Welcome to Cape Town! You have arrived and it was a long journey so we are going to take our time here. With a rental car (be sure to request an automatic transmission if needed, which are available but not the default) and an appetite for adventure, you can easily self-drive this South African food and wine odyssey. Of course, if you prefer to sit back and enjoy, ground transportation and local logistics can all be sorted out for you.

Here’s my ideal way to spend the next five days:

On a Saturday or Sunday morning, head to one of my favorite places on earth - a roving brunch at the Neighbourgoods Market, one of the world’s coolest urban markets showcasing delectable goods by local artisans and entrepreneurs. Most importantly, you can eat your way through the diverse culinary offerings of the community from Cape Malay cuisine to Mexican street food, and be sure not to miss one of the longest-standing traders at the market, Mother Shucker Oyster. Neighbourgoods Market helps you instantly see why Cape Town is a foodie’s heaven. You’ll have some busy days ahead, so spend the afternoon relaxing, wandering, or at the spa.

Check out the lively and serious coffee scene in Cape Town. Two of my favorite coffee shops to linger awhile are: Origin Bagels and Coffee and Truth Coffee. Post coffee, experience the views atop Table Mountain (check before heading over to make sure the aerial cableway is operating as it closes on windy days.) You can hike Table Mountain, but know that it’s not an easy hike so expect a moderately challenging route! Or for more leisurely hiking and exploration, drive around to Kirstenbosch National Botanical Garden, nestled at the eastern foot of Table Mountain.

Roam the V&A Waterfront, a bustling mixed-use neighborhood and working harbor. While it’s one of the more touristy parts of Cape Town, the big reason to head there is to catch a ferry from the Nelson Mandela Gateway over to Robben Island. There you’ll face history with an unforgettable tour of where Nelson Mandela was imprisoned for 18 of his 27 years in jail. The island, also a UNESCO World Heritage Site, has since become a symbol of the triumph of democracy, freedom and the human spirit over oppression.

Spend a day exploring the Cape Peninsula. From your hotel, drive south along Chapman's Peak. If you’ve seen Big Sur in California, the drive along Chapman’s Peak is, dare I say, even more splendid! Continue on to visit the penguins in Simon’s Town (made world famous by the Netflix documentary Penguin Town.) From there you can continue south to the epically beautiful Cape Point in the Cape of Good Hope, or call it and head back to town. But either way, when your eyes are tired of all the natural beauty you saw today, head to Steenberg Farm for a well-deserved glass of estate wine and a snack at Bistro 1682. (Bonus: get lost in the sculpture gardens of Norval Foundation Art Museum, minutes away from Steenberg.)

With your last day in Cape Town, explore the historical Bo Kaap neighborhood and the District Six Museum. From Bo Kaap, pop into Publik Wine Bar for an incredibly thoughtful perspective on South African wine, come share a glass in this intimate yet approachable wine bar. Or you can head to the V&A Waterfront for the Zeitz Museum of Contemporary Art Africa. The Zeitz MOCAA is the world’s largest museum of contemporary African art, designed to rival the Whitney in NYC or the Tate Modern in London.

These epic few days in Cape Town would not be complete without a few key dinner reservations. Here are my favorites:

La Colombe - When I think back to a memorable dinner with friends that I did not want to end I am transported to La Colombe. Putting forth contemporary South African cuisine in a fine dining setting, this is one of Cape Town’s most loved and awarded restaurants. The multi course Chef’s tasting menu will run you ~$105 USD + wine, and would easily command 3x that if located in NYC (Alternatively, check out Petit Colombe when you get to Franschoek.)

Test Kitchen Fledglings - After closing his wildly successful restaurant Test Kitchen in 2021, Chef Luke Dale Roberts along with his wife Sandalene, have forged on with their newest restaurant concept which couples excellent food and a training program aimed at providing culinary experience to individuals who may otherwise be sidelined by a lack of access to opportunity.

Aubergine - You will not regret a visit to this longstanding Cape Town institution. Located in a historic building, the space is intimate, elegantly understated and authentic. The food is classic, steadfast and always quality driven. Rounding out this fine dining experience is a spectacular wine list.

Gold Restaurant - A cultural experience unto itself, a meal at Gold is an unforgettable & immersive experience that will take you on a “14-dish taste-safari” of traditional Cape Malay and panAfrican cuisine.

Today you’ll meander to the town of Stellenbosch in South Africa’s Winelands region. An easy 45 minutes outside of Cape Town, all of your senses will awaken as you are quickly surrounded by the rolling green hills of vineyards and majestic oak trees. Viticulture and winemaking are king here, so let’s get right to it.

The first stop is Meerlust, famous for its smooth and silky Rubicon, a blend of Cabernet Sauvignon, Merlot, Cabernet Franc and Petit Verdot. White wine lovers will be very happy with the Meerlust Chardonnay as well.

Second, you’ll tour winery production and sip Bordeaux style wine at De Toren. This cult wine would be exceptional to drink anywhere, but adding to its splendor are the estate’s breathtaking vistas that extend as far as Table Mountain in the West, Cape Point and False Bay in the South, and the Stellenbosch Mountains in the East.

Head to your hotel to check-in, nap, or relax in the sunshine because tonight you will dine at the memorable Rust en Vrede. Its historic Dutch architecture and wine farm setting will transport you back in time to a place oozing with tranquility and charm. While enjoying the top flight service, you can contemplate just how well wine plays with food. The six course menu comes in at ~$50USD + wine pairing.

In the morning, enjoy a walk in the vineyard and then linger over breakfast before heading to Franschoek.

Franschoek, which feels more like a village, has been described as the food and wine capital of South Africa. If you choose a hotel in town, you can walk to dinner, shop boutique and be only a stone’s throw away from some of the best wineries and restaurants in South Africa.

Head a just a few blocks from town to Boekenhoutskloof. You’ll be hosted by their winemaker to taste the portfolio, but don't miss their special bottling of The Chocolate Block. A syrah blend with intrigue, it does not really taste like chocolate, or does it?

Schedule a lunch tasting at GlenWood Vineyards for oaky full-bodied chardonnay and a surprise sushi kitchen in a gorgeous setting that exudes rustic luxury, if that’s possibly a thing.

Unwind at Camelot Spa at Le Franschhoek Hotel & Spa for a complete retreat from stress.

Dinner

La Petite Colombe - If you didn’t get to La Colombe in Cape Town, or if you did and loved it, check out their follow-up restaurant in a lush vineyard setting.

Le Coin Francais - Where elegant French cuisine gets a locavore’s twist.

Head back to Capetown to depart for your next adventure or head home with a full belly, an uplifted mind, and a hearty dose of wine and adventure.

Be on the lookout for dishes featuring ostrich or springbok - my two favorite game meats widely offered on South African menus.

Seek out Cape Malay dishes like savory lamb bredie stew or beef bobotie, or the sticky-toffee like dessert called malva pudding. These are the 3 dishes I learned to cook while living there that I still make whenever I am missing South Africa!

Nandos - South African fast casual food at its finest known for its grilled peri-peri chicken.

Not ready to go home yet? Add on to this itinerary with:

• Head east for the safari of a lifetime in Kruger National Park.

• Road trip east along the coastal Garden Route, stay in a lux treehouse and gorge on fresh Indian Ocean oysters.

• Head north to Johannesburg SA, a modern city in constant evolution with many distinct personalities and a complex history to reckon with.

• Head north to Victoria Falls, Zimbabwe to an unforgettable luxury lodge at an elephant sanctuary.

• Head west to see the highest sand dunes in the world where ocean meets desert in Namibia’s Namib-Naukluft National Park.

• Head east to an unspoiled ecolodge on the white sand beach of Mozambique.