Curated Tours

Browse our Food & Wine, Art & Culture and Adventure & Wellness Tours

Wine & Food
Book Tour

Hidden Gems Wine Tour

This exclusive tour will take you to the wine estates less well known, but producing some of the most sought-after wines the region has to offer.

From / person
  • Full Day Private Tour
Wine & Food Helicopter Tours
Book Tour

Cape Winelands Helicopter Tour

Take to the skies and explore the winelands in your private helicopter with a personal wine specialist guide. This exclusive curated experience showcases the absolute best of the Cape Winelands.

From / person
  • Full Day Private Tour
Wine & Food Constantia Helicopter Wine Tour
Book Tour

4×4 Wine Tasting & Helicopter Flight

Take to the skies for a scenic helicopter flight over the Cape Peninsula before touching down at a historic Constantia estate for a unique wine tasting experience.

From / person
  • 2-3 Hours
Wine & Food
Book Tour

4×4 Wine Tasting Experience

Explore a historic Constantia wine estate by 4x4, followed by a full wine tasting and delicious canapés as you look over the breathtakingly beautiful valley below.

From / person
  • 2 - 3 hours
Romantic Getaways Romantics-Urban-Adventure
Book Tour

Romantics’ Urban Adventure – A Day in the City

A little adventure mixed with a dose of romance. Start your day with a hike up Table Mountain or kayak along Table Bay as the sun rises over the city, visit colourful Bo-Kaap, stroll through the exquisite Kirstenbosch Gardens and end the day with a sunset cycle along the coast.

From / person
  • Full Day Private Tour
Romantic Getaways Table-Mountain-4x4
Book Tour

Romantics’ Table Mountain Escape

Endless views, a bottle of bubbles and a delicious picnic – a taste of what to expect on this romantic day on the slopes of Table Mountain. Head off the beaten path on this truly unique adventure during your stay in Cape Town.

From / person
  • Full Day Private Tour
Romantic Getaways
Book Tour

A Romantic Day on the Cape Peninsula

Fall in love with Cape Town's seaside. Spend the day taking in unbelievable views as you explore the Cape Peninsula's beautiful coastline. Visit the famous African penguins, lounge in the sunshine with a bottle of wine and delicious picnic, stroll through quaint seaside towns.

From / person
  • Full Day Private Tour
Romantic Getaways Top Proposal Ideas in the Winelands
Book Tour

Wind down in the Winelands

Combine relaxation and incredible wines on this perfect full-day experience. Explore vineyards, wander through beautiful gardens, taste exceptional wines, and let go of life's every-day stresses with a massage in a serene setting.

From / person
  • Full Day Private Tour
Wine & Food Hot air balloon floating above vineyards in Napa Valley California
Book Tour

Napa Valley: A Luxury Vacation in Northern California

Get ready to explore one of the world’s top wine regions complete with unparalleled views, award-winning wines and mouth-watering cuisine.

From / person
  • Full-Day Private Experience
Wine & Food Unique architecture at a Hungarian winery
Book Tour

Hungary: The Ultimate Hungarian Wine Experience

Beautiful architecture, incredible scenery and an endless flow of amazing wines are just a few of the things that make Hungary a must-visit destination. 

From / person
  • Full-Day Private Experience
Wine & Food Harvested red grapes in crate
Book Tour

Portugal: An Exclusive Wine Harvest Experience in the Douro Valley

An occasion that rolls around once a year deserves to be celebrated. Set in the world’s first-ever wine-producing region, we’re bringing you the ultimate Douro Valley wine harvest experience.

From / person
  • Full-Day Private Experience
Wine & Food
Book Tour

Alentejo: A Journey of Castles, Cork and Countryside in Portugal

Castle-topped hills, towering cork forests, olive groves and amazing wines, this full-day experience through Portugal’s Alentejo region is the leisurely breakaway from the country’s buzzing hotspots that you’re looking for.

From / person
  • Full-Day Private Experience
Wine & Food View of the Douro Valley in Portugal
Book Tour

Douro Valley: A Vine to Wine Experience in Portugal

This full-day experience will take you on a magical journey through the world’s oldest wine region, shining a light on what Explore Sideways knows best, the wonderful world of wine.

From / person
  • Full-Day Private Experience
Adventure & Wellness
Book Tour

Porto: An Adventure of Bikes, Beaches and Bridge Climbing in Portugal

Hear that? It’s the city of Porto calling your name.  This adventure-packed full-day experience in Porto will take you from the banks of the Douro River to the waves of Matosinhos. 

From / person
  • Full-Day Private Experience
Wine & Food Moliceiros boat in a canal in Aveiro Portugal
Book Tour

Aveiro & Bairrada: From Canals to Vineyards in Central Portugal

This full-day experience will take you on a magical journey through Central Portugal. Get your daily dose of culture as you explore a vibrant and colourful city of Aveiro, before getting whisked away into the beautiful Bairrada region to enjoy some of the country’s best wines.

From / person
  • Full-Day Private Experience

Load more

Why Book With Us

PRIVATE TOURS & EXPERIENCES
All our tours & experiences are provided in a private vehicle & with your own personal guide.
SPECIALIST GUIDES
All our guides are specialists in their respective fields with years of valuable experience & knowledge.
SIDEWAYS APPROVED
Every one of our tours & experiences has been curated & approved by our team of local experts.
FLEXIBLE & PERSONALISED
All our tours are flexible & can be tailored to suit your unique personal preference & taste.

Sign In