Luxury Vacations in California

Why should you travel on a luxury California vacation with us?

Whether you’re taking a once-in-a-life road trip down the Pacific Coast Highway, or dipping into a city or two, a trip to California is set to be a core life memory. But first: the planning. We’ll listen to what you want – and what you need – and weave together a luxury California vacation that serves up something truly unforgettable.

That could mean soaring over Los Angeles’ Hollywood sign in a chopper, pedalling across the Golden Gate Bridge in San Francisco, or taking a taco tour in San Diego. Or you may prefer an off-the-beaten track hike in Yosemite or Sequoia National Parks, a pause for wine tasting in the sun-dappled Napa Valley, whale spotting in the peaceful ocean, and long days diving into the surf at one of the state’s sun-kissed beaches. Perhaps you’re keen on all of that – or more than that.

With teams on the ground exploring every corner of the state, we have a pretty epic list of the best places to visit in California, but we’re also here to help you uncover the lesser-known places that feel distinctly “you”. Roof down. Volume up. Let’s get started.

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What to see and do in California

Explore Yosemite with a Conservancy Naturalists

Sure, you could explore Yosemite National Park solo, but to really uncover into this rural wonderland – which we consider one of the best places to visit in California – we’ll arrange a Conservancy Naturalist to join you. Their step-by-step in-depth accounts will elevate your hike from “just good views” to extraordinary insights into the region’s culture and history. If you have kids with you, we’ll arrange for them to play park ranger for the day, giving them responsibility and connecting them to the land.

Spot whales in Monterey Bay

There are few wildlife encounters as exhilarating as spying whales breaching in a vast, glittering ocean. On this humbling excursion you’ll get a rarely-gained insight into California’s nature from your own private Zodiac (an inflatable speed boat). As you watch them from safe respectful distances, your expert naturalist will tell you about the lives of these majestic animals that call the California coastline home.

Float over Napa Valley at sunrise

It’s worth every second of your pre-dawn wake up call to experience this – one of the most spectacular things to do in California. After a briefing at the hot air balloon launch site, you’ll soon be lifting into the air to float over the rolling northern valleys of the world-famous Napa Valley. Up in the sky, life feels very different. Soak in the sounds as you drift over the vineyards and countryside.

Cruise the Pacific Coast Highway

Almost all of our California luxury vacations include a drive along the 656-mile-long Pacific Coast Highway. This is more than just a way to get from A to B, but a journey of fresh air, freedom, and feel-good fun. Depending on the stretch you drive (we’ll craft an itinerary that best suits you), you’ll skim along the coastline, witnessing the natural beauty on a drive that’s studded with state parks, lighthouses, redwood forests, kitsch coastal towns, and see-it-to-believe-it bays.

Explore San Francisco on two wheels

You’ll cover so much ground on an easy-breezy electric bike tour of San Francisco. This is a trip that we can tailor to you and your group, but we love to share our intel on the hippest bars, galleries, and secret viewpoints of the city – before letting you loose to explore yourself. We’ll begin at Fisherman’s Wharf, skim the waterfront to Fort Point and cross the iconic Golden Gate bridge to the quaint fishing village of Sausalito. Hungry? We’ll park up at the oldest Chinatown in North America for pillowy dim sum and sweet moon cakes.

Live it up in LA

To truly understand a city as vast as Los Angeles, you need to see it with a local. This half-day private tour begins with an exciting glimpse into the city’s glamorous side, seeing the Hollywood Sign, strolling along Rodeo Drive, and seeking out your favorite celebrity’s brass star on the Hollywood Walk of Fame. Then it’s on to the coast, for a laid-back afternoon kicking back on the sand, soaking in the heady mix of sunshine and surf, before cocktails with a view over cocktails looking out over the bright lights of Santa Monica pier.

The best of California

FAQs

Everything you need to know about visiting California with Black Tomato

What is the best time to visit California?

California’s seasons vary dramatically by region, which makes it a genuinely year-round destination. San Francisco is at its warmest and driest May through October, though the city’s famous fog is most prevalent in June and July. Southern California — Los Angeles, Santa Barbara, Palm Springs — is reliably sunny most of the year, with peak warmth September through November. Yosemite is best visited May through October when roads are fully open and wildflower meadows are at their peak. Napa Valley’s harvest season, September through November, is the most atmospheric time for wine country. We factor all of this into every itinerary.

How much does a luxury California vacation cost?

Luxury California vacations typically start from around $5,000 per person for a five-night itinerary focused on a single area — wine country, Los Angeles, or Yosemite. A comprehensive two-week road trip combining San Francisco, Napa, Yosemite, Big Sur, and Los Angeles usually falls between $10,000 and $18,000 per person depending on accommodation and pacing. Properties like Post Ranch Inn in Big Sur and the Majestic Yosemite Hotel are priced at the higher end; city hotels in LA and San Francisco offer more flexibility. We price every vacation individually based on your dates, group size, and exactly what you want to do — and there are no planning fees.

What are the best luxury experiences in California?

The experiences that consistently define luxury California vacations are a hot air balloon over Napa Valley at sunrise, a private drive of the Pacific Coast Highway in a convertible with a knowledgeable guide calling the stops, whale watching from a private Zodiac in Monterey Bay, exploring Yosemite with a Conservancy naturalist who knows the park in all its moods, and a private cooking class with a chef sourcing local California produce. For families, having children play park ranger for the day in Yosemite is consistently one of our most requested additions. We build every itinerary around which of these suit your group.

Is California good for a luxury family vacation?

California is one of the most family-friendly luxury destinations in the United States — partly because the range of experiences is so wide that every age group finds something extraordinary. Children are captivated by Yosemite’s wildlife and waterfalls; teenagers love the surf culture and city energy of Los Angeles; parents appreciate Napa’s restaurants and Big Sur’s stillness. We design every California family vacation around your group’s specific mix of ages and interests, with private guides, flexible pacing, and properties that work for families of all sizes.

Can you combine California with another US destination?

Yes, and two combinations stand out. California and Hawaii is a popular pairing — the Pacific Coast energy flows naturally into island life, and the flight between Los Angeles and Honolulu is around five hours. California and New York suits those who want to balance West Coast ease with East Coast culture on a longer US trip. Both work best over two to three weeks. Your travel expert will design the routing so the journey feels intentional rather than rushed.

What are the best places to visit in California?

California’s standout destinations each offer something entirely different. Yosemite National Park delivers wilderness and scale that is genuinely difficult to find elsewhere in the United States. San Francisco rewards those who go beyond the Golden Gate Bridge into its neighbourhoods, food scene, and bay. Los Angeles is best experienced by neighbourhood — Beverly Hills and the coast have a different energy to Silver Lake or Malibu. Big Sur is non-negotiable on any coastal road trip. Napa and Sonoma reward slower itineraries built around tastings, cycling between vineyards, and Michelin-level meals. We’ll build your California itinerary around whatever combination makes sense for your group and timeline.

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