The trip in a nutshell
9 days/8nights
The Cycladic islands are the prototypical “Greek islands”. Whitewashed houses, turquoise blue seas, olive groves and sun parched landscapes. It is here where man lived in harmony with the environment for thousands of years. We believe that island hopping is the best way to connect with this past and get to know the islands, each of them stamped with its own unique character.
The trip starts in Athens, and after exploring the city during a foodie walking tour and visiting Acropolis you will fly to Santorini. Probably you know how it looks like. Photos of vibrant blue waters overlooked by whitewashed stone homes nestled above multicolored cliffs are constantly fueling wanderlust around the world.
Next stop is Naxos, the biggest and one of the most beautiful islands of the Cyclades, if one can be in position to choose. It is an island with incredible landscape interchanges, Venetian castles and traditional villages perched on the cliffs of its mountains.
Last destination, is Mykonos, Greece’s most famous cosmopolitan island, a whitewashed paradise in the heart of the Cyclades. Here the Cycladic architecture creates a distinctive character with a sophisticated personality.
Trip type
Discover Greece in style with our meticulously crafted journey, blending cultural exploration, gastronomic delights, and seaside relaxation. Whether you are a history enthusiast, a food lover, or simply seeking a rejuvenating seaside escape, this journey caters to diverse tastes. Join us for a trip that seamlessly weaves together the threads of Greece’s rich heritage, leaving you with memories to savor long after the journey ends.
Physical rating
For this tour, you don’t need significant athletic preparation. It’s enough that you are accustomed to medium-length walks. Special equipment is not necessary either. What you need to train is your gaze for beauty.
Entry requirements
Visas: Generally, American, Australian, British, and Canadian citizens traveling to Greece for stays of fewer than 90 days usually do not require a visa. However, there could be exceptions, and it remains the traveler’s responsibility to verify visa requirements. Starting from 2025, non EU citizens will need ETIAS to travel to Europe.
A journey through Greece's timeless wonders: Athens, Santorini, Naxos and Mykonos
$6,798.00
Single room +$1,699.50
You can reserve your spot with a deposit. Select this option from your trip summary.
What’s included?
Local Guide and 1 Gay Up Travel Host from beginning to end of tour
Great 4 star hotels
Daily breakfast, 2 lunches and 5 dinners as indicated in the itinerary
Transfers during the trip
All activities mentioned in the program
Ferry tickets from Santorini to Naxos, Naxos to Mykonos, Mykonos to Athens
Flight tickets from Athens to Santorini
Entrance fees to the Acropolis archaeological site and Delos archaeological site
Tourist guide for the archaeological site of Acropolis and for Delos archaeological site
Cooking class and wine tasting
A $50 USD donation to The LGBT Asylum Project to support the resettlement of LGBTQ+ refugees.
What isn’t included?
International flight
Travel insurance is mandatory for all travellers
Gratuities for Group Leader (budget approximately $60-$120 USD)
Other items of a personal nature (Medical expenses, drinks, laundry, etc)
Other items of a personal nature
Anything not mentioned above under “What’s included?”
DAY 1
- Athens Arrival
- Unveiling the Ancient Wonders
Upon your arrival at the airport, our dedicated driver will be ready to escort you to our centrally located 4-star hotel overlooking the Acropolis. After our tour presentation we’ll have a delightful Greek welcome dinner, providing the perfect setting to get acquainted and set the tone for the exciting journey ahead!
DAY 2
- Discovering Athens
- Food Tour and Acropolis.
Often referred to as the cradle of Western civilization, Athens has been continuously inhabited for the last 7,000 years. Everywhere you turn, you encounter ancient ruins or buildings evoking imagery of Greek gods or the thoughts of philosophers. In the morning, we’ll embark on a culinary journey through the bustling streets of downtown Athens with a Foodie Walking Tour. We’ll uncover the city’s hidden gems and indulge in delicious, locally sourced delicacies from family-owned stores and artisanal producers.
Later in the day, accompanied by a specialized guide, we’ll make our way to the Acropolis. No matter how many photographs you’ve seen, nothing can prepare you for witnessing it in person, standing after thousands of years.
DAY 3
- Flight to Santorini
- Wine Tasting Amidst Volcanic Splendor.
In the morning we will fly to Santorini, which is going to take your breath away. It is dramatic and unique, formed from the remains of a volcanic crater and even the most jaded traveler succumbs to the spectacle of this surreal landscape. A world-famous destination where a sophisticated lifestyle and Greek culture merge with spectacular landscapes.
Our afternoon will be spent at one of the island’s finest wineries. As we savor diverse grape varietals like the indigenous Assyrtiko, we’ll explore the best of Santorini’s ancient vineyards and uncover the profound influence of volcanic soils on its winemaking traditions.
DAY 4
- Sailing the Caldera
- A Maritime Symphony
Get ready for today’s experience because it’ll be amazing. Sailing in the caldera is a really unique experience. The caldera is a large depression formed when a volcano erupts or collapses after an eruption. Filled with seawater, it creates a unique and spectacular environment for exploration and relaxation. In the caldera of Santorini, there is a large lagoon surrounded by the cliffs of the island, offering breathtaking scenery and unique opportunities for activities such as sailing, swimming, and relaxing in hot springs. We’ll have the opportunity to swim in the invigorating hot springs renowned for their therapeutic properties. We’ll enjoy a delightful onboard barbecue, and immerse ourselves in the breathtaking hues of Santorini’s world-renowned sunset.
DAY 5
- Naxos
- Ancient Temples, Mountain Villages, and Olive Mills
As the ferry sails towards the island, you catch the first glimpse of the Portara, a marble gateway on the headland, all that remains of an ancient temple to Apollo. This marks the beginning of your adventure here, where you will uncover the rich tapestry of local customs and traditions that bring the spirit of Naxos to life. Your journey commences with a visit to the archaic temple of Goddess Demeter, constructed a hundred years before the Parthenon. Continuing on, you will embark on a scenic drive, ascending to the mountain village of Apeiranthos, renowned for its marble streets and medieval architecture, where you will enjoy lunch. En route back to the main town, you will pass through one of Naxos’s oldest remaining olive mills in the village of Eggares, dating back to at least the late 1800s, when it pressed locally-grown olives for the village community.
Overnight in Naxos
Breakfast and dinner included
DAY 6
- Exploring Naxian Cuisine
- Cooking class in a traditional village
Greek cuisine mirrors the abundant agricultural output of this small yet blessed country, providing us with indirect insights into the land’s economy, history, social life, customs, and even the people’s religious beliefs. Today, you will have the opportunity to learn how to prepare a typical Greek family meal using the renowned pure Naxian products. This culinary experience will take place in a traditional house located in Kaloxylos, a village nestled in the heart of the island.
Overnight in Naxos
Breakfast and lunch included
DAY 7
- Glamorous Mykonos
- Exploring the island and its Little Venice
Today, you will embark on a ferry journey to Mykonos, the renowned glamour island of Greece. Mykonos Town greets you with its enchanting labyrinth, adorned with chic boutiques and dazzling white houses adorned with bougainvillea and geraniums. Explore its narrow streets lined with small museums and picturesque churches. Don’t miss the iconic Little Venice, where the sea kisses the edge of restaurants and bars, and the famous hilltop windmills that grace the island’s skyline.
Later in the evening, indulge in dining experiences at some of the finest restaurants in the Mediterranean. Award-winning chefs will treat you to a fusion of local and international cuisines, ensuring a memorable culinary journey.
Overnight in Mykonos
Breakfast included
DAY 8
- Sail trip to Delos and Farewell Dinner
- Ancient Treasures in a great UNESCO site
In the morning, you will set sail by boat for the island of Delos. This UNESCO World Heritage Site stands as one of Greece’s most significant archaeological sites. Accompanied by your guide, you will delve into the awe-inspiring architectural wonders of an urban center dating back over 2000 years. Among other highlights, you will visit the impressive House of Dionysus, renowned for its exceptional mosaics, well-preserved marble columns, and wall paintings. You will also stroll along the celebrated Lion Street.
In the afternoon, we will explore the neighborhoods of the island’s main town and conclude our journey with a farewell dinner.
Overnight in Mykonos
Breakfast and dinner included
DAY 9
- Farewell to Greece
- A Ferry to Athens
Check out of your hotel and meet your private driver for your transfer back to the Mykonos port for your ferry to Athens. Say farewell to Greece as you board your flight back home.
Breakfast included