Greek Islands Getaway
September 17-24, 2026
Full Price: $5895
Activity Level — Moderate
This tour is not suitable for those in a wheelchair or with mobility issues.
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:
Buzzing Athens for two nights
The volcanic beauty of Santorini for two nights
The chill island-vibes of Naxos for three 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?
“This was a marvelous trip! It was my first time traveling “alone” although I wasn’t really alone. Met some incredible women from different walks of life. ”
MAIN ATTRACTIONS
Relax as an expert facilitator manages your vacation logistics
Explore Akrotiri, a Bronze Age Minoan settlement
Embrace your inner mermaid as you swim in the sea off Naxos’ beaches
Take in dramatic caldera views on Santorini
Wander the winding cobblestones in Athens, Santorini, and Naxos
Devour fresh Greek food and sip local wines
Indulge in rest and relaxation on quiet Naxos Island
Discover shops, restaurants, and cafes in Athen’s historic center (great shopping!)
Taste local specialties on an island foodie adventure
Find Greek pottery and textiles to take home with you
Pop on your sunnies for a private catamaran tour off Naxos
Stay in beautiful hotels
Meet other bold women who love travel as much as you do!
Activity Highlights
Food tour
Archaeological site visit
Catamaran island tour
Swimming off pristine beaches
Ferry ride to both Naxos and Athens
Visit to stunning Oia
Relaxing by the pool or on the beach
Connecting with other Bold Spirit women
DETAILED Itinerary
Day 1: Your Greek Adventure Begins
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 transfer 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 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: Orama Hotel and Spa 5* or similar
Day 2: Postcard Perfect in Oia
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: Orama Hotel and Spa 5* or similar
Day 3: Ferry Hopping to Naxos
Our private transfer 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.
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 driver will pick us up at the port and transfer us to our home for the next three nights. You’ll be staying in a cozy boutique hotel in a traditional village.
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 - exclusive or elegant room category
Day 4: Delicious Day Out
Wake up slowly, sleep in, and lingering over breakfast. There is no rush.
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. 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
Day 5: 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. 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).
Meals: Breakfast, Lunch
Hotel: Nastasia Village Boutique Hotel or similar
Day 6: On Our Way to Athens
Alas, we’ll leave sweet 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 transfer will meet our group and transfer the group 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 - superior room
Day 7: Old Meets New in Athens
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.
And 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.
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 - superior room
Day 8: Farewell, Greece
Alas, our adventure has come to an end.
After breakfast at the hotel, there will be one group transfer 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
Hotel: n/a
What’s Included:
Eight days and seven nights at beautiful hotels (based on double occupancy; we will pair you with a roommate unless you choose a private upgrade)
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 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
Mandatory travel insurance
Optional private room upgrade (limited number available)
Early hotel check-in
Room service/minibar
Spa services
Laundry
Tips for tour leaders, drivers, local guides
What to Bring on This Adventure:
Comfortable walking shoes and sandals
Bathing suit & cover-up
Day pack or bag
Reusable water bottle
Beach towel for boat trip and beaches
You will receive a detailed packing list upon registering
Travel Insurance
Purchase travel insurance for your Bold Spirit trip.
We highly recommend that you obtain adequate coverage for cancellation, curtailment, and loss of luggage and personal effects. Your deposit and final trip balance can then be recovered via a claim to your insurance provider in the event that you must cancel your adventure due to unforeseen circumstances.
Check out insurance options at Tinleg, Squaremouth, GlobeHopper Senior, WorldTrips and Travel Guard.
No refunds are issued 90 days or fewer from departure.
Other Considerations
Our itinerary is subject to change based on availability and unforeseen conditions.
The minimum group number for this trip to run is six participants. Note: Please do not book any flights until the trip is confirmed.
Payment dates:
* Deposit: upon registering
* 2 subsequent payments
Greek Protocols:
You must abide by Greek rules and health protocols. Bold Spirit Travel is not responsible if you cannot enter Greece due to lack of vaccination or other entry requirements.
Visas: Make sure you know the latest about ETIAS.
Luggage:
* 1 wheel-on bag, limit 50lbs
* 1 day pack
* 1 purse
* You will need a beach towel for the catamaran day trip
Please do not bring more than the allowed luggage on the trip as we have limited space in the van.
Recommended Reading:
The Odyssey by Homer. Translated by Richmond Lattimore.
Brush up on your ancient Greek mythology.
Internet and Data:
You must have internet on your phone during the trip via an international data plan with your carrier or a SIM/E-SIM.
We use WhatsApp during the trip and we will communicate with you through your internet connection. If you are lost or something else comes up, we will call you, or you will call us, on WhatsApp. Make sure you have a data plan before you arrive in Greece and start the tour.
Refund amounts are determined as follows:
120+ days before trip: Full refund minus non-refundable deposit
120–90 days before trip: 50% of balance minus non-refundable deposit
No refund after June 1st, 2026. This is due to hotel deposits on the islands.
We use your deposit to secure your hotel room and guides. This is why it is not refundable. Please get travel insurance to protect your purchase (see above).
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