Jonathan Epstein's 14-day Ireland Itinerary

Ashford Castle, County Mayo, Ireland
Photo: Design Pics/The Irish Image Co/Getty Images

Jonathan Epstein is a member of Travel + Leisure’s A-List, a collection of the top travel advisors in the world, and can help plan your perfect getaway. Below is an example of the type of itineraries he creates. To work with Jonathan, you can contact him directly at

Day 1: Arrive in Dublin

Today you will arrive into Dublin Airport on, where you will catch a taxi to The Westbury in Dublin. After dropping off your bags and freshening up, you can explore Dublin independently. We suggest a walk through the heart of Georgian Dublin and the 22-acre park of St. Stephen's Green. You will certainly enjoy Powerscourt Townhouse, which is located just beside The Westbury. In the evening, enjoy a meal in one of Dublin's authentic pubs or casual restaurants.

Stay: The Westbury

Day 2: Dublin

This morning, explore more of the city independently, visiting sites such as Sheridans Cheesemongers — to enjoy a taste of authentic Irish farmhouse cheeses — and the Chester Beatty Library, which is home to what many consider the finest private collection of manuscripts. This afternoon, you will be met by your expert walking guide for a half day overview tour of Dublin, taking in all the highlights along the historic "Golden Kilometre." In the evning, visit St. Patrick’s Cathedral, the largest church in Ireland, for their daily choral evensong. Dinner reservations at Wilde.

Stay: The Westbury

Day 3: Dublin

You will be met by your driver and separate guide to explore more of Dublin. Begin your day touring Kilmainham Jail to learn about its important role in the Irish Revolution and some of its famous past occupants. Then, visit the National Gallery of Ireland, followed by Trinity College to see the famous Book of Kells and the Long Room. Enjoy dinner in one of Ireland's finest restaurants, Chapter One.

Stay: The Westbury

Day 4: Connemara

Youu will be met by your driver guide in the morning for a transfer to Ashford Castle, in the Connemara region. One of the world's finest hotels, we have worked closely with our friends at the castle on all elements of your stay. En route, you can visit Clonmacnoise, on the River Shannon, which is one of Ireland’s holiest sites with a history that spans centuries. This afternoon, relax at the hotel and enjoy a walk through the Walled Garden and their beautiful grounds.

Stay: Ashford Castle

Day 5: Connemara

Relax at the hotel and also enjoy some of the activities on the estate. We have worked with our friends on property to build a robust schedule, including a boat trip on Lough Corrib, horseback riding, and the property's famous "Hawk Walk." Dinner is booked at their sister hotel, The Lodge at Ashford.

Stay: Ashford Castle

Day 6: Connemara

Enjoy more activities at Ashford Castle: in the morning, we have booked a fishing experience with a wonderful ghillie, and in the afternoon, you will enjoy clay target shooting. You can also take a walk into the nearby village of Cong. Dinner is booked at George V, their fine dining restaurant.

Stay: Ashford Castle

Day 7: County Clare

In the morning, transfer with a private driver to Gregans Castle in County Clare. On the way, you can explore the boglands, lakes, and mountains that make up the Connemara National Park. Visit the market town of Clifden before stopping for lunch in the vibrant city of Galway, where you can walk around the many shops and restaurants of the Latin Quarter and explore Eyre Square. At Gregans Castle, we have booked a room with an incredible view over The Burren. Dinner tonight is booked in the local village of Ballyvaughan.

Stay: Gregans Castle

Day 8: County Clare and the Burren

Meet your driver in the morning for a visit to the Cliffs of Moher, some of the world's highest sea cliffs with stunning views of the Atlantic Coast. Then, head to Burren National Park to meet up with your walking guide and enjoy a walk through the park's vast limestone plateaus and diverse botanical wildlife. If time permits, you can also visit the Burren Perfumery, famous for using local wildflowers and herbs in their soaps and other products.

Stay: Gregans Castle

Day 9: County Kerry

Meet your driver in the morning for your transfer to Killarney Park Hotel in County Kerry. En route, stop in the charming village of Adare, best known for its quaint thatched-roof cottages. Upon arrival in Killarney, you can visit some of the nearby sites along the Ring of Kerry — Ross Castle, Muckross House & Gardens, Torc Waterfall, and the panoramic viewpoint of Ladies View.

Stay: Killarney Park Hotel

Day 10: County Kerry and the Dingle Peninsula

With your drive, explore the Dingle Peninsula, a narrow 40-mile stretch of land famed for its rugged and remote beauty. Here you can stop in some of the many shops of the local craftsmen, such as Louis Mulcahy’s pottery and Murphy’s Ice Cream; we have also booked a special experience with one of our friends, a local crystal maker. Later, drive along the beautiful Slea Head Drive, where you can see some of the many ancient Fahan "beehive" huts, inhabited until the 13th century.

Stay: Killarney Park Hotel

Day 11: County Kerry

Spend the day independently, perhaps hiking in the National Park or exploring the shops and pubs of Killarney. In the evening, we have organized a comparative whiskey tasting of a number of Irish and Scottish Whiskeys.

Stay: Killarney Park Hotel

Day 12: County Laois and Ballyfin

Meet your driver and travel to Ballyfin, visiting the Rock of Cashel, one of Ireland’s most important historical sites, along the way. This is where Saint Patrick reputedly converted the King of Munster. Upon arrival, you can relax at the hotel and explore the beautiful grounds, before joining their guided tour of Ballyfin and the property's kitchens. In the evening, enjoy pre-dinner drinks with Ballyfin's resident pianist and dinner at the Cellar Bar.


Stay: Ballyfin

Day 13: County Kilkenny

Take a full day private tour of the medieval city of Kilkenny, with highlights including Kilkenny Castle, home of the fabulous Butler Art Collection, and the Kilkenny Design Centre, where you will find locally made jewelry and pottery. Kilkenny also has a thriving arts and crafts scene and a couple of our favorite local artisans include Chesneau Leather and Jerpoint Glass, where you can enjoy a glassblowing demonstration.

Stay: Ballyfin

Day 14: Depart from Dublin

Transfer to the airport for your onward flight home.

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