19-Day Yachtsman’s Caribbean & Atlantic Passage

Philipsburg is the gateway to an intriguing little Caribbean island with a dual personality: the Dutch side, St. Maarten, is the livelier of the two, with shopping malls, casinos and more of a nightlife scene, while French-speaking St. Martin is a more refined (and more expensive) affair, with a laid-back, continental air and a host of exclusive resorts and restaurants. Travelling between the two halves of the island is hassle-free, and both sides boast beautiful beaches, friendly locals and pleasant little towns and villages.

The beach at South Friars Bay is a lovely sweep of golden sand at the southern end of St Kitts, although it can get a little busy when the larger cruise ships are docked on the island. There are several bars and restaurants along this half-mile stretch, with watersports equipment and loungers available to rent.

Trois-Îlets is perhaps best known for the plantation La Pagerie, the birthplace and childhood home of Joséphine Bonaparte. The main beach, Anse Mitan, is a picturesque spot with a few shops and restaurants close by, and you can catch a ferry across the bay to Martinique’s bustling capital, Fort-de-France.

Bequia is an incredibly friendly, laid-back island blessed with pristine golden sand beaches and some excellent restaurants. It’s also a popular sailing destination; the yachts tend to congregate around Admiralty Bay, where you’ll find the little waterfront town of Port Elizabeth.

Browse the markets of charming St George’s, fragrant with the scent of cinnamon and nutmeg, and you’ll soon understand why Grenada is known as the ‘isle of spice’. This is one of the Caribbean’s most enchanting islands, fringed by gorgeous beaches and largely unsullied by mass market tourism.

There’s more to Barbados than just beaches; the delightful architecture of the old garrison in Bridgetown, the capital, is fully deserving of its UNESCO World Heritage status, and the island interior is littered with old sugar plantations and natural wonders such as Harrison’s Cave.

Castries, Saint Lucia’s diminutive capital, is home to some interesting markets and colonial buildings. The island’s highlights are situated elsewhere, however, and we’d recommend either heading south towards Soufrière, where the iconic Piton mountains guard a beautiful bay, or north to the bars, restaurants and beaches of Rodney Bay.

Funchal, Madeira’s bustling capital, tumbles down a dramatic hillside towards a beautiful sweeping bay. Highlights include colourful markets, wine lodges and the spectacular cable car ride up to the village of Monte, home of the famous toboggan run.

Portimão is a bustling fishing port and gateway to the Algarve, with a pleasant riverside promenade where the smell of sizzling sardines fills the air. The most popular attraction is Praia da Rocha just to the south, one of the Algarve’s loveliest beaches.

Spread across steep hillsides that overlook the Rio Tejo, Lisbon’s colourful cityscape includes Gothic cathedrals, majestic monasteries and quaint museums. But for many the best times will be had wandering the narrow lanes of Lisbon’s lovely backstreets, with their great local food, wine and music.