190+ Guided Tours in Greece - Expert-Led Experiences

Greece Sailing Adventure: Cyclades Islands

No booking fees

Best price guaranteed

Picture yourself cruising the cerulean waters of the Cyclades—this Greece Sailing Adventure offers a ten-day island-hopping tour from Santorini, weaving through Amorgos, Ios, Mykonos, and other gems of the Aegean Sea. Travelers can expect a blend of relaxed yachting, regular swims in turquoise bays, and insider access to ancient towns and lively beachside hotspots. Guided by a knowledgeable local, you’ll enjoy the freedom to explore secluded coves, indulge in fresh seafood, and sip local wines as sunsets paint the horizon. The trip’s moderate activity level keeps the pace lively—perfect for those seeking a balance of exploration and relaxation, with opportunities for snorkeling, walking tours, and cultural immersion. What sets this sailing tour apart is its seamless blend of adventure and local flavor, ensuring every day reveals a new facet of Greek island life. If you’re after a trip that combines iconic destinations with the spontaneity and comfort of life at sea, this package is your ticket to an unforgettable Mediterranean escape.

Sailing, yachting and motor boating

Tour Type

Small Group Tour

Accommodation

Hotel, Yacht Cabin

Age Range

15-99 yrs

Operated in

english

Destinations

Santorini, Amorgos, Small Cyclad

Santorini, Amorgos, Small Cyclades, Naxos, Syros, Mykonos, Sifnos, Folegandros

Duration10 days

View Tour

Sail Greece: Santorini to Mykonos

No booking fees

Best price guaranteed

Dreaming of Greek island bliss? The Sail Greece: Santorini to Mykonos tour is an eight-day sailing adventure through the Cyclades, including iconic stops in Santorini, Ios, Amorgos, Naxos, and Mykonos. Travelers are treated to days filled with sun, sea, and exploration: swim in crystalline bays, wander whitewashed villages, and savor fresh Greek cuisine straight from the sea. With moderate activity and a lively, relaxed vibe, this trip is perfect for those who seek both adventure and downtime. Explore olive groves, historical ruins, and vibrant nightlife before returning to your yacht for a peaceful night’s sleep under the stars. What sets this tour apart is the perfect balance of Greek culture, scenic beauty, and the comfort of life at sea—making it an ideal trip package for anyone wanting to experience the Cyclades in style.

Sailing, yachting and motor boating

Tour Type

Small Group Tour

Accommodation

Yacht Cabin

Age Range

15-99 yrs

Operated in

english

Destinations

Mykonos, Santorini, Ios, Small C

Mykonos, Santorini, Ios, Small Cyclades, Amorgos, Naxos

Duration8 days

View Tour

Sail Greece: Skiathos, Skopelos & Alonnisos

No booking fees

Best price guaranteed

If you’re seeking paradise, then this eight-day adventure aboard a catamaran might be calling your name. With an experienced skipper, you’ll sail between the lesser-known islands of Skiathos, Skopelos and Alonnisos, seeing the Greek Islands from a new perspective. Enjoying the comfort of your private yacht, you’ll spend days sailing, stand-up paddleboarding in the National Marine Park of Sporades, where dolphins and monk seals call their home. Spend your nights watching the sunset over calm waters and spending your free time seeking local tavernas for deliciously fresh cuisine and a glass of the local vino. Yiamas!

Sailing, yachting and motor boating

Tour Type

Small Group Tour

Accommodation

Yacht Cabin

Age Range

15-99 yrs

Operated in

english

Destinations

Thessaly, Skiathos, Skopelos, Panagia

Duration8 days

View Tour

Greece Sailing Adventure: Corfu to Kefalonia

No booking fees

Best price guaranteed

Sail the sparkling Ionian Sea and explore the hidden gems of Greece on this eight-day Greece Sailing Adventure: Corfu to Kefalonia. Perfect for those seeking a moderate blend of relaxation and activity, this sailing tour visits Paxos, Lefkadas, Ithaca, and more—each island offering sun-drenched beaches, Venetian architecture, and warm local tavernas. Swim in crystal-clear bays, watch sunsets from the deck, and spend evenings discovering lively island towns. With daily opportunities for walking on white sands and uncovering secluded coves, this trip delivers an immersive taste of Greek island life. The unique selling point of this sailing tour package lies in its exclusive access to remote beaches and coves, promising an unforgettable journey for those who long for adventure off the beaten path.

Sailing, yachting and motor boating

Tour Type

Small Group Tour

Accommodation

Yacht Cabin

Age Range

15-99 yrs

Operated in

english

Destinations

Corfu, Kefalonia, Paxos, Lefkada

Corfu, Kefalonia, Paxos, Lefkadas, Ithaca

Duration8 days

View Tour

Sail & Hike Greece: Athens to Mykonos

No booking fees

Best price guaranteed

Spend eight sun-kissed days island-hopping, swimming and hiking your way through the Cyclades. Kick things off in the port town of Lavrio near Athens, then set sail across the Aegean on a private yacht. Dropping anchor at some of Greece's lesser-known islands, you’ll hike through sleepy villages and along craggy cliffs, share a homemade dinner with a local family in Syros and uncover the stories of ancient civilisations on the UNESCO-listed Delos. With an experienced skipper leading the way, daily sea dips and plenty of free time to soak up the slower rhythm of island life, this is the Cyclades at their best.

Sailing, yachting and motor boating

Tour Type

Small Group Tour

Accommodation

Yacht Cabin

Age Range

15-99 yrs

Operated in

english

Destinations

Athens, Mykonos, Kea, Kythnos, S

Athens, Mykonos, Kea, Kythnos, Serifos, Syros, Lavrio

Duration8 days

View Tour

Sail & Hike Greece: Mykonos to Athens

No booking fees

Best price guaranteed

Spend eight salty-skinned days sailing, hiking and swimming your way through some of the lesser-known Cyclades. Starting in lively Mykonos, you’ll cruise the sparkling Aegean Sea aboard a private yacht and drop anchor at islands that seem unchanged by time. Hike to a clifftop castle in Kythnos, share a homemade dinner with a local family in Syros and unearth the stories of legendary gods and ancient civilisations on the UNESCO-listed Delos. With a passionate skipper at the helm, daily swims and plenty of free time to enjoy the Cyclades’ laidback pace, this is Greek island hopping done right.

Sailing, yachting and motor boating

Tour Type

Small Group Tour

Accommodation

Yacht Cabin

Age Range

15-99 yrs

Operated in

english

Destinations

Mykonos, Syros, Kythnos, Serifos

Mykonos, Syros, Kythnos, Serifos, Kea, Lavrio

Duration8 days

View Tour

Greece Sailing Adventure: Kefalonia to Corfu

No booking fees

Best price guaranteed

Explore the enchanting Ionian islands on the "Greece Sailing Adventure: Kefalonia to Corfu," an eight-day journey that promises both relaxation and discovery. Ideal for those who relish moderate physical activity and the freedom of the open sea, this sailing trip unveils secluded coastlines, private islands, and charming towns like Paxos, Meganisi, and Lefkadas. Swim in crystal-clear bays, wander Venetian-inspired villages, and savor evenings in local tavernas. The highlight: exclusive access to hidden beaches and coves only reachable by boat, making this tour package a truly unique Greek island-hopping experience.

Sailing, yachting and motor boating

Tour Type

Small Group Tour

Accommodation

Yacht Cabin

Age Range

15-99 yrs

Operated in

english

Destinations

Corfu, Kefalonia, Ithaca, Megani

Corfu, Kefalonia, Ithaca, Meganisi, Lefkadas, Paxos

Duration8 days

View Tour

Greece Guided Tours and Trips

Create a 100% personalized and guided trip to Greece

Page 2 of 17 Guided and Escorted Trips in Greece with 51 Reviews