The Mariner in the Mediterranean: A Gentlemen’s Guide to Island Hopping

The mariner in the mediterranean - a gentleman's guide to island hopping

Picture it now: you’re lounging dockside on a tropical island with turquoise waters in every direction. The sweet soundtrack of Antônio Carlos Jobim plays in the background as you slowly sip a tropical cocktail.

The island-hopper’s life is a dream, especially if you know what to pack for your adventure. Taking cues from old-school sailors and navigators — and maybe a little bit of Hemingway circa his time in Bimini — we’ll embark on a journey of all the essential gear and accessories made for the stylish and sensible seafarer. It doesn’t matter if you’re careening along the coastline of Curaçao aboard a catamaran or yachting inshore on the Mediterranean, we’re here to help you pack like a pro.


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Whether your style is old-school cool or classic and sophisticated, you’re going to want to pack some modern accessories to round out the experience. Here is what you’ll need.

  • A Good Navigation System — Sailing sans skipper? You’ll need a reliable GPS system that gets you from port A to port B without the use of internet or cell phone service. Pick a handheld GPS by a reliable maker like Garmin. Note that if you charter a vessel, it will be equipped with the essential navigation and safety gadgets that you’ll need to get around the high seas.
  • A High-Tech Compass — Every mariner needs a reliable compass to guide him or her. Pick a hand bearing mariner’s compass (the Vion Mini 2000 is a solid choice) so that you don’t take up too much precious suitcase space. You’ll want a compass with a light for nighttime use, so consider one that’s solar powered. Even better, pack a maritime watch with a compass built in to the mechanism.

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  • A Solid Sports Camera — GoPro is the obvious choice, but there are a lot of options for high-tech adventure cameras that are well suited for marine environments. The bottom line when selecting your island-hopping camera is that you need something with a battery that lasts. There’s nothing worse than parasailing off the coast of an Instagram-worthy private island without documentation. A waterproof drone makes a great pre-vacation investment too.

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Exploring the tropics is especially appealing to dive enthusiasts, and there will be plenty of opportunity on your island-hopping adventure.

  • Essentials That You Don’t Want to Rent — First-time and casual divers will likely prefer to rent their tanks and regulators, and this is the best option for short-term and guided journeys. With that being said, there are some things you’ll want to bring yourself.We recommend investing in a high-quality snorkel, a mask and flippers. This way, if you decide to take a quick snorkeling jaunt, you’ll be equipped with everything you need to indulge the whim.
  • A Protective Wetsuit — Assuming that you’ll be headed to a tropical or sub-tropical climate, you’ll benefit from investing in a full-body wetsuit (also called a steamer) that keeps you warm and safe in deep-sea diving environments. For sailing and dockside wear, invest in a shorty wetsuit that will provide ample UV protection without the risk of overheating.


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During your day-to-day life, you likely wear your watch to reflect your style and dedication to performance. In the mariner’s world, though, a good watch goes above and beyond chronology.

  • mens fashionable watch in forest greenA Mariner’s Watch — In terms of the best specialty timepieces, it’s hard to pick just one. With that being said, we can definitely vouch for the Rolex Yacht-Master; it’s waterproof up to 100 meters and has some amazing marine-specific features, like a built-in regatta timekeeper with a programmable countdown dial.
  • A Swiss-Made Watch Band — We can’t stress this enough. Don’t wear your expensive gold or leather watch band in the water! Instead, opt for one of our precision vulcanized Swiss rubber watch bands with tang buckles, which provide steadfast style coupled with the ability to withstand extreme temperatures and exposure to UV rays and water. The sleek, streamlined design works well with your diving gear, and it won’t get in your way.


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Make no mistake about it; a little bit of sun does wonders for the soul. Still, you want to be extra careful to avoid too much exposure on your island-hopping adventure. The last thing you want is a sunburn to get in your way.

  • Waterproof Sunscreen — This should go without saying, but every day on the island is an opportunity for sun damage. Pack plenty of sunscreen and wear it every day. We recommend a minimum of 30+ SPF (waterproof, of course).

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  • A Windproof, Waterproof Jacket — The serene, crystal-blue sea along the coast is one thing, but the rough waters that you have to navigate through to get there are quite another. You may not encounter full foul-weather if you’re hopping in tropical climates, but you still want to make sure you’re getting proper protection against the elements in the event of a downpour.Pick a lightweight, packable technical sailing jacket and make sure that it’s waterproof, not just water resistant. Most manufacturers of technical sailing gear focus on waterproof fabrics and use taped seams for extra water resistance.
  • UV Protective Gear — Besides breezy linen shirts and shorts, you’ll want to pack some sun-protective layers that guard you from damaging UVA/UVB rays. Look for base layers and T-shirts that have UPF 50+ specifications. Follow the same convention when shopping for sun hats.



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They say sun and saltwater are the best medicine for a range of woes. But if you find yourself feeling nauseous or experience an unexpected bout of seasickness, it’s best to be prepared. According to Yachting World, 90 percent of seafarers have suffered at least once from seasickness.

three boats out on tropical waters

  • Over-the-Counter Remedies — Opting for an OTC seasick remedy is the best option, since you never know what kind of access you’ll have to fresh herbs and produce. Cited as the most used seasickness medicine by the Royal Navy, Stugeron (cinnarizine) can help curb nausea and vomiting associated with motion sickness. Scopolamine patches are another good solution, especially if you can’t stomach an oral medicine.
  • Natural Remedies — There are endless non-medicinal ways to treat seasickness, ranging from elastic, nerve-stimulating wristbands to quell nausea to salty snacks. Some people swear by ingesting ginger root and fruits with a high concentration of vitamin C to treat symptoms of seasickness.


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There are two distinct types of tropical travelers: the one who indulges in Hawaiian shirts and the one who prefers breezy linen and classic khakis. Regardless of which style suits you, the key is to pick choose accessories that correspond to your activities.

  • Sunglasses — Just like all the other gear on our island-hopping packing list, your sunglasses should be stylish and technical. If you can’t find a pair that offers both (we love this season’s Kaenon polarized sun specs, for example), then be sure to pack one pair for looks and one pair for performance.
  • Hats — If there’s one beach trip requisite for the sophisticated traveler, it’s got to be the packable straw hat. Keep things trendy when you ditch the overplayed fedora for something a bit less common, like the porkpie or safari hat. For sporting endeavors, pack a moisture-wicking ball cap or visor or add extra sun protection with a UPF 50+.
  • Swimwear — You’re going to need some dependable swim trunks on your Mediterranean adventure. This season, men’s swimwear makers have taken some serious cues from the trunks of the 1950s and ‘60s, with shorter inseams in colorful, retro menswear prints.

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Thankfully, when you’re packing for a beach trip, you can check your wingtips and winter boots at the door and opt instead for lighter options that don’t take up much suitcase space. You’ll need two types of shoes for all your maritime adventures.

  • Deck Shoes — You may be tempted to pack your Top-Siders (and we don’t blame you, classic as they are), but it’s a good idea to sport something aboard with a bit more traction on the underside. The best set of deck shoes should be designed for both style and sensibility, with high-grip soles to keep you safe on board. We love the ridiculously cool Swims Lace Loafer, for example — and they’re water friendly too. Side note: if you’re committed to the classic leather loafer, opt for one made with marine-grade leather.
  • Street Shoes — When you’re ready for a cultural jaunt into town, take advantage of the laid-back tropical style with a pair of men’s sandals in a textured croc or alligator leather.  Streetwear enthusiasts will find a good middle ground between casual and dressy with sportier options, like Soloviere sneakers.


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Provided that you’re heading out for a relatively short trip, you can get away with just two pieces of luggage: a soft-sided carry-on and a stylish rolling suitcase.

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  • A Stylish, Soft-Sided Bag — This piece of luggage doubles as your carry-on and your day pack, perfect for excursions and day-long offshore adventures. Choose a rugged men’s weekender made of canvas or marine leather, and make sure it has a comfy, padded strap.
  • Waterproof Luggage — Ensure that all your gear is safe on and off the water with waterproof or water-resistant luggage. Super-sporty and practical styles by Pelican are a good choice, especially if you’re traveling with your expensive electronics. You can also shop around to find one that has segregated wet and dry compartments so you can stash wet gear without drenching your dry clothing.


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Don’t forget the essentials.

  • Earplugs — A good pair of reusable earplugs make a solid investment for those who travel frequently. Not only are they essential for long-distance flights, they’ll also help you tune out the extraneous noise when you’re trying to catch some rest on the beach or deck. Choose a washable pair for an eco-friendlier option.
  • Toiletries — Customize your toiletries bag with stuff that’ll keep you looking and feeling great during long days in the sun. Pack waterproof sunscreen, over-the-counter seasick medicine, travel-sized analgesics, translucent deodorant, a quality travel-friendly razor and shaving cream, toothpaste, a toothbrush and extras like cotton swabs and cotton balls. Make sure to pack any prescription medications, glasses and contact lens solution in your carry-on in case your luggage gets lost.
  • Books — When else are you going to get the chance to sit down and read? Before you leave, stock up on best sellers and e-books from your local bookstore so you’re well-stocked for your trip.
  • Music — Any good island-hopping playlist should include the following: Antônio Carlos Jobim, Stan Getz, Astrud Gilberto and João Gilberto (is it even a beach trip if you don’t play “The Girl from Ipanema” on repeat?). Keep an upbeat vibe with a playlist jam-packed with island favorites — Bob Marley and the Wailers, The Beach Boys, Rihanna and plenty of Brazilian jazz, reggaeton and salsa.

sunset at sea on classic sailboat

Wherever your travels take away, you’re now all geared up for your next seafaring adventure. Channel your inner Aristotle Onassis and enjoy the azure ocean waters of the Mediterranean Sea in style.

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