You can't miss this amazing trip!

Start in Dubrovnik, Croatia, finish in Montenegro's Bay of Kotor, and spend seven days in between exploring UNESCO-listed old towns, walking the famous City Walls, boating through the Elaphiti Islands, and hiking above the coast. We'll eat and drink our way through two cuisines, from fresh Dalmatian seafood and Konavle wines to smoked Njeguši ham and a hands-on Montenegrin cooking class. The pace is balanced on purpose, with active mornings, long lunches, and free time to wander on your own. May brings warm days, long golden evenings, and the summer crowds still to come.

Come for the old towns and the island days. Stay for the group dinners, the golden-hour views, and the women you'll be sharing them with.

This trip requires a minimum number of travelers to run. Please wait to book flights and purchase travel insurance until we confirm the minimum has been met.

Arrive in Dubrovnik, settle into our hotel, and meet your fellow travelers. We'll take a first stroll through the UNESCO-listed Old City, then gather for a welcome dinner and our first taste of Dalmatian seafood.

Overnight: Dubrovnik

We start first thing in the morning on Dubrovnik's famous City Walls, before the crowds, with rooftop and sea views at every turn. Then we'll take a guided walking tour of the Old City and linger over a long lunch. The afternoon is free, with an optional cable car ride up Mount Srđ for sunset.

Overnight: Dubrovnik

We board a boat to a few of the Elaphiti Islands, such as Koločep, Lopud, and Šipan, for island walks, a long lunch, and a slow afternoon in the spring sun. Back in Dubrovnik, the evening is yours.

Overnight: Dubrovnik

After breakfast, we head south, stopping in the harbor town of Cavtat and the Konavle wine valley for lunch and a tasting. Then we cross the border into Montenegro and arrive in Kotor by late afternoon, in time for a stroll through its UNESCO-listed Old Town and dinner together.

Overnight: Kotor

We explore the Bay of Kotor by land, wandering the baroque waterfront of Perast and taking a short local boat hop to Our Lady of the Rocks, a tiny man-made island topped with a church. Back in Kotor, we'll cook together in a hands-on Montenegrin cooking class, then sit down to enjoy lunch. The late afternoon is free, with an optional golden-hour climb up Kotor's fortress.

Overnight: Kotor

We wind up the famous serpentine road above Kotor into Lovćen National Park for a moderate hike (conditions permitting) and sweeping views over the bay. Then it's on to the village of Njeguši, known for its smoked ham and local cheese, for a long, tasty lunch. Back in Kotor, we celebrate with a farewell dinner.

Overnight: Kotor