The 10 Best Sailing Voyages For the Epic Explorer

Ryan Rudnansky
by Ryan Rudnansky
Last updated: 5:35 PM ET, Sun January 12, 2014

The documentary "Maiden Trip" - scheduled to open in theaters nationwide on Jan. 17 - is the inspirational story of a 14-year-old girl named Laura Dekker who set out to defy the odds and become the youngest person to sail solo around the world.

Sailing is a source of adventure and enlightenment. Once you're out on the open seas, you leave everything behind. And what you discover can oftentimes be mind-blowing, whether it's the unbridled scenery or the various people in different regions of the world.

In honor of Dekker and sailors everywhere, here are some of the best sailing voyages on the planet.

SeaScape Sailing, Greece, Turkey

SeaScape Sailing travels to a variety of beautiful settings, but the Dodecanese islands in Greece was the original sailing area.

During the Dodecanese voyage, passengers will set sail from the home port in Leros. The itinerary includes visits to stylish Patmos, the tiny island paradise of Marathi, mountainous Kalymnos and the volcanic island of Niseros (new to 2014).

On top of that, SeaScape will be opening up another home base in Skiathos in the Sporades islands in 2014. The trip will include stops at rich-green Skopelos, Alonnisos' marine park and the undeveloped Pelion region.

For those who want an ever more extensive trip, SeaScape also offers voyages to Turkey's Turquoise Coast and a combo package that includes both Turkey and Greece. The combo package spans for either 10 days or two weeks, depending on your preference.

Another perk of sailing with SeaScape is the fact that the company's routes are specifically designed to stay away from the high-traffic tourist areas, giving passengers a better local feel.

Star Clippers, French Polynesia

Aboard Star Clippers' Star Flyer ship, passengers will travel to the French Polynesia tropical islands.

Seven-, 10- and 11-night cruises are offered, spanning destinations such as Tahiti, Bora Bora, Moorea, Rangiroa and Huahine.

On board, there isn't a strict schedule of events. Passengers are free to do as they wish, whether they want to check out the elegant bars or read a book at an Edwardian-style library.

Those familiar with the works of historic writer Jack London already know a little about French Polynesia.

Pirates of the Caymans, Grand Cayman Island

The "Pirate Adventure Cruise" by Pirates of the Caymans is a two-hour voyage that sets sail from the George Town harbor.

Not only does the trip present you exquisite views of the Cayman Islands, it also comes complete with a crew of pirates who reenact daily life a few centuries ago (that includes pirate trials, sword fights and "attacks" on cruise ships).

The cruise makes a 40-minute stop along the way so passengers can go snorkeling.

Other activities for passengers include hoisting the sail, firing the canon and walking the plank.

Complimentary rum punch and fruit punch is included in the itinerary.

San Juan Cruises, San Juan Islands, Washington

The Whale Watching Adventure cruise through San Juan Cruises departs from Bellingham in Washington and heads for the picturesque San Juan Islands.

During the cruise, don't be surprised if you see a variety of whales, as well as sea lions, seals, porpoises and even bald eagles. The tour is fully narrated and includes a Northwest salmon lunch and a two-hour visit of San Juan Island.

The cruise lasts a total of eight hours as deep blue waters, dark green forests and snowy mountain peaks surround you.

Yeah, life is tough.

Sailing Ship Adventures, Brazil to Nova Scotia

For those of you looking for a grander expedition, you'll want to check out Sailing Ship Adventures' 44-night trip from Brazil in South America to Nova Scotia in Canada.

The first 2014 trip from Brazil to Nova Scotia sets sail in June, crossing the Equator before arriving at Nova Scotia's capital region of Halifax.

Along the way, passengers will get chances to take the steering wheel, learn how to navigate by the sun and the stars, experience local cultures and be treated to views of whales, dolphins and flying fish traveling through.

Discovery Thailand, Andaman Sea, Thailand

Through Discovery Thailand, travelers can take a six-day cruise through Andaman Sea.

You can either depart from Krabi or Phuket. During your voyage, you will travel through breathtaking and famous locations, including Phra Nang Princess Beach, Phi Phi Island, Phang Nga Bay Marine National Park and James Bond Island in Phang Nga Bay (featured in the James Bond film "The Man with the Golden Gun").

For a little extra, you can also go kayaking through a cave labyrinth at James Bond Island.

Fans of the film "The Beach" may also recognize some of the surrounding area.

Oceanwide Expeditions, Disko Bay, West and South Greenland

For a look at the Greenland area, hop aboard Oceanwide Expeditions' voyage through Disko Bay and West and South Greenland.

During the 21-day trip, passengers can expect to come across whales and birdlife and giant icebergs while learning about the country's culture. And, if you're lucky, you may even be treated to surreal sights of the Northern Lights.

From the town of Aasiaat to the colorful and magnificent mountains, adventurers can't go wrong with this trip.

You may want to bring some warm clothes, though.

Contrary to what Greenland's name may lead you to believe, 80 percent of the country's surface area is covered by ice.

Windward Islands, Seychelles Islands

About 600 nautical miles from the east coast of Africa, you come across the Seychelles Islands in the Indian Ocean.

The choral islands boast white sand beaches, topaz waters, lush hills, glistening lagoons and alien-like glacis boulders.

The voyage courtesy of Windward Islands spans four main islands of Mahe, Praslin, Silhouette and La Digue, as well as several other small islands. Whether you are traveling through old pirate hideouts in Praslin or the spectacular beach of Anse Source d'Argent at La Digue, there is no shortage of magical locations.

Rederij Bark Europa, Antarctica

Taking a voyage with Rederij Bark Europa doesn't just ocean lovers. From photographers to bird lovers to artists, a wide range of people go through the company to travel to Antarctica.

All 22-day voyages that start in Ushuaia, Argentina, continue through the famous "Drake Passage" and the Antarctic Peninsula. On the way, you'll come across various birdlife, whales, and penguin colonies, as well as spectacular glaciers, mosses and lichen.

Like in Greenland, you'll want to bundle up, but the views will more than make up for the chilly temperatures. Plus, ironically enough, January is one of the area's warmest months, so now is the perfect time to set sail to the vast continent.

Footprint, Vietnam

Footprint has received a great deal of publicity since opening up 13 years ago, and for good reason.

One of the company's most popular trips is the three-day cruise through Ha Long Bay, Thien Canh Son Cave and Bai Tu Long Bay in Vietnam. The scenic adventure takes passengers through lush islands littered with enormous caves and thick jungle. The unique limestone karsts (geographical formations) leave some visitors spellbound.

On top of that, you'll also meet cultures from fishing villages and be treated to some delectable, fresh seafood.

Oh yeah, and you will be traveling on an ancient Chinese junk ship the whole time … so that's cool.

Any particular voyage or company I should have highlighted?

Contact me at [email protected].

Follow me on Twitter @RyanRudnansky.


For the latest travel news, updates and deals, subscribe to the daily TravelPulse newsletter.

Topics From This Article to Explore

More From TravelPulse

Related Videos

Ryan Rudnansky

Ryan Rudnansky

Born and raised in Santa Rosa, California. Graduated from San Diego State with a B.A. in journalism. Worked for Bleacher...

Grow Your Travel Business With Certified Courses

Travel Agent Academy
Travel Agent Academy
Los Cabos Specialist ProgramSell the magic of Los Cabos: luxury, adventure, and endless sunshine.
Travel Agent Academy
Travel Agent Academy
Majestic Resorts Specialist ProgramDiscover all-inclusive luxury at Majestic Resorts in paradise.
Travel Agent Academy
Travel Agent Academy
Allianz Specialist ProgramProtect every journey with Allianz Partners Travel Insurance.
Travel Agent Academy
Travel Agent Academy
Los Cabos Specialist ProgramSell the magic of Los Cabos: luxury, adventure, and endless sunshine.
Travel Agent Academy
Travel Agent Academy
Majestic Resorts Specialist ProgramDiscover all-inclusive luxury at Majestic Resorts in paradise.
Travel Agent Academy
Travel Agent Academy
Allianz Specialist ProgramProtect every journey with Allianz Partners Travel Insurance.

Don't Miss These Travel Agent Events and Trainings

Upcoming Webinar
MSC Cruises: A Year in Motion — Learn More, $ell MoreMonday, September 21, 2026
2:00pm Eastern
MSC Cruises just wrapped its first-ever Alaska season, and it's only the beginning. Join Erin Douglas...
Upcoming Webinar
Destination Weddings & HoneymoonsTuesday, September 22, 2026
2:00pm Eastern
Join Travel Weekly TravelAge West, and TravelPulse as we showcase romantic hotels and resorts designed...
Upcoming Webinar
The Islands of the Bahamas: 16 Islands, Endless LuxuryWednesday, September 23, 2026
2:00pm Eastern
The modern luxury traveler demands far more than breathtaking aesthetics, they seek effortless...
Upcoming Webinar
MSC Cruises: A Year in Motion — Learn More, $ell MoreMonday, September 21, 2026
2:00pm Eastern
MSC Cruises just wrapped its first-ever Alaska season, and it's only the beginning. Join Erin Douglas...
Upcoming Webinar
Destination Weddings & HoneymoonsTuesday, September 22, 2026
2:00pm Eastern
Join Travel Weekly TravelAge West, and TravelPulse as we showcase romantic hotels and resorts designed...
Upcoming Webinar
The Islands of the Bahamas: 16 Islands, Endless LuxuryWednesday, September 23, 2026
2:00pm Eastern
The modern luxury traveler demands far more than breathtaking aesthetics, they seek effortless...