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?
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.
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!
We’re planning a Greece trip to celebrate our 25th anniversary in September 2017 We plan to arrive in Athens and directly take train to Kalambaka/Meteora (2 nights), then down to Delphi (hotel stay in Athens), a day to see sights in Athens, a day trip to Nafplio and then leave to explore islands. Our plan is to go to Naxos for 4-5 nights, then to Santorini (for our anniversary) for 4 nights, and then to Crete for 5-6 nights. I would like to see Delos and wonder if it’s possible to stop in Mykonos, do the tour to Delos and still be able to catch ferry to Naxos the same day?
The busiest and hottest months. If you like beach parties and packed clubs then Mykonos is the place to be. The less-busy islands (Antiparos, Sifnos, Ikaria, Folegandros, Milos) have short tourists seasons and this is when they’re fully open and running. Santorini, Crete, Rhodes, and Corfu are in peak-season but all are large enough to retain their charm.
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.
We’re planning a Greece trip to celebrate our 25th anniversary in September 2017 We plan to arrive in Athens and directly take train to Kalambaka/Meteora (2 nights), then down to Delphi (hotel stay in Athens), a day to see sights in Athens, a day trip to Nafplio and then leave to explore islands. Our plan is to go to Naxos for 4-5 nights, then to Santorini (for our anniversary) for 4 nights, and then to Crete for 5-6 nights. I would like to see Delos and wonder if it’s possible to stop in Mykonos, do the tour to Delos and still be able to catch ferry to Naxos the same day?
Crete, Santorini, and Naxos look quite doable within the 12-day block, but Crete’s beaches are scattered throughout a very LARGE island, Santorini really only has Kamari and Perissá (and some southern coast bays) and Naxos does have nice places to swim. If you choose only to visit those three islands in your relatively short time, you will do well.
This long and slender island is the most historic of the Out Islands, with the first English settlers arriving back in 1648.  Much of the architecture and way of life was influenced by these British Loyalists. Here you will find some of the island’s luxury resorts, massive coral reefs that create breathtaking backdrops, and miles and miles of beautiful beach that can often be enjoyed all to yourself, with many stretches of sand relatively deserted thanks to their secluded locales. Although Eleuthera is the fourth most populated island in The Bahamas, home to about 11,000, most who live here either fish for bounty or farm the rolling acres of pineapple plantations. The bakeries lure visitors in with their mouth-watering pineapple tarts from the island’s signature crop – Henry Sands homemade bread even won him an invitation to Princess Di’s wedding.
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.
Private jet is the best new way for VIPs to travel south: Casa Marina, A Waldorf Astoria Resort, now offers direct seaplane air service with Key West Seaplanes from Florida airports to the property’s private beach pier. Slightly farther north on Key Largo, Playa Largo Resort & Spa debuted last summer with signature Sunshine State coral reefs and sea glass, plus 144 rooms and suites, 10 secluded bungalows and a standalone luxury guesthouse.
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.
Bermuda is recognized as one of the most elegant of the Caribbean islands, and also on the formal side. It has a strong British influence, and you can still find many places that serve traditional afternoon tea. Cricket matches are also easy to find. Bermuda is also a great destination for golfers, as the island has many world class courses. This island is extremely convenient to reach from the Eastern U.S. Flights from New York to Bermuda are only two hours.
My fiancé and I are interested in the Greek Islands for our honeymoon in early August. I know it’s not the ideal time to go, but it’s right after our wedding. We are two women in our late thirties. We’d fly into Athens and then I was thinking Santorini for 4 nights and then possibly one other island. We’re into the beach, snorkeling/boat trip, maybe a hike or bike ride and amazing food. We’re not interested in the party scene, but definitely want to explore amazing restaurants. You know, the perfect amount of romance and relaxation combined with culture and epic scenery. Suggestions? Thanks in advance!
Bermuda is recognized as one of the most elegant of the Caribbean islands, and also on the formal side. It has a strong British influence, and you can still find many places that serve traditional afternoon tea. Cricket matches are also easy to find. Bermuda is also a great destination for golfers, as the island has many world class courses. This island is extremely convenient to reach from the Eastern U.S. Flights from New York to Bermuda are only two hours.
We are planning our honeymoon in Greece. We can probably take up to two weeks. One of the places we want to go is Santorini. We would like to visit one or maybe two other places if possible. The other places we were looking at are Athens, Mykonos & Crete. Which of these would you recommend with Santorini if we were thinking of visiting 2 or 3 places total?
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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Hi Dave, going to Greece in September from the 3rd to 18th. Paros and Milos are pretty much decided but we are not sure about adding a 3rd island. We arrive in Athens early in the day from an overnight flight so will be jetlagged. My husband is staying on for an additional week near Thessaloniki. We have already visited Athens, Aegina, Crete, Santorini, Mykonos, Paros, and Rhodes. My husband isn’t really a beach person and I love the beach so we do need a mix of things to do. We are pretty fit and enjoy being Active. Great restaurants are a must. Any suggestions?
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.)
We are wanting to hit 3 islands and have narrowed it down to Corfu, Crete, and Santorini. I was feeling pretty good about this but I haven’t seen a lot of hype for Corfu. I was thinking it would be more unique as compared to the other 2 with its proximity to Italy and Turkey and Albania. Am I missing something, do you have any insight you could provide, please?

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.
Can you see all the major sights in Athens in one day? No. But you can see the Acropolis, Acropolis Museum, and the top historical sites of the Plaka in one day. If you had an extra half-day then visit the Archaeological Museum in Exarcheia. That still leaves many great sights but you will have seen all of the iconic Athens attractions. Adding Naxos is always a good idea. You might even enjoy it more than Mykonos (but no nightlife like Mykonos).
Be cautious with Santorini and kids. Some hotels don’t do kids (check carefully) and not all hotels are suitable for kids along the caldera lip. Many steps, confined spaces and other guests who don’t actually want to hear kids … Here’s an idea – look for a child-friendly hotel (perhaps on the beach at Perissá) and base yourself where the kids will like it and then take them to the caldera scene. There are a couple of child-friendly hotels on the Caldera, but they get booked very early in the year. 

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.
The Greek islands have beautiful weather in the months just before and after peak season. It’s a great time to see the islands, save money, avoid the crowds, and still have great weather (though not as hot as July and August). If you want to see the super-popular islands of Santorini, Rhodes, Corfu, and Crete without the tourists then this is a great time to visit.
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.
Fabulous site Dave! I am taking my daughter to Greece for 12 days in late May 2017 as a grad gift (yeah I know…, I think my Dad gave me a Timex watch, but I digress) and we are flying into Santorini expecting to spend 5-6 days there then ferrying over to Mykonos (not really sure why?) for a couple days. A couple days there and then flying into Athens for 2-2.5 days to inject some culture into what is otherwise somewhat hedonistic trip. I was wondering, after reading about other islands whether it is worth going to Mykonos. I’d love to go to Crete but it seems to be tough to squeeze that in. The original plan was to go to Istanbul for a couple days but it seems really sketchy right now. So is Naxos a better idea than Mykonos? Should we stay longer in Santorini? Is 2.5 days too much for Athens? Any and all info is appreciated.
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).
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!
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