Between fascinating ancient ruins, beautiful whitewashed architecture and glistening beaches that wash against the Aegean and Ionian Seas, the Greek Islands spark the imagination in more ways than one. Although well-established stars such as Santorini, Ios and Mykonos tend to grab all the headlines, Greece boasts more than 6,000 islands and islets, each with their own sheltered bays, sandy beaches and coastal caves waiting to be explored. Across the Greek archipelago, there’s truly an unlimited amount of exquisite cultural experiences, captivating mythology and mouthwatering cuisine that’s waiting to enchant you at every move. When packing your bags for these sun-kissed islands, it helps to keep it easy breezy, relaxed, playful and just a pinch of glamorous.

Natasha Oakley

Island Hopping

Simply put, it would be a crime to come all the way to Greece and limit yourself to just one place. For those looking to take advantage of Greece’s breathtaking diversity, the very best option lies aboard a luxury yacht charter. This way, you’ll be able to creep to hidden corners of ancient civilization, drop anchor in your own pristine slice of paradise and watch those famous Santorini sunsets–all in the span of a single day. Whether you find a secluded pebble beach or prefer to swim aboard, this Haight Marcella Bikini was designed to maximize both comfort and flexibility. Carefully adapting to the figure, the flattering fit comes in a rich amber hue that’s sure to give you just the right amount of pop. When you’re breezing along and enjoying the view, toss on this lightweight Asceno Oversized Linen-Poplin Shirt, which keeps you effortlessly cool and snug.

Mr. Porter

Seaside Dining

Taking advantage of its unique Mediterranean position, the local flavors keep it fresh, abundant and uncomplicated. Breezing through the Greek Archipelago is a culinary adventure in itself and a tour of regional cuisine with each region putting forth its own traditional dishes heaped with generations of pride. Many of Greece’s charming local restaurants take advantage of their picturesque surroundings with some of the most lovely terraces you will find, so keep these Oliver Peoples Cary Grant Sunglasses close by. This vintage-inspired pair is crafted from glossy acetate and lends its stylish round frames for an on-trend look that will also protect you from the sun’s harsh rays. Keep the relaxed fit going with this Lanvin Striped Camp Collar Cotton-Poplin Button-Up, which keeps it simple with its light fabrics and loose-fitting nature. Equal parts stylish and functional, the Rolex GMT-Master II is the perfect finishing touch, allowing you to keep track of three separate time zones to boot.

Mister Zimi

Exploring Ancient Ruins

From secluded hilltops to narrow laneways, no matter what islands you find yourself on throughout the archipelago, walking is generally the best way to explore. As the cradle of Western civilization, much of your time in Greece will also be spent exploring some of the most magnificent archaeological ruins and cultural treasures that the world has to offer. That being said, it’s more than wise to come prepared with a pair of flats such as these Ancient Greek Sandals Meloivia Leather Sandals. Made with classic leather soles, these sandals offer slender top straps covered in a metallic finish, complemented by the buckled ankle strap that will keep you secure and comfortable for extended periods of movement. You’ll also want to opt for a stylish pair of frames to protect you from those UV rays, such as these Thierry Lasry Sunglasses that come with a traditional cat-eye silhouette. This Little Liffner  Leather Crossbody Bag makes for the perfect all-around option that will take you from day to night with ease. The clean-lined design is topped off with a gold-tone shell push lock.

Faithfull the Brand

Island Life

From the legendary nightlife of Mykonos that extends well into the night to the sophisticated cocktail scene of Caprice, the Greek Islands offer endless versatility when the sun begins to set. You’ll want to bring a few outfits that can effortlessly take you from day to night and back. Designed from gorgeous crepe and adorned in a pale yellow zebra print, this Faithfull the Brand Rafa Midi Dress offers a flattering waistline and fit. The puffed sleeves and plunging neckline are chic touches that make all the difference. A nice touch of jewelry goes a long way and these Alighieri Apollo’s Song Earrings do just the trick.