Syros May 2026 Tours and Trip packages

Accommodations

BudgetSimple stays with essential amenities. Typically guesthouses, hostels or hotels rated below 3 stars — clean, no-frills, and great for value-conscious travelers.
Mid-rangeComfortable and reliable 3-star stays. Expect private rooms, en-suite bathrooms, and solid amenities — a great balance between comfort and cost.

Sailing Greece - Santorini to Santorini - May 2026

(10 reviews )

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Best price guaranteed

Overall it was an amazing experience combining the exploration of several beautiful Greek islands with the excitement of travelling on a yacht . The guests on board all worked together well to help sail the yacht under the careful eye and patient tuition of Captain Phil

Sailing, yachting and motor boating

Tour Type

Small Group Tour

Accommodation

Yacht Cabin

Age Range

16-100 yrs

Operated in

english

Destinations

Santorini, Ios, Mykonos, Syros

Duration10 days

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Sailing Greece - Mykonos to Athens - May 2026

(8 reviews )

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Best price guaranteed

This was definitely one of the top 3 sailing experiences I have had over the years.

Sailing, yachting and motor boating

Tour Type

Small Group Tour

Accommodation

Yacht Cabin

Age Range

16-100 yrs

Operated in

english

Destinations

Athens, Mykonos, Syros, Northern Cyclades

Duration8 days

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Sailing Greece - Mykonos to Mykonos - May 2026

(7 reviews )

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Best price guaranteed

This Greece Islands sailing adventure was so memorable! It exceeded all of our expectations, every day sailing to explore a different island and experience local culture and food as well as gain knowledge about the history and culture of the region. Our skipper CEO Mack was highly knowledgeable about the region and very passionate about sailing as well as sharing his knowledge and providing opportunities for each of us to learn and experience it for ourselves. Our only recommendation is for G Adventures to include more information about the need to pay in cash at restaurants and establishments in the Greek islands (Euros). We thought we would be using our credit card for dinners but learned we really needed to have cash instead.

Sailing, yachting and motor boating

Tour Type

Small Group Tour

Accommodation

Yacht Cabin

Age Range

16-100 yrs

Operated in

english

Destinations

Mykonos, Syros, Santorini, Ios

Duration10 days

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Sailing Greece - Athens to Mykonos - May 2026

4.9

(9 reviews )

No booking fees

Best price guaranteed

An awesome and relaxing way to see many quieter Greek islands and get a more local experience!

Sailing, yachting and motor boating

Tour Type

Small Group Tour

Accommodation

Yacht Cabin

Age Range

16-100 yrs

Operated in

english

Destinations

Athens, Mykonos, Syros, Kea

Duration8 days

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Sailing Greece - Athens to Santorini - May 2026

4.8

(5 reviews )

No booking fees

Best price guaranteed

I had a wonderful time and saw and came to understand the different Greek Islands in the best possible way.

Sailing, yachting and motor boating

Tour Type

Small Group Tour

Accommodation

Yacht Cabin

Age Range

16-100 yrs

Operated in

english

Destinations

Athens, Santorini, Naxos, Syros

Athens, Santorini, Naxos, Syros, Kea, Mykonos

Duration15 days

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Sail Greece: Mykonos to Santorini - May 2026

(1 review )

No booking fees

Best price guaranteed

This was the absolute best trip ever. Ive traveled many times. I have to say this was one of the best experiences and adventures of all. Our skipper, Rita was simply amazing. The best! Wonderful skipper, skilled sailor, knowledgeable, so friendly, helpful, genuinely caring of her boat mates. Shes a dream to sail with! If anyone sails, Id highly recommend requesting her.

Sailing, yachting and motor boating

Tour Type

Small Group Tour

Accommodation

Yacht Cabin, Hotel

Age Range

15-99 yrs

Operated in

english

Destinations

Mykonos, Santorini, Syros, Naxos

Mykonos, Santorini, Syros, Naxos, Cyclades, Amorgos, Ios

Duration8 days

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Greece Sailing Adventure: Cyclades Islands - May 2026

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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

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Sail & Hike Greece: Athens to Mykonos - May 2026

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

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Sail & Hike Greece: Mykonos to Athens - May 2026

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

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Tours and Trip Packages to Syros in May 2026

Get a customized trip to Syros in May 2026

9 Trips in Syros during May 2026 with 40 Reviews

9 Trips in Syros during May 2026 with 40 Reviews

Sailing Greece - Santorini to Santorini - May 2026

Sailing Greece - Mykonos to Athens - May 2026

Sailing Greece - Mykonos to Mykonos - May 2026

Sailing Greece - Athens to Mykonos - May 2026

Sailing Greece - Athens to Santorini - May 2026

Sail Greece: Mykonos to Santorini - May 2026

Greece Sailing Adventure: Cyclades Islands - May 2026

Sail & Hike Greece: Athens to Mykonos - May 2026

Sail & Hike Greece: Mykonos to Athens - May 2026

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Tours and Trip Packages to Syros in May 2026

Get a customized trip to Syros in May 2026

9 Trips in Syros during May 2026 with 40 Reviews

9 Trips in Syros during May 2026 with 40 Reviews