Cyclades Islands Vacation Packages 2026 from $1,767

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Your Cyclades Islands Vacation

Make organizing your next great adventure easy with a Cyclades Islands vacation package. If it's culture, gift and craft shops and views you're searching for, you won't be disappointed. Start your trip to Cyclades Islands with some time in Oia visiting popular sights like Kamari Beach and Santorini Caldera. Platis Gialos is another top city that lures crowds from near and far. Ornos Beach and Paradise Beach are two of the top places to see in this destination. Start packing your suitcase, because your Cyclades Islands vacation is just clicks away with Expedia.

The Latest Cyclades Islands vacation packages

Price found within the past 48 hours. Click for updated prices.

Million Stars Mykonos

Save 100% on your flight

$1,767

per person

Oct 14 - Oct 20

found 16 hours ago

Roundtrip non-stop flight included

New York (NYC) to Mykonos (JMK)

10/10 Exceptional! (4 reviews)

Grand Ambassador Santorini Hotel

Save 100% on your flight

$2,732

per person

Oct 24 - Oct 28

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Thira (JTR)

9.4/10 Exceptional! (256 reviews)

Phōs The Boutique Luxury Hotel & Villas

Save 100% on your flight

$3,020

per person

Oct 7 - Oct 13

found 23 hours ago

Roundtrip non-stop flight included

Boston (BOS) to Thira (JTR)

9.6/10 Exceptional! (40 reviews)

5 stars! Great spot in Santorini with an amazing view!

Reviewed on Jun 11, 2026

Art Maisons Oia Castle

Save 100% on your flight

$2,147

per person

Oct 26 - Oct 31

found 1 day ago

Roundtrip non-stop flight included

Newark Liberty Intl. Airport (EWR) to Thira (JTR)

9.6/10 Exceptional! (123 reviews)

Everything was amazing!

Reviewed on Jul 27, 2026

Santorini Princess Presidential Suites

Save 100% on your flight

$1,779

per person

Oct 14 - Oct 19

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Thira (JTR)

10/10 Exceptional! (71 reviews)

The property, service and food were amazing! Highly recommend.

Reviewed on Jul 3, 2026

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Where to stay in Cyclades Islands

Find the best Cyclades Islands areas and neighborhoods for the activities you enjoy most. Learn more about Cyclades Islands

A coastal town with white buildings, a dock, and a boat.

Adamas

Adamas is known for its waterfront views, and you can plan a trip to Papikinou Beach and Adamas Port while you're in town.

A densely packed white village with terraced buildings on a hillside.

Old Town Naxos

1 out of top 10 points of interest in this area

The pristine beaches and captivating waterfront views are top of the list for many visitors to Old Town Naxos. A stop by Port of Naxos or Naxos Kastro might round out your trip.

A coastal village with white buildings, a prominent mountain, and a clear blue sky.

Plaka

The beaches and restaurants are a few reasons travelers visit Plaka. Though there aren't many top sights in the neighborhood, you can visit Catacombs of Milos and Plathiena Beach, a few notable attractions nearby.

A coastal landscape with white cliffs and the ocean.

Apollonia

Unique features of Apollonia include the beaches and restaurants. Make a stop by Pollonia Beach or Pollonia Dock while you're exploring the area.

A calm sea with a clear sky and a hilly landscape in the distance.

Tripití

Tripití is popular for its waterfront views, and you can check out Milos Folk and History Museum, a top attraction in the neighborhood.

Stay near popular Cyclades Islands attractions

A marina with numerous yachts docked, a large cruise ship, and a coastal town with white buildings.

Mykonos New Port

8.8/10 (3,440 reviews)

Explore the waterfront in Tourlos with a trip to Mykonos New Port. Wander the beautiful beaches and seaside in the area.

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A coastal road with a steep drop-off, a clear blue sea, and rocky cliffs.

Athinios Port

8.4/10 (4,035 reviews)

Explore the waterfront of Athinios Port and enjoy activities such as boating in Órmos Athiniós. Stroll along the beautiful beaches or discover the area's beautiful sunsets.

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A pebbled beach with sun loungers and thatched umbrellas.

Kamari Beach

9.0/10 (3,927 reviews)

Nothing says vacation like spending a lazy day at Kamari Beach, a popular beach in Santorini. Wander the seaside or discover the area's volcano viewpoints.

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A coastal view with waves crashing onto the shore and a distant shoreline with buildings.

Port of Naxos

9.0/10 (1,141 reviews)

Explore the waterfront in Naxos Town with a trip to Port of Naxos. Wander the beautiful beaches and waterfront in this quaint area.

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A coastal town with white buildings, a harbor with boats, and a stone wall.

Port of Parikia

9.0/10 (825 reviews)

Explore the waterfront in Parikia with a trip to Port of Parikia. Wander the beautiful beaches and waterfront in this quaint area.

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A coastal town with white buildings, a beach, and boats in the water.

Ornos Beach

9.0/10 (1,946 reviews)

Nothing says vacation like spending a lazy day at Ornos Beach, a popular beach in Ornos. While in this romantic area, you can savor the top-notch restaurants.

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A coastal town with white buildings, a pier, and clear blue waters.

Mykonos Old Port

9.2/10 (3,631 reviews)

Explore the waterfront in Mykonos Town with a trip to Mykonos Old Port. Stroll along the area's waterfront or simply enjoy its restaurants.

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Cyclades Islands Hotel Deals

Santorini Palace

Fira town Santorini Santorini Island

$144 nightly

$175 total

Sep 5 - Sep 6

Total with taxes and fees

9/10 Wonderful! (810 reviews)

"Everything was very good, nothing to complain about."

Reviewed on Aug 21, 2026

Cresanto Luxury Suites

Imerovigli Santorini

$263 nightly

$316 total

Sep 6 - Sep 7

Total with taxes and fees

9.6/10 Exceptional! (431 reviews)

"Excellent experience that started as soon as we got there. Attentive service, incredible facilities, perfectly clean, and great location that's close enough to Imerovigli for anything you need but just separated enough for the hotel to feel like its own community. If I went back to Santorini I would ..."

Reviewed on Aug 23, 2026

DIAMOND on the cliff Hotel &Suites

imerovigli 1 Santorini Cyclades

$361 nightly

$412 total

Sep 14 - Sep 15

Total with taxes and fees

8.4/10 Very Good! (20 reviews)

"This property was in the perfect spot with amazing views of Skaros rock. Many restaurants nearby and only about a 15 minute walk to Fira. Staff was very friendly and helpful. Only slight negative is that parts of the room are very low so if you’re taller then 6 feet you may find yourself hitting ..."

Reviewed on Aug 17, 2026

See all 14,926 properties in Cyclades Islands

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Find the Best Cyclades Islands Vacation Packages

Things to do near Cyclades Islands

The Cyclades Islands offer an ideal getaway for beach lovers, culture enthusiasts, and couples seeking romance. Enjoy stunning sunsets and embark on sailing trips to explore the beautiful waters. Don't miss the chance to join sightseeing tours and embrace the unique Cycladic adventure that awaits you. With plenty of options for beach vacations and sailing tours, the Cyclades promise an unforgettable experience filled with relaxation and exploration.

Shopping

Discover the charm of Old Market Street, a vibrant shopping area located 21 miles from the Cyclades Islands. Enjoy a mix of local boutiques and artisanal shops, perfect for finding unique gifts and souvenirs that capture the essence of Greek culture.

Recreation

Experience the soothing waters at Paros Fish Therapy, where you’ll unwind as tiny fish gently exfoliate your skin. For a dose of culture, visit the Odysseas Elytis Theatre, where you can enjoy captivating performances in a romantic setting, perfect for families and couples alike.

Adventure

Aqua Paros Water Park, located 15 miles from Cyclades Islands, offers thrilling slides and family-friendly fun, ensuring a day packed with excitement. Similarly, Aqua Fun Water Park, situated 19 miles away, promises wave pools and adventure activities perfect for all ages, creating unforgettable memories in the sun.

Nightlife

The Cyclades Islands offer vibrant nightlife, especially in Mykonos, where you can dance at iconic clubs like Cavo Paradiso. For a more laid-back vibe, Santorini's bars, such as the trendy Koo Club, provide stunning sunset views and cocktails. Enjoy a memorable evening under the stars.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Find the best attractions near Cyclades Islands

The Cyclades Islands in Greece are perfect for beach, culture, and romantic getaways. Visitors can explore beautiful beaches, nudist spots, and charming harbors. Key highlights include the vibrant Mykonos Island and the serene Syros Island, offering a mix of relaxation and cultural experiences. Whether you seek sun-soaked shores or rich history, the Cyclades cater to every traveler’s desire for an unforgettable vacation.

Agios Nikolaos Beach: Experience the perfect beach vibes at Agios Nikolaos Beach, just 6 miles from Cyclades Islands. Relax on the soft sands, swim in the crystal-clear waters, and soak up the sun while enjoying stunning views of the Aegean Sea.
Cave of Antiparos: Venture 2 miles away to the Cave of Antiparos, an adventurous destination filled with impressive stalactites and stalagmites. Explore the mystical underground chambers and feel the thrill of discovery in this natural wonder.
Butterfly Valley: Located 7 miles from Cyclades Islands, Butterfly Valley is a serene nature reserve where you can witness thousands of butterflies during the summer months. Stroll along the peaceful trails and enjoy the vibrant flora and fauna.

Best time to go to Cyclades Islands

The best time to visit Cyclades Islands is dependent on what kind of holiday you are seeking. August is its hottest month on average. At this time, visitor numbers are high and weather is sunny with no rain. January is its coolest month on average. At this time, visitor numbers are low and weather is mostly sunny with light rain.

Calendar Month	Temperature	Precipitation	Cloudiness	Occupancy	Pricing
January	54.3°F (12.4°C)	Light Rain	Mostly Sunny	Low	Moderately Low
February	54.7°F (12.6°C)	Light Rain	Mostly Sunny	Low	Moderately Low
March	56.1°F (13.4°C)	No Rain	Mostly Sunny	Average	Average
April	59.9°F (15.5°C)	No Rain	Sunny	Average	Average
May	65.8°F (18.8°C)	No Rain	Sunny	Average	Average
June	72.5°F (22.5°C)	No Rain	Sunny	Average	Moderately High
July	76.6°F (24.8°C)	No Rain	Sunny	High	Moderately High
August	77.4°F (25.200000000000003°C)	No Rain	Sunny	High	Moderately High
September	73.6°F (23.1°C)	No Rain	Sunny	High	Average
October	67.6°F (19.8°C)	No Rain	Sunny	Average	Average
November	62.8°F (17.1°C)	No Rain	Mostly Sunny	Average	Average
December	57.6°F (14.2°C)	Light Rain	Mostly Sunny	Low	Moderately Low

Tips to save on your trip to Cyclades Islands

Combine your flights, hotels and car rentals on Expedia—bundling can result in significant savings.
Consider traveling during the off-peak season (typically December to February) for more affordable package holidays to Cyclades Islands.
Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.