tuquoise blue water and white sand beach Fiji

How to Choose the Perfect Island

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An island getaway is pretty much the ideal vacation for many people. But which of the thousands of islands in the world is best for you?  Whether you’re thinking about the Caribbean, the South Pacific, the Mediterranean, or someplace even more far-flung, each island destination offers something a little bit different and each has its own unique flavor.

A travel advisor can help you find the right destination, and save you time and stress in the planning process. But you’ll still need to do some thinking in advance to help your agent narrow things down. 


Start your decision process by deciding why you want to go on a tropical island vacation. What about an island getaway MOST excites you, and what do you see yourself doing while you’re there. It might be a whole mix of things but there is sure to be one thing that rises to the top.

restaurant on a beautiful beach Fiji
[Photo Credit: Annie via Shared Adventures — read about her adventure in Fiji here!]

To Relax in the Sunshine

Does your perfect island vacation involve soft white sand for sunbathing, a massage in the resort spa, and a piña colada by the pool? Are you looking to relax and restore after too many busy days at work?  Your perfect island has a luxury resort, calm soothing waters and a sunbed ready for you each day. This vacation is all about chilling on the beach and soaking up the sun.

Amazingly soft sands, calm waters, and beaches perfect for sunbathing:
Milos, Anguilla, Turks & Caicos, The Cook Islands, Martinique, Grenada, Aruba, Maui

Incredible resorts that cater to your wellness. Stylish spas and relaxing pools:
Santorini, St Lucia, The Bahamas, The Cayman Islands, Nevis/St. Kitts, Bora Bora.

To Eat Amazing Food & Explore Other Cultures

Are you a foodie? Are you interested in the local culture of the islands and always looking to explore outside the resort? Then you’ll want to look at islands that offer more than just a beach – they should have established cities or towns that have their own unique flavor, with lots of interesting and delicious restaurants and a strong cultural presence that you can connect with. 

Amazing food with lots of unique cuisines:

Crete, St. Maarten, and O’ahu

Vibrant nightlife:

Mykonos & Barbados

Lots of historical and cultural sites:
Jamaica, Puerto Rico, Curacao and Bermuda

a view of the Moorea mountains from the sea
[Photo Credit: Meagan via Shared Adventures — read about her Mo’orea honeymoon here!]

To Spend Time in the Sea

Of course you’ll want to enjoy the water on your island vacation! But is it the main reason you’re going? Do you want to spend your days swimming, snorkeling, or scuba diving? Or are you excited to try your hand at water sports like kayaking, jet skis, and kitesurfing? Perhaps even going out on a boat to see the island from a new perspective. If the water is where you plan on spending most of your time, you’ll want to look at islands that highlight it as their best feature. 

For water sports, boating and diving:

Paros, St. John, Aruba, Bonaire, British Virgin Islands, Antigua, and Maui.

For over-water bungalows and lots of marine life:
French Polynesia and The Maldives

To Explore Nature & See Wildlife

Some islands have incredible mountains and colorful plants and animals that make the land almost as enticing as the sea. Do you want to take an island vacation to get out into nature, and to enjoy tropical landscapes that are completely different from your city life? Perhaps your ideal vacation is all about hiking to the top of the lush peak to see a stunningly dramatic view. Look for islands that highlight eco-tourism, hiking, wellness & nature escapes.

Incredible views, lush mountain peaks, and great hiking:

Ikaria, St. Lucia, Fiji, Mo’orea, Kaua’i, and Hawai

For eco-tourism and ziplining:

St. Kitt, Rapa Nui (Easter Island), The Solomon Islands, Moloka’i, St. John, and Domenica

ocean sunset with sailboat in Aruba
[Photo Credit: Helen Pereira via Shared Adventures]

When to Go

Now that you’ve discovered why you’re excited to go on an island vacation, it’s worth taking a moment to consider the when and the how. 

Sometimes we get to decide when we’re going to take our vacation and sometimes it’s dictated by work, school, or other responsibilities. If you have a limited and specific timeframe, then you want to look at things like weather and sea conditions. Are you dreaming of only warm sunny days without a cloud in the sky? Do you despise humidity with every fiber of your being? Can you only travel in September during hurricane season? Consider the seasonality:

The Caribbean:

Dry Season: February – May

Wet season: June- November

High Season: December – April

Mediterranean

Best Weather: May- October

Best for Honeymoon:
June & September

Low Season: November- April

French Polynesia

Dry Season:
June- August

Wet Season:
November- April

Hot with high humidity:
December- March


No matter which island you choose, you are sure to find incredible water, beautiful beaches, and a variety of accommodations. While some islands will be better suited to your adventure priorities than others, you simply can’t go wrong with an island getaway! If you’re feeling inspired to find the perfect island for you — let us know!

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You provided excellent guidance for us. I appreciated that you really had us think about what was most important to us when we were selecting the right cruise – and not to totally focus on what other people had to say. THANK YOU for helping to make this a memorable trip for our family! It really was a trip of a lifetime!

Clare and Mark (family cruise to Alaska)

The level of service we experienced was out of this world (and we did NOT make it easy on Ann). We weren’t quite sure where we wanted to go, when we would be able to go, or what “vibe” we were going for. After asking us some key questions (what we liked, didn’t like, why, etc.) Ann helped us narrow down our trip details and planned the honeymoon of our dreams. She helped book some of our excursions, answered some emergency questions while abroad and was always available/willing to help. I think it’s safe to say we won’t be using anyone else for future travel planning – Ann is a rockstar!

Carli (Italy and Spain)