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Lake Como

Amalfi Coast

Paros

Santorini

Athens

22-Day Italy and Greece Island Escape

22 days

5 cities

82 experiences

5 hotels

5 transports

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Chicago

Lake Como

Aug 24 – 28

Amalfi Coast

28 Aug – 1 Sep

Paros

Sep 1 – 6

Santorini

Sep 6 – 11

Athens

Sep 11 – 13

Chicago

Days 1-5

Aug 24 – 28

Lake Como

Hey there! Your upcoming stay in Lake Como from August 24 to 28, 2027, promises a perfect blend of luxurious lakeside relaxation and breathtaking natural beauty. You'll enjoy exploring charming towns, indulging in exquisite Italian cuisine, and soaking in the serene atmosphere of one of Italy's most iconic destinations. This leg is a fantastic way to unwind before heading to the vibrant Amalfi Coast!

Stay

Days 1-5

Aug 24 – 28

4 nights

Mandarin Oriental, Lago di Como

Deluxe Room, 1 King BedBreakfast included

9.4

Wonderful502 reviews

Itinerary

Days 1-5

Aug 24 – 28

Day 1•Aug 24•

29°C•3 Experiences

Arrival and Lakeside Relaxation in Como

Day 2•Aug 25•

27°C•4 Experiences

Historic Como and Private Boat Exploration

Day 3•Aug 26•

29°C•3 Experiences

Culinary Delights and Balbianello Splendor

Day 4•Aug 27•

30°C•4 Experiences

Gardens and Serene Nature in Bellagio

Day 5•Aug 28•

30°C•1 Experience

Departure to Amalfi Coast

Days 5-9

28 Aug – 1 Sep

Amalfi Coast

Get ready to be enchanted by the Amalfi Coast, Italy, from August 28 to September 1, 2027. This leg of your trip offers a perfect blend of breathtaking coastal views, charming cliffside villages, and luxurious yet authentic Italian experiences. After the serene beauty of Lake Como, immerse yourself in the vibrant culture, delicious cuisine, and stunning Mediterranean landscapes that make the Amalfi Coast a must-visit destination before heading to the idyllic Greek island of Paros.

Stay

Days 5-9

28 Aug – 1 Sep

4 nights

Borgo Santandrea

Deluxe Room, Sea ViewBreakfast included

10.0

Wonderful34 reviews

Itinerary

Days 5-9

28 Aug – 1 Sep

Day 5•Aug 28•

33°C•2 Experiences

Arrival and Settling into Positano

Day 6•Aug 29•

32°C•4 Experiences

Exploring Positano and Roman History

Day 7•Aug 30•

29°C•4 Experiences

Ravello Charm and Gardens

Day 8•Aug 31•

29°C•3 Experiences

Hiking the Path of the Gods and Amalfi Town

Day 9•Sep 1•

29°C•1 Experience

Departure from the Amalfi Coast

Days 9-14

Sep 1 – 6

Paros

Experience the charming and authentic Greek island life in Paros, known for its beautiful beaches, traditional villages, and vibrant local culture. From September 1 to 6, 2027, enjoy relaxing seaside moments and exploring quaint streets that perfectly balance tranquility and lively atmosphere. This leg offers a perfect blend of relaxation and cultural immersion before heading to the iconic Santorini.

Stay

Days 9-14

Sep 1 – 6

5 nights

Summer Senses Luxury Resort

Deluxe RoomBreakfast included

9.6

Wonderful144 reviews

Itinerary

Days 9-14

Sep 1 – 6

Day 9•Sep 1••3 Experiences

Arrival in Paros and Relaxed Evening in Naoussa

Day 10•Sep 2••3 Experiences

Coastal Highlights and Naoussa Dining

Day 11•Sep 3•

29°C•3 Experiences

Countryside Riding and Village Charm

Day 12•Sep 4••4 Experiences

Farm to Table Cooking and Antiparos Exploration

Day 13•Sep 5••3 Experiences

ATV Adventure and Marble History

Day 14•Sep 6••3 Experiences

Final Morning in Parikia and Departure to Santorini

Days 14-19

Sep 6 – 11

Santorini

Experience the iconic beauty of Santorini from September 6 to 11, 2027, where you'll enjoy the breathtaking caldera views and the charming village of Oia. This leg of your trip offers a perfect blend of romantic sunsets, luxury accommodations, and unique volcanic beaches, making it an unforgettable highlight of your Greek island adventure. Dive into the local culture, savor exquisite cuisine, and relax in one of the most picturesque settings in the world.

Stay

Days 14-19

Sep 6 – 11

5 nights

Santorini Princess Spa Hotel

Double room with caldera viewBreakfast included

10.0

Wonderful1,001 reviews

Itinerary

Days 14-19

Sep 6 – 11

Day 14•Sep 6••3 Experiences

Arrival in Oia and Sunset at Amoudi Bay

Day 15•Sep 7•

31°C•5 Experiences

Exploring Oia Red Beach and Akrotiri Ruins

Day 16•Sep 8•3 Experiences

Caldera Hiking and Fine Dining in Pyrgos

Day 17•Sep 9•4 Experiences

Volcano Adventure and Hot Springs Exploration

Day 18•Sep 10•3 Experiences

Monastery Views and Full Island Sunset Tour

Day 19•Sep 11•3 Experiences

Final Morning and Departure to Athens

Days 19-21

Sep 11 – 13

Athens

Experience the heart of ancient civilization in Athens, Greece, where you can explore iconic landmarks like the Acropolis and Parthenon. Enjoy the vibrant city life, rich history, and delicious Mediterranean cuisine during your stay from September 11 to 13, 2027. This leg perfectly blends cultural immersion with modern comforts, making it an unforgettable part of your European adventure.