I’m traveling to Greece for the first time, and I’m so fortunate to be staying for about 9 weeks (peak season, unfortunately, I’m an educator and it’s summer!). I have ample time planned in Athens, and the Peloponnese (with rental car). Here’s where I need some help and suggestions. I have 5 weeks saved for the islands and I’m still trying to figure out how to spend them. I’m not sure if I’d like to cover just a few islands and soak them in a bit deeper with longer stays…or to travel at a quicker pace covering several islands in each main area (the Cyclades, Ionians, Crete-Rhodes Dodecanese, Eastern Islands) I’m an easy traveler and enjoy diversity. I crave spending time with locals and interacting with families – home stays at times, I enjoy the water and I’m an avid diver, I like hiking and exploring. Also, want to perhaps relax a bit – food/wine tasting welcomed). I’m excited about the trip and my ideas are racing all over. Do you have some ideas and suggestions to share? A rough sketch itinerary for Greece? Thanks so much!
Yes, it’s possible. Get the SeaJet ferry from Athens to Mykonos. It should arrive at 9:30am or shortly after. You’ll have to hurry to store you’re luggage at the Sea and Sky travel agency across from the Old Port and then buy tickets for Delos. The last ferry to Delos leaves at 11am or maybe 11:30am. Ferry to Delos is about 30 minutes. Last ferry back is at 3pm which will give you plenty of time before the last ferry of the day to Naxos (at 6:15pm on SeaJet). All the ferries mention here use the Old Port. Don’t book any ferries that use the New Port or you’ll have trouble making the connections.
Patmos has an indefinable je ne sais quoi - an otherworldly quality that radiates from its crowning glory, the medieval monastery of St John. This turreted fortress, bursting with Byzantine relics, is named after John the Divine, who conjured up his apocalyptic revelations in a cave nearby. Pure-white Chora, a World Heritage Site, is where A-listers and fashion editors stay. High walls and heavy doors conceal magnificent mansions dating back to the 16th century.
Toward the end of the century, a new style of low cost airline emerged, offering a no-frills product at a lower price. Southwest Airlines, JetBlue, AirTran Airways, Skybus Airlines and other low-cost carriers began to represent a serious challenge to the so-called "legacy airlines", as did their low-cost counterparts in many other countries.[42] Their commercial viability represented a serious competitive threat to the legacy carriers. However, of these, ATA and Skybus have since ceased operations.

They are located north of Australia and east of Bali and offer stunning tropical scenery, a remarkable history, friendly villages, and some of the globe’s most pristine, biologically diverse coral reefs. The only way to reach them is to island-hop the Indonesian archipelago by small planes, ferry services, or eco-friendly cruises for serious divers but it is more than worth the trouble.
Ferries between Naxos and Milos don’t start until June 7th (one each way, every day after that). Ferries between Santorini and Milos start April 28th and there is one every day in each direction. And there are always ferries between Naxos and Santorini. So if the dates work I would fly to Santorini (the longest leg) then ferry to Milos then Naxos and back to Athens. But if you need to travel between Naxos and Milos before the 7th then ferry Athens to Milos to Santorini to Naxos and back to Athens.
Close to this island is a little island that provides excellent snorkeling opportunities. You may even spot a few reef sharks. Bathtub-warm water and fine sand beaches kept me here for over three weeks. It will do the same for you. Visit between November and March for the best weather and the fewest people. May through October sees a harsh monsoon season that shuts the island down. The best way to get there is by boat from Pak Bara.
Zakynthos, or Zante, has shrugged off its reputation as a destination for lads on tour (as long as you avoid Lagana and the built-up south coast) by rebranding itself as Greece's greenest island. It's not just the emerald hills sliding into the electric blue Ionian: much of the south coast is a nature reserve where endangered loggerhead turtles hatch in the sand. The turtle beaches are off limits, but there are countless coves in every hue of green and blue. Favourites are tiny Xigia, with its bubbling underwater springs, and craggy Porto Limnionas, with sunbeds wedged between the rocks and palm-frond umbrellas positioned between the pine trees. Skinari is the starting point for boat trips to the most famous landmarks, the Blue Caves and Shipwreck Beach, where a rusting liner leans into the chalky cliffs. From Keri, you can cast away for Marathonisi island, another turtle sanctuary.
The Island of Hawaii (i.e., the Big Island) contains 10 of the world’s 14 climate zones — the only spot on the planet with so many condensed into one small region. Lush tropical terrain rules the green, wet, windward side of the island (see Akaka Falls and Waianuenue/Rainbow Falls), while more arid beauty is on display at Hapuna Beach Park. You can even enter an ice climate at the mystical summit of Mauna Kea volcano, as well as Lake Waiau, one of the highest lakes in the United States.
A complicating factor is that of origin-destination control ("O&D control"). Someone purchasing a ticket from Melbourne to Sydney (as an example) for A$200 is competing with someone else who wants to fly Melbourne to Los Angeles through Sydney on the same flight, and who is willing to pay A$1400. Should the airline prefer the $1400 passenger, or the $200 passenger plus a possible Sydney-Los Angeles passenger willing to pay $1300? Airlines have to make hundreds of thousands of similar pricing decisions daily.
It’s a tough call. The good news is that whatever you decide, it will feel like the right thing after you’ve done it. You’ll almost certainly say to yourself, “I’m so glad we saw both islands” or “I’m so glad we had 6 full days on Santorini.” In deciding I would ask whether a return trip to Greece is likely or possible in the next couple of years. If so, then spend your 6 days on Santorini and explore that island, then return to Crete at some time in the future for a deserving 7 to 10 days. But if this is a one-time deal for the foreseeable future then do 3 days on Santorini and 3 days in Crete. (Whatever you decide don’t do a day trip to the other island as it’s not worth the time and effort.)
Thank you for putting together such a great site. My husband and I are planning a trip to the Islands in May – neither of us have been and, honestly, have no idea where to even start putting together an itinerary. We have at least 14 nights to spend there (and may be able to push that to 17). I’m in my early 30s, my husband’s in his early 40s. Our priorities are culture and history, swimming, beautiful views, nice towns, and food and drink. We’re not interested in clubbing at all, but more laid-back late night bars definitely appeal. This is probably our one big holiday this year so while the budget is more mid-range than sky-high, we can push it a bit for the right places or experiences. We’re happy to take in quite a few islands, or with a mix of longer and shorter stays.
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