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Living in Bermuda, Real Estate in Bermuda, Choosing Your Island Home

Bermuda vs The Hamptons vs Martha's Vineyard vs Nantucket

7 minute read

The condo lifestyle is the dream for a lot of people. So, in order to live the dream lifestyle, you need to live in the dream location. Choosing a luxury vacation home is a big commitment and is not one you should stroll into lightly without thinking about the potential consequences.

It’s normal to be confused and not know where to start looking for your dream condo, so don’t worry. This post will cover Bermuda, The Hamptons, Martha’s Vineyard and Nantucket and will help you choose which one is the perfect condo location for your dream lifestyle.

We’ll cover:


Forget about the stresses of everyday life and relax in the ultimate paradise that is Bermuda. This sophisticated island offers the perfect time travel experience and is a popular choice with condo buyers.

And it’s easy to see why.

Bermuda’s sub-tropical climate means it is warmer all year round here than its US eastern seaboard rivals. Plus, short haul flights from New York, Boston, Philadelphia make Bermuda very easily accessible.

Bermuda is the ultimate paradise with stunning coral sand beaches, breathtaking views and a deep, interesting history. As soon as you step off the plane, you’ll realise how great this country is. With a perfect culture that’s steeped in character, this really is a sub-tropical paradise with the friendliest of locals to welcome you with open arms.

If it’s action you’re looking for, look no further. Bermuda is home to some of the prettiest cycling routes. Or you can hike across the various different trails and take in the country’s natural beauty. If history is more your thing, head to Hamilton, or The Royal Naval Dockyard, which is definitely not to be missed.

Tourism started in Bermuda for the first time in the Victorian era when the wealthy and elite classes of America would vacation to the island to escape North American winters. These days Bermuda is accessible to all. Wake up in the morning and draw back the curtains to a stunning ocean view. The peace, tranquillity and sheer beauty of Bermuda when the sun comes up is truly something to behold. The perfect place for the condo you’ve always dreamed of.

The Hamptons

The Hamptons are a collection of different seaside communities and are always a popular hit when it comes to summer destinations. The Hamptons is home to long stretches of lovely beaches and structures of stunning 18th-century architecture, that really give this place a great character. East Hampton is home to high-end restaurants, bars and designer boutiques and is the perfect luxury to have on the doorstep of your condo.  

The Hamptons, especially East Hampton is famed for its celebrity lifestyle. But with that prestige, comes the price tag. Seaside properties in this area are the ultimate luxury, but your wallet will likely be left with a huge dent in it afterwards.

Head to the various beach clubs. Spend glorious hours in the sun while being waited on and brought the tastiest shrimp skewers, hot dogs and lobster rolls. Or, better still, wash them down with amazingly refreshing pineapple mojitos. Now doesn’t that sound fantastic?

If shopping is your thing, you’ll definitely be in heaven. Both men and women can enjoy browsing the shops and boutiques of high-end fashion designers including Louis Vuitton, Gucci and Christian Dior.

However, if you’re looking for all-year round sunshine, the Hamptons only offers a short season. June - September are the peak temperature months in which they reach over 20°C, but other than that temperatures can reach as low as 4°C in January.

Nobody wants to go for a dip in the ocean at these temperatures, especially when the water temperatures can reach 1°C in their coldest months.

Martha’s Vineyard

Martha’s Vineyard is an island just off Massachusetts that encompasses harbor towns, sandy beaches and farmland. It’s awesome and is the popular favorite of many well-known celebrities and figureheads.

Barack Obama and his family often visit Martha’s Vineyard. Bill Gates is another familiar face too. Reese Witherspoon and Jake Gyllenhaal have also been seen on the island back when they dated. But perhaps most importantly, Oprah Winfrey really loves the place and visits frequently throughout the year. Fancy having a condo in the same location as these heavy rollers? Who doesn’t?

One great way to see “the Vineyard” is by renting a Jeep and touring the island. Of course, having a car isn’t essential and taxis are easy to come by, but to get the true feel for Martha’s Vineyard, tripping from beach to beach in an open top Jeep is a great experience.

For the food lovers and craft beer enthusiasts, you’re in luck. Both are popular here. The fresh fish is a big hit and can often be seen dominating the menus of many of the amazing restaurants on offer.

Although a lot of bars don’t have full licences to serve alcohol, those that do, rock! Craft beer is huge here and the various breweries that specialize in them are ace. A must try.

Martha’s Vineyard is a three and a half hour flight from Philadelphia and just under two hours from New York. Temperatures peak at 26°C in July but reach as low as 4°C in January. This means the season is really short and doesn’t offer that 12-month sunshine ridden paradise that most condo owners crave.


Nantucket is a tiny, isolated island off Cape Cod, Massachusetts. The cobbled streets of the Town of Nantucket are lined with restaurants, high-end boutiques and steepled churches. It’s beautiful and a very popular choice amongst condo buyers.

Once you spend some time in Nantucket, you won’t want to leave. The picturesque sunset and white sand beaches are sights to behold. The beauty of this place will never cease to amaze you. The island has a great charm to it that’ll make you feel at home straight away. Relax and unwind in this condo buyer’s dream location.

Although Nantucket is perfect for you and the family to go and unwind, it can certainly be lively too. Entertainment and outdoor activities are great for getting you out and about during the day.

And as for the nightlife, be sure to stop for drinks in one of the many great jazz bars - you definitely won’t regret it.

Temperatures in Nantucket reach the mid-20’s at peak season, but the winter months are bitterly cold and temperatures drop as low as 2°C. And the ocean temperature doesn’t get much higher than that. At its coldest, it drops to a mere 3°C, so you can kiss goodbye to those dreams of a relaxing dip in the winter months.

Our Verdict

So, which is actually best for your dream vacation condo?

The rich cultures of all these places might have some similarities. Beautiful beaches, intriguing history and welcoming locals are common in all of these places, but there are definitely major differences between them all which make them all terrifically unique.

It all depends on what kind of experience you prefer when you get away and can de-stress. Whether it’s luxury and high-end or a heartfelt trip to a sub-tropical island, there’s certainly something in each of these places for everybody.

Ultimately, our personal favorite is Bermuda. We can’t see past its sheer beauty and are yet to hear of anybody who doesn’t share the same opinion as us.

It's sub-tropical climate means it has a longer summer season than the other destinations mentioned in this list. With summers more temperate than the Caribbean and the southern States and winters where temperatures never fall below a balmy 60 F, Bermuda is heaven on earth.

It has everything, from deep sea fishing and whale watching, sophisticated restaurants and nightlife, to its quirky maritime Anglo-Portuguese-Caribbean history, it’s the perfect place to de-stress and unwind. What’s more it is only a two hour flight from New York and less than three hours from most North American east coast cities. 

Make Sure Your Condo is Perfect For You

Buying a condo is a big commitment, both financially and from a lifestyle perspective. Therefore, you have to be sure that the condo you’re looking at buying is perfect for you. Otherwise, you’re not going to benefit from that dreamy condo lifestyle.

We’ve created a checklist that will enable you to determine whether a condo is the one for you or not. Download it for free today and take the first step to purchasing your very own dream condo.

Buying a Vacation in Bermuda Guide