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14 Day Sailing itinerary from Dubrovnik

About this program

This is a 14-day sailing trip starting from Dubrovnik and is meant for people who love to go island-hopping while on vacation. The sailing route starts and ends on Saturday. When you find your yacht, you may want to choose a bareboat or skippered yacht charter, or even luxury yachts charters, to follow the route.


About the route

Welcome to the breathtaking coastal charm of Dubrovnik, Croatia’s crown jewel, where azure waters caress ancient walls and captivating history meets modern allure. Brace yourself for an unforgettable 14-day sailing odyssey that will sweep you off your feet and onto the open seas.
Picture yourself aboard a graceful sailboat, wind whispering through your hair, as you embark on a voyage that blends adventure, relaxation, and discovery in perfect harmony. From Dubrovnik’s sun-kissed shores to the hidden coves and enchanting islands that adorn Croatia’s coastline, our sailing itinerary promises an immersive experience like no other.
So, grab your sun hat, pack your sense of wonder, and join us on this delightful escapade as we set sail to explore the wonders of Croatia.


Day 1

Day 1: Exploring Dubrovnik’s Old Town

The first day of your perfect route takes you to the captivating streets of Dubrovnik’s Old Town, a historical gem that will enchant you at every turn. Meander through the ancient limestone alleys that connect to Stradun, the main old street, where tales of old seafarers and adventurous traders come alive.

As you wander, soak in the grandeur of the city walls that stand tall, guarding the secrets of a bygone era. Lace up your explorer shoes and venture atop the walls for a panoramic view that will steal your breath away. Discover the iconic Onofrio’s Fountain, a centuries-old landmark that whispers of its fascinating past. Oh, and do not miss the impressive Rector’s Palace, where history unfolds before your eyes.

The Old Town of Dubrovnik promises a mix of history, culture, and seaside charm, setting the stage for the nautical escapades that lie ahead of your 14-day island-hopping sailing itinerary.

Day 2
Mljet Island

Day 2: Sailing to Mljet Island

Begin your 14-day sailing route by sailing to Mljet Island, known for its unspoiled beauty. This island paradise offers an idyllic escape from the bustling world.

Explore the charming village of Polače, where ancient Roman ruins stand tall as a testament to the island’s rich history. Wander through picturesque olive groves and vineyards, indulging in the island’s local flavors. Then, you may want to visit the tranquil St. Mary’s Island, home to a stunning 12th-century Benedictine monastery that exudes peace and serenity.

While on Mljet Island, do not miss the mystical Odysseus Cave, a captivating sea cave that inspired ancient tales of Homer’s Odyssey. Paddle into its surreal depths and be enchanted by the play of light and shadows, creating an otherworldly atmosphere. A must-visit gem that will leave you in awe of nature’s artistic wonders on your sailing journey.

Day 3
Mljet National Park

Day 3: Exploring the National Park of Mljet

The third day of your thrilling sailing vacation beckons you to enjoy the enchanting National Park Mljet. Hoist your sails and let the gentle Adriatic Sea breeze guide you to this nature lover’s paradise—a pristine oasis of lush greenery and crystalline lakes.

Drop anchor near the National Park Mljet and plunge into an underwater wonderland while snorkeling in the serene lake waters. Note that you should check in advance where it is allowed to anchor within the area of the national park.

Traverse the island’s rugged trails, where ancient myths and legends intertwine with the lush Mediterranean landscape.

Day 4

Day 4: Sailing to Korčula

On the fourth day, your sails unfurl toward the captivating island of Korčula.

Embrace the winds of excitement as you approach the island’s shores, a haven of culture and natural wonders. As you dock, prepare to be amazed by the mystical beauty of the Moreška Sword Dance, an age-old tradition that brings history to life with its spirited performances.

Delight in the island’s renowned vineyards, where luscious wines beckon for a tasting adventure like no other. The vineyards’ lush greenery provides the perfect backdrop as you indulge in Croatia’s finest vintages.

As the sun sets, revel in the enchanting ambiance and lose yourself in the island’s captivating tales. With every moment on Korčula Island, your sailing journey is bound to become a treasure trove of unforgettable memories.

Day 5
Town of Korčula

Day 5: Exploring the Town of Korčula

While on Korčula Island, you may want to discover its charismatic heart, Korčula Town.

Prepare to be whisked away to a fairytale setting as you stroll through its charming, cobbled streets. Meet the mysterious Moreška dancers, whose vibrant swordplay echoes ancient legends and folklore. Pause at the majestic St. Mark’s Cathedral, an architectural masterpiece that stands tall, overlooking the town’s orange-tiled rooftops. Step into the Marco Polo House, where the legendary explorer’s tales come alive, and you might just feel the winds of adventure beckoning you to new horizons. Delight in the quaint boutiques and artisanal shops, offering unique souvenirs and delectable local treats.

Prepare for a day filled with wonder and laughter, as Korčula Town weaves its magic into your sailing escapade.

Day 6

Day 6: Sailing to Hvar

Now, your sailing adventure brings you to the sun-kissed shores of Hvar Town, a captivating gem on the island of Hvar.

As you moor, the first landmark to behold is the iconic Hvar Fortress, perched atop a hill, offering panoramic views of the azure Adriatic and the charming town below. Meander through the narrow streets to discover the Renaissance-era St. Stephen’s Cathedral, adorned with stunning artworks and a mesmerizing bell tower.

Once the sun sets, Hvar Town truly comes alive with its legendary nightlife. Gather your crew and set out to explore the bustling bars and clubs, where laughter and music fill the air. Sailing with friends becomes even more memorable as you dance the night away under the stars, embracing the joyous spirit of Hvar Town and the camaraderie of your nautical journey.

Day 7
Exploring Hvar

Day 7: Exploring the Island of Hvar

As you venture beyond Hvar Town’s allure, the island of Hvar unfurls a treasure trove of sights and wonders waiting to be explored.

Set sail to the enchanting Pakleni Islands, a stunning archipelago where hidden coves and secluded beaches beckon for your exclusive anchor drop. Dive into the crystal-clear waters, unveiling a kaleidoscope of marine life that will leave you in awe.

Step back in time and wander the charming streets of Stari Grad, lined with centuries-old buildings, and immerse yourself in the captivating blend of rich culture and natural beauty that this ancient town has to offer.

As you sail with the wind in your hair and the sun on your face, the island of Hvar promises endless adventures and the thrill of discovering nature’s hidden gems.

Day 8
Vis town

Day 9: Sailing to Vis

Your next voyage takes you to the captivating island of Vis, where the enchanting Vis Town awaits your exploration. Dock your vessel and step ashore to discover this charming Mediterranean gem.

Lose yourself in the town’s quaint streets lined with vibrant houses and bustling cafes. Savor local delicacies at the bustling farmer’s market, relishing the flavors of freshly caught seafood and succulent fruits. Immerse yourself in history at the Archaeological Museum, which unravels the island’s intriguing past, or explore the impressive Fort George, offering breathtaking vistas of the azure sea.

Find yourself enchanted by the warm hospitality and lively atmosphere, making your day in Vis Town an unforgettable memory of your seafaring escapades.

Day 9
Island of Vis

Day 10: Exploring the Island of Vis

Komiža, a picturesque fishing village, offers a glimpse into traditional Dalmatian life, where colorful boats bob in the harbor, and the aroma of freshly caught seafood fills the air.

Meanwhile, a short sail away lies Stiniva Cove, a secluded gem hidden between towering cliffs. As you approach this breathtaking paradise, you will be mesmerized by the stunning turquoise waters and the intimate pebble beach, creating a serene oasis for relaxation and exploration.

Raise your binoculars and spot the ethereal Blue Cave on Biševo Island, where sunlight paints the underwater world in mesmerizing shades of blue. Navigate through the labyrinthine bays, feeling like a true explorer as you encounter ancient ruins and charming fishing villages.

Day 10

Day 11: Sailing to Šolta

Your sailing journey from Vis to Šolta promises an exhilarating experience on the open seas. Feel the thrill of the waves beneath your vessel as you navigate through the azure expanse and keep an eye out for playful dolphins that may join you on your voyage.

Upon reaching Šolta, venture into the charming village of Grohote, where time seems to stand still among the rustic stone houses and lush olive groves. Immerse yourself in the island’s authentic atmosphere, relishing in the warm hospitality of the locals and savoring the delectable traditional cuisine.

Do not miss the chance to visit the enchanting village of Maslinica, a postcard-worthy bay dotted with luxury yachts, charming stone houses, and a picturesque seventeenth-century castle, adding a touch of history and allure to your sailing adventure on Šolta.

Day 11
Beaches of Šolta

Day 12: Enjoying the Local Beaches on Šolta

A blissful summer awaits you on Šolta’s pristine beaches. Picture yourself lounging on the soft golden sands, basking in the warm Mediterranean sun. As you dip into the crystal-clear waters, your worries dissolve, and tranquility envelops you.

Each beach on Šolta offers its own enchanting charm – from the secluded coves of Livka and Zaglav, ideal for peaceful seclusion, to the family-friendly beach of Šešula, where laughter fills the air, making it a perfect spot for sailing with family. Swim in the refreshing sea, feeling the gentle embrace of the waves, or indulge in leisurely sunbathing, allowing the cares of the world to drift away.

Whether you seek solitude or camaraderie, Šolta’s beaches offer the perfect haven for relaxation, swimming, and sun-kissed summer bliss.

Day 12

Day 13: Sailing to Lopud

Your sailing adventure leads you to the enchanting Lopud Island, where idyllic beauty and rich history beckon. As you approach the island’s shores, be mesmerized by the picture-perfect sandy beaches, like Šunj Beach, offering a paradise for relaxation and swimming.

Embark on a leisurely stroll through the charming village of Lopud, where car-free paths lead you to historical treasures, like the Franciscan Monastery and its lush botanical garden. Hike up to the spectacular Lopud Fortress, standing as a testament to the island’s past. Dive into the azure sea to discover underwater wonders or try your hand at water sports for an adrenaline rush.

Whether you seek moments of serenity or exhilarating adventures, Lopud Island promises an unforgettable sailing escapade filled with nature’s splendor and cultural marvels.

Day 13

Day 14: Return to Dubrovnik

As your 14-day sailing itinerary comes to an end, the memories of your epic nautical odyssey in Croatia will forever linger in your heart. From the ancient charm of Dubrovnik’s Old Town to the hidden paradises of Mljet, Korčula, Hvar, Vis, Šolta, and Lopud islands, you have uncovered a world of breathtaking beauty and untamed adventures. The Adriatic’s azure waters and the warm embrace of the sun have become your loyal companions throughout this enchanting journey.

But fret not, for the call of the sea will always beckon you back to Croatia’s stunning coastline. So, if you crave endless horizons, secluded coves, and a true escape from the ordinary, do not hesitate to get in touch with us and book your 14-day sailing vacation in Dubrovnik!


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Have a question about this route?
We have answers to your questions. So don’t hesitate to get in touch with our team today!

Picking a boat type

Picking out the type of boat to go with will generally come down to your budget, the group size, and preferred method of sailing. Moreover, different sailboats available can be chartered independently or with a fully-staffed crew.

Find your yacht
sailing boat with full sails up and people on the side
2-12 people
Choose a Sailboat if you are an active traveler or you’re looking for a romantic getaway. Sailboat offer the classic sailing experience and tend to vary in size from 30 up to 64 feet
Starting from 160 EUR per day
luxury catamaran on the water aerial view
2-12 people
Catamaran is a top choice if you’re looking for a smoother sailing experience compared to sailboats. Since the size ranges from 38 to 70 feet, this is a right vessel for bigger groups or families
Starting from 500 EUR per day
Motor yacht on the water | Sebastus Sailing
Motor yacht
2 – 12 people
Depending on what you’re looking for, you may find motor yachts from one up to five cabins and their size tend to range from 30 to 100 ft. These beautiful vessels are perfect for a luxurious touch on sailing vacation
Starting from 500 EUR per day
luxury wooden gulet cruising on a sunny day
8-20 people
Most of Gulets have six cabins and come with three or four crew members, which makes it amazing for larger groups. The sip sizes tend to range between 60 to 100 feet, so you can be sure that everyone has more than enough space.
Starting from 600 EUR per day
Waves icon | Sebastus Sailing

Have a question?
We have the answer!

You ask yourself what kind of boat to choose? Which places to visit? We have answers to those questions and many more. So don’t hesitate to get in touch with our friendly team today!