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Hi Dave. Thank you for your amazing website! We (30’s / 40’s couple – no kids) used your recommendations last year in September and visited Santorini (7days), Milos (3days) and Crete (12days) before spending 3 days in Athens. The trip was amazing and Greece is calling us to go back again this year! We have a conundrum which we are hoping you can assist (well, many of them really!)
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Located in southern Thailand, this semi-off-the-map island is one of my favorites and the month I spent here remains one of my most fond memories. Here on Ko Lipe, the super-friendly locals bring in the daily catch for amazing seafood, as the island’s water is teeming with life. Accommodation is still basic, and most places turn off the electricity around midnight. 

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.
Went to Fiji for my honeymoon and i don’t think that trip can be topped. We wanted seclusion, privacy and romance and thats what we got. Our bure was 20 feet from the beach where we could relax and maybe see 1 or two people all day. It was incredible. The resort was called Matangi island resort. Great staff, great food…. It’s as close to perfect as you can get.
I need to finalize plans for a mid-June trip, looking to stay 9-10 nights. Traveling with my wife and two sons (24 and 16). Definitely want to go to Santorini, Mykonos and Athens. Was considering 3 nights at each, but after reading on your site, I am thinking about stealing a night from Athens and spending 2 nights at Naxos. We want to see the major sights in Athens, can we do that in a day? Any comments on the itinerary given our group is welcome.
Im here in Vermont and love it here but want more and Im antsy to move in the future. I dont know where to start, but I do know I want a tropical place warm year round. I guess I need a break from this cold weather. I own and operate an herbal shop for I am a Holistic Practitioner , Master Herbalist, Nutritional consultant and much more. Iam looking to relocate my business and myself with my 2 boys!!! Anyone have any locations that I may visit that might be a new future location with a high call for my type of work please oh please let me know. Namaste! Cold here in Vermont!!!!
To sum up: a lot depends on your own stamina because island hopping means packing and unpacking, getting on and off buses and ferries. Limit your choice of islands to perhaps one or two less than you think you can manage. Maximise transport links to avoid backtracking or port-transferring and since you are traveling high season be aware that you will usually need bookings ahead at most places. It is possible to turn up on an island and not find a place to stay or have to make do with a third-rate option.
These groups are generally better connected among themselves than with other groups, so you are probably better advised to target them on this basis. As it’s your first time to Greece, you may want the full-on Greek island experience and you could easily fill your five weeks flitting from one island to the other in the Cyclades. You could start in Kea and work your way down to Milos via Kythnos, Serifos and Sifnos then segue to Paros and Naxos. Dip down to Santorini, up to Mykonos and back to Piraeus. The map will also show plenty of other Cyclades islands to pick and choose from such as Ios, Sikinos, Folegandros, Amorgos, Syros, Tinos and Andros – yes! too many choices, but you will find that sticking to one group it will be easier to get between them. Realistically for a period of five weeks you will not want to be doing more than 6-8 islands.
Also, if there are any other suggestions you have in general for Athens and Santorini I would love to hear them. I would like to be able to leave Athens early morning on Day 3 so that we can have almost a full day on our first island. We would like to see as much as we can without feeling like we are running around from island to island the whole time.

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!


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.
They’re all great choices. Athens (1 to 2 full days) is great for historical sightseeing. Mykonos for beaches and nightlife (2 to 4 days). Crete for historical sightseeing, greek culture and towns, some beaches but spread out (4 to 7 days). Santorini has great sightseeing, tours, and some history (4 to 7 days). If visiting outside of June to September then drop Mykonos and do the other 3 for sure.
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. 

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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).
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I would recommend Naxos over Mykonos and with 12 days you could easily add Paros too. With Santorini, Paros, and Naxos you’ll get a good mix of different delights and some ferry island hopping too which is fun in itself. 1.5 days in Athens is perfect for most – 1 day for the Plaka, Parthenon, Acropolis Museum area; and a half-day to visit the Archaeological Museum which is a short drive or walk from the Plaka but hard to fit in one day along with the other sights. 

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.

Remote and unspoiled Crooked Island has little in the way of tourist facilities, but it does boast gorgeous beaches, bat caves and flamingos, and also serves as a turtle nesting spot. One of the four islands that form an atoll hugging the striking shallow waters of the Bight of Acklins, it hasn’t much changed since Columbus sailed down the leeward side through the narrow Crooked Island Passage. There are miles of untouched, white powdery sands, coral gardens, limestone caves and cliffs, remnants of slave and cotton plantations, ancient churches, fortifications and mangrove-lined waterways.

It’s best to visit Greek islands within the same group. For example, I wouldn’t recommend visiting Corfu and Santorini on the same trip as they’re on opposite sides of the country. Instead, visit islands in the same island group: the Cyclades, the Sporades, the Dodecanese, the Ionian, the Saronic, and the Northeastern Aegean. For one, they’re close to each other. And two, they have frequent ferry connections with each other. For first time visitors to Greece, the Cyclades make the most natural and convenient introduction.
It’s best to visit Greek islands within the same group. For example, I wouldn’t recommend visiting Corfu and Santorini on the same trip as they’re on opposite sides of the country. Instead, visit islands in the same island group: the Cyclades, the Sporades, the Dodecanese, the Ionian, the Saronic, and the Northeastern Aegean. For one, they’re close to each other. And two, they have frequent ferry connections with each other. For first time visitors to Greece, the Cyclades make the most natural and convenient introduction.
We are having trouble deciding on another island to go to besides Santorini (we both want to go there). I was hoping you might be able to make a suggestion. We are not really into late night partying/night life. We LOVE good food..quite possibly the most important item on our list. We also like to hike, my husband is very into history, we love beer/wine, we could definitely be into in a less populated/touristy type spot. Gorgeous beaches and great views are also a plus.
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)?
I loved you website, congratulations. Me, my wife and a couple of friends are traveling to Greece in march/2018 (I know it’s not the best time of the year to visit Greece, but it’s the time we have available). We are in our late 30’s and are looking forward to some beautiful views, chill out time and good food. We’re not after huge parties but some local music wouldn’t be bad. We have 13 days in our hands, so by reading your texts I’m considering spending some 2 days in Athens, 3 days in Mykonos, 4 days in Santorini, 4 days in Chania.
Those are 3 great islands. Corfu is much more green than Crete and Santorini and does have a different feel (more Italian but it’s no where near Turkey). The trouble with doing all 3 is that Corfu is on the opposite side of Greece from Crete and Santorini so you’d need to fly via Athens. It’s better for most people to visit another Cycladic island (Naxos, Paros, Milos, Folegandros) instead of splitting up their trip between the two sides of the country.
These groups are generally better connected among themselves than with other groups, so you are probably better advised to target them on this basis. As it’s your first time to Greece, you may want the full-on Greek island experience and you could easily fill your five weeks flitting from one island to the other in the Cyclades. You could start in Kea and work your way down to Milos via Kythnos, Serifos and Sifnos then segue to Paros and Naxos. Dip down to Santorini, up to Mykonos and back to Piraeus. The map will also show plenty of other Cyclades islands to pick and choose from such as Ios, Sikinos, Folegandros, Amorgos, Syros, Tinos and Andros – yes! too many choices, but you will find that sticking to one group it will be easier to get between them. Realistically for a period of five weeks you will not want to be doing more than 6-8 islands.
Travel here is now easier than ever thanks to recent renovations at both international airports. One of Grand Cayman’s first hotel openings in years, Kimpton Seafire Resort + Spa opened in November, with 266 design-centric guest rooms along a 500-foot coral sand stretch of Seven Mile Beach. At the grass-and-teak filled, flip-flop friendly Margaritaville Beach Resort, which will open in early 2017 with 286 guest rooms, kids can cruise down the two-story waterslide and you’ve got a License to Chill at the bar with the same name.
I would recommend Naxos over Mykonos and with 12 days you could easily add Paros too. With Santorini, Paros, and Naxos you’ll get a good mix of different delights and some ferry island hopping too which is fun in itself. 1.5 days in Athens is perfect for most – 1 day for the Plaka, Parthenon, Acropolis Museum area; and a half-day to visit the Archaeological Museum which is a short drive or walk from the Plaka but hard to fit in one day along with the other sights.
I’m a little worried I’ll get bored in Milos. My husband likes to stay in one place, but I like exploring. We would have split our time more evenly but we want to stay on the caldera and it’s just too expensive to stay any longer than two or three nights. Alternatively, we could stay in Santorini for longer but move to a cheaper hotel. Perhaps Santorini 6 nights and Milos 6 nights?
– Any advice on where to go after for around 5 nights? Back to Naxos (we didn’t really move from the town last year unlike in Paros where we rented a car and saw the whole island)? What about Folegandros? Tinos? Milos? We would like somewhere with a nice town to walk around, upmarket, more couple less family, nice bars and things to see during the day bit also nice beaches etc?
Of the above groups the Dodecanese probably constitute the best opportunity to mix islands between groups. You could, for example, take the Blue Star Ferries and map an island-hopping route that essentially heads in the same direction. In this way you could take in some of the Cyclades – Syros, Mykonos, Patmos, Naxos and some of the Dodecanese – Patmos, Leros, Kos, Chalki, and Rhodes – without any backtracking. Hellenic Seaways is another major ferry company whose routes you may want to explore.
Unlike its luxurious Caribbean neighbors, here you’ll only find more budget-friendly hotels and guesthouses. Everything needs to come by ship or airplane, so it’s not super cheap. However, since no non-natives can own property there is no influx of overdevelopment, keeping the island simple but beautiful. For a more rustic, non-touristy getaway, this might be the island for you!
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