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.


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?
Barbados is one of the most multifaceted Caribbean islands, offering a wide range of accommodations and activities. It has places to stay for visitors of every budget, and a diversity of landscapes and cultural activities. Visitors especially enjoy visiting the lively city of Bridgetown, which dates back to the 17th century. One of the island’s most spectacular attractions is Harrison’s Cave, an amazing formation that can be seen on a tramway.
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.
Culebra Island is beautiful. I just got back to Canada from Puerto Rico. I was there for a month. I loved Culebra so much I went back twice. On my second trip I spent two nights camping at Playa Flamenco. I paid $20 USD per night for a sweet little camping spot (section E). I saw turtles, amazing, colourful fish and met some wonderful people. The snorkelling was okay in terms of being able to see under water but the reefs are not healthy. There was plenty of coconut to pick to drink the water inside and eat the meat. I found passion fruit, mangoes (not ripe), almonds (not ripe) and another really weird looking fruit I don’t know the name of. While I didn’t enjoy the main island of Puerto Rico as much as I’d hoped, I would go back to Culebra if the opportunity ever arose. I made some friends (Perri and Hector–owners) at a little place in town called, “Aqui Me Quedo” who I will never forget their kindness and hospitality.
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).

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.


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!
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! 

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.
Considering your interests (great food, hiking, beaches, nightlife unimportant) then Naxos should definitely be your other island. (And Naxos has many daily ferry connections with both Santorini and Athens.) Also, Athens needs at least one full day to explore so you should drop any thoughts about Delphi or Nafplio. Also, I would look into flights from Athens to Santorini on your night of arrival. If you could get to Santorini that night (and move your day in Athens to the end of your trip) you’d almost gain an entire day and could spend two nights on Naxos.
Argostoli is the capital on the mid-west flank of the island and is not really a destination itself, that moniker falling to the contiguous beach scene running from Lourdata south eastward to Skala. While development might have caught up here by now, it should still be a pleasant beach scene and focus for a relaxing stay. The Melissani Cave on the east coast is a must attraction and while it can be visited on a day excursion from anywhere on Kefallonia the two villages or Agia Efthymia and Poros are low-key ‘resorts’ pulling in a regular crowd of travellers and may warrant a look-in. The port of Pesada (just west of Lourdata) is the home of the local ferry to Zakynthos (Zante).
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).

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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.
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.
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.
They are packaged tourist places, though not quite in the extreme league of the north coast of Crete, but certainly they look to the ‘managed’ traveller more than the individual. September is a good time, though the start of September is still pretty close to high season and you will need to make bookings in advance. The waters of the Ionian are a bit chillier than the Aegean, but the islands sport some very spectacular beaches and seaside resorts. They are very popular with Italian travellers in their boats and motorhomes.
Hi! I have fallen in love with the cyklades and have visited Santorini, Ios, Naxos and Folegandros in late june. Folegandros was the best, a fantastic island. We are now thinking about going to Paros the last week in September. Naoussa seem to be a great place. What’s the weather like in late September? Is it still quite warm? I also wonder about the sea conditions. May the sea be rough at that time of the year? I don’t like wavy ferry rides 😨 Thank you for a good sight!
The Abacos is situated in the Northern Bahamas, made up of its own 120-mile-long island chain, with Great Abaco Island and Little Abaco serving as the “mainland,” and a string of barrier islands separating them from the Atlantic. Known as the most accessible of the Out Islands, this family-friendly destination boasts white and pink sandy beaches as well as the four national parks, where parrots, orchids and all types of exotic marine life can be spotted. Seeing the famous swimming island pigs makes a visit to this archipelago and especially unforgettable experience. One of the most popular attractions in this remote region, you can see them adorably lounging on the beach, soaking up the Bahamian sun and treading through the clear azure waters. There are also villages that seem locked in another time, turquoise flats, spectacular coral reefs, untouched forests and uninhabited cays, all waiting to be explored. 

Chania is a great choice. A wonderful charming town. Elounda is great for a quiet laid back stop, Agios Nikolaos has a more interesting vibe and is more of a real town. Also very charming. I prefer Ag Nik but Elounda has more luxurious hotels. (Crete hotels.) Naxos has lots to see in the interior so if you didn’t explore then certainly consider that. Folegandros and Milos are both incredible. Folegandros is more suited to walking and relaxing (and has some top notch restaurants and hotels). On Milos you need to do a tour and get out and actively explore to do it justice. Geologically Milos is stunning. A little like Santorini but with better beaches.
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.
This small island isn’t quite as popular as some of its neighbors, and many visitors consider that a good thing. Vieques is perhaps the best Caribbean island for truly getting away from it all. It has fewer than 10,000 inhabitants, giving it a bit of a deserted island look. The island is a popular honeymoon destination and it’s also a favorite of eco-tourists, who are drawn to the protected area known as Mosquito Bay.

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.
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While technically a subtropical island, the Azores make for a great getaway if you’re looking for something beyond the standard resort getaway. The islands boast tons of hiking and beautiful nature. Rent a car and explore the winding roads of the main island, São Miguel Island, taking it secluded beaches and picturesque waterfalls. Best of all, it’s close to both Europe and North America and makes for a great stopover point if you’re traveling between the two.
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.
Jamaica attracts travelers of many different types. Some come to see the amazing flora and wildlife, including many exotic species of birds. Others come to experience the famous Reggae music scene, which had its birthplace on this island. Others are drawn to the many great deals available on Jamaica, especially when it comes to all-inclusive resorts. Finally, many golfers come to Montego Bay, known for having the best golf courses in all of the Caribbean.
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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. 

Java, with a population of 140 million, makes its first appearance on this list. Celebrated for its ancient culture, breathtaking vistas, and UNESCO World Heritage sites like the Borobudur Temple Compounds, the island also offers the opportunity to indulge in modernity (five-star hotels abound). Waterfalls, volcanoes, protected parks, and white-sand beaches also allow visitors to get away from the thrum.
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