Fall / Autumn 2025 Tours & Vacation Packages Greek Islands
135 Greek Islands vacation packages in September, October and November
Greece Sailing Adventure: Cyclades Islands
Greece Sailing Adventure: Cyclades IslandsDid 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!
- 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
Sailing Greece - Mykonos to Santorini
Sailing Greece - Mykonos to SantoriniSailing with G Adventures with Mariusz as our skipper was such a wonderful experience. The islands,beaches, sites and restaurants were great places to make memories with our new friends and it was such a great way to experience Greece together !
- 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
Cultural Athens & Island Hopping Mykonos - Santorini (Self-guided)
Cultural Athens & Island Hopping Mykonos - Santorini (Self-guided)We had to cancel our trip, and the team behind our trip was very helpful and very speedy in their responses. We received a full refund, and that will be used for our new trip.
- 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
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)Everything about my experience with Dot Travel was great. All of the hotels and transportation were great. We loved the itinerary and thanks Dot Travel for making our dreams of Greece come true. The hotels were great, though a couple were not in main towns, so make sure you understand you will need to find transportation. All of the staff at the hotels were awesome! The Atlantis hotel in Syros was great, our hosts were the sweetest people.
- 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
Athens, Santorini & Mykonos with 3 Guided Tours | SemiPrivate | 10 Days
Athens, Santorini & Mykonos with 3 Guided Tours | SemiPrivate | 10 DaysFantastic tours! Great service, friendly staff, wonderful hotel accommodations. Overall it was excellent!
- 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, Spanish
- Operator
- Travel Zone This operator has the highest review ratings and fastest responses to enquiries
35% Off- Duration
- 10 days
- Price per day
- $228
- From $3,504
- US$2,278You save $1,226
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
Sailing Greece - Santorini to Mykonos
Sailing Greece - Santorini to MykonosMax was an amazing Skipper and went to great lengths to ensure we all had an amazing experience. I highly recommend this trip and will definitely be coming back for future adventures.
- 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
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
Greek Island Wanderer
Greek Island WandererThe tour materials and routes chosen were just what we needed and the accommodations were generally just right - not fancy but nice people, clean and comfort room and all basics required. Just right for our demographic (65+).
- Destinations
- Athens, Piraeus, Galissas, Vari, Azolimnos, Ermoupolis, Paros, Lefkes, Prodromos, Antiparos, Parikia, Santorini, Thirasia, Thera, Oia, Naxos, Delos, Mykonos+16 more
- Age Range
- 16 to 85 year olds
- Regions
- Greek Islands, Aegean Islands, Cyclades Greece, Athens Santorini & Mykonos+3 more
- Operated in
- English
- Operator
- Explore! This operator has high review ratings and responds promptly to enquiries
6% Off- Duration
- 14 days
- Price per day
- $186
- From $2,760
- US$2,600You save $160
Greek Island Hopping | SemiPrivate with 4* Hotels | 11 Days
Greek Island Hopping | SemiPrivate with 4* Hotels | 11 DaysEverything was perfectly organized and on time
- 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
Sailing Greece - Santorini to Santorini
Sailing Greece - Santorini to SantoriniIt was not what I expected, but the experience and the care I received from the skipper Max was exceptional. There's no question that it was an adventure. I would recommend it to people who want to learn to sail and don't care about the amenities or sightseeing the ruins as much as the water experience. My children are taking a similar trip this Friday to the Galapagos Islands.
- 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
Greek Island Hopping (Plus, 11 Days)
Greek Island Hopping (Plus, 11 Days)Phenomenal time with a great group. It was a real party! And with a large group, you are sure to find your people.
- Destinations
- Athens, Mykonos, Paros, Santorini, Ios+3 more
- Age Range
- 18 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
46% Off- Duration
- 11 days
- Price per day
- $167
- From $3,387
- US$1,833You save $1,554
Premium Greece Cyclades Islands
Premium Greece Cyclades Islands- Destinations
- Athens, Paros, Naxos, Santorini+1 more
- Age Range
- 15 to 99 year olds
- Regions
- Greek Islands, Aegean Islands, Cyclades Greece, Santorini, Mainland Greece, Aegean, Athens Santorini & Mykonos+6 more
- Operated in
- English
- Operator
- Intrepid Premium This operator has the highest review ratings and fastest responses to enquiries
25% Off- Duration
- 9 days
- Price per day
- $496
- From $5,955
- US$4,466You save $1,489
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
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
What people love about Greek Islands Tours in Fall / Autumn
- 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!
- 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
- Cultural Athens & Island Hopping Mykonos - Santorini (Self-guided)
I am glad that I took this package. It helped us have a stress free trip. Transfer from day 1 was seamless. I want to mention Kristos, the driver that picked us up from the airport who gave us a lot of useful information that kicked our trip to a good start. He served as a tour guide from the airport to the hotel. The hotels we stayed in were located near the must see places, especially our hotel in Athens. The person at the reception in all the hotels we stayed in was very helpful. George of Dot Travel was very prompt in answering my queries before our trip. It was a good package to take. We were satisfied.
Departure
- September 2025 (134)
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- November 2025 (24)
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