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?
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!
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.
Unlike its luxurious Caribbean neighbors, here you’ll only find more budget-friendly hotels and guesthouses. Everything needs to come by ship or airplane, so it’s not super cheap. However, since no non-natives can own property there is no influx of overdevelopment, keeping the island simple but beautiful. For a more rustic, non-touristy getaway, this might be the island for you!
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.
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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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. 

Hi everyone.Went back home (seychelles)for 7 weeks,it was amazing!Just the island way of life(no stress),the weather,the families,creole food especially the fresh fish and of course the beautiful beaches with amazing sceneries.You need to get off the main road sometimes to see the secluded beaches,Some beaches can be seen while driving.My favourite is ANSE ROYALE where i grew up,ANSE PARNEL,PETITE ANSE,ANSE COPRA,ANSE TAKAMAKA,L’INTENDANCE,AND OF COURSE PORT LAUNAY.I also went on PRASLIN AND LA DIGUE ISLAND(WOW)it blew me away.I left seychelles at 17,missed so much,one thing for sure i will be back(hopefully for good one day)THANK YOU
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.
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.

You’d have to check the schedule for your specific dates but I think Santorini then Milos then Paros then Naxos and Athens would probably be the best order. 3 days in each sounds great. Or a small tweak: 2 days in Milos and then 4 days in Santorini (splitting time between 2 of the 4 caldera towns) or even 4 days in Paros (splitting time between Naousa and Parikia).
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.
Im here in Vermont and love it here but want more and Im antsy to move in the future. I dont know where to start, but I do know I want a tropical place warm year round. I guess I need a break from this cold weather. I own and operate an herbal shop for I am a Holistic Practitioner , Master Herbalist, Nutritional consultant and much more. Iam looking to relocate my business and myself with my 2 boys!!! Anyone have any locations that I may visit that might be a new future location with a high call for my type of work please oh please let me know. Namaste! Cold here in Vermont!!!!

Hi Dave. Thank you for your amazing website! We (30’s / 40’s couple – no kids) used your recommendations last year in September and visited Santorini (7days), Milos (3days) and Crete (12days) before spending 3 days in Athens. The trip was amazing and Greece is calling us to go back again this year! We have a conundrum which we are hoping you can assist (well, many of them really!)


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.
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?
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? 

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.
Hi Dave. Thank you for your amazing website! We (30’s / 40’s couple – no kids) used your recommendations last year in September and visited Santorini (7days), Milos (3days) and Crete (12days) before spending 3 days in Athens. The trip was amazing and Greece is calling us to go back again this year! We have a conundrum which we are hoping you can assist (well, many of them really!)
I think that’s a great plan. Santorini is a must and Milos and Naxos are two islands that have both great beaches and lots to do and see away from the beach. Renting a car and exploring the interior villages of Naxos is a must-do and so is a boat tour around Milos. If you’re willing to cut Athens to 2 days, I would recommend Santorini 5 days, Milos 3 days, Naxos 3 days, and Athens 2 days.

These little coral islands are surrounded by excellent diving, snorkeling, and white sand beaches, and are filled with friendly locals. Private resorts litter the islands, and a vacation here is also very pricey. Luckily, Bangkok Airways offers cheap flights to and from Thailand. The best time to go to the Maldives is from November to May, when the weather is cool and dry. June through October sees wetter and hotter weather due to the monsoon season.
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