Travel at your own pace through majestic mountain ranges, stunning coastlines along the Adriatic Sea, captivating European cities, formidable fortresses, bewildering caves, historical architecture, and majestic bays from San Marino to Montenegro. This ~1,220-mile (1,963 km) road trip, mostly through the Balkan Peninsula, journeys through 6 countries (San Marino, Italy, Slovenia, Croatia, Bosnia and Herzegovina, and Montenegro) and at least 9 cities.
Travel Tips and Practicalities
Winetraveler selected Milan (MXP) as the starting point based on the ease of Winetravelers worldwide arriving in Milan. You can easily tack on a few extra days to explore Milan. For those just passing through with an overnight layover, there is a Sheraton conveniently connected to the MXP airport. From Kotor, fly home via Podgorica (TGD). Renting a car or arranging private transfers will be your most convenient option. Daytrip is an alternative option and offers flexible customizable private transfers with local drivers with the option of adding side trips.
This itinerary is perfect for all travelers (including travelers with babies or young children). For those traveling with little Winetravelers, all the hotels mentioned are family-friendly and at least fairly recently had cribs or Pack n Plays. Always confirm and reserve at the time of booking.
NOTE: Not all of these countries in this itinerary are presently open for US tourists, and those that are have restrictions in place. Before traveling, visit the Embassies of Italy, Slovenia, Croatia, Bosnia and Herzegovina, and Montenegro websites for the most current visa and tourist information. With Covid-19 restrictions and regulations constantly changing, stay current and confirm all openings.
San Marino, San Marino
San Marino is a tiny country completely landlocked by Italy and situated on the slopes of Mount Titano in the Apennine Mountain range near the Adriatic Sea. It’s one of the world’s smallest countries with a claim to being the oldest surviving republic. This micro-state spanning 23.6 square miles is the third smallest country in Europe after Vatican City and Monaco. It contains rich history, medieval fortifications, charm, dramatic views, and of course, wine. Three defensive fortifications are perched on top of Mount Titano’s three peaks in the capital city. They’re connected by medieval stone walls and cobbled paths. As you explore fortresses, churches, and museums, you may be reminded of a time when Italy and other parts of Europe were made up of independent city-states.
The Hotel La Grotta, San Marino is a charming boutique family-friendly hotel arranged over 3 floors conveniently located in historic San Marino walking distance to all the top sites.
Winetraveler has previously covered Venice at length. As described by Winetraveler author, Kristy Wenz, Venice “is unlike any other, with a charm and intrigue all its own. Colorful buildings rise above the narrow canals. Uneven brick-lined walkways and quaint bridges (of which there are 400) beckon with romanticism. Gleaming gondolas float lazily past adorned with fire engine red plastic roses and mesmerized faces.”
Venice has plentiful hotel options. The Riva del Vin Boutique Hotel offers deluxe rooms with canal views looking out toward the Rialto Bridge. Being near the Grand Canal and close to water taxi stops, it has a prime location, too. After just a short ~9 minute walk, you can be at the Basilica di San Marco and Piazza San Marco. The Bridge of Sighs is ~3 minutes longer.
Lake Bled, a lake reminiscent of a fairy tale, is tucked between lush forestry and the Julian Alps. A quaint island with a church floats in the middle. Bled Castle, believed to be the oldest castle in Slovenia, is perched high above the lake on top of a gray cliff. Slovenia offers nearly unending possibilities for adventurous spirits. From mountains soaring above valleys, waterfalls, rivers, and lakes, to an underground world full of caves. It’s the perfect place to breathe in the fresh mountain air while seeking out active adventures by day and then indulge in fine dining paired with local Slovenian wines by night.
Old Bled House is a small 300-year old farmhouse featuring cozy home-style décor and walking distance to Lake Bled. It has a romantic rustic feel whilst being a welcoming retreat for families. Affordable two-bedroom suites make this house an attractive choice to comfortably accommodate families. The restaurant provides the opportunity to taste authentic Slovenian dishes. Across the hall from the restaurant is the Old Cellar Bled that boasts a selection of more than 70 different Slovenian wines, most of which are served by the glass.
Plitvice Lakes National Park, Croatia
While the surrounding countryside is beautiful, the drive can be sobering at times. Parts of the drive to Plitvice Lakes National Park provide a stark reminder of a recent tragic past. You may pass by villages that appear to be completely abandoned with rundown homes that seem to have been destroyed and covered in bullet holes.
The Plitvice Lakes National Park is the oldest and largest national park in the Republic of Croatia. Nearly 80% of the park is covered in forestry. The park is famous for its plentiful waterfalls and turquoise lakes. The lake system is separated into the Upper and Lower lakes. The landscape is exceptionally biologically diverse. There are plentiful hiking trails around the falls, and ferries to take you to different hiking spots.
Winetraveler Tips: When in the national park, drive carefully to avoid large potholes that could result in flat tires. As of May 2021, tickets to the park are required to be purchased in advance at the official park’s website. Click here for more information and to purchase tickets.
Fenomen Plitvice is a resort blending luxury and wilderness with exceptional service. The quaint wooden houses/cabins are nestled in the woods within walking distance to the majestic waterfalls and located conveniently in the heart of Plitvice Lakes National Park. The restaurant on-site is aesthetically pleasing with a fireplace and charming wood furnishings. It is an excellent place to try local foods and local Croatian wine and beers.
Soaring mountains, long tunnels, and quaint towns surround you en route to Split. For those with time, stop at the Krka National Park on the way. Sites not to miss include the Cathedral of St. Domnius, Diocletian’s Palace, Kliss Fortress, Split Marina, Pjaca Square, and Gregory of Nin Statue. Snack on a cheese plate and try local wines at Paradox Wine & Cheese Bar. The Tribidrag Riserva Grabavoc was recommended and delightfully enjoyed.
Winetraveler Tip: For Game of Thrones fans, the Klis Fortress is a beautiful fortress on a mountain that had been used as the city of Meereen on the show.
Prima Life Spalato is an affordable hotel option connected to a shopping center and within walking distance to many of the top sites.
Mostar, Bosnia and Herzegovina
Expansive countryside, vineyards, and mountain views will surround you while heading to Mostar in Bosnia and Herzegovina. Buildings shattered with bullet holes provide a reminder of not-so-distant past strife with turmoil. Mostar is known for its old Turkish homes and its famous reconstructed bridge, Stari Most. Stroll along cobbled pathways with shops, restaurants, and surrounding mosques. Taste local dishes, such as Čevapčići, Ražnjići, and Kajmak, and local wine and beer at Podrum, located just a two-minute walk from the bridge.
Winetraveler Tip: Pay a small entrance fee by the Koski Mehmed Pasha Mosque for an unobstructed view of the iconic Stari Most.
If time permits, while traveling to Dubrovnik, pass through Neum. This will extend the duration of the trip, but many will find the views of the Adriatic Sea to be worth it.
The walled medieval town of Dubrovnik is considered to be the “Pearl of the Adriatic.” The top things to do in Dubrovnik, as previously covered by Winetraveler, include: meandering along the city walls, wine tasting within the medieval walls, visiting the Lovrijenac Fortress, basking in the sun at Banje Beach or Sveti Jakov Beach, sipping wine overlooking the sea, taking a 20-minute ferry to Lokrum Island, strolling the streets, kayaking the waters, and taking the cable car up to Srd Hill at sunset. For a truly unique experience for the more adventurous Winetravelers, head over to Edivo Underwater Winery that combines diving and wine tasting. It is only an hour from Dubrovnik. Click here to read Winetraveler’s full article detailing the best things to do, see, and drink in Dubrovnik.
The lovely seaside Hotel Excelsior Dubrovnik provides enchanting views of the Adriatic Sea and the ancient old town, restaurants facing the Adriatic, an indoor swimming pool, a beach, gardens, and a spa and fitness center. If you get a sea view room, the balcony is the perfect place to sip on wine overlooking the walled town.
Breathtaking views are offered from nearly anywhere you venture in Montenegro. Shortly after entering Montenegro, taste quality wines at the quaint family-owned Savina Winery while soaking in the dazzling bay and mountain views. The setting up on a hill is pleasant and calming, and the captivating views are visible from the tasting terrace, tasting room, and the vineyards slanted up the slope. Advanced reservations are required.
Stay or stop in Perast as you continue southward to Kotor. The charming small town of Perast, with a population of fewer than 400 people, looks out toward the narrowest part of the bay, Verige Strait, and two islets: the small island of St. George, and the artificial man-made island of Our Lady of the Rocks with a small Roman Catholic Church resting on top. Legend claims the latter was built by residents of Perast piling rocks and sinking ships around the spot fishermen found an icon of the Virgin Mary until the islet was formed.
Kotor lies along the edge of the majestic Bay of Kotor (Boka Kotorska). The turquoise bay appears to slice apart the dramatic grayish-colored mountains with speckled shrubbery encircling the city. Medieval city walls extending for nearly 3 miles surround Kotor’s Stari Grad (Old Town) and up into the mountain above the city forming a loop. The grayish-colored stone walls blend into the mountain slopes during the day. At night, the weaving walls are illuminated showcasing the perimeters of the defensive structure.
Climb up the old city walls that snake up the mountainside to the Castle of San Giovanni, and dine and wine in Kotor’s old town. Take day tours to Njegos Mausoleum, a must-see monument in Lovćen National Park for epic views and fascinating history, and Skadar Lake, the largest lake on the Balkan Peninsula. Tour nearby wineries, such as Vinarija Ivan, Vinarija Mrkan, Vinarija Vukmirović, and Vinarija Mašonović.
Stay at the historic Hotel Cattaro. The hotel is a member of the Historic Hotels of Europe and shares a portion of the town’s old walls located in Armory Square. Many rooms overlook the iconic clock tower.
Winetraveler Tip: Enhance your stay in Montenegro with the knowledge of a local guide. Montenegro M Tours provides excellent personalized tours.
If you enjoyed this itinerary, consider joining the Winetraveler Facebook Group for additional insight and travel inspiration around the world.