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10 best Cyclades trips in May 2026
Paros and Naxos 7 Days
5.0 (1 traveler review)"The hotels were very nice. All information was communicated in a timely manner and in detail."
- Duration
- 7 days
- Destinations
- Paros, Antiparos, Despotiko Island, Náousa, Naxos, Eggares,Ano Koufonisi Island+1 more
- Age Range
- Ages 18+
- Islands
- Greek IslandsCyclades Greece+1 more
- Operated in
- English
- Operator
- Oxygen Tours
- From
- US$1,048per person
Price based on Private Double Room1 May, 202610 spaces left2 May, 202610 spaces left
IREMIA | Athens, Naxos and Santorini (+sightseeing in Athens, ferries and flight)
5.0 (3 traveler reviews)"Really great Service and atenttion from greca team."
- Duration
- 7 days
- Destinations
- Athens, Naxos, Santorini
- Age Range
- All Ages Welcome
- Islands
- Greek IslandsAegean IslandsCyclades Greece+2 more
- Operated in
- English
- Operator
- Greca
- From
- US$1,548per person
Price based on Private Double Room1 May, 202610+ spaces left2 May, 202610+ spaces left
Island Hopping Greek Islands Delights: Mykonos, Paros, Santorini
4.3 (3 traveler reviews)"The hotels were lovely, the breakfasts were incredible. We would love to go back to Greece, this trip is a must!"
- Duration
- 8 days
- Destinations
- Mykonos, Paros, Marpissa, Prodromos, Lefkes, Santorini, Oia,Akrotiri,Thirasia+2 more
- Age Range
- All Ages Welcome
- Islands
- Greek IslandsAegean IslandsCyclades Greece+2 more
- Operated in
- English
- Operator
- Destination Services Greece
10% Off- From $992
- US$893per person
Price based on Private Double Room4 May, 202610 spaces left5 May, 202610 spaces left
10-Day Island Honeymoon Adventure: Mykonos, Santorini, Crete & Athens
4.0 (1 traveler review)"The vacation was set up well and we highly enjoyed it."
- Duration
- 10 days
- Destinations
- Athens, Mykonos, Santorini, Crete
- Age Range
- All Ages Welcome
- Islands
- Greek Islands
- Operated in
- English
- Operator
- Private Tours Greece
25% Off- From $4,037
- US$3,028per person
Price based on Private Double Room1 May, 202610 spaces left2 May, 202610 spaces left
Mykonos & Santorini Tour - 5 Days - Premium
4.8 (25 traveler reviews)"Each island had its unique charm. The ferry transfers were seamless and the accommodation was top notch."
- Duration
- 5 days
- Destinations
- Athens, Mykonos, Santorini
- Age Range
- All Ages Welcome
- Regions
- Greek IslandsAegean IslandsCyclades GreeceMykonosAthens Santorini & Mykonos+4 more
- Operated in
- English, Spanish
- Operator
- Travel Zone
25% Off- From $2,208
- US$1,656per person
Price based on Private Double Room2 May, 202610+ spaces left3 May, 202610+ spaces left
2 Greek Islands Tour - 5 Days - Paros & Santorini - Premium
4.8 (45 traveler reviews)"Great people. Great views. Great food."
- Duration
- 5 days
- Destinations
- Athens, Paros, Santorini
- Age Range
- All Ages Welcome
- Islands
- Greek IslandsAegean IslandsCyclades Greece+2 more
- Operated in
- English
- Operator
- Travel Zone
25% Off- From $2,100
- US$1,575per person
Price based on Private Double Room2 May, 202610 spaces left3 May, 202610 spaces left
Paros, Naxos, Santorini & Milos with Guided Tours - Premium
4.3 (3 traveler reviews)"The trip was perfect. 9 days between the islands with all hotels and tours booked."
- Duration
- 9 days
- Destinations
- Athens, Paros, Antiparos, Naxos, Santorini, Milos
- Age Range
- All Ages Welcome
- Islands
- Greek IslandsAegean IslandsCyclades Greece+2 more
- Operated in
- English
- Operator
- Travel Zone
15% Off- From $4,074
- US$3,463per person
Price based on Private Double Room2 May, 202610+ spaces left3 May, 202610+ spaces left
Greek Island Dream Paros, Naxos & Santorini- 7 Days (Self-Guided Package)
5.0 (8 traveler reviews)"The hotels were comfortable and clean."
- Duration
- 7 days
- Destinations
- Athens, Paros, Naxos, Santorini
- Age Range
- All Ages Welcome
- Islands
- Greek IslandsAegean IslandsCyclades Greece+2 more
- Operated in
- English
- Operator
- Travel Zone
25% Off- From $2,196
- US$1,647per person
Price based on Private Double Room2 May, 202610+ spaces left3 May, 202610+ spaces left
Santorini, Paros & Naxos Islands with Guided Tours - Premium
4.3 (14 traveler reviews)"Service has been stellar along with the magnificent locations. Greatly recommended."
- Duration
- 7 days
- Destinations
- Athens, Paros, Naxos, Santorini
- Age Range
- All Ages Welcome
- Islands
- Greek IslandsAegean IslandsCyclades Greece+2 more
- Operated in
- English
- Operator
- Travel Zone
25% Off- From $2,935
- US$2,201per person
Price based on Private Double Room2 May, 202610+ spaces left3 May, 202610+ spaces left
Mykonos & Santorini Experience - Premium
4.7 (3 traveler reviews)"Expectations was great. Hotel selection was excellent especially in Santorini."
- Duration
- 5 days
- Destinations
- Athens, Mykonos, Delos, Santorini
- Age Range
- All Ages Welcome
- Regions
- Greek IslandsAegean IslandsCyclades GreeceMykonosAthens Santorini & Mykonos+4 more
- Operated in
- English
- Operator
- Travel Zone
25% Off- From $2,677
- US$2,008per person
Price based on Private Double Room2 May, 202610+ spaces left3 May, 202610+ spaces left
Greek Island Hopping | Semi guided Tour | 11 Days
4.7 (127 traveler reviews)"Communication was excellent and the itinerary was well balanced. Highly recommended!"
- Duration
- 11 days
- Destinations
- Athens, Mykonos, Paros, Naxos, Santorini
- Age Range
- All Ages Welcome
- Islands
- Greek IslandsAegean IslandsCyclades Greece+2 more
- Operated in
- English
- Operator
- Travel Zone
25% Off- From $2,918
- US$2,189per person
Price based on Private Double Room1 May, 202610+ spaces left2 May, 202610+ spaces left
Cultural Athens & Island Hopping Mykonos - Santorini (Self-guided)
4.6 (97 traveler reviews)"The hotels were charming boutiques and in excellent locations. We all agreed our holiday was perfect."
- Duration
- 7 days
- Destinations
- Athens, Mykonos, Santorini
- Age Range
- All Ages Welcome
- Regions
- Greek IslandsAegean IslandsCyclades GreeceMykonosAthens Santorini & Mykonos+4 more
- Operated in
- English, German,French,Dutch+2 more
- Operator
- Dot Travel
10% Off- From $1,165
- US$1,049per person
Price based on Private Double Room1 May, 202610+ spaces left2 May, 202610+ spaces left
Athens, Santorini & Mykonos Tour - 7 Days -
4.8 (25 traveler reviews)"The beauty of Santorini was spectacular. The tour was well organized and all the assistants and drivers very polite."
- Duration
- 7 days
- Destinations
- Athens, Mykonos, Santorini
- Age Range
- All Ages Welcome
- Regions
- Greek IslandsAegean IslandsCyclades GreeceMykonosAthens Santorini & Mykonos+4 more
- Operated in
- English, Spanish
- Operator
- Travel Zone
25% Off- From $2,295
- US$1,722per person
Price based on Private Double Room1 May, 202610+ spaces left2 May, 202610+ spaces left
Sailing Greece - Mykonos to Santorini
4.6 (54 traveler reviews)"Loved the route and flexibility to customize."
- Duration
- 8 days
- Destinations
- Mykonos, Naxos, Paros, Antiparos, Ios, Sifnos, Folegandros,Santorini+1 more
- Age Range
- Ages 18+
- Ship
- G Adventures Sailing Yacht
- Islands
- Greek IslandsAegean IslandsCyclades Greece+2 more
- Operated in
- English
- Operator
- G Adventures
50% Off- From $1,899
- US$950per person
Price based on Private Double Room2 May, 20262 spaces left23 May, 20262 spaces left
Greek Island Hopping (Standard)
4.8 (812 traveler reviews)"If your thinking about going do it! You won't regret it."
- Duration
- 11 days
- Destinations
- Athens, Mykonos, Paros, Santorini, Ios
- Age Range
- Ages 18-35
- Islands
- Greek IslandsAegean IslandsCyclades Greece+2 more
- Operated in
- English
- Operator
- Contiki
10% Off- From $1,825
- US$1,643per person
Price based on Shared Room2 May, 20261 space left4 May, 20268 spaces left
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Joachim
Expert in Cyclades at TourRadar
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