The Caribbean has some of the most beautiful vacation destinations in the world. This makes it popular with tourists worldwide. Many people, however, have trouble deciding which island to visit. Although it may seem that every Caribbean island is equally desirable and perfect, the fact is there are significant differences among them. Let’s look at the top ten Caribbean islands and what type of traveler each is best suited for.
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 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?


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.
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.
Zakynthos is an island of certain extremes: beauty and crass, mass tourism of the worst sort. The islands – like all the Ionian islands is lush and verdant and boasts the now famous ‘shipwreck beach’ (Navagio) that many seek to travel to and swim at. Yes, it’s worth it and numerous excursion boats make the run from ports on the west side of the island. Environmentalists and capitalists clash daggers at Laganas where the mass tourism trade is carried out to the detriment of the Caretta Caretta, or loggerhead turtle that loves the beach as much as British tourists on a binge. Read this page for the background. There is an alternative scene to Laganas at Vasilikos over to the east, but it is much more low-key and less busy.

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.
Travel & Leisure is part of the Travel & Leisure Group. CopyRight 2019 Meredith Corporation. Travel & Leisure is a registered trademark of Meredith Corporation Travel & Leisure Group All Rights Reserved, registered in the United States and other countries. Travel & Leisure may receive compensation for some links to products and services on this website. Offers may be subject to change without notice. Privacy Policy | Terms of Service | Ad Choices | Your California Privacy Rights | EU Data Subject Requests
Lefkada is an island, but is connected to the mainland by a causeway at the northern tip and its access airport is on the mainland at Aktio (Preveza). It is an island popular with Greeks and mainly European visitors. Italians and Brits predominate. It is green, verdant, has good beaches and facilities and is compact enough to get around easily. Tourism is centred on the east coast around the port village of Nydri. It is low-key accommodation with villas and small family-run hotels predominating. Off-shore from Nydri are a couple of islands worth visiting on excursions: the sizeable Meganisi (car ferries run to and fro’) and the private Skorpios Island which belong to the Onassis family. On your own hired motor boat, you can heave-to on just one private beach on the north side of the island and swim and claim boasting rights to having swum on Aristotle Onassis’ private piece of Greece.
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.
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?

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?

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.
While you will need a respectable budget, if you give Bermuda a chance you’ll find an island home to some of the most beautiful beaches in all of North America and the Caribbean. The locals are incredibly friendly people and you can find some world-class food here too. To keep you busy, there is tons of snorkeling, some caves to explore, lots of hiking, and tons more!
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.
Nine weeks in Greece is a dream itinerary it certainly gives you lots of flexibility. As you seem to have Athens and the Peloponnese sorted, you just need to sort out your five weeks on the islands. What you need to realize, however, is that the islands are not all mutually interconnected, but rather they are ‘grouped’ – both administratively and from the point of view of transport routes. Here are the main groups.
Nine weeks in Greece is a dream itinerary it certainly gives you lots of flexibility. As you seem to have Athens and the Peloponnese sorted, you just need to sort out your five weeks on the islands. What you need to realize, however, is that the islands are not all mutually interconnected, but rather they are ‘grouped’ – both administratively and from the point of view of transport routes. Here are the main groups.
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.
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?
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.
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)?
Lefkada is the island that’s not an island. You can drive to it across the causeway from the mainland, but it feels every bit an island. Aristotle Onassis bought the satellite island of Skorpios here as his own bit of getaway paradise. Beaches, windsurfing, boat hire, good food and wine are all here and there are few built-up package resorts. The main tourist area is centred on Nydri.
Great list Matt! Indeed, there obviously there are some spots on this globe I have to visit. Can confirm the Maldives though. Has changed over time, but then again, the first time they were still “exploring” their “tourist economy” potential. Been there twice now and although definitely more crowded still holds its appeal. Be prepared for culture shock though. If you return to the “civilised world” you will wonder about the rest of the grubby world and catch yourself day dreaming regularly. 😉

Antigua is a small island that is often grouped with its nearby neighbor Barbuda. A popular gambling destination, Antigua has a good selection of casinos. It also has plenty of other exciting nightlife, including great restaurants, cafes and discos. The beaches are also spectacular, and you can find literally hundreds of them, with both white and pink sand.


I’m sorry if you covered this in another part of your site, (either I’m technically challenged or there just isn’t a search function for your site) but I’m curious about Corfu. From what I can tell, you mentioned it once in your site under your post about best beaches. The Paleokastritsa area is something that has caught my attention for a while and is on my list, and then I saw pictures of Nissakids Bay and that looked kind of amazing.
Vegas.com has the best deals on Las Vegas hotels of every type to help you find the perfect room that will fit your budget. Looking for a cheap stay in a clean cubby? No problem. How about suites of epic grandeur in luxury Las Vegas resorts? Yep, got 'em too. Before you make your Las Vegas hotel reservations read hotel reviews from people who've actually stayed there…so you'll know you're making the right choice.

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.


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.
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. 
×