3 Luxury Sailing Vacations to Go On Before You Die

luxury sailing vacations cuba italy fiji captain cook cruises boat ship
Sometimes the best way to explore is by water. Travelers adventurous enough to sail around a country are often afforded a view of their destination that few others will ever appreciate. Here are three unique sailing vacations worth a look.

Cuba

G Adventures’ Sailing Cuba sailing vacations boat

Cuba is, of course, much more than Castro, old cars, and fancy cigars. Passengers on G Adventures’ Sailing Cuba trip begin their journey in Havana before being whisked away to Cienfuegos to board a modern catamaran. The small ship tour (with a maximum of just 14 passengers) focuses on the Canarreos Archipelago, where visitors spend most of their eight-day journey leisurely exploring the beautiful island chain from the water. Relaxed days are spent sunbathing on deck, strolling pristine beaches, snorkeling, and checking out the archipelago’s more remote islands. Standard pricing starts at $1,999, including a twin-share room and most meals (booze is extra).

Italy

Sailing Collective Sail Sicily sail vacations boat italy

If you fancy your relaxation with a bit more luxury, Sailing Collective specializes in small ship cruising that includes whole cabin booking (no sharing with strangers), plus private chefs and unique land-and-sea itineraries. Most of the catalog features bespoke cruise itineraries where guests travel by flotilla with up to five ships together. The Sail Sicily itinerary, in particular, takes passengers on a week-long journey around Italy’s famous Aeolian Islands. The volcanic archipelago is both rugged and pristine, surrounded by impossibly blue waters. The fact that it’s UNESCO-protected makes it a worthwhile destination in its own right. The daily schedule blends sea- and land-based exploring, however, the crew leaves it largely up to the passengers to decide the specific excursions. Pricing starts at $2,200 per person double occupancy and includes most meals (booze is extra).

Fiji

Captain Cook Cruises Fiji sailing vacations boat ship

If a four-cabin catamaran is a bit too claustrophobic for your liking, Captain Cook Cruises’ tall ships offer plenty of room to spread out. The company has a fleet of vessels, from a rustic, 88-foot pirate ship to the Fiji On, one of the area’s most luxurious charter boats capable of transporting up to 160 passengers. The Fijian islands are among the most exotic and beautiful in the world: pristine coral reefs, cobalt blue waters, and perfect tropical weather year-round. Captain Cook offers day and lunch cruises around the archipelago. However, the company specializea in custom, multi-day itineraries (with custom pricing) that allow passengers to explore as much of Fiji as they like.

If you prefer your travel experiences with less cocktail-sipping relaxation and a more hands-on approach, these sailing adventures put you in the captain’s seat in some of the world’s most beautiful waters.

Travel

5 Easy Tips for Protecting Your Digital Data While Traveling

Travel smart — don't become an identity theft statistic.
Travel

Burstner Harmony 3 Is One of the Sexiest Camper Concepts We’ve Ever Seen

Sometimes "roughing it" should include an espresso maker and a rainfall shower.
Auto

Get Lost On Your Terms With Hudway Sight AR Helmet

With this helmet-mounted display, motorcycle riders are only ever a command away from navigation.
Living

No Pool, No Problem: Book Your Own Private Pool by the Hour with Swimply

Who says you have to own a pool to throw a pool party?
Auto

Ducati’s New Scrambler Icon Gets More Style and Tech for 2019

Ducati's refreshed moto still looks tough, but gets a bit smarter.
Travel

Dive In to the Best Beaches and Rum During Your St. Croix Vacation

If you’ve been considering a tropical vacation, now is a fantastic time to head to the Caribbean.
Travel

Sanctuary Retreats is the Name to Know for Luxury African Safaris

Each camp is a unique reflection of its natural environment and often, the wildlife viewing from your balcony or the pool is as good as any safari truck.
Travel

A Visit to a Maasai Village in Africa (Photos)

Unlike many other, far more private indigenous groups, the Maasai are known to welcome visitors to their villages to learn about their customs and way of life.
Travel

What It’s Like to Go On a Once-in-a-Lifetime African Safari (Photos)

"We’d been in the Serengeti for all of ten minutes before we heard the baby elephant’s panicked trumpeting in the distance."
Travel

How to Pack Your Suitcase, Backpack, or Duffel Bag Like a Pro

Despite the many horrors of modern air travel, it’s never been easier to get organized for your next trip.
Food & Drink

How to Eat Your Way Across Texas Barbecue Country

Brisket, brisket, and more brisket. Here’s how to eat it like a king in Texas barbecue country.
Food & Drink

Ohio Is Home to the World’s First Brewery Hotel (with In-room Taps!)

In-room taps and well-stocked shower fridges? Sign us up!
Food & Drink

Win a Luxurious Travel Cocktail Set In Honor of The Manual Spirit Awards

Only two can win. Will it be you? Enter to find out.
Travel

Tips for Staying Healthy on the Road from People Who Get Paid to Drink

Though spirits brand ambassadors have pretty much the coolest job ever, constant travel can take a serious toll. Here's how some of the best stay balanced on the go.