Greek Islands Tour for Women

Welcome to island life. You are now officially in vacation mode.

Your Bold Spirit journey kicks off in Santorini, the most famous of the Cyclades Islands.

Arrive at the Santorini Airport (JTR) and travel in our group van to your dreamy hotel. You may wish to arrive the day before the tour starts in order to experience more of Santorini and get over jet lag. (See early arrival hotel options.)

Take some time to settle in at the hotel and freshen up. See that glittering pool? You may want to jump in or enjoy a drink at the bar.

Later in the afternoon, meet up with the Bold Spirit Travel crew for orientation.

In the evening,  enjoy a group welcome dinner together. Get to know the other women sharing in this adventure while tucking into Greek dishes and local wines.

*There will be one group transfer in a private van today from the Santorini airport to the hotel. If you plan to come early to Santorini or at a different time, we can set up a private driver for you at an additional cost, or you can take a taxi on your own.

**You could fly into Athens and then fly into Santorini. Or, you can fly directly into Santorini and then out of Athens. Ask us about your options. We recommend coming early to get over jet lag and see more of Athens.

Meals: Welcome dinner & orientation drinks

Hotel: Santorini Palace or similar

After breakfast, get ready to be whisked away by your driver and guide to Akrotiri Prehistoric Settlement. Akrotiri is one of the most impressive ancient sites in all of Greece. Back around 1650 B.C., a massive volcanic eruption wiped out the town—but here’s the wild part: the ash and lava actually preserved everything (sort of like Pompeii in Italy).

You’ll get to explore the site with a guide who’ll share all the fascinating stories, history, and myths that make Akrotiri legendary.

We won’t go too far for lunch. Enjoy a group meal together by the seaside near Akrotiri.

Next, it’s time for a dreamy guided stroll through the fairy-tale village of Oia.

Perched on the northern edge of Santorini’s caldera, Oia is basically the supermodel of Greek villages—picture-perfect from every angle. Think whitewashed houses and iconic blue-domed churches that’ll have your camera working overtime.

Wander the narrow little streets packed with inviting shops, artsy galleries, cozy cafes, and swanky restaurants. Oia has that perfect mix of charm and chic. You will have free time here to shop, take photos, or just enjoy a drink and the view.

Dinner is on your own this evening. Grab a Bold Spirit friend and head into Fira or have dinner at the onsite restaurant.

*Fira is the larger town on Santorini and our hotel sits just outside it, away from the bustle but close enough that you can still enjoy all Fira’s shops, cafes, bars, and many restaurants. It’s a short walk from our hotel to Fira or you can take a taxi.

Meals: Breakfast, Lunch

Hotel: Santorini Palace or similar

Wake up slowly, sleep in, and linger over breakfast. There is no rush.

Today we leave Santorini behind and head to laid-back Naxos, the largest of the Cyclades Islands. This Aegean gem is known for its towering mountains, stunning sandy beaches, and charming little villages.

Our private van will take us down to the port where we will catch the jet ferry. Settle in and enjoy the ride across the Aegean Sea. This is part of the adventure! This is the fast ferry option.

Because today is a travel day, we will not have a group lunch. Plan to have a snack at the port or on the ferry as we cruise across the Aegean Sea. This ferry has a cafe.

Upon arrival on Naxos, our private driver will pick us up at the port and take us to our home for the next three nights. You’ll be staying in a cozy boutique hotel in Naxos town, right in the center where you’ll be able to walk to everything.

Unpack and unwind. Indulge in some downtime. This is a place for you to deeply relax and decompress.

Later, we will meet for dinner together in the evening. Watch the boats bob in the tranquil water and drink in the beauty all around you.

Meals: Breakfast, Dinner

Hotel: Nastasia Village Boutique Hotel or similar

Get ready for a delicious day of exploring Naxos—one bite at a time.

First stop: the charming neoclassical village of Chalki, where you’ll visit the island’s oldest distillery and sip on Naxos’ famous citron liqueur (yes, it’s as tasty as it sounds).

Next up: Kaloxylos, a village built on the slope of a hill, covered with olive groves and vineyards. Here, you’ll get to try locally produced olive oils.

Need a little pick-me-up? We’ve got you covered with a coffee break in the lovely village of Filoti. Then it’s off to a local farm to learn the secrets of traditional cheese making—yes, there will be samples.

And to top it all off, you’ll land in the stunning marble village of Apiranthos for a laid-back lunch packed with village-style recipes.

It’s a full day of flavor, fun, and Greek tradition, so bring your appetite and your curiosity.

In the late afternoon, we’ll return to the hotel for downtime. You are within walking distance to shops, cafes, restaurants, and the beach.

Dinner is on your own tonight. Grab a Bold Spirit buddy and try out one of the town’s many eateries. Life is good!

Meals: Breakfast, Food Tour Lunch

Hotel: Nastasia Village Boutique Hotel or similar

Today is a full day of sun, sea, and fun. We’re setting sail from the port of Naxos and cruising on the Aegean. First stop? A dreamy beach where you can dive into crystal-clear waters like an ancient Greek naiad.

Then it's off to another soul-stirring spot with emerald-green water and soft golden sand—perfect for a splash or a lazy lounge. While you’re soaking it all in, your catamaran crew will be whipping up a traditional Greek meal for lunch.

After lunch, the adventure isn't over. We’ll cruise back toward Naxos, with plenty of time for more swims at picture-perfect locales.

In the late afternoon, we’ll make our way back to the hotel. Enjoy free time and maybe a siesta.

Dinner is on your own this evening with your Bold Spirit buddies. Dolmades, anyone?

Important: You will need to bring a beach towel and/or sarong for this day trip; they are not provided on the boat. You will also need your bathing suit, walking shoes, and sunscreen (and a hat is a good idea, too).

*Itinerary is subject to change based on weather conditions.

Meals: Breakfast, Lunch

Hotel: Nastasia Village Boutique Hotel or similar

We leave tranquil Naxos behind today for the bustle of big-city Athens.

We’ll board the jet ferry and cruise along, arriving in Piraeus-Athens port in the afternoon. This is the fast ferry to Athens.

Because today is a travel day, we will not have a group lunch. Plan to have a snack at the port or on the ferry as we cruise across the Aegean Sea. This ferry has a cafe.

Once in Athens, a private van will meet our group and take us to the hotel.

Athens—the legendary heart of Europe, where democracy was born and brilliant minds like Socrates and Plato once roamed the streets. There is so much to see here (and you may want to add a day or two more to your trip). Tomorrow, we’ll explore Athens together.

Take time to settle into your hotel room.

Tonight, we’ll have a group dinner together at a nearby restaurant.

Meals: Breakfast, Dinner
Hotel: Amalia Hotel or similar

Whether you're a foodie, a Greek mythology superfan, or swoon for ancient architecture, Athens has something to make your smile.

Most travelers make a beeline for the Acropolis — not us.

Instead, we are taking you on a Tour of Six Neighborhoods, ranging from working-class havens to boutique boulevards. We want you to step into Athenian local life for a few hours.

On the Six Neighborhoods walking tour:

• Discover how Athens went from a sleepy little town to the modern city it is today—all while its ancient past looms large in the background.

• Wander through hidden corners packed with stories and fun finds—whether it’s something tasty, some local fashion, or a little souvenir to take home.

• Take a coffee break in a secret courtyard tucked away in the middle of all the hustle and bustle.

• Get a feel for what Athens is up to now—because this city definitely isn’t stuck in the past. Athens buzzes with hot spots and a dynamic creative scene.

In the afternoon, you’ll have free time to enjoy lunch on your own, shop, or head to the Acropolis, which is definitely worth the visit!

Important: The Acropolis is made of slick rock. If you choose to visit this site on your own (well worth it), then wear good shoes and bring a hat, as there is little shade. Walking poles are recommended for those with balance issues.

In the evening, meet up with the group for a farewell dinner. Let’s toast to our week together in Greece and new friends.  

Meals: Breakfast, Farewell Dinner
Hotel: Amalia Hotel or similar

Alas, our adventure has come to an end.

After breakfast at the hotel, there will be one group transfer in a private van to the airport (time to be confirmed) that aligns with most guests’ departure times.

Or choose to stay in Athens another day on your own to see more of this dynamic, historic city. (This would be a good option if you want to spend an entire day at the Acropolis and the Acropolis Museum).

You will depart from Greece today with a camera roll full of memories and a few new travel friends. There are 6,000 islands and islets scattered in the Greek Seas — so there is plenty to see if you return to this beautiful country one day!

Meals: Breakfast