Greek Island Hopping: Santorini, Mykonos, Ios, Hydra, Athens & more!

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Overview

Greek Island Hopping: Santorini, Mykonos, Ios, Hydra, Athens & more!
Athens, Greece
Sep 22 - Oct 1, 2026
The Wanderlust Rose image
The Wanderlust Rose
$3,800
Deposit: $600

About this trip

Greece is truly one of my favorite countries in the world, and after multiple trips, I’m so excited to share what I believe is the perfect itinerary. This journey blends hidden local gems with the experiences Greece is most famous for like the magic of Santorini and the energy of Mykonos.

We’ll begin in Athens before spending 3 nights on the stunning island of Hydra, a boutique haven where cobblestone streets and timeless charm set the tone for the trip. From Hydra, we’ll also explore two of my favorite neighboring islands, giving you a taste of authentic Greece. Along the way, we’ll enjoy olive oil tastings, wine tastings, and a very fun hands-on cooking class on a beautiful organic farm, all while surrounded by the most beautiful blue waters you can imagine.

From there, we’ll dive into the vibrant side of Greece: dancing to ABBA under the stars in Mykonos, joining a lively pub crawl in Ios, and soaking up the dramatic beauty of Santorini.

In some islands, it's impossible to reserve twin rooms. We cannot guarantee a twin room. Everyone will be in a King bed in our beautiful Santorini hotel.

What's included

Daily breakfast

All ferries

Comfortable transportation to each island

Olive oil tasting

5 different olive oils, by an olive oil maker and expert

Wine tasting in Poros

Try 8 local wines

Cooking class

3 course cooking class + pool

Welcome dinner in Athens

Goodbye dinner

Santorini Live Show

My big fat greek wedding show in Santorini

2 lunches

Swim Stops

Private transport

From harbours to hotels

All accommodation

In central 4 & 5 star boutique hotels

Professional photos

Ios Pub Crawl

This island is known for it's nightlife!

Mykonos Photo Walk

Santorini Sunset Photos

Hydra Beach Bar

Visit Poros Clock Tower

Oia Morning Visit

Visit the 3 iconic blue domes of Oia

Visit Mykonos Windmills

Hydra Sunset Bar

What's not included

International Airfare

Travel insurance

Airport Transfers

Day 1

Day 1 image

Welcome to Athens

You are able to take an uber or the train directly to Athens city centre.

We will have welcome dinner included tonight.

Day 2

Day 2 image

Hydra

We’ll take an early ferry from Athens and arrive on the island of Hydra around noon. After dropping our bags, we’ll head straight to the water to enjoy the afternoon at Rock Beach Bar and Spilia Beach Bar, two beautiful spots perfect for swimming and relaxing by the sea. Later, we’ll check in and head out for a photo walk through Hydra’s charming streets before stopping by Poem Box. As the sun sets, we’ll enjoy the views from a favorite sunset bar, and then end the night with drinks and dancing in one of my favorite bars on the Island.

Day 3

Day 3 image

A day in Poros

Today we will make our way to Poros, a small island known for its relaxed atmosphere. Our time here begins with a hands-on cooking class, where we’ll not only learn to prepare traditional Greek dishes but also enjoy some poolside time at the villa. In the afternoon, we’ll take part in a wine tasting and then head out to explore Poros at a leisurely pace. After a full day of food, wine, and island charm, we’ll sail back in the evening.

Day 4

Day 4 image

Beach and olive oil tasting

We’ll set out in the morning and sail to one of the most beautiful beaches in Greece, where we’ll spend time swimming in the clear blue water before enjoying a relaxed lunch by the sea. In the afternoon, we continue to Ermioni, this is a very cute island and we go to a family-run olive grove, where a local olive oil maker will guide us through a tasting surrounded by 3,000-year-old olive trees.

Day 5

Day 5 image

Mykonos

After a morning sail back to Athens, we’ll make our way to Mykonos and check in to our beautiful hotel overlooking the island. With stunning views and the perfect base for exploring, the afternoon is yours to settle in, enjoy the scenery, and soak up the Mykonos atmosphere before the evening’s adventures begin.

Day 6

Day 6 image

Exploring Mykonos

In Mykonos, we’ll start the day with a leisurely walk, exploring the island’s charming streets and capturing beautiful photos along the way. For lunch, we’ll head to Teo’s, a local favorite known for its fresh, flavorful dishes. In the evening, we’ll enjoy dinner at a beautiful restaurant a cozy spot perfect for relaxing and soaking in the atmosphere. Afterward, the night is yours to experience the vibrant energy of Mykonos, whether that means dancing, exploring, or simply enjoying a drink under the stars.

Day 7

Day 7 image

Ios

We’ll sail to Ios in the morning and start the day by relaxing at the hotel pool, taking in the sun and the stunning surroundings. Later, we’ll wander through the charming streets of Ios, capturing some beautiful photos and exploring the island’s scenic town. In the evening, we’ll enjoy a delicious Greek dinner before heading out for a lively pub crawl, experiencing the island’s vibrant nightlife.

Day 8

Day 8 image

Santorini

We’ll sail to Santorini in the morning and settle in at our hotel, where we can relax by the pool overlooking the iconic Santorini caldera. In the evening, we’ll enjoy a fun and unforgettable experience at the Big Fat Greek Wedding show, immersing ourselves in laughter, music, and the island’s unique charm.

Day 9

Day 9 image

Explore Oia

We’ll spend the day exploring Oia, one of Santorini’s most iconic villages. Known for its whitewashed buildings and blue-domed churches, Oia offers picture-perfect streets, stunning sea views, and plenty of charming spots to wander and take photos. It’s the perfect place to soak in the beauty of Santorini and enjoy the unique atmosphere of this world-famous village.

Day 10

Day 10 image

Time to say goodbye!

All photos will be in the google drive!

Location

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1. Athens, Greece

Athens, Greece

About your organizer

Hi, I'm Emily Rose! In 2018, I sold all my stuff and moved into my suitcase to travel full time and work around the world! After 33 countries and 29 states, I decided to start bringing others along on my adventures with me! Check out my website TheWanderlustRose.com or my Instagram (@thewanderlust_rose) for all things travel and adventure. I can't wait to meet you!

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