Toll-Free1.855.295.9200

16

days

Charms of Cyclades

16 days

4.7 See Our Reviews
|

Our freedom packages provide the perfect balance between organization and independence. Airport transfers, high-quality accommodations, and more are included in all our trips. These packages allow you free time to explore each destination at your own pace while sparing you the headaches of planning.

16-day hassle-free Greek Island hopping package with flights! Discover Athens, Mykonos, Paros, and Santorini! Experience one of our most popular hassle-free package to Greece.

PACKAGE INCLUDES

  • international flights
  • welcome & transfers
  • hotels
  • breakfasts
  • fast ferries
High demand. We recommend booking at your earliest convenience to secure best rate and availability.
Make a request to receive details on flights, itinerary, price and more.
June 2026
Departure Date Return Date Starting rate    
Mon Jun 15 Tue Jun 30 $4,998/person
Departure
Mon Jun 15
Return
Tue Jun 30
$4,998/person

Fri Jun 19 Sat Jul 04 $6,198/person
Departure
Fri Jun 19
Return
Sat Jul 04
$6,198/person

Tue Jun 23 Wed Jul 08 $6,198/person
Departure
Tue Jun 23
Return
Wed Jul 08
$6,198/person

Sat Jun 27 Sun Jul 12 $6,498/person
Departure
Sat Jun 27
Return
Sun Jul 12
$6,498/person

July 2026
Departure Date Return Date Starting rate    
Wed Jul 01 Thu Jul 16 $5,998/person
Departure
Wed Jul 01
Return
Thu Jul 16
$5,998/person

Sun Jul 05 Mon Jul 20 $6,198/person
Departure
Sun Jul 05
Return
Mon Jul 20
$6,198/person

Thu Jul 09 Fri Jul 24 $5,998/person
Departure
Thu Jul 09
Return
Fri Jul 24
$5,998/person

Mon Jul 13 Tue Jul 28 $6,498/person
Departure
Mon Jul 13
Return
Tue Jul 28
$6,498/person

Fri Jul 17 Sat Aug 01 $7,298/person
Departure
Fri Jul 17
Return
Sat Aug 01
$7,298/person

Tue Jul 21 Wed Aug 05 $6,998/person
Departure
Tue Jul 21
Return
Wed Aug 05
$6,998/person

Sat Jul 25 Sun Aug 09 $7,298/person
Departure
Sat Jul 25
Return
Sun Aug 09
$7,298/person

Wed Jul 29 Thu Aug 13 $6,698/person
Departure
Wed Jul 29
Return
Thu Aug 13
$6,698/person

August 2026
Departure Date Return Date Starting rate    
Sun Aug 02 Mon Aug 17 $6,998/person
Departure
Sun Aug 02
Return
Mon Aug 17
$6,998/person

Thu Aug 06 Fri Aug 21 $6,398/person
Departure
Thu Aug 06
Return
Fri Aug 21
$6,398/person

Mon Aug 10 Tue Aug 25 $6,298/person
Departure
Mon Aug 10
Return
Tue Aug 25
$6,298/person

Fri Aug 14 Sat Aug 29 $5,998/person
Departure
Fri Aug 14
Return
Sat Aug 29
$5,998/person

Tue Aug 18 Wed Sep 02 $5,598/person
Departure
Tue Aug 18
Return
Wed Sep 02
$5,598/person

Sat Aug 22 Sun Sep 06 $5,998/person
Departure
Sat Aug 22
Return
Sun Sep 06
$5,998/person

Wed Aug 26 Thu Sep 10 $5,598/person
Departure
Wed Aug 26
Return
Thu Sep 10
$5,598/person

Sun Aug 30 Mon Sep 14 $5,798/person
Departure
Sun Aug 30
Return
Mon Sep 14
$5,798/person

September 2026
Departure Date Return Date Starting rate    
Thu Sep 03 Fri Sep 18 $5,598/person
Departure
Thu Sep 03
Return
Fri Sep 18
$5,598/person

Mon Sep 07 Tue Sep 22 $5,598/person
Departure
Mon Sep 07
Return
Tue Sep 22
$5,598/person

Fri Sep 11 Sat Sep 26 $5,998/person
Departure
Fri Sep 11
Return
Sat Sep 26
$5,998/person

Tue Sep 15 Wed Sep 30 $5,898/person
Departure
Tue Sep 15
Return
Wed Sep 30
$5,898/person

Sat Sep 19 Sun Oct 04 $5,998/person
Departure
Sat Sep 19
Return
Sun Oct 04
$5,998/person

Wed Sep 23 Thu Oct 08 $5,698/person
Departure
Wed Sep 23
Return
Thu Oct 08
$5,698/person

Sun Sep 27 Mon Oct 12 $5,698/person
Departure
Sun Sep 27
Return
Mon Oct 12
$5,698/person

October 2026
Departure Date Return Date Starting rate    
Thu Oct 01 Fri Oct 16 $4,998/person
Departure
Thu Oct 01
Return
Fri Oct 16
$4,998/person

Mon Oct 05 Tue Oct 20 $4,498/person
Departure
Mon Oct 05
Return
Tue Oct 20
$4,498/person

Fri Oct 09 Sat Oct 24 $4,498/person
Departure
Fri Oct 09
Return
Sat Oct 24
$4,498/person

Tue Oct 13 Wed Oct 28 $4,798/person
Departure
Tue Oct 13
Return
Wed Oct 28
$4,798/person

April 2027
Departure Date Return Date Starting rate    
Tue Apr 20 Wed May 05 $4,498/person
Departure
Tue Apr 20
Return
Wed May 05
$4,498/person

Sat Apr 24 Sun May 09 $4,598/person
Departure
Sat Apr 24
Return
Sun May 09
$4,598/person

Wed Apr 28 Thu May 13 $4,598/person
Departure
Wed Apr 28
Return
Thu May 13
$4,598/person

May 2027
Departure Date Return Date Starting rate    
Sun May 02 Mon May 17 $4,398/person
Departure
Sun May 02
Return
Mon May 17
$4,398/person

Thu May 06 Fri May 21 $4,498/person
Departure
Thu May 06
Return
Fri May 21
$4,498/person

Mon May 10 Tue May 25 $5,398/person
Departure
Mon May 10
Return
Tue May 25
$5,398/person

Fri May 14 Sat May 29 $5,498/person
Departure
Fri May 14
Return
Sat May 29
$5,498/person

Tue May 18 Wed Jun 02 $5,598/person
Departure
Tue May 18
Return
Wed Jun 02
$5,598/person

Sat May 22 Sun Jun 06 $5,598/person
Departure
Sat May 22
Return
Sun Jun 06
$5,598/person

Wed May 26 Thu Jun 10 $5,598/person
Departure
Wed May 26
Return
Thu Jun 10
$5,598/person

Sun May 30 Mon Jun 14 $5,598/person
Departure
Sun May 30
Return
Mon Jun 14
$5,598/person

June 2027
Departure Date Return Date Starting rate    
Thu Jun 03 Fri Jun 18 $5,598/person
Departure
Thu Jun 03
Return
Fri Jun 18
$5,598/person

Mon Jun 07 Tue Jun 22 $5,698/person
Departure
Mon Jun 07
Return
Tue Jun 22
$5,698/person

Fri Jun 11 Sat Jun 26 $5,898/person
Departure
Fri Jun 11
Return
Sat Jun 26
$5,898/person

Tue Jun 15 Wed Jun 30 $5,998/person
Departure
Tue Jun 15
Return
Wed Jun 30
$5,998/person

Sat Jun 19 Sun Jul 04 $6,198/person
Departure
Sat Jun 19
Return
Sun Jul 04
$6,198/person

Wed Jun 23 Thu Jul 08 $6,298/person
Departure
Wed Jun 23
Return
Thu Jul 08
$6,298/person

Sun Jun 27 Mon Jul 12 $6,298/person
Departure
Sun Jun 27
Return
Mon Jul 12
$6,298/person

July 2027
Departure Date Return Date Starting rate    
Thu Jul 01 Fri Jul 16 $6,298/person
Departure
Thu Jul 01
Return
Fri Jul 16
$6,298/person

Mon Jul 05 Tue Jul 20 $6,398/person
Departure
Mon Jul 05
Return
Tue Jul 20
$6,398/person

Fri Jul 09 Sat Jul 24 $6,598/person
Departure
Fri Jul 09
Return
Sat Jul 24
$6,598/person

Tue Jul 13 Wed Jul 28 $6,798/person
Departure
Tue Jul 13
Return
Wed Jul 28
$6,798/person

Sat Jul 17 Sun Aug 01 $6,998/person
Departure
Sat Jul 17
Return
Sun Aug 01
$6,998/person

Wed Jul 21 Thu Aug 05 $6,998/person
Departure
Wed Jul 21
Return
Thu Aug 05
$6,998/person

Sun Jul 25 Mon Aug 09 $6,998/person
Departure
Sun Jul 25
Return
Mon Aug 09
$6,998/person

Thu Jul 29 Fri Aug 13 $6,998/person
Departure
Thu Jul 29
Return
Fri Aug 13
$6,998/person

August 2027
Departure Date Return Date Starting rate    
Mon Aug 02 Tue Aug 17 $6,998/person
Departure
Mon Aug 02
Return
Tue Aug 17
$6,998/person

Fri Aug 06 Sat Aug 21 $6,998/person
Departure
Fri Aug 06
Return
Sat Aug 21
$6,998/person

Tue Aug 10 Wed Aug 25 $6,998/person
Departure
Tue Aug 10
Return
Wed Aug 25
$6,998/person

Sat Aug 14 Sun Aug 29 $6,798/person
Departure
Sat Aug 14
Return
Sun Aug 29
$6,798/person

Wed Aug 18 Thu Sep 02 $6,598/person
Departure
Wed Aug 18
Return
Thu Sep 02
$6,598/person

Sun Aug 22 Mon Sep 06 $6,398/person
Departure
Sun Aug 22
Return
Mon Sep 06
$6,398/person

Thu Aug 26 Fri Sep 10 $6,298/person
Departure
Thu Aug 26
Return
Fri Sep 10
$6,298/person

Mon Aug 30 Tue Sep 14 $6,298/person
Departure
Mon Aug 30
Return
Tue Sep 14
$6,298/person

September 2027
Departure Date Return Date Starting rate    
Fri Sep 03 Sat Sep 18 $6,298/person
Departure
Fri Sep 03
Return
Sat Sep 18
$6,298/person

Tue Sep 07 Wed Sep 22 $6,198/person
Departure
Tue Sep 07
Return
Wed Sep 22
$6,198/person

Looking for a Date in the Future?

Add your email to be notified when new dates open up.

Subscribe to new dates Alerts for Charms of the Cyclades

You will receive an email when new dates are added for this package. You can unsubscribe from this email any time.

*The advertised starting rate is available from Toronto on Oct 2026
**All prices are subject to change without notice

FAQ

Reviews

4.7  (32)
STARTING AT:
CAD $4,098 *
PER PERSON/TAXES INCL
See Dates and Prices
See Dates and Prices
Pay in two installments of $2,049

New Agency

Thank you, we will contact you shortly

Representative Name

It seems that you are visiting us from the US. Would you like to be redirected to the American version of wingbuddy?

Subscribe to our newsletter

Subscribe to our newsletter

And receive exclusive deals and discounts