As a starter to explore ferry services, go to the Ferryhopper.com and punch in your route searches. Note: air travel between islands is not generally good. Air travel is normally only feasible between Athens (or other mainland destinations) and the island in question. Some exceptions do exist – Rhodes Kastellorizo, Kos-Leros-Astypalaia, Thessaloniki-Limnos-Ikaria etc. but again you will need bookings weeks in advance. 

Hawaii’s biggest island has everything you could ever want to do and more. But what separates it from the other islands is Volcano National Park. Explore volcanoes, climb through old lava tubes, and watch as new lava oozes into the ocean. Then there are all the waterfalls on the island, too. Big Island has it all. I mean it’s Hawaii — how could you go wrong?!
Puerto Rico is a commonwealth of the U.S., so citizens do not need a passport to visit this island. This is a bustling island full of activities. Cities such as San Juan and Ponce offer lots of historical sites as well as great food and nightlife. There are lots of different kinds of beaches, making it equally attractive for surfers, snorkelers or people who simply want to relax. Puerto Rico also has quite a few casinos both large and small.
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.
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.
Which of these great locations would you recommend for a family with teenagers who like to dive and surf? We have been to Hawaii, Costa Rica and Tahiti. We are looking for a safe, yet different, cultural experience with exotic plants, fish and animals. We would prefer to stay in one villa, as opposed to multiple rooms in a hotel. We don’t mind if it is far away from Southern California. I realize this may be painful financially.
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!
This 80-mile-long island is home to one of the oldest dive operations in the Bahamas. It hosts multiple shallow and deep dive sites, but is most well known for Dean’s Blue Hole, the deepest recorded blue hole in the archipelago at over 600 feet. Friendly turtles and tiny sea horses come to the warm, saltwater pool for a break from the ocean currents, while the coral caves and sand banks on the side of the entrance harbor all types of tropical reef life, from colorful tropical fish to groupers and snappers. The western shoreline of  Long Island has soft, sandy beaches edged with rich green mangroves. With the Atlantic to the east, the island is also a fishing, sailing, and yachting paradise.
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.
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.
To island-hop some of the most beautiful havens in the world, book a trip to Asia, which lays claim to six of this year’s top 15 destinations. But if you only have a week, you’ll hardly suffer. Each of the islands on this list is worth a visit on its own, from the perennial World’s Best list-makers Maui and the Galápagos to Portugal’s rising star, the Azores, with its friendly locals and awe-inspiring landscapes.

This 80-mile-long island is home to one of the oldest dive operations in the Bahamas. It hosts multiple shallow and deep dive sites, but is most well known for Dean’s Blue Hole, the deepest recorded blue hole in the archipelago at over 600 feet. Friendly turtles and tiny sea horses come to the warm, saltwater pool for a break from the ocean currents, while the coral caves and sand banks on the side of the entrance harbor all types of tropical reef life, from colorful tropical fish to groupers and snappers. The western shoreline of  Long Island has soft, sandy beaches edged with rich green mangroves. With the Atlantic to the east, the island is also a fishing, sailing, and yachting paradise.
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.
This 80-mile-long island is home to one of the oldest dive operations in the Bahamas. It hosts multiple shallow and deep dive sites, but is most well known for Dean’s Blue Hole, the deepest recorded blue hole in the archipelago at over 600 feet. Friendly turtles and tiny sea horses come to the warm, saltwater pool for a break from the ocean currents, while the coral caves and sand banks on the side of the entrance harbor all types of tropical reef life, from colorful tropical fish to groupers and snappers. The western shoreline of  Long Island has soft, sandy beaches edged with rich green mangroves. With the Atlantic to the east, the island is also a fishing, sailing, and yachting paradise.
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.
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?
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.
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. 

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.


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.
Hawaii’s biggest island has everything you could ever want to do and more. But what separates it from the other islands is Volcano National Park. Explore volcanoes, climb through old lava tubes, and watch as new lava oozes into the ocean. Then there are all the waterfalls on the island, too. Big Island has it all. I mean it’s Hawaii — how could you go wrong?!
Ferries are not really cheap any more – certainly not like they used to be – but the vessel fleet is better, safer and faster than in previous years so the cost is justified. You can get exceptionally cheap deals on longer-haul routes if you are prepared to forego a booked seat: €14 v €40 on a run to a mid-distant island, but it’s probably wise to consider taking fast catamarans to get to core islands (Mykonos, Santorini, Paros etc.) and even then, go the extra 10/15% for Business or even VIP class for the extra comfort. On longer hauls it can be cheaper to fly if you seek out flights online and book beforehand.
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.
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.

Hi dave – very cool and informative site! We’re a family of 6 (all adults) traveling to Greece for the first time…and most likely the last time. We’d like to visit some historic sites, but more interested in experiencing Greek life in small towns. Beaches and nightlife are not important. I’m looking to put together a balanced itinerary covering 10 days (11 nights) and had the following in mind: 

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).
My husband and I are planning a trip to Greece in late May/early April. We already plan to spend a few nights on Santorini, and are trying to choose one other island to pair with it (will have 3 nights on other island). We are in our late 20s and are more interested in outdoors (hiking, exploring, beaches, boat trips). I’d like to keep travel time to a minimum, so I have been looking at the closer islands – Milos, Paros, and Naxos. Do you have any recommendations or thoughts on a good island to pair with Santorini?
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.
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. 😉
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.

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).
Kefallonia was severely shaken by an earthquake in 1953 and thereafter lost its quaint gloss. The picturesque northern port of Fiskardo however, escaped much of the destruction and remains to this day one of the main focal points for visitors to the island, so is a good spot for a stay of 2-3 days. Pretty, waterfront cafés and restaurants and a cosy, folksy feel predominate. Asos, between Fiskardo and Argostoli is a west coast ‘resort’ village that pulls in its fair share of visitors and the view down to Asos from the main island road is one of the most photographed spots on Kefallonia.
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.
Though this country has some 322 islands, less than a third are inhabited. Most of the action happens in the western islands, but no matter where you go, this is heaven. Any time the name Fiji is heard, visions of beaches and tropical ocean dance in people’s head. There’s a good reason for that – because this place is one of the best places to go in the world, and with so many islands, you’re bound to find one you like.
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