Join us for a sun-soaked adventure through two of Europe’s most stunning coastal destinations—Croatia and Montenegro! We’ll kick things off in Dubrovnik, wandering the iconic Old Town, tasting incredible local wines, and soaking up those sparkling Adriatic views.
Then it’s on to Montenegro, where dramatic mountains, turquoise bays, and charming seaside towns await. Think private boat day along the coast, breathtaking cable-car views, and evenings spent wandering the storybook streets of Kotor.
sunshine and coastal vibes
OUR ITINERARY
Arrive at Dubrovnik Airport (DBV) and make your way to our hotel, just a quick 35-minute ride from the airport. Taxis and Ubers are easy to find, making your transfer smooth and hassle-free. Your group host will be waiting at the hotel to greet you, help with check-in, and get you settled in for the adventure ahead.
If you’re arriving early, we’ll share our favorite nearby spots—perfect for a relaxed stroll, a bite to eat, or a little exploring at your own pace.
That evening, we’ll gather for a welcome dinner at a beautiful coastal-view restaurant, the perfect place to meet your fellow travelers and kick off our Croatian escape together.
WELCOME TO dubrovnik
Day 1
Enjoy a slow and easy morning—sleep in, lounge by the pool, wander into town, or head to a nearby beach for some Adriatic sunshine. This is your time to recharge and explore however you’d like.
In the afternoon, we’ll make our way into wine country, visiting a couple of charming family-owned vineyards where you’ll meet the winemakers and sample a variety of their signature wines. Between tastings, we’ll stop in the lovely coastal town of Cavtat for a stroll and some free time to soak in the seaside charm.
We’ll finish the day with a drop-off in Dubrovnik’s Old Town, giving you plenty of time to explore, shop, and enjoy dinner at your leisure.
FREE MORNING AND WINERIES
Day 2
This morning, we’ll dive into Dubrovnik’s rich history with a guided walking tour of Old Town. Led by a local expert, you’ll hear stories of the city’s past and stop by several iconic Game of Thrones filming locations—perfect for fans and photo lovers alike.
The afternoon is yours to enjoy however you’d like. Explore museums, wander the picturesque streets, or relax with a coffee while soaking in the Old Town atmosphere.
In the evening you can join us for an optional dinner cruise or dine on your own.
DUBROVNIK OLD TOWN
Day 3
Today is all about customizing your perfect Dubrovnik experience. Take an optional day trip to Mostar in Bosnia and Herzegovina, spend the day swimming, cliff jumping, and relaxing at a lively beach bar, unwind by the hotel pool, or explore Lokrum Island—a must for Game of Thrones fans. However you choose to spend the day, it’s all about doing what excites you most.
In the evening, those who’d like can come together for an optional group dinner, the perfect way to share stories from the day and enjoy our last night in Dubrovnik.
FREE DAY in Dubrovnik: YOUR DAY, YOUR WAY
Day 4
It is time to say goodby to Dubrovnik! In the morning we’ll head to Montenegro by private transportation, taking in stunning coastal and mountain views along the way. We’ll arrive at our hotel in the afternoon, giving you plenty time to relax by the water and unwind before dinner at a nearby restaurant.
DEPART FOR MONTENEGRO
Day 5
Sleep in and savor a slow morning—there’s no rush today! Then we’re off to the Kotor Bay chairlift for a ride up the mountain with jaw-dropping views. At the top, you can grab a bite, sip a drink while soaking in the scenery, hike along scenic trails, or thrill yourself on the mountain coaster.
Later, we’ll explore the storybook charm of Kotor’s Old Town. Stroll the cobblestone streets, peek into local shops, and soak up the historic atmosphere before enjoying an optional dinner in town. Afterward, we’ll head back to our hotel to relax and unwind.
Soaring Views & OLD TOWN CHARM
Day 6
Montenegro’s sparkling bays and stunning coastline are a must-see, and today we’ll experience them in style—by private boat! We’ll set off in the morning, cruising along the bays and stopping at charming coastal towns and iconic landmarks.
After lunch at a waterside restaurant, the afternoon is all about the water. Take a refreshing swim in a secluded spot, lounge on the boat soaking up the sun, or simply admire the breathtaking views around you. It’s the perfect mix of adventure and relaxation.
As the sun begins to set, we’ll return to our hotel. Dinner is on your own tonight—choose a quiet solo meal or join the group at a nearby restaurant. Either way, it’s a magical way to end a day on Montenegro’s stunning waters.
BOAT DAY
Day 7
Enjoy a full day to do exactly what you like! Wander the charming streets of Kotor’s Old Town, relax by the pool or on the beach, or embark on a day trip—our team will be happy to share recommendations for whatever sparks your interest.
In the evening, we’ll come together one last time for a farewell dinner, celebrating the adventures, friendships, and memories from an unforgettable trip.
FREE DAY
Day 8
It’s hard to say goodbye! Travelers can head home from nearby Tivat Airport or, if it’s easier, we can help arrange transportation to Dubrovnik for your flight. If you’re not ready to say farewell to Montenegro just yet, we’re happy to share recommendations for extending your stay and making the most of your adventure.
DEPARTURE
Day 9
$4,100 shared room | $5,750 Single room**
PAYMENT PLAN AVAILABLE
Due at Registration: $650 Nonrefundable Deposit
Payment 2 Due 1/20/26 $875 Shared | $1,275 Single
Payment 3 Due 3/1/26: $875 Shared | $1,275 Single
Payment 3 Due 4/10/26: $850 Shared | $1,275 Single
Final Payment Due 5/15/26: $850 Shared | $1,275 Single
**Reflects $150 early bird discount through 1/10/26
Pricing & inclusions
what's included
- Accommodations: 4 nights in a 4* hotel in Dubrovnik and 4 nights in a 5* hotel in Kotor Bay
- Daily Breakfasts & Selected Meals: Enjoy breakfast every day & 3 group dinners and 1 lunch
- Winelands Tour & Tastings: Explore 2 stunning family-owned wineries along the Croatian coast, complete with tastings and insights into local winemaking traditions.
- Dubrovnik Walking Tour: Discover the history and charm of Dubrovnik’s Old Town with a knowledgeable local guide.
- Boat Day in Kotor Bay: Spend a day on the water, exploring charming coastal towns and sites, with plenty of time for swimming and relaxing.
- Evening in Old Town Kotor: Wander the cobblestone streets, shop, and soak up the atmosphere of this picturesque historic town.
- Kotor Cable Car & Scenic Outlook: Ride to the mountaintop for incredible views of Kotor Bay, with options to enjoy a drink or take a rid on a mountain coaster at the summit
- Dedicated Guides and Hosts: Local experts guides plus an on-site trip host to ensure you have a seamless trip.
- Convenient Transfers: Transfer from Dubrovnik to Montenegro and all transportation to included activities
- Exciting Surprises Along the Way!
what's excluded
- International airfare
- Tips for local guides
- Meals not listed
- Optional add-on activities
- Traveler's Insurance (required)
- Souvenirs
- Transportation during free time
READY to join us?
How do meals work?
All activities outlined above are included in the price. There will be plenty of free time on this trip, but we will have optional group activities you can join for an additional cost. You can also use your free time to explore at your leisure and we will provide recommendations for those who want to explore independently.
Will there be free time during the trip?
Yes! Most people joining this trip will be strangers. We will coordinate a meetup before the trip for all confirmed travelers to come and meet your travel host as well as other travelers. If you are looking for a shared room, we will match you up with another girl for the trip.
I don't have anyone to go with is that ok?
We price all of our trips for both single and double occupancy. We do this to make sure travelers are as comfortable as possible, but if you want to have your own room during the trip it does increase the price. If you are interested in rooming with another traveler, please express that in our pre-registration form. We will help coordinate with other girls who express interest in sharing a room. We will be staying in handpicked luxury 5 star hotels during our trip.
What are the accomodations?
All travelers should be comfortable walking. Part of the fun of a trip to Europe is wandering down streets to shop or stop into a local cafe. We will be walking 3-8 miles most days. Both Dubrovnik and Kotor are unesco world heritage sites and although they are absolutely beautiful, most of the sidewalks will be cobblestone streets and don't allow cars. Both towns also have some slight elevation. If you are uncomfortable walking that much, you are welcome to take taxis to meet the group at your own cost.
Who is this trip for?
Meals outlined above in the "What's Included" section are included in the price. All other meals will be at your own expense. We will have an optional group dinner most evenings on the trip you can join or head out on your own. We will work to accommodate dietary restrictions as much as possible throughout our trip.
What flight should I book for this trip?
The tip will start in Dubrovnik and end in Kotor. For your arrival you can fly into Dubrovnik airport (DBV). We recommend you arrive before 3pm to ensure you have time to get through customs and check-in to the hotel before we head out to our welcome dinner. For your departure flight, you can fly directly out of Tivat airport (TIV). As we have nothing planned for the departure day you can book any flight that works with your schedule. It may be easier to fly back out of Dubrovnik which is just a 2 hour drive away, we will help coordinate transportation back to Dubrovnik for those that choose to fly out from DBV.
What is the Cancellation Policy?
Every traveler that registers and joins us for our trips need to ensure they have read the terms and conditions which include our standard cancellation policy.
FAQ's
*We currently have local communities in Chicagoland Area, Wisconsin and New York City. If you are not in one of those locations, please still include your city as we are looking to add more in the future!
