Alaska
Australia, New Zealand & Tahiti
Canada
Central & South America
Eastern USA
Europe, Africa & the Middle East
Hawaii
Southern USA
West & Mid-West USA
View All Destinations
Hosted By: Jerre Fuqua
President
Holiday Vacations
View Biography
Experience luxury cruising along the gorgeous coastlines of Italy (including Sicily), Montenegro, and Croatia aboard the world’s largest sailing ship, holding just over 300 guests! Begin discovering Italy’s cultural treasures with two captivating days in Rome, where we explore famous landmarks like the Vatican Museums, the Sistine Chapel, and the Colosseum. Then, board Windstar Cruises’ award-winning Wind Surf for an eight-night Mediterranean voyage through the Tyrrhenian, Ionian, and Adriatic Seas. Enjoy several breathtaking ports of call: Sorrento, Giardini Naxos, Kotor, Dubrovnik, Split, and Rovinj. While there are plenty of opportunities to create your own adventures with spectacular optional excursions, we’ve handpicked a variety to include, from walking through ancient Pompeii’s ruins and gazing upon 12th-century Baroque architecture to visiting a historic man-made islet and sampling the region’s best wine. After disembarking, we cruise the canal to Venice for a guided walking tour and quintessential gondola ride before concluding with a Farewell Dinner.
October 15th, 2025 - October 27th, 2025
Occupancy
Price Per Person
Double Stateroom
$9299
Double Suite
$11099
Single Stateroom
$12599
Single Suite
$15699
Final Payment Date: 06/07/2025
Day 1 : Fly to Europe
Our adventure begins with an overnight flight across the Atlantic Ocean.
Day 2 : Buongiorno Rome
Our English-speaking local guide greets us at the airport upon arriving in the beautiful city of Rome. After checking in to our accommodations with time to rest, we get to know fellow travelers over a Welcome Dinner.
Day 3 : Vatican City & Leisure Afternoon
We begin our Italian adventure with a guided tour of the iconic Vatican Museums. Browse the galleries to see some of the most renowned classical sculptures and Renaissance art around the globe, then step into the remarkable Sistine Chapel for views of its illustrious ceiling fresco, painted by Michelangelo. Our discoveries in Vatican City continue with a special tour of St. Peter’s Basilica, one of the most extraordinary churches to ever exist and home to the Catholic Church. The rest of the day is yours to explore more of Rome’s treasures.
Day 4 : Ancient Rome & Set Sail
This morning, we discover the most pivotal landmarks of ancient Rome! Our first stop is the largest amphitheater in the world, the Colosseum, where we can walk in the steps of the mighty gladiators. Next, we tour the Roman Forum, home to several well-preserved pieces of architecture, including the Arch of Constantine. Lastly, take in views of the stunning Trevi Fountain before boarding Windstar’s Wind Surf to experience the luxury of yacht-style cruising. This newly renovated sailing ship is small enough to venture into ports beyond the reach of larger vessels, yet expansive enough to provide high-class amenities.
Day 5 : Sorrento & Pompeii
Our first port of call is the stunning coastal town of Sorrento. Revel in the opportunity to uncover one of the most significant moments in history with an included excursion to Pompeii. Our rigorous walk along ancient, uneven footpaths in this preserved archaeological site is led by a private guide who recounts the city’s cataclysmic destruction after Mount Vesuvius erupted in 79 AD. Later, we return to Sorrento for time at leisure.
Day 6 : Giardini Naxos, Sicily
We dock in Giardini Naxos today, an enchanting village in Sicily known for its ancient Greek history. There are a variety of optional excursions available, such as a boat ride into the famous Blue Grotto sea cave or wine tasting near Mount Etna, Europe’s most active volcano. Windstar’s complimentary Watersports Platform is also available so you can enjoy the sparkling waters of the Ionian Sea.
Day 7 : Day at Sea
Take advantage of the ship’s wonderful amenities today as we sail towards the Adriatic Sea. Go for a dip in the whirlpool, indulge in a treatment at World Spa by Windstar, attend a cooking demonstration, or dance the night away with live music.
Day 8 : Montenegro & Kotor Bay
Our ship arrives in Montenegro this morning, docking in UNESCO World Heritage-listed Kotor. We take an excursion to Perast, a pedestrian-only Baroque village, where a local guide leads us on a walking tour that includes views of the Cathedral of St. Nicholas, the Parish Church, and more. Next, savor a taste of authentic Baroque sweets before our private motorboat ride to Our Lady of the Rocks, a man-made islet in the Bay of Kotor. Explore its Catholic church, which holds over 60 paintings by famous 17th-century artist, Tripo Kokolia. This afternoon, enjoy a walking tour of Old Town Kotor to admire its bright red rooftops, 12th-century Baroque palaces, and impressive fortress before time to explore independently.
Day 9 : Dubrovnik & Croatian Wines
We go where larger ships cannot today and anchor within the renowned walled city of Dubrovnik! An included excursion takes us to a family-owned winery in the small village of Komaji. Taste some of the finest wines in the region as we get to know a third-generation winemaker who shares his firsthand knowledge of Croatian wines. Afterwards, we return to Dubrovnik’s Old Town for a guided walking tour that immerses us in centuries of history with sights such as the Franciscan Monastery and Sponza Palace. The rest of the afternoon is yours at leisure.
Day 10 : Split, Croatia
Today’s port of call is the gorgeous city of Split, nestled along the eastern shore of the Adriatic Sea. Its lively harbor boasts wonderful cafes and Old Town holds the most famous attraction: Diocletian’s Palace, which was built around 300 AD for the Roman emperor. Stroll the charismatic streets or create your own adventures with an optional excursion, such as a cooking class, river rafting adventure, or tour of UNESCO World Heritage Sites.
Day 11 : Rovinj, Croatia
Discover the Istrian peninsula this morning as we dock in the beautiful fishing port of Rovinj. The day is yours to explore as you wish! Wander through the maze of cobbled streets in Old Town to St. Euphemia Cathedral or select an optional excursion.
Day 12 : Venice City Tour & Gondola Ride
We disembark this morning and take a boat ride on the canal to Venice. Enjoy a guided walking tour of the stunning “Floating City” and discover grand examples of Byzantine architecture in St. Mark’s Square, such as St. Mark’s Basilica, the Bridge of Sighs, and the Doge’s Palace, a former royal residence. Afterwards, explore on your own before our quintessential gondola ride on Venice’s charming waterways. This evening, we celebrate our travels at a Farewell Dinner and settle into our hotel near the airport.
Day 13 : Fly Home
We board our flight and return home with wonderful memories of our Dalmatian Coast adventure.
Jerre Fuqua is president of Holiday Vacations. A career veteran in travel and tourism, Jerre is a fifth-generation Colorado native and has been active in the outdoors from an early age. His love for travel began with a subscription from his grandparents to National Geographic. Each month he would anxiously watch the mailbox for the next magazine.
In addition to Holiday Vacations, Jerre has a rich background in leading specialist travel brands that created over 500 unique itineraries. His experience includes luxury guided tours, walking and biking tours, private jet excursions around the world, small-ship cruises as well as ocean and river cruises, plus tailor-made travel to over 150 countries.
He is most proud of changing lives through travel, fully believing that a tourist can leave home and return as a traveler, forever changed to make a positive impact in the world.
Tour days tend to be shorter in length, at a relaxed pace, and include lots of unscheduled time for leisure. Expect standing and walking for extended periods of time on flat surfaces, mostly low altitudes, and consistent temperatures.
Tour days usually move at a leisurely pace. Some days’ scheduled activities last longer than others. Expect standing and walking for long periods of time on occasionally uneven terrain. You may experience changes in altitude or temperature.
Tour days tend to be long, move at a consistent pace, and may include long travel days. Expect standing and walking for long periods of time on uneven surfaces. Some destinations may have changes in altitude and/or temperature.
Tour days tend to be long, move at a brisk pace, and may include lengthy travel days. Expect long periods of walking and standing on uneven surfaces. Scheduled activities may require physical effort or have distinct changes in altitude or temperature.
Tour days tend to be long, move at a vigorous pace, and may include lengthy travel days. Expect long periods of walking and standing on rough surfaces. Scheduled activities may require physical effort or have distinct changes in altitude or temperature.