8 day Cape Town & the Winelands
You've chosen to stay put in one region and relax. Sensible, really: You're in one of the most beautiful cities in the world, surrounded by vineyard-carpeted valleys and a whale nursery off the coast -- why rush off? This tour starts off in Cape Town then takes you out of the city -- but not too far.
Having arranged for an airport transfer through your lodgings (where you have booked for 4 nights), spend the first day sleeping late. Then take a stroll around the Victoria & Alfred Waterfront in the late afternoon before dining at a table with a view of the iconic Table Mountain, magically lit up at night. We recommend either Den Anker (for delicious Belgian-inspired cuisine) or the more flashy Baia (for seafood). Be sure to book ahead for either (in the summer, make your reservation even before you leave home). Alternatively, if you want to watch Capetonians at play, head for the tiny piazza at Cape Quarter and grab an outside table at one of the restaurants there; or, if you're a dedicated foodie (and ready for a bit of nightlife), book a table at Jardine in the city. If you've still got energy after your meal, stroll the sidewalk through heady Long Street, one of the city's key nightlife nodes, and get a glimpse of Cape Town's "real" city action.
With any luck, at the start of your second full day, your batteries will be fully recharged. Your rental car should be delivered to you this morning. Spend the morning on the eastern slopes of Table Mountain exploring Kirstenbosch Botanical Gardens. From Kirstenbosch, make your way farther south to lunch at the manor house at Constantia Uitsig, for pastoral vineyard views and old-style elegance. Alternatively, if you're a beach lover, skip the gardens and take a book, sunscreen, and sunglasses to Clifton Beach, where it's a short drive to a fabulous lunch at Rumbullion (again, reserve well ahead), set in a forest overlooking palm-fringed Camps Bay. Or worship the sun on Camps Bay and saunter over to The Grand for lunch. Weather permitting, ascend Table Mountain in the late afternoon to watch as the sun sinks into the western horizon and the city lights start to sparkle.
By the third day, you'll set off on the peninsula drive to cruise the awesome Chapman's Peak Drive (if it's open) and get off the beaten track in the Cape Point Nature Reserve. (If you've not yet done Kirstenbosch Gardens, stop there in the morning.) It's also an opportunity to wander through the boho fishing town of Kalk Bay, where you'll get your fill of galleries and antique shops. Have lunch at Harbor House for the close-up views of crashing waves and seals catching fish. Rather than head back to the city, consider overnighting at uber-elegant Rodwell House in teensy St James, where you can kick off your shoes, hang with the local surfers, or join the old-timers in the famous tidal pool. Alternatively, book a night at cool-white Zensa Lodge, in idyllic Scarborough. Your first night here will make you thankful you've booked another, with time to explore the laid-back villages that surround Cape Point.
The next day, set off fairly early for Stellenbosch, where the majority of South Africa's award-winning wines are grown. Arrange in advance for a personal wine guide to take you to select wine estates. Lunch at Overture (the views are beautiful; the food is divine), then spend the late afternoon exploring Stellenbosch's bustling town on foot. The town is alive with students, except in mid-summer, and it's packed with great restaurants. For the best take on New South African cuisine, book your place at Cognito for dinner. Then see if you can catch a local band later in the evening, before retiring at either River Manor or Asara. Alternatively, get to Franschhoek by midafternoon to spend the night at the gorgeously located Le Petite Ferme, where you'll spend the night lording over the valley below. Next day, continue your oeno-expedition.
You could easily spend another night in Stellenbosch (for the myriad restaurant options alone). But if it's whale-watching season (June-Nov), keep following the magnificent Coastal Road south from Gordon's Bay to Hermanus, whale-watching capital of the world, approximately 112km (69 miles) from Cape Town. Spend the night here (preferably at the Marine), and check out some of the world's biggest fish at Shark Alley before returning to Cape Town. If it's not yet whale season, head from Stellenbosch in the opposite direction, passing through Paarl and stopping there for lunch if you're hungry. Then head up over the sublime Bain's Kloof Pass to reach unspoiled Tulbagh, a gem of a village, packed with charming historical houses and surrounded by vineyards. Stay in a treehouse at Vin Doux, or imbibe the country hospitality at the guesthouse on Church Street, where dozens of Cape Dutch houses are lined up for viewing.
Extend your stay by 1 day and celebrate with a meal at the Roundhouse (same venue as Rumbullion, but this time indoors); the food, service, and formidable list of South African wines and top-class spirits will put you in the mood for a party. Make sure you preorder a taxi, and if it's the right night of the week, hit a bar or club of your choice. Whether you dance or mourn on your final night, you'll forever be dreaming of your return.