Greek Islands Tours & Trips in May 2025
137 tour packages in Greek Islands in May 2025
Greek Island Explorer (10 Days)
Greek Island Explorer (10 Days)We had a very good time and had a wonderful tour agent to help us all the way. She went above the call of duty every day for us all. The only event that was beyond the control of Tour Radar is the hotel in Mykonos which considered a lower level room as a 50 Euro upgrade for seniors and persons with disabilities. They preferred to leave those rooms vacant than allow them at the same rate.
- Destinations
- Athens, Santorini, Mykonos+1 more
- Age Range
- up to 80 year olds
- Regions
- Greek Islands, Aegean Islands, Cyclades Greece, Mykonos, Athens Santorini & Mykonos+4 more
- Operated in
- English
- Operator
- Costsaver This operator has high review ratings and responds promptly to enquiries
10% Off- Duration
- 10 days
- Price per day
- $279
- From $3,095
- US$2,786You save $309
3 May, 202510+ spaces left6 May, 202510 spaces left
Sailing Greece - Mykonos to Santorini
Sailing Greece - Mykonos to SantoriniLoved this sailing adventure and plan to do another one in the near future. The Captain Marius was excellent with a wealth of knowledge in all aspects of sailing and taking care of his passengers. Our group gelled well and we all had fun swimming, eating on board and going out to dinner and playing cards. I would definitely do this adventure again
- Destinations
- Mykonos, Naxos, Paros, Antiparos, Ios, Sifnos, Folegandros, Santorini+5 more
- Age Range
- 16 to 70 year olds
- Ship
- G Adventures Sailing Yacht
- Regions
- Greek Islands, Aegean Islands, Cyclades Greece, Athens Santorini & Mykonos+3 more
- Operated in
- English
- Operator
- G Adventures This operator has the highest review ratings and fastest responses to enquiries
40% Off- Duration
- 8 days
- Price per day
- $126
- From $1,679
- US$1,007You save $671
10 May, 20257 spaces left
Charms of the Cyclades
Charms of the CycladesGoing in, we give Wingbuddy extra points for customizing their packages to meet the clients wishes. Since this was the first trip booked through Wingbuddy, it was unknown how reliable they are, but coming out of this experience, I would say that we are very pleased. All the transfers were handled seamlessly. The drivers were always prompt, friendly and helpful. The accommodations were just fine. We came to realize that this company oversees your trip in the background to ensure that everything runs smoothly for you. We recommend them to others and would book again with Wingbuddy.
- Destinations
- Athens, Mykonos, Paros, Santorini+2 more
- Age Range
- 1 to 99 year olds
- Regions
- Greek Islands, Aegean Islands, Cyclades Greece, Athens Santorini & Mykonos+3 more
- Operated in
- English
- Operator
- Wingbuddy This operator has high review ratings and responds promptly to enquiries
40% Off- Duration
- 15 days
- Price per day
- $132
- From
- US$1,979
2 May, 202510+ spaces left5 May, 202510+ spaces left
Bewitching Greece with All Inclusive beach stay
Bewitching Greece with All Inclusive beach stayThe best part of the tour was the communication with Rose, Wendy, Sam and Alberto. The promptness, clarity and helpfulness in their communication was impressive. Their role in organising transport etc was commendable. Many good wishes for their good work! My suggestions for some other aspects: 1. If a person opts for a group tour, at least inform them in advance that it will be not be a group tour if it so happens, rather than leaving it to them to discover when they find themselves alone on reaching the destination. 2. Select your hotels carefully keeping in mind that your customers are paying you money to have an enjoyable tour experience that a tourist looks for. If you give a hotel which is located at a completely secluded place and does not offer even the basic facilities, it spoils a tourist's experience to a large extent. 3. Prepare a standard guiding document for your various tours, like many good tour companies do. This type of document includes helpful suggestions on what to expect, what to pack, what kind of weather, what precautions to take, currency suggestions, location and shopping scenarios etc. If you have a ready and comprehensive document like this, you can share it with all your customers for a particular tour well in time. This will avoid their having to ask many questions individually. Good luck. Madhavi
- Destinations
- Athens, Oia, Santorini, Crete+2 more
- Age Range
- up to 99 year olds
- Regions
- Greek Islands, Aegean Islands, Cyclades Greece, Santorini, Athens Santorini & Mykonos+4 more
- Operated in
- English
- Operator
- Wanderful Holidays LLC This operator has good review ratings and responds to all enquiries
40% Off- Duration
- 9 days
- Price per day
- $255
- From
- US$2,299
3 May, 202510 spaces left4 May, 202510 spaces left
Greek Island Hopper (10 Days)
Greek Island Hopper (10 Days)3 days in each location gave us time to explore the area, culture and people . We had plenty of time for shopping, dining, checking out local places of interest at our own pace
- Destinations
- Athens, Santorini, Mykonos+1 more
- Age Range
- up to 99 year olds
- Regions
- Greek Islands, Aegean Islands, Cyclades Greece, Mykonos, Athens Santorini & Mykonos+4 more
- Operated in
- English
- Operator
- Trafalgar This operator has the highest review ratings and fastest responses to enquiries
10% Off- Duration
- 10 days
- Price per day
- $441
- From $4,895
- US$4,406You save $489
3 May, 202510+ spaces left6 May, 202510 spaces left
Sailing Greece - Santorini to Santorini
Sailing Greece - Santorini to SantoriniOur Captain Martin is superb.
- Destinations
- Santorini, Ios, Naxos, Mykonos, Syros, Paros, Sifnos, Folegandros+5 more
- Age Range
- 16 to 70 year olds
- Ship
- G Adventures Sailing Yacht
- Regions
- Greek Islands, Aegean Islands, Cyclades Greece, Athens Santorini & Mykonos+3 more
- Operated in
- English
- Operator
- G Adventures This operator has the highest review ratings and fastest responses to enquiries
20% Off- Duration
- 10 days
- Price per day
- $172
- From $2,149
- US$1,719You save $429
3 May, 20258 spaces left13 May, 20258 spaces left
Authentic Greek Islands
Authentic Greek IslandsWe did the Greek Island hopping vacation in June 2022. It was the best experience ever. We were completely looked after for transportation (air, land and ferry) and accommodations. It couldn’t possibly have been better organized and I will travel with Wingbuddy again. We are looking at the South Africa tour right now.
- Destinations
- Athens, Paros, Naxos, Santorini+1 more
- Age Range
- 1 to 99 year olds
- Regions
- Greek Islands, Aegean Islands, Cyclades Greece, Athens Santorini & Mykonos+3 more
- Operated in
- English
- Operator
- Wingbuddy This operator has high review ratings and responds promptly to enquiries
20% Off- Duration
- 15 days
- Price per day
- $117
- From
- US$1,749
2 May, 202510+ spaces left5 May, 202510+ spaces left
Best of Greece
Best of GreeceOutstanding Service! Excellent communication throughout the process, from booking to final checkout. Even in the single instance when weather did not cooperate and forced to cancel a sailing activity, the team helped finding and booking a good alternative. Great hotels and highly professional local services. Perfect if you are looking for a fun, stress-free, fully organized vacation. Beats the crazy self-planning/booking/coordination hassle many times over.
- Destinations
- Athens, Mykonos, Santorini+1 more
- Age Range
- up to 99 year olds
- Regions
- Greek Islands, Aegean Islands, Cyclades Greece, Mykonos, Athens Santorini & Mykonos+4 more
- Operated in
- English
- Operator
- Wanderful Holidays LLC This operator has good review ratings and responds to all enquiries
20% Off- Duration
- 9 days
- Price per day
- $200
- From
- US$1,799
3 May, 202510 spaces left8 May, 202510 spaces left
Athens to Santorini
Athens to SantoriniA well organised fun tour that gave a great overview of the different islands ( and types of ferry transport. Our tour guide was excellent. Highly recommended.
- Destinations
- Athens, Syros, Mykonos, Santorini+2 more
- Age Range
- 15 to 99 year olds
- Regions
- Greek Islands, Aegean Islands, Cyclades Greece, Mykonos, Athens Santorini & Mykonos+4 more
- Operated in
- English
- Operator
- Intrepid Travel This operator has the highest review ratings and fastest responses to enquiries
20% Off- Duration
- 8 days
- Price per day
- $305
- From $3,050
- US$2,440You save $610
3 May, 202510+ spaces left5 May, 202510+ spaces left
Greece Sailing Adventure: Cyclades Islands
Greece Sailing Adventure: Cyclades IslandsMy daughter and I just got back from sailing around 9 greek islands starting in Santorini n finishing there. The whole experience was sensational and I highly recommend it. The group got on really well we had a blast of a time. The Skipper Antonios was totally awesome in assuring our safety n explaining the different parts of the yatch n he gave us an opportunity to sail the boat I totally loved sailing the boat what an experience it was. Ill never forget the deep blue sea i was mesmorised by the colour. Antonios did great job at telling us about the islands n where to catch the bus if we wanted n guided us in best way possible. I loved everything about this holiday the only downfall was how tiny the cabins were pretty tight n squishy but we survived, we were there for 3wks but it felt like 3 months in a fantabulous way. Will definately do it again 1 day. Love love loved it. Cat and Bonnie xo
- Destinations
- Santorini, Ios, Amorgos, Cyclades, Naxos, Syros, Mykonos, Sifnos, Folegandros+7 more
- Age Range
- 15 to 99 year olds
- Regions
- Greek Islands, Aegean Islands, Cyclades Greece, Athens Santorini & Mykonos+3 more
- Operated in
- English
- Operator
- Intrepid Travel This operator has the highest review ratings and fastest responses to enquiries
20% Off- Duration
- 10 days
- Price per day
- $199
- From $2,490
- US$1,992+$121 local paymentsYou save $498
3 May, 202510+ spaces left13 May, 20258 spaces left
Best of Greece (15 days) Athens & 4 Islands in 15 days (Self-Guided)
Best of Greece (15 days) Athens & 4 Islands in 15 days (Self-Guided)We have never experinced this kind of tour. It was spot one. Every detail was well thoughtout and executed with precision. It was remarkable. I highly recommend TourRadar for a remarlable travel experience. Marilyn and Elizabeth
- Destinations
- Athens, Syros, Mykonos, Santorini, Crete+3 more
- Age Range
- 12 to 99 year olds
- Regions
- Greek Islands, Aegean Islands, Cyclades Greece, Athens Santorini & Mykonos+3 more
- Operated in
- English, German, French, Dutch+3 more
- Operator
- Dot Travel This operator has high review ratings and responds promptly to enquiries
25% Off- Duration
- 15 days
- Price per day
- $110
- From $2,200
- US$1,650You save $550
1 May, 202510+ spaces left2 May, 202510+ spaces left
Cultural Athens & Island Hopping Mykonos - Santorini (Self-guided)
Cultural Athens & Island Hopping Mykonos - Santorini (Self-guided)I’ll pick ups were on time. All accommodations were beautiful and everyone was friendly. I will do this again
- Destinations
- Athens, Mykonos, Santorini+1 more
- Age Range
- 1 to 99 year olds
- Regions
- Greek Islands, Aegean Islands, Cyclades Greece, Mykonos, Athens Santorini & Mykonos+4 more
- Operated in
- English, German, French, Dutch+3 more
- Operator
- Dot Travel This operator has high review ratings and responds promptly to enquiries
16% Off- Duration
- 7 days
- Price per day
- $131
- From $1,094
- US$920You save $175
1 May, 202510+ spaces left2 May, 202510+ spaces left
Greek Island Hopping | SemiPrivate with 4* Hotels | 11 Days
Greek Island Hopping | SemiPrivate with 4* Hotels | 11 DaysThe arrangements were seamless and took all the hassle out of the trip so we could just relax and enjoy. Personal touch such as hand delivery of documents and attention to detail such as breakfast boxes for an early start, were special . All worth every penny
- Destinations
- Athens, Mykonos, Paros, Naxos, Santorini+3 more
- Age Range
- 1 to 99 year olds
- Regions
- Greek Islands, Aegean Islands, Cyclades Greece, Athens Santorini & Mykonos+3 more
- Operated in
- English
- Operator
- Travel Zone This operator has the highest review ratings and fastest responses to enquiries
25% Off- Duration
- 11 days
- Price per day
- $229
- From $3,351
- US$2,514You save $837
1 May, 202510+ spaces left2 May, 202510+ spaces left
Sail Greece: Santorini to Mykonos
Sail Greece: Santorini to MykonosWe had a great time meeting lots of new friends who all got on from many nationalities. At a restaurant one evening another group asked if we were a family which is how we ended up but without the disputes! Our skipper, Rita displayed wonderful leadership & sailing skills telling many interesting stories. Twice we has difficult dockings in strong crosswinds & other boats were messing it up big time but Rita nailed it both times & I was informed she received applause at Mykonos from the people on the dock. She also spent lot of time producing a video of our trip that she gave to us all. If your other CEO’s are half as good as her you have a very good team. Please note that you may only use my first name publically for this review, Peter!
- Destinations
- Santorini, Ios, Cyclades, Amorgos, Naxos, Syros, Mykonos+5 more
- Age Range
- 15 to 99 year olds
- Regions
- Greek Islands, Aegean Islands, Cyclades Greece, Athens Santorini & Mykonos+3 more
- Operated in
- English
- Operator
- Intrepid Travel This operator has the highest review ratings and fastest responses to enquiries
30% Off- Duration
- 8 days
- Price per day
- $147
- From $1,680
- US$1,176+$110 local paymentsYou save $504
3 May, 202510+ spaces left13 May, 202510+ spaces left
Sailing Greece - Mykonos to Mykonos
Sailing Greece - Mykonos to MykonosWe had a wonderful time sailing through the Greek Isles! We were able to visit several islands, including some that larger ships can't get to. Our captain, Kristina, was terrific, and she even led us to some spots where we could jump off the boat and swim to a cave, snorkel over a wreck of a World War 1 German plane, and just a random swim in the Mediterranean. G Adventures was excellent and had our back when a couple of unforeseen issues occurred. It wasn't a luxurious trip because we lived on a sailboat instead of a cruise ship, but it was a great adventure!
- Destinations
- Mykonos, Syros, Paros, Folegandros, Santorini, Ios, Naxos+4 more
- Age Range
- 16 to 70 year olds
- Ship
- G Adventures Sailing Yacht
- Regions
- Greek Islands, Aegean Islands, Cyclades Greece, Athens Santorini & Mykonos+3 more
- Operated in
- English
- Operator
- G Adventures This operator has the highest review ratings and fastest responses to enquiries
50% Off- Duration
- 10 days
- Price per day
- $107
- From $2,149
- US$1,075You save $1,074
3 May, 20258 spaces left13 May, 20258 spaces left
What people love about Greek Islands Tours in May
- Greek Island Explorer (10 Days)
We had a very good time and had a wonderful tour agent to help us all the way. She went above the call of duty every day for us all. The only event that was beyond the control of Tour Radar is the hotel in Mykonos which considered a lower level room as a 50 Euro upgrade for seniors and persons with disabilities. They preferred to leave those rooms vacant than allow them at the same rate.
- Sailing Greece - Mykonos to Santorini
Loved this sailing adventure and plan to do another one in the near future. The Captain Marius was excellent with a wealth of knowledge in all aspects of sailing and taking care of his passengers. Our group gelled well and we all had fun swimming, eating on board and going out to dinner and playing cards. I would definitely do this adventure again
- Charms of the Cyclades
The train from Athens literally fell off the tracks. And the people at Tour Radar were waiting for us when our bus for the train finally arrived at the terminal. They went way out of their way to give us a nice tour of as many sights as we had time for. The train ride was pretty awful but the tour was worth the ride.
Other Regions in Greece
- Mainland Greece (402)
- Aegean Islands (399)
- Cyclades Greece (371)
- Athens Santorini & Mykonos (362)
- Peloponnese Islands (112)
- Mykonos (87)
- Central Greece (63)
- Northern Greece (59)
- Crete (51)
- Ionian Islands (31)
- Santorini (24)
- Attica (21)
- Dodecanese Islands (15)
- Eastern Aegean Islands (14)
- Saronic Islands (6)
- Sporades Islands (5)
Seasons
- Spring 2024 tours (300)
- Summer 2024 tours (403)
- Fall / Autumn 2024 tours (403)
- Winter 2024 / 2025 tours (49)
- Spring 2025 tours (152)
- Summer 2025 tours (140)
- Fall / Autumn 2025 tours (135)
- Winter 2025 / 2026 tours (18)