Yes, I would agree that 8 or 9 days is too long for Naxos – unless you’re happy sitting at the beach for several of those days. But if you’re looking to be semi-active and explore then you’d be best to add Paros and spend 4/5 days on each. Crete, on the other hand, would be perfect for an 8/9 day road trip. Start in Heraklion (where the ferry arrives from Santorini) head east and then south and finally ending up in the western town of Chania where you can fly up home from.
Excellent choice of islands, though getting between them presents one or two challenges (they are not as conveniently connected like the Cycladic or Dodecanese islands so island hopping is not as popular in this island group). All three islands are served by airports with year-round connections to Athens and in the Summer with international charter flights from Europe. Let’s take the pros and cons of each island.
I think Naxos would be the best island for you: incredible beaches, wonderful villages, great restaurants, and some very good hotels (though I don’t think I’d go so far as to call them hip – but nice, for sure). The farther south you go from Naxos Town the quieter the beaches get – so keep going to find the balance you prefer. If you want an island with a little more hip but beaches not quite as perfect then try Paros. If you want to err on the quieter and idyllic side then Antiparos or Ikaria.
This quiet island is waking up. Luxe boutique Zemi Beach House recently opened with classic details and a laid-back vibe that call to the local natural beauty of Shoal Bay East beach. On Merrywing Bay next to sister property CuisinArt Golf Resort & Spa, The Reef by CuisinArt recently unveiled 80 new suites. Here, farm-to-table fare means local fish and fresh produce from the on-site Hydroponic Farm. The Four Seasons Resort and Residences Anguilla took over the former Viceroy Anguilla with villas that overlook white-sand beaches and the rugged coral coastline. 

The other groups are best tackled individually. For example, the Ionians have no ferry connections to the rest of the Greek islands; the same story with the Sporades and the Argo-Saronics. The NE Aegean islands do have a link to the Dodecanese and the Cyclades but are probably best left for another trip once you have got the feel of the rhythm of the Greek islands.

Another South Pacific island group (see a pattern here?), the Cook Islands are pretty far off the map. OK, not too far, but they are considerably less visited than some of their neighbors. These tiny islands are named after James Cook, the intrepid man who discovered them. With few amenities, this is the best place to find your inner castaway and escape modern life. The islands see similar weather to the rest of the area, with temperatures hot and humid all year round.
Question: Is it worth taking the evening ferry on the 4th Sep to Crete (Heraklion) from Santorini, then the bus onto Chania so that we can do the Samaria Gorge on the 5th? Spending the full day in Chania on the 6th and taking the last flight out of Chania that night back to Athens? (or do you think this is trying to squeeze in too much in too little time)?

Transport between them can be patchy, but a new service linking Zakynthos with Corfu which started this year now brings all the islands (bar Kythira) together. Zakynthos is otherwise linked to Kefallonia with an old-style open deck ‘slipper’ ferry; Kefallonia includes Ithaki on its local small ferry route to Nydri on Lefkada. There is no link (except for the new service) from Lefkada to Paxi/Corfu. Corfu has links to Paxi and its little know satellite islands just to the north. Kythira has an airport with flights to Athens and ferries to Crete (Kissamos) and the Peloponnese (Gythio, Kalamata, and Neapoli).

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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!
The Ionian Islands are a quite different entity to the more familiar Aegean islands. There are in effect only seven of them plus a sprinkling of satellite islands that make for a very enjoyable package. They are different from the point of view of flora – they are greener and less barren than their Aegean cousins and they share a different history to the rest of Greece and the other islands, having absorbed much Venetian and Italian influences over the years. This is particularly apparent in the Old Town of Corfu where you could be forgiven for thinking you might be somewhere in Italy.
Anguilla is most famous for its white beaches, and there are more than 30 of these to choose from. It’s one of the Caribbean’s smaller islands, so you can easily see the whole island if you’re there for a few days. This island is perfect for people looking for a quiet and less touristy Caribbean experience. At the same time, you can find some interesting nightlife here to stimulate you after a day relaxing on the beach.
Naturally, there are some amazing coral reefs for snorkeling and diving and pristine beaches (my favorite is Whitehaven Beach). Upon arrival, you’ll instantly see why this is one of the best tropical islands in the world — and why over half a million people visit a year. One of the most popular way to see the islands is via a multi-day sailing tour (which is what I did when I visited). It was an amazing experience — especially diving! Prices start around 450 AUD for multi-day sailing tours. 

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Between Nydri and the next main tourism centre is the little port and beach of Mikros Gialos (small bay) that is a great little base for individual travellers for a day or three. The port village of Vasiliki on the southern underbelly of Lefkada is a haven for windsurfers: see this page or this one for more information. The little village is very pretty and is a good base for general holiday-making (as are the two other places). From Vasiliki there is a regular local ferry that runs to Fiskardo on Kefallonia (via Ithaca/Ithaki).
Panama is an underrated destination in Central America, including the San Blas Islands. This is a popular spot for sailing and boat tours, though there are also some resorts in case you’re looking for a more luxurious stay. Generally, the islands are quite rustic and make for a great off-the-grid island getaway. There are tons of beautiful spots for good sailing, diving, and snorkeling.
Comfortable accommodation in May for 2 persons can be found for between €40 and €80 per night. A meal for two that includes a starter, two main meals, salad and a litre carafe of local wine will cost you around €25-35. This can vary widely depending of level of establishment you eat at. A cheap vegetarian dish (pulses or vegetable) will set you back by no more than €5-6 a plate. If you get your breakfast included at the hotel, that is good because breakfast can add another €15 for the two of you per day.
You’d have to check the schedule for your specific dates but I think Santorini then Milos then Paros then Naxos and Athens would probably be the best order. 3 days in each sounds great. Or a small tweak: 2 days in Milos and then 4 days in Santorini (splitting time between 2 of the 4 caldera towns) or even 4 days in Paros (splitting time between Naousa and Parikia).
My sister (32 years young) and myself (28 years young) are traveling to Greece from 22nd Aug – 6th Sept 2017. This will be the first visit for my sister and my second visit so I am trying to show her my favourite places as well as visit new ones myself (i have only ever been to mykonos and santorini). Our trip starts in Athens for 2 days, Mykonos for 6 days, Santorini for 5 days and leaving us with 3 days to spare at the end of the trip. (4th Sept – 7th Sept) We fly out of Athens in the am on the 7th Sept so need to be back in Athens prior to this.
The island’s next hotspot may be The Shore Club, the only development on Providenciales’ Long Bay Beach with 106 ocean view suites and six luxury villas on a nine-acre stretch. On popular, pristine Grace Bay Beach, Grace Bay Club’s tropical-chic redesign led by interior designer Thom Filicia includes redesigned lobby and guest rooms, the new Infiniti Restaurant and Raw Bar and The Residences, a trio of freestanding, beachfront villas. To get off the radar, the eco-conscious Sailrock Resort debuts this year on untouched South Caicos Island — secluded beaches are the buzz.
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Since St. John is part of the U.S. Virgin Islands, U.S. citizens can visit without a passport. There are quite a few bargains on both St. Thomas and St. John right now, so it’s a good choice for travelers on a budget. Snorkelers should not miss visiting Trunk Bay, one of the best snorkeling spots in all of the Caribbean for seeing amazing marine life.

Aruba offers a diverse number of activities for people of all ages. On the one hand, it’s extremely family friendly, with many resorts catering to families with kids. On the other hand, you can find many adult-centered activities, such as nightlife and a wide assortment of casinos. Aruba also has a slightly different landscape from many Caribbean islands, having more of a desert appearance rather than forests.
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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.
Yes, I would agree that 8 or 9 days is too long for Naxos – unless you’re happy sitting at the beach for several of those days. But if you’re looking to be semi-active and explore then you’d be best to add Paros and spend 4/5 days on each. Crete, on the other hand, would be perfect for an 8/9 day road trip. Start in Heraklion (where the ferry arrives from Santorini) head east and then south and finally ending up in the western town of Chania where you can fly up home from.
Hi Dave! Your website is so detailed and helpful! I’m starting to plan a trip for late May-early June. We were interested in visiting Santorini, Naxos (we opted for Naxos instead of party-filled Mykonos) and Milos. Our main airport of arrival is Athens. What order should we visit all three islands (in terms of convenience of ferry/flight availability) and how many nights do you recommend allotting to each? Thanks in advance for your time!
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.
Kate Hudson, Goldie Hawn and Amy Schumer were among the first guests at Four Seasons Resort Oahu at Ko Olina, a 642-acre that opened in May 2016 on the island’s west coast 17 miles from Honolulu. Closer to the action of Waikiki, the Surfjack Hotel opened in May with a dose of vintage 1960s Hawaii, down to its painted murals and birds of paradise wallpaper by local artists that are just begging to be Instagramed. Pacific Beach Hotel re-emerges in the fall as Alohilani Resort Waikiki Beach, whose $115 million upgrades include two new restaurants by celebrity chef Masaharu Morimoto.
The largest of the Bahama islands, Andros is also the least populated, offering the chance to own a piece of your own island without the high price tag.  Here, locals make waterproof straw baskets, batik and other crafts, and visitors will also find mesmerizing blue holes, excellent bonefishing and diving. The island is home to the world’s oldest dive shop, the second largest coral reef in the Western hemisphere, and is covered with vast areas of wetlands that create channels perfect for bonefishing. Many visitors come to experience this “Bonefishing Capital of the World,” by staying at Bair’s Lodge, a plantation-style lodge situated between Deep and Middle Creek on the south end of the island offering a beachfront paradise with a picture-perfect white sand beach, swaying palms, fire pit and access to a flats skiff. The tidal paths found on this part of Andros provides water pathways to access the famous west side while offering protection from the winds, and creating a fertile, bait-rich environment that bonefish prefer.
My fiancee and I are heading to Greece in July. We’ve been to Naxos, Paros, Mykonos, and Santorini. This time we plan on being there July 1 to 23. We’re definitely including Milos, and one of Paros or Naxos. Any recommendations for other islands? Any particular ferry routes we should consider? Some “less touristy” islands are a must (for at least one island). We can be lively or very chilled. Thanks and best wishes!
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