international airfare to/from Greece and Italy not included

📅 Day-by-Day Itinerary

Day 1
Jun 26
Santorini
Arrival at Santorini Airport (JTR). Private transfer to Perivolas Lifestyle Houses in Oia. Afternoon free to settle into your cave-style suite and enjoy sweeping caldera views; evening at leisure to watch the famous Oia sunset.
Day 2
Jun 27
Santorini
Full day at leisure to explore the whitewashed villages of Oia and Fira, or join an optional wine-tasting tour of Santorini’s volcanic-soil vineyards.
Day 3
Jun 28
Santorini
Optional catamaran cruise around the caldera with stops for swimming near the volcanic hot springs, or a visit to the Akrotiri archaeological site and Red Beach.
Day 4
Jun 29
Santorini → Lake Como
Private transfer to Santorini Airport (JTR). Fly via Athens to Milan Malpensa (MXP). Private transfer to Villa Flori in Bellagio, on the shores of Lake Como.
Day 5
Jun 30
Lake Como
Full day to explore Bellagio’s lakeside promenade, gardens, and boutiques, or join an optional boat excursion to Villa del Balbianello.
Day 6
Jul 1
Lake Como
Optional guided visit to Villa Carlotta, or a private boat tour of the lake’s villages, including Menaggio and Tremezzo.
Day 7
Jul 2
Lake Como → Positano
Private transfer to Milan Linate Airport (LIN). Fly to Naples (NAP). Private transfer along the Amalfi Coast to Villa Franca in Positano.
Day 8
Jul 3
Positano
Day at leisure to enjoy Positano’s beaches and boutiques, or an optional boat trip to Capri.
Day 9
Jul 4
Positano → Naples
Private transfer to Naples. Check in to Grand Hotel Parker’s; afternoon free to explore Naples’ historic center, or an optional day trip to Pompeii.
Day 10
Jul 5
Departure
Private transfer to Naples Airport (NAP) for your onward or international flight home. Trip concludes.

🏨 Where You’ll Stay

Santorini · Jun 26–29, 3 Nights
Perivolas Lifestyle Houses — Breakfast Included
Lake Como · Jun 29–Jul 2, 3 Nights
Villa Flori — Breakfast Included
Positano · Jul 2–4, 2 Nights
Villa Franca — Breakfast Included
Naples · Jul 4–5, 1 Night
Grand Hotel Parker’s — Breakfast Included

💎 What’s Included

✔ All private transfers — airport, hotel, and inter-destination transfers throughout the journey
✔ Regional flights between Santorini and Milan, and Milan and Naples
✔ 9 nights of handpicked boutique hotel accommodations, including daily breakfast
✔ Private transfer service in every city
✔ Personalized assistance throughout your journey
✘ Round-trip international airfare to/from Greece and Italy is not included
Investment Per Person
$6,800
Double Occupancy · International airfare not included
Subject to availability
Request This Trip  →

This is a private, customized journey designed exclusively for you. Spaces are limited.

Who Is This Trip For?

This Santorini & Lake Como Signature Trip is ideal for couples and honeymooners who want romance, elegance, and variety in one journey — Santorini’s caldera sunsets, Lake Como’s lakeside serenity, and the pastel cliffs of the Amalfi Coast — all without the stress of planning any of it themselves.

How to Book Your Santorini & Lake Como Signature Trip

Ready to reserve your spot on this extraordinary journey? Contact New Way Travel Corp today at (305) 551-1314, by email at nwtravel1@newaytravels.com, or via WhatsApp at +1 (786) 374-4816. A deposit of $500 per person secures your place, with the balance due 90 days prior to departure.

Travel With Peace of Mind

We strongly recommend travel protection for this international trip, so you can enjoy every city, view, and sunset with peace of mind.