Day 1 San Juan (Puerto Rico), Puerto Rico

If you associate Puerto Rico's capital with the colonial streets of Old San Juan, then you know only part of the picture. San Juan is a major metropolis, radiating out from the bay on the Atlantic Ocean that was discovered by Juan Ponce de León. More than a third of the island's nearly 4 million citizens proudly call themselves sanjuaneros. The city may be rooted in the past, but it has its eye on the future. Locals go about their business surrounded by colonial architecture and towering modern structures.By 1508 the explorer Juan Ponce de León had established a colony in an area now known as Caparra, southeast of present-day San Juan. He later moved the settlement north to a more hospitable peninsular location. In 1521, after he became the first colonial governor, Ponce de León switched the name of the island—which was then called San Juan Bautista in honor of St. John the Baptist—with that of the settlement of Puerto Rico ("rich port").Defended by the imposing Castillo San Felipe del Morro (El Morro) and Castillo San Cristóbal, Puerto Rico's administrative and population center remained firmly in Spain's hands until 1898, when it came under U.S. control after the Spanish-American War. Centuries of Spanish rule left an indelible imprint on the city, particularly in the walled area now known as Old San Juan. The area is filled with cobblestone streets and brightly painted, colonial-era structures, and its fortifications have been designated a UNESCO World Heritage Site.Old San Juan is a monument to the past, but most of the rest of the city is planted firmly in the 21st century and draws migrants island-wide and from farther afield to jobs in its businesses and industries. The city captivates residents and visitors alike with its vibrant lifestyle as well as its balmy beaches, pulsing nightclubs, globe-spanning restaurants, and world-class museums. Once you set foot in this city, you may never want to leave.

Day 2 Gustavia, Saint Barthélemy

You can easily explore all of Gustavia during a two-hour stroll. Some shops close from noon to 3 or 4, so plan lunch accordingly, but stores stay open past 7 in the evening. Parking in Gustavia is a challenge, especially during vacation times. A good spot to park is rue de la République, alongside the catamarans, yachts, and sailboats.

Day 3 Saint John's, Antigua and Barbuda

With its superb beaches, historical attractions and beautiful coral reefs, Antigua provides a host of diversions. It is said that the island contains 365 beaches, one for every day of the year. Antigua maintains its traditional West Indian character, with gingerbread-house style architecture, calypso music and carnival festivities. St John's has been the administrative capital since the island's colonisation in 1632, and has been the seat of government since it gained independence in 1981. From the port you can explore the colourful Redcliffe district, with its restored wooden houses, and Heritage Quay with its shopping mall and craft shops. The city has some fine examples of Colonial architecture, including the twin-towered cathedral, built in 1845 and considered one of the finest church buildings in the Caribbean. All coaches in Antigua are operated by smaller vehicles, and commentary will be given by a driver/guide.

Day 10 Funchal, Madeira, Portugal

Formed by a volcanic eruption, Madeira lies in the Gulf Stream, about 500 miles due west of Casablanca. Discovered by Portuguese explorer João Gonçalves Zarco in 1419, this beautiful island became part of Portugal's vast empire and was named for the dense forest which cloaked it - 'Madeira' means 'wood' in Portuguese. Sugar plantations first brought wealth here, and when King Charles II of England granted an exclusive franchise to sell wine to England and its colonies, many British emigrants were drawn to the capital, Funchal. Today's travellers come to Madeira for the varied and luxuriant scenery, from mountain slopes covered with vines to picturesque villages and a profusion of wild flowers. The natural beauty of the island has earned it many pseudonyms such as ‘The Floating Garden of the Atlantic', 'The Island of Eternal Springtime' and ‘God's Botanical Gardens' and our selection of excursions aim to show you why.

Day 12 Tangier, Morocco

Tangier can trace its origins back to the Phoenicians and ancient Greeks. It was named after Tinge, the mother of Hercules' son, and its beginnings are embedded in mythology. It was subsequently a Roman province, and after Vandal and Byzantine influences, was occupied by the Arabs with Spain, Portugal, France and England also playing a part in the city's history. With such a diverse past it is perhaps not surprising that Tangier is such an individual city. Overlooking the Straits of Gibraltar, the city lies on a bay between two promontories. With its old Kasbah, panoramic views, elegant buildings, squares and places of interest, there is much to discover in both the new and old parts of the city.

Day 13 Motril, Spain

Motril is located in the Spanish region of Andalucia on the Costa Tropical. It is the biggest town on the Costa with a thriving commercial, fishing and leisure port. An hour and a half's drive east of Malaga and within easy reach of the magnificent Sierra Nevada mountain range, Motril makes an ideal base for exploring the many delights of the Andalucian coastline and its hinterland. Halfway between the resorts of Malaga to the west and Almeria to the east, nestling in the foothills of the Sierra Lujar mountains, Motril is at the heart of one of the most fertile and productive agricultural areas of Spain. The Costa Tropical takes its name from its sub-tropical climate which enables the cultivation of exotic fruits and crops such as sugar cane, oranges, lemons, apples, avocadoes, mangoes and bananas. One of the sights of Motril is the 17th-century church of Nuestra Señora de la Cabeza, dedicated to the town's patron saint.

Day 14 Alicante, Spain

The provincial capital of the Valencian Community serves as a gateway to the huge influx of tourists that flock to the Costa Blanca resorts every year. Alicante is popular with holidaymakers who arrive for the warm, Mediterranean climate and seemingly endless golden beaches. However, there is much more to this city than sand and sun. With a picturesque waterfront, a hugely impressive castle, buzzing nightlife and a rich, complex history, Alicante is a fascinating destination all year round.

Day 15 Barcelona, Spain

The infinite variety of street life, the nooks and crannies of the medieval Barri Gòtic, the ceramic tile and stained glass of Art Nouveau facades, the art and music, the throb of street life, the food (ah, the food!)—one way or another, Barcelona will find a way to get your full attention. The capital of Catalonia is a banquet for the senses, with its beguiling mix of ancient and modern architecture, tempting cafés and markets, and sun-drenched Mediterranean beaches. A stroll along La Rambla and through waterfront Barceloneta, as well as a tour of Gaudí's majestic Sagrada Famíliaand his other unique creations, are part of a visit to Spain's second-largest city. Modern art museums and chic shops call for attention, too. Barcelona's vibe stays lively well into the night, when you can linger over regional wine and cuisine at buzzing tapas bars.

Day 16 Mahón, Menorca, Spain

The capital of Menorca since 1721, Mahon has a impressive natural deep water harbour, which is one of the largest in the world. This, coupled with its strategic location, has made it a stronghold for many nations throughout history. Mahon has an abundance of historical buildings, the oldest being the Arch of Saint Roc which is all that remains of the wall that once encircled the whole town. The island was occupied by the British during the 18th century and Lord Nelson is thought to have stayed there. Indeed, San Antoni Mansion, located on the north side of the harbour, houses a collection of Nelson memorabilia. The legacy of colonial rule can be seen in the muted Georgian style of some of the buildings, but Mahon still boasts attractive examples of neo-Classical, Baroque and Romanesque architecture. With narrow streets to explore, pleasant shaded squares and welcoming pavement cafés, there is something for everyone to enjoy. Please be aware that most shops in town close for a siesta between 1330 and 1730.

Day 17 Sète, France

The fishing village of Sète serves as gateway to Montpellier, in the North. Other noteworthy destinations in this area include Carcassone, Aigues Mortes, the Abbaye de Fontfroide, and Pezenas. For a look at the real fisherman's life, however, stay right where you are. Sète is the Mediterranean's biggest fishing port. Canals winding through town make it fun to stroll around, and there are a number of good walking paths leading to the beach (about 30 minutes to the west). Although it's small and unspectacular, Plage de la Corniche has calm, pristine waters that are perfect for swimming. For a panoramic view of the area, climb Mont St-Clair or Les Pierres Blanches and pick a beach to settle down on.

Day 18 Sanary-sur-Mer, France

Day 19 Monaco, Monaco

The 202-hectare Principality of Monaco is located east of France's Mediterranean coast. Known for its royal family, especially Prince Albert of Monaco, its casinos and racetracks and for being a wealthy state with no applied taxes. Monaco is reachable by air through the French airport of Nice Côte d'Azur, located approximately 16 miles from the principality.

Day 20 Portofino, Italy

One of the most photographed villages along the coast, with a decidedly romantic and affluent aura, Portofino has long been a popular destination for the rich and famous. Once an ancient Roman colony and taken by the Republic of Genoa in 1229, it's also been ruled by the French, English, Spanish, and Austrians, as well as by marauding bands of 16th-century pirates. Elite British tourists first flocked to the lush harbor in the mid-1800s. Some of Europe's wealthiest drop anchor in Portofino in summer, but they stay out of sight by day, appearing in the evening after buses and boats have carried off the day-trippers.There's not actually much to do in Portofino other than stroll around the wee harbor, see the castle, walk to Punta del Capo, browse at the pricey boutiques, and sip a coffee while people-watching. However, weaving through picture-perfect cliffside gardens and gazing at yachts framed by the sapphire Ligurian Sea and the cliffs of Santa Margherita can make for quite a relaxing afternoon. There are also several tame, photo-friendly hikes into the hills to nearby villages.Unless you're traveling on a deluxe budget, you may want to stay in Camogli or Santa Margherita Ligure rather than at one of Portofino's few very expensive hotels. Restaurants and cafés are good but also pricey (don't expect to have a beer here for much under €10).

Day 21 Livorno, Italy

Livorno is a gritty city with a long and interesting history. In the early Middle Ages it alternately belonged to Pisa and Genoa. In 1421 Florence, seeking access to the sea, bought it. Cosimo I (1519–74) started construction of the harbor in 1571, putting Livorno on the map. After Ferdinando I de' Medici (1549–1609) proclaimed Livorno a free city, it became a haven for people suffering from religious persecution; Roman Catholics from England and Jews and Moors from Spain and Portugal, among others, settled here. The Quattro Mori (Four Moors), also known as the Monument to Ferdinando I, commemorates this. (The statue of Ferdinando I dates from 1595, the bronze Moors by Pietro Tacca from the 1620s.)In the following centuries, and particularly in the 18th, Livorno boomed as a port. In the 19th century the town drew a host of famous Britons passing through on their grand tours. Its prominence continued up to World War II, when it was heavily bombed. Much of the town's architecture, therefore, postdates the war, and it's somewhat difficult to imagine what it might have looked like before. Livorno has recovered from the war, however, as it's become a huge point of departure for container ships, as well as the only spot in Tuscany for cruise ships to dock for the day.Most of Livorno's artistic treasures date from the 17th century and aren't all that interesting unless you dote on obscure baroque artists. Livorno's most famous native artist, Amedeo Modigliani (1884–1920), was of much more recent vintage. Sadly, there's no notable work by him in his hometown.There may not be much in the way of art, but it's still worth strolling around the city. The Mercato Nuovo, which has been around since 1894, sells all sorts of fruits, vegetables, grains, meat, and fish. Outdoor markets nearby are also chock-full of local color. The presence of Camp Darby, an American military base just outside town, accounts for the availability of many American products.If you have time, Livorno is worth a stop for lunch or dinner at the very least.

Day 22 Civitavecchia, Italy

Italy's vibrant capital lives in the present, but no other city on earth evokes its past so powerfully. For over 2,500 years, emperors, popes, artists, and common citizens have left their mark here. Archaeological remains from ancient Rome, art-stuffed churches, and the treasures of Vatican City vie for your attention, but Rome is also a wonderful place to practice the Italian-perfected il dolce far niente, the sweet art of idleness. Your most memorable experiences may include sitting at a caffè in the Campo de' Fiori or strolling in a beguiling piazza.