A private Solo in Style slowcation in the idyllic Greek islands! Join a small group of just 12 women, along with Deborah Ives, founder of Solo in Style, and Monica, your Globe Drifters host, for a relaxed and unforgettable island escape.

Slow travel, not rushed travel: Spend several nights on each island instead of constantly packing and moving. With ample free time, you'll have plenty of time to relax, explore at your own pace, or simply enjoy Greek island life.

Island hopping made easy: Travel between Santorini, Naxos, and the beautiful village of Naousa on Paros, experiencing three very different sides of the Cyclades during one unforgettable trip.

Boutique hotels in exceptional locations: Stay in carefully selected boutique hotels—one perched above Santorini's caldera and another directly on an idyllic beach in Naxos, just steps from the sea and beach bars as well as Naxos' town center.

Welcome to Greece! Upon arrival in Santorini, you'll be met at the airport or ferry port and transferred to your charming boutique hotel perched on the cliffs overlooking the sparkling Aegean Sea. After settling into your room, spend the afternoon relaxing by the pool or take the hotel's complimentary shuttle into Fira to explore the island's lively capital.

As the sun begins to set, join your fellow travelers for a delicious Greek welcome dinner at the hotel, the perfect way to kick off your island adventure.

Arrival Information: Complimentary airport or ferry port transfers are included only for arrivals on Day 1. If you arrive before the tour begins, you'll need to make your own way to the hotel.

Included: 

• Activities: Santorini hotel transfer on arrival day only

• Meals: Dinner

• Accommodation: Boutique hotel

Start the day early with a visit to Oia, arriving before the crowds when the village is still peaceful, and its shops and cafés are just beginning to open. Enjoy time to explore its narrow lanes, whitewashed buildings, and sweeping caldera views before continuing to Megalochori, a traditional village known for its quiet streets and local character.

Afterward, visit Venetsanos Winery for a tasting of five Santorini wines accompanied by a light lunch of local specialties, including cold cuts, dips, fava, tomato fritters, and dessert. Return to the hotel in the early afternoon, with the rest of the day free to relax.

Included:

• Activities: Santorini island tour, Wine tasting, Free time

• Meals: Breakfast, Lunch

• Accommodation: Boutique hotel

Start your day at your own pace—enjoy breakfast, sleep in, relax by the pool, or wander through Fira’s winding streets. Later, we’ll board our private catamaran for an afternoon and evening on the water. There will be plenty of time to swim, soak up the sunshine, and simply enjoy Santorini’s spectacular coastline from the sea. As the sun sets, we’ll enjoy a freshly prepared meal onboard while taking in the beautiful views before returning to shore.

Included:

• Activities: Free time; Santorini private sunset cruise with dinner

• Meals: Breakfast, Dinner

• Accommodation: Boutique hotel

Today, we’ll travel by ferry from Santorini to Naxos, the largest island in the Cyclades. Steeped in history and mythology, Naxos is known for its traditional villages, green landscapes, beautiful beaches, and relaxed atmosphere.

Upon arrival, we’ll transfer to our hotel right on the beach. The rest of the day is yours to settle in and enjoy at your own pace. Relax by the sea, explore the nearby restaurants, cafés, and beach bars, or take a short taxi ride into Chora, Naxos’ lively main town, for shopping, sightseeing, and dinner by the waterfront.

Included:

• Activities: Naxos by ferry; Naxos free time

• Meals: Breakfast

• Accommodation: Boutique hotel

Get ready to explore the quieter, more traditional side of Naxos, an island rich in history, culture, and fertile farmland.

We’ll begin at a family-run citron farm that has been passed down through generations. Here, you’ll see the citron trees, learn how the fruit is grown, and visit the small factory where it is transformed into the island’s traditional citron liqueur.

Afterwards, enjoy a tasting of citron liqueur and local wine, accompanied by jams, cheeses, cured meats, and olives that have been produced or grown nearby and carefully paired with each tasting.

Next, we’ll continue to Chalki, a charming village in the heart of the island. You’ll have free time to wander its narrow streets, browse the small boutiques dotted throughout the village, and enjoy its relaxed atmosphere.

Our final stop will be Apeiranthos, one of Naxos’ most distinctive mountain villages. Here, we’ll sit down to a delicious lunch in a beautiful setting beneath the shade of a large tree, surrounded by the remains of old stone ruins. Because Apeiranthos is located high in the mountains and away from the coast, the village is especially known for its meat dishes and hearty local specialties. You’ll be able to choose from several traditional dishes and enjoy a relaxed meal in one of the island’s most memorable settings.

Included:

• Activities: Naxos Island private tour

• Meals: Breakfast, Lunch

• Accommodation: Boutique hotel

Set sail on a private catamaran for a relaxing day at sea. Explore hidden coves and secluded beaches, with time to swim or simply unwind on the sundeck while taking in the coastline. A delicious lunch featuring local products will be served onboard, along with complimentary beer, raki, wine, and other cold drinks. After returning to shore, the evening is yours to enjoy at your own pace, whether you prefer dinner in town, a quiet drink, or some free time to explore.

Included:

• Activities: Full-day private catamaran tour with lunch; Free time

• Meals: Breakfast, Lunch

• Accommodation: Boutique hotel

Enjoy a free morning and early afternoon to relax on the beach, explore Naxos, browse the local shops, or simply spend the day however you wish.

Later in the afternoon, we’ll board a speedboat and make our way to Naousa, a beautiful whitewashed village on the island of Paros. Its narrow cobbled streets are lined with boutiques, cafés, and bistros, making it a lovely place for some shopping, a leisurely stroll, or a drink by the harbor. Even if shopping is not your thing, the maze of charming lanes and picture-perfect corners makes Naousa a wonderful place to explore.

As the day comes to an end, we’ll return to Naxos by speedboat, timing our journey so we are out on the water at sunset. Sit back and enjoy the views as the sun sets over the South Aegean Sea.

*In case of high winds, the boat trip will be rescheduled or canceled.

Included:

• Activities: Naousa boat trip

• Meals: Breakfast

• Accommodation: Boutique hotel

Try not to fill up at breakfast this morning because today, you will prepare a Greek feast. Head to a traditional village on the north side of the island to spend the morning with a lovely family, visit and learn about their farm, and pick fresh produce for a cooking class. Then, enjoy a hands-on private culinary experience as you cook and eat your way through some of Naxos' specialties.

Included:

• Activities: Farm visit and cooking class with lunch; Free time

• Meals: Breakfast, Lunch

• Accommodation: Boutique hotel

Your final day in Naxos is completely free to enjoy however you wish. Spend the day relaxing on the beach, return to Chora for a little more shopping and exploring, or simply settle into the island’s slower pace with a long lunch and nowhere you need to be.

This evening, we’ll come together for one final dinner in Naxos at a beachfront restaurant beneath a beautifully lit tree. As the sun sets over the Aegean, we’ll enjoy dinner, live music, and one last relaxed evening together by the sea.

Included:

• Activities: Naxos free day (optional activities at your own expense); Farewell dinner

• Meals: Breakfast, Dinner

• Accommodation: Boutique hotel

Say farewell to the Greek Islands and your new friends. Today is the last day of your trip. We hope to see you on one of our next adventures!

Included:

• Activities: Departure (at your own expense); Free time

• Meals: Breakfast

*Itinerary is subject to change.