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Greek Islands Getaway 2027

June 13-20, 2027
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Small-Group Women-Only Trip to Greece with Bold Spirit Travel

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Trip Overview

Pack your sunglasses and join us for an epic eight-day, women-only island getaway to the The Cyclades in Greece. On your itinerary are Santorini and Naxos—with a stop in Athens, too! The Cyclades are some of the world’s most breathtaking islands. We’ll soak up the sunshine, wander through charming coastal towns, check out ancient ruins, and take in those dreamy blue seas Greece is famous for.

Here’s what’s on your itinerary:

  • The volcanic beauty of Santorini for two nights

  • The chill island-vibes of Naxos for three nights

  • Buzzing Athens for two nights

This Bold Spirit trip is all about the good stuff—making new friends, enjoying nature, kicking back and relaxing, and eating amazing Greek food.

Ready to join the adventure?

Journey Highlights

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At a Glance

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Trip Overview

Day 1: Your Greek Adventure Begins

Day 1: Your Greek Adventure Begins image

Arrive in Santorini and Begin Your Island Adventure

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Arrive at Santorini Airport and Group Transfer

Arrive at the Santorini Airport (JTR) and travel in our group van to your dreamy hotel. 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.
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Group Orientation

In the afternoon, meet up with the Bold Spirit Travel crew for group orientation.

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Welcome Dinner

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

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Meals: Dinner

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Hotel: 4-star Cycladic-style resort in the Firostefani area of Santorini, just a short 10-15 minute walk from Fira

Day 2: Postcard Perfect in Oia

Day 2: Postcard Perfect in Oia image

Explore Akrotiri, Oia, and Santorini’s Charms

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Breakfast at the Hotel

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Guided visit 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 the ash and lava preserved everything. Explore the site with a guide who’ll share all the fascinating stories, history, and myths that make Akrotiri legendary.
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Group Lunch

Enjoy a group meal together by the seaside near Akrotiri.
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Guided Stroll through Oia

Take a dreamy guided stroll through the fairy-tale village of Oia. Perched on the northern edge of Santorini’s caldera, Oia is picture-perfect with whitewashed houses and iconic blue-domed churches. Wander the narrow streets packed with shops, galleries, cafes, and restaurants. Free time to shop, take photos, or enjoy a drink and the view.
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Evening at Leisure

We return to the hotel in the late afternoon.

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

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Meals: Breakfast, Lunch

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Hotel: 4-star Cycladic-style resort in the Firostefani area of Santorini, just a short 10-15 minute walk from Fira

Day 3: Ferry Hopping to Naxos

Day 3: Ferry Hopping to Naxos image

Jet Ferry to Naxos and Settle In

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Breakfast at the Hotel

Wake up slowly, sleep in, and linger over breakfast. There is no rush. After breakfast, check out of your room and load your luggage into our van for a private group transfer to the port.

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Jet Ferry to Naxos

Settle in and enjoy the ride across the Aegean Sea. This is part of the adventure! This is the fast ferry option.

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Arrive on Naxos

Arrive in Naxos, the largest of the Cyclades Islands. Our private driver will pick us up at the port and take us to our home for the next three nights. Unpack and unwind. Indulge in some downtime. This is a place for you to deeply relax and decompress.

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Group Dinner

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.

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Meals: Breakfast, Dinner

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Hotel: Cozy boutique hotel in Naxos town, within walking distance to shops, cafes, restaurants, and the beach

Day 4: Delicious Day Out

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Explore Naxos Villages and Food Traditions

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Breakfast at the Hotel

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Food Tour of Naxos Villages

Get ready for a delicious day of exploring Naxos—one bite at a time. Visit the neoclassical village of Chalki for citron liqueur, Kaloxylos for olive oils, Filoti for a coffee break, a local farm for cheese making, and end in Apiranthos for a laid-back lunch.

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Evening at Leisure

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!

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Meals: Breakfast, Lunch

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Hotel: Cozy boutique hotel in Naxos town, within walking distance to shops, cafes, restaurants, and the beach

Day 5: Aegean Catamaran Adventure

Day 5: Aegean Catamaran Adventure image

Sailing, Swimming, and Greek Island Lunch

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Breakfast at the Hotel

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Aegean Catamaran Adventure

Get ready for 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.

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

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Lunch on Catamaran

While you’re soaking it all in, your catamaran crew will be whipping up a traditional Greek meal for lunch.
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Evening at Leisure

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?

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Meals: Breakfast, Lunch

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Hotel: Cozy boutique hotel in Naxos town, within walking distance to shops, cafes, restaurants, and the beach

Day 6: On Our Way to Athens

Day 6: On Our Way to Athens image

Jet Ferry to Athens and Group Dinner

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Breakfast at the Hotel

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Travel from Naxos to Athens

Leave sweet Naxos behind for the bustle of big-city Athens. Board the jet ferry and cruise along, arriving in Piraeus-Athens port in the afternoon. This is the fast ferry to Athens.

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 the group to the hotel.

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Group Dinner

Tonight, we’ll have a group dinner together at a nearby restaurant.
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Meals: Breakfast, Dinner

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Hotel: Modern 4-star hotel in the heart of the city

Day 7: Old Meets New in Athens

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Six Neighborhoods Tour and Farewell Dinner

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Breakfast at the Hotel

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Six Neighborhoods Walking Tour

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, take a coffee break in a secret courtyard, and get a feel for what Athens is up to now.
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Free Time in Athens

In the afternoon, you’ll have free time to enjoy lunch on your own, shop, or head to the Acropolis.

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Farewell Dinner

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

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Hotel: Modern 4-star hotel in the heart of the city

Day 8: Farewell, Greece

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Departure from Athens and Group Transfer

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Breakfast at the Hotel

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Group transfer to Athens airport

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.
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Optional extra day in Athens

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).
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Map

1. Santorini (Thira) Airport (JTR)

Santorini Airport, Thira 847 00, Greece

2. Firostefani Area (Santorini)

Φηροστεφάνι, Thira 847 00, Greece

3. Akrotiri Prehistoric Settlement (Santorini)

Akrotiri, Santorini 847 00, Greece

4. Oia Village (Santorini)

Oia, Santorini 847 02, Greece

5. Naxos Town (Chora)

Naxos Town, Naxos 843 00, Greece

6. Chalki Village (Naxos)

Chalki, Naxos 843 02, Greece

7. Kaloxylos Village (Naxos)

Kaloxylos, Naxos 843 02, Greece

8. Filoti Village (Naxos)

Filoti, Naxos 843 02, Greece

9. Apiranthos Village (Naxos)

Apiranthos, Naxos 843 02, Greece

10. Naxos Port

Naxos Port, Naxos 843 00, Greece

11. Piraeus Port (Athens)

Piraeus Port, Akti Miaouli, Piraeus 185 38, Greece

12. Athens National Garden

Athens 105 57, Greece

13. Acropolis of Athens

Acropolis, Athens 105 58, Greece

14. Acropolis Museum

15 Dionysiou Areopagitou, Athina 117 42, Greece

15. Athens International Airport (ATH)

Athens International Airport, Spata 190 04, Greece

What's Included

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What's included

Eight days and seven nights at beautiful hotels

An English-speaking Bold Spirit tour leader accompanying you every step of the way

All group meals as indicated in the detailed itinerary

Private land transfers for the Bold Spirit group throughout the entire adventure and ferries

A small group experience

Expert bilingual guides

All equipment needed for activities

An online session where you can meet the other guests on the trip before the trip (usually one month before departure)

A packing list

A WhatsApp group to connect you with the other women on the trip

Gratuities for servers at group meals

Group airport pick-up in Santorini on Day 1

Group airport transfer on Day 8 to Athens Airport

What's not included

Round-trip airfare (you must meet us on Santorini on Day 1; many international flights fly directly to Santorini)

Cost for additional activities (not outlined in the detailed itinerary) such as an Acropolis visit

Meals not outlined in the detailed itinerary

Alcoholic beverages, unless otherwise specified (most meals include 1 glass of wine or beer)

Personal expenses, such as souvenirs

Travel insurance

Early hotel check-in

Room service/minibar

Spa services

Laundry

Tips for tour leaders, drivers, local guides

Pricing

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