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Another South Pacific island group (see a pattern here?), the Cook Islands are pretty far off the map. OK, not too far, but they are considerably less visited than some of their neighbors. These tiny islands are named after James Cook, the intrepid man who discovered them. With few amenities, this is the best place to find your inner castaway and escape modern life. The islands see similar weather to the rest of the area, with temperatures hot and humid all year round.
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.

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Hi, Dave! My husband and I will be going to Greece 8/26 – 9/4. We are flying into and out of Athens for cost efficiency. We really want to see Navagio Beach on Zakynthos for a day, and we realize this will likely be an overnight trip, or even 2 nights depending on the travel options. What is the best way to get from Athens to Zykanthos? What is the best way to get from Zakynthos to Santorini? Or is it best to just go from Zakynthos back to Athens and then to Santorini? We are trying to avoid additional flights but realize we may have to fly from Zakynthos to Santorini. 

We are planning to come back at the start of September for 2 weeks to visit different islands for some beach and sun. To give you some background, we loved Santorini, Milos and the quieter / smaller places in Crete (Loutro, Falassarna, Samaria Gorge). We enjoy beach time, some hiking, site seeing, good wine / food and good / buzzy atmosphere at night for dinner / tavernas.
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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.
Fiji is poised for a comeback after 2016’s Tropical Cyclone Winston, the most severe on record. The quintessential Fijian Jean-Michel Cousteau Resort on Savusavu Bay reopened in September with 25 newly thatched houses known as bures. For total seclusion, guests are ferried via seaplane to the remote Kokomo Island, a new collection of 21 bures and five villas on uninhabited Yaukuve Island.
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.
We’re on a budget (think €50 per person per day) and would like to go someplace warm and sunny where there’s also a combination of culture and nature. So we can explore in the mornings and relax at the beach in the afternoon. Preferably a sandy beach. We don’t need a lot of nightlife but it would be nice if not the whole island is closing down already. Do you have a suggestion?
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.
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.
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.
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?
Barbados is a vibrant island with a great nightlight. Bridgetown is one of the nightlife capitals of the area, so if you’re looking to stay up until the wee hours then this might be the island for you! Like Bermuda, you’ll find amazing beaches and caving here. You’ll also find some world-class surfing. The food here is amazing, and you’ll be able to enjoy expensive, delicious meals alongside cheap local food.
Under a constellation of dazzling lights, the Strip throngs with glamorous folk and star-struck visitors. The Eiffel Tower is illuminated against the night sky, boats punt along Venetian canals, and the roulette tables heat up with anticipation. Las Vegas is the city of fantasy, where dreams are realized and where fortunes are lost and won. It’s bold, brash, and it doesn’t hold back – you have to surrender to this exhilarating city and let it do with you whatever it desires.

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Thank you for putting together such a great site. My husband and I are planning a trip to the Islands in May – neither of us have been and, honestly, have no idea where to even start putting together an itinerary. We have at least 14 nights to spend there (and may be able to push that to 17). I’m in my early 30s, my husband’s in his early 40s. Our priorities are culture and history, swimming, beautiful views, nice towns, and food and drink. We’re not interested in clubbing at all, but more laid-back late night bars definitely appeal. This is probably our one big holiday this year so while the budget is more mid-range than sky-high, we can push it a bit for the right places or experiences. We’re happy to take in quite a few islands, or with a mix of longer and shorter stays.
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.
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.
U.S. citizens don’t need a passport to explore this trio of Caribbean islands (St. Thomas, St. John and St. Croix). While the 133-square-mile chain has history in spades — Christopher Columbus touched down in 1493 — 2017 marks a banner year as the USVI celebrates its Centennial, with special events (festivals, parades and presumably lots of rum cake) continuing throughout the year. Also historic, Caneel Bay, the 60-year-old, 170-acre escape in St. John’s Virgin Islands National Park founded by environmentalist and preservationist Laurance Rockefeller, just celebrated its diamond anniversary. The property is bringing back the original beauty of its pared-down, 1950s-inspired Scandinavian style.
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.
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Hi Dave! I’m planning my honeymoon for early September, starting from Santorini. I’d like to hit Naxos, Paros and finally Milos before returning to Athens. Is this order of islands doable? I’m most concerned about ferries being available to each of the islands, especially Paros to Milos. Are ferries routinely available daily in September? Also, for all these islands would three full days each be too much or not enough? My wife and I aren’t into nightlife, just looking for relaxation, great beaches, beautiful water and amazing food! Thanks!
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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? 

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:
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’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?
But Indonesia has more than just Bali. The nearby Gili Islands are another incredible island getaway. Both destinations make for a more active tropical vacation and the weather remains pretty constant all year round (though April to October sees slightly drier weather). Both Bali and the Gili Islands are close enough that you should be able to visit them both on your trip to really get the most out of this idyllic corner of the world.
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?
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