Head up the slope and across the drawbridge to enter Old Town where you'll find narrow, winding cobbled streets and great views. Plenty of restaurants, shops, art galleries, etc. At the top are a castle and the Santa Maria de les Nues cathedral. Unfortunately not much was open when we were there but we enjoyed the walk (climb!) and the views overlooking the harbor.
Continue walking up and you reach Carrer Sant Ciriac. On the corner you find Capella de Sant Cristofol and nice inexpensive souvenir shop Shambala across the street from the chapel. Carry on up the Csant Ciriac and you will find a small chapel built in 1754 in honor of the saint from whom the street takes its name. According to the legend, the chapel marks the exact point where King Jaume’s troops entered the walled area and took the city over. From the chapel you turn left and continue your way up along Carrer Major (every town has the Main Street), which leads you to the highest point in Dalt Vila. The houses along the street date back to the 15th century. One of them (on your left) contains the only hotel in the Old Town called Torre del Canonico – it worth brief visit even if you are not going to spend a night here.
Carrer Major ends at Plaça de la Catedral at the top of the hill. Apart from taking in a magnificent overview of the port and the city, here you have the opportunity to visit 2 old buildings. First of all, the Cathedral, built in 14th – 16th centuries, remodeled in the 18th, as a result combining Gothic with Baroque. Next to the Cathedral you see la Universitat – the political institution that governed Eivissa from 13th to the 18th century (it houses Archeological Museum now). Leaving Plaça de la Catedral, follow a narrow passage to the bastion of Sant Bernat, which gives you overview of the sea with the island of Formentera in the distance.
You can go down through the bastion to the terrace below it. Above the bastion, you see the Castel / Castle , not in the best shape today. Continuing your walk along ronda de Joan Baptista Calvi (yes, the guy who designed the fortifications) and come to the bastion de Sant Jordi. From here you have magnificent view over the Necropolis of Puig des Molins. From the bastion we went back retracing our steps along the same route, but you can find your own way.
During this tour we are going to visit a part of the area which UNESCO declared a World Heritage Site. We start our walking tour at the main gate called the Portal de les Taules. The current drawbridge was added in 1990 and was rebuilt using old photographs. The niches alongside the gates contain the statues of the Goddess Juno and Cayo Julio Tiron Cetutico. Above the gate you see the stone coat of arms of Felipe II as well as inscription in remembrance of the year the gate was built: 1585. Once beyond the gate, you see the statue of Lucio Oculacio. Former ancient market, today lovely plaça de Vila will be on your right but you turn left and walk up along sa Carrossa (do not miss the Macabich monument) towards bastion Santa Llúcia. From here you will enjoy marvelous view of the Dalt Vila (the Old Town) above you and spectacular seascape. Continuing your way up along G. Balansta and passing the church of Santo Domingo (built in the 16th century), turn left at miniscule square Plaça d’Espanya (wonderful view over the sea) and visit local Ajuntament – the former Dominican convent which now houses the Eivissa Town Council. First room on the right contains very interesting portraits; returning to the main hall, go left and enjoy quiet courtyard. Continue the climb up Calle Pere Tur (18th and 19th century stately homes) and come to Career Joan Roman, where the former Seminari is found. A little further up you will see the cloister convent of the Augustine nuns.