Skip to main content

3 Luxury Sailing Vacations to Go On Before You Die

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
Image used with permission by copyright holder

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).

Recommended Videos

Italy

Sailing Collective Sail Sicily sail vacations boat italy
Image used with permission by copyright holder

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
Image used with permission by copyright holder

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.

Mike Richard
Mike Richard has traveled the world since 2008. He's kayaked in Antarctica, tracked endangered African wild dogs in South…
Avoid the awkward: 5 basic flight etiquette rules you should always follow
Because nobody wants to be that passenger everyone remembers for the wrong reasons
Interior of a passenger airplane

A few months ago, I was on a red-eye flight trying to catch some sleep, and just as I started to doze off, the person in front of me suddenly reclined their seat with full force, nearly knocking my laptop into my lap. Moments later, someone a few rows over had their shoes off and feet resting on the bulkhead. It was a crash course in why flight etiquette matters.

Air travel puts hundreds of strangers in a small, shared space for hours at a time. When everyone follows a few unspoken rules of courtesy, the experience can end up being smoother and more comfortable for everyone. So, here are five flight etiquette basics that make a big difference.
1. The middle airplane seat gets both armrests

Read more
Visiting Norway? A new fee may change how much your trip costs
The tax could be implemented as soon as next summer
Bergen Norway

Norway, famous for its dramatic fjords and Arctic beauty, is the latest country to introduce a tourism-related fee in response to growing concerns over overtourism. In 2024, Norwegian accommodations recorded more than 38 million guest nights, placing increasing pressure on infrastructure in many of the country's most scenic areas. Now, following the lead of cities like Venice and Barcelona, lawmakers have approved a measure that allows municipalities to implement a 3% “visitor’s contribution” tax on overnight stays and cruise ship passengers.

Unlike nationwide tourist taxes in other countries, Norway’s version will be locally applied. Municipalities must apply for approval by demonstrating that tourism has significantly strained public services. Once approved, the 3% tax can be levied on hotels, guesthouses, Airbnbs, and cruise passengers. However, camping vans, tents, and recreational boats will be exempt.

Read more
New technology offers US citizens seamless entry back into the country
Dallas Fort Worth International Airport

United States Customs and Border Protection (CBP) is expanding a new program, Enhanced Passenger Processing (EPP), which allows U.S. residents traveling internationally to have uninterrupted entry back home. The technology uses biometric scanning and high-tech software to clear travelers as they walk through the international arrivals area. Best of all, there are no application fees, memberships, or interviews.

The program is an even better alternative to Global Entry, which offers pre-approved, low-risk passengers a quick, smooth arrival back to the U.S. But even then, travelers have to stop at kiosks, and there’s a $120 nonrefundable application fee.

Read more