Greek Islands Tours & Trips in September 2025
134 tour packages in Greek Islands in September 2025
Greece Sailing Adventure: Cyclades Islands
Greece Sailing Adventure: Cyclades IslandsGreat way to see and experience the cyclades.
- 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
4 Sep, 20258 spaces left10 Sep, 202510+ spaces left
Greek Island Explorer (10 Days)
Greek Island Explorer (10 Days)I LOVED this tour, 3 days in each place was perfect to get to know them and do what you want! Our tour guide Kiki from Costsaver was phenomenal and when I had my back give out, she went to the ER in Santorini with me and helped me a lot BC she knew Greek and I didn’t! Santorini was my favorite! Would definitely visit Greece again!
- 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 Sep, 20258 spaces left6 Sep, 20257 spaces left
Bewitching Greece with All Inclusive beach stay
Bewitching Greece with All Inclusive beach stayWe did experience some glitches but Wanderful was quick to correct the and even reimbursed a tour we missed due to a 3rd party problem. They were easy to work with.
- 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
10% Off- Duration
- 9 days
- Price per day
- $255
- From
- US$2,299
1 Sep, 202510 spaces left3 Sep, 202510 spaces left
Sailing Greece - Santorini to Mykonos
Sailing Greece - Santorini to MykonosGreat country, excellent tour leader but very poor comfort...so think about it twice before taking the tour, little space in a boat, no real shower...and I won't comment the toilets. ..and in august, it's very windy so you will never be able to relax in the deck..just watch the others being sick...Just so you know.....but the country is nice and worth exploring.
- Destinations
- Santorini, Folegandros, Sifnos, Ios, Antiparos, Paros, Naxos, Mykonos+7 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
30% Off- Duration
- 8 days
- Price per day
- $160
- From $1,829
- US$1,280You save $548
6 Sep, 20258 spaces left21 Sep, 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
30% Off- Duration
- 15 days
- Price per day
- $117
- From
- US$1,749
1 Sep, 202510+ spaces left5 Sep, 202510+ spaces left
Athens to Santorini
Athens to SantoriniOur guide was amazing. She was kind, thoughtful, looked out for the good of everyone in the group.
- 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
1 Sep, 202510+ spaces left3 Sep, 202510+ spaces left
Sailing Greece - Mykonos to Santorini
Sailing Greece - Mykonos to SantoriniAmazing trip and fantastic skipper. Very professional and friendly, plus super helpful
- 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
14 Sep, 20258 spaces left21 Sep, 20258 spaces left
Greek Island Hopper (10 Days)
Greek Island Hopper (10 Days)Great sites and had a blast with our tour group! Our Tour Director was awesome!
- 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 Sep, 20258 spaces left6 Sep, 20257 spaces left
Best of Greece
Best of GreeceOverall, our 8-day trip to Greece in September of 2023 was fantastic! Our trip started in Athens where we had excellent accommodations (including breakfast) and a great tour of the Acropolis, the museum, and the Temple of Poseidon. We arrived in Mykonos on Day 3 to find our hotel had moved to a different location on the island. The company accommodated us with a vehicle as the hotel was in a completely different part of the island. Thankfully someone in our group was willing to drive! The hotel was really nice and located within walking distance of shops/dining. Our final part of the trip was in Santorini. The tours in Santorini were amazing (afternoon/dinner/sunset cruise on a catamaran and a bus tour of the island with wine tasting)! However, the hotel accommodations we less than desirable in Santorini. Our room was very old and rundown. All transfers to/from the airports/ferries were excellent, as well! I would highly recommend utilizing Tourratdar for your upcoming holiday! They were accommodating and communicative throughout the entire process. Personally, in hindsight, we would've planned for 1 additional day in Athens and 1 additional day in Santorini.
- 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
10% Off- Duration
- 9 days
- Price per day
- $200
- From
- US$1,799
1 Sep, 202510 spaces left5 Sep, 202510 spaces left
Charms of the Cyclades
Charms of the CycladesThe 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.
- 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
10% Off- Duration
- 15 days
- Price per day
- $132
- From
- US$1,979
1 Sep, 202510+ spaces left5 Sep, 202510+ spaces left
Greece Islands w/4 Star stays & fast Ferries
Greece Islands w/4 Star stays & fast FerriesThe team were very accomodating of any requests made
- Destinations
- Athens, Santorini, Crete+1 more
- Age Range
- 2 to 89 year olds
- Islands
- Greek Islands
- Operated in
- English
- Operator
- Wonderful Holidays UK
10% Off- Duration
- 9 days
- Price per day
- $156
- From
- US$1,405
6 Sep, 202510 spaces left7 Sep, 202510 spaces left
Sail Greece: Mykonos to Santorini
Sail Greece: Mykonos to SantoriniFantastic trip! Highly recommend
- Destinations
- Mykonos, Naxos, Syros, Cyclades, Amorgos, Ios, Santorini+4 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
10% Off- Duration
- 8 days
- Price per day
- $189
- From $1,680
- US$1,512+$110 local paymentsYou save $168
9 Sep, 202510+ spaces left13 Sep, 202510+ spaces left
Greek Island Hopping | SemiPrivate with 4* Hotels | 11 Days
Greek Island Hopping | SemiPrivate with 4* Hotels | 11 DaysGreece is a beautiful country with plenty of history. We have a great extra days in Athens visiting most of the historical places. Great shops and foods in trendy Plaka and Monastiraki. The island hopping to Mykonos, Naxos, Paros and Santorini was perfect though the ferry queuing was a challenge but manageable. An extra day in Santorini could have been better as the wooden boat tour time consumed the full day activity. The itinerary description was perfect, guided us through all the way to the last day of the tour.The pick-up and transfers were prompt. Thank you!
- 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 Sep, 202510+ spaces left2 Sep, 202510+ spaces left
Sailing Greece - Santorini to Athens
Sailing Greece - Santorini to AthensIncredible trip. Skipper was fantastic, knowledgeable, and looked after our every need. Accommodations were a bit tight, but that was to be expected on a trip of this nature. We visited interesting islands, ate at excellent restaurants, and had good company.
- Destinations
- Santorini, Folegandros, Ios, Kimolos, Sifnos, Antiparos, Paros, Naxos, Mykonos, Syros, Kythnos, Kea, Hydra, Aegina, Athens+14 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
25% Off- Duration
- 15 days
- Price per day
- $174
- From $3,479
- US$2,609You save $869
6 Sep, 20258 spaces left21 Sep, 20258 spaces left
Greek Island Hopping (Standard, 11 Days)
Greek Island Hopping (Standard, 11 Days)My experience with the Greek Island Hopping Tour was amazing! I liked having the freedom to do excursions (which were all amazing), or have the day to myself. Ellen was an amazing guide and ensured everything went smoothly. Would definitely do another Contiki in the future!
- Destinations
- Athens, Mykonos, Paros, Santorini, Ios+3 more
- Age Range
- up to 35 year olds
- Regions
- Greek Islands, Aegean Islands, Cyclades Greece, Athens Santorini & Mykonos+3 more
- Operated in
- English
- Operator
- Contiki This operator has the highest review ratings and fastest responses to enquiries
20% Off- Duration
- 11 days
- Price per day
- $186
- From $2,555
- US$2,044You save $511
2 Sep, 202510+ spaces left4 Sep, 202510+ spaces left
What people love about Greek Islands Tours in September
- Greece Sailing Adventure: Cyclades Islands
Did the 10 day sailing trip around greece! Had an amazing time. Lots of time spent on the boat, beautiful swimming spots and a great way to spend a short time at lots of islands. Spent most of the day out on the water and afternoon/nights exploring different greek islands. We had the most amazing skippers (George and Orestis). They mad the trip so fun and we’re full of information about Greece and the history. Definitely recommend this trip! Best skippers ever!
- 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.
- Bewitching Greece with All Inclusive beach stay
The 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
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)