9 Ways to Plan the Ultimate, Adventurous Road Trip – That’s Luxurious, Too

By Aimee Heckel

Luxury and road trips don’t typically go together. But it’s time to rewrite the possibilities of a road trip. 

Especially with the current challenges of air travel, like spiked costs and thousands of canceled flights. Add to that the ripple effects from Covid-19, including the risk of being quarantined or sick in another country, and it’s no wonder road trips are a favorite vacation idea for 2022. In fact, more than 90% of people said they planned to take a road trip this year, according to Outdoorsy. 

But luxury travelers still want high-end experiences. 

Here are nine ways in nine days to plan the ultimate, adventurous road trip (mostly) down the scenic Pacific Coast Highway – that’s luxurious, too. We’ll take you from north to south, Napa to San Diego, hitting the best attractions, hotels, restaurants, and hidden gems along one of the country’s most scenic routes.

Ride in Style

The most important piece in a road trip is locking down the perfect vehicle. Whether you live in California or are flying in, avoid putting mileage on your own vehicle and travel in comfort and style when you rent a car from Outdoorsy.com. 

While Outdoorsy is called “the Airbnb of RVs,” it’s actually much more than just RVs (although it’s a definite level-up to take a road trip in a cushy RV). You can find camper vans, Airstreams, even converted school buses and a Polaris. Our pick: a Land Rover or Jeep equipped with a pop-up camper on top. 

Even if you don’t want to sleep in the rooftop tent, it provides your own private, mobile hangout at any beach you stop at along the way. Too exhausted to make it to your next destination? Whether it’s a power nap or overnight, you’re never without a comfortable resting point. 

Depending on the vehicle, Outdoorsy can hook you up with pretty much anything you want to live large on the road, like a portable cooler/fridge, cargo box for extra storage, a drone, beach/camping chairs, a Gskyer Telescope, hammock, GoPro camera, a lithium ion battery with solar panels, outdoor shower to rinse the sand off your feet, a wifi hotspot and more. 

Outdoorsy has seen a major surge in interest over the past year, and it’s no wonder. A basic rental car company just can’t compete.  

Arrange a pick-up and drop-off wherever and whenever you want. No Ubers and shuttles. Just step off the plane and take the keys. 

Day 1: Napa Valley

Napa Valley kicks off this road trip in style, especially for wine-lovers. While you could plan your own tour (and DD) from vineyard to vineyard, the most relaxing way to see the highlights of Napa and taste its wines is aboard the elegant Napa Valley Wine Train. All views and flavors with no stress.

Sit back in beautifully restored, vintage Pullman rail cars and enjoy a multiple-course gourmet meal with wine served to you. This train is one of the few active, historic passenger trains in the nation. Choose from a variety of experiences, including a three-hour lunch in the two-story, glass-topped Vista Dome observation car. If you can only do one thing in Napa, make it this; the time flies by, and you’re welcome to walk the full length of the historic train and watch the grape fields pass by on the multiple, outdoor decks. 

The wine train also serves dinner, afternoon tea, and a longer “Legacy Experience” with stops at vineyards and tastings there. 

After lunch, check in to the River Terrace Inn, just steps away from the train depot. While rooms are comfortable and the hotel offers a stunning bar, restaurant, and weekly live music, the location is what makes the River Terrace Inn the best place to stay in Napa. Walk out the back doors and you’re right on the banks of the bubbling Napa River and nature preserve; at night, the outdoor lounge area glows with party lights and fire pits. Walk out the front doors and you’ll be in downtown Napa in a few minutes. 

Browse the shops and wine tasting rooms until dinner, when you’ll want to make sure you secure a reservation for a rooftop table at AVOW, right in the heart of Napa and one of the few rooftop options in town. AVOW is run by fifth-gen Napa winemaker Joe Wagner and serves fun, whimsical, California-style fare with creative cocktails, many that use Wagner’s wines.

New executive chef Daniel Ziebell is what really elevates this restaurant above anywhere else in town, though. He’s created a farm-to-table menu that’s as fun and unique as the decor and atmosphere – like nothing else in Napa Valley. Try roasted bone marrow served with fruit, roasted coconut, and pineapple gastrique, and when the marrow is gone, you can use the bone as a whiskey luge. 

Seriously, try it. Bone marrow is incredibly healthy and tasty. Plus, how often can you do a whiskey shot from a bone? 

The pan-seared wild king salmon with sweet corn escabeche pairs great with the AVOW Spritz with elderflower and lemon. And don’t miss the lobster, shrimp and yellowfin tuna tacos.

Day 2: San Francisco

A short hour and a half (ish) drive will bring you to San Francisco, such a vibrant city with a completely different energy than Napa Valley. The best place to stay in San Francisco is the Argonaut Hotel, a Four Diamond, historic, elegant hotel ideally located right on Fisherman’s Wharf. The Argonaut is stunning, with exposed brick, Golden Gate Bridge views from bed, and a comfortably elegant lobby. 

Want to test your quads on the hills or skip the traffic to view the bridge? The Argonaut offers free bike rentals. 

San Francisco is packed with fresh seafood restaurants (check Pier 39); half the fun is wandering around the weirdness to find your personal favorite combo of views and food. The Argonaut also is home to the Blue Mermaid Restaurant, with fire pits and games. 

But there’s one hidden gem you cannot miss in San Fran. A scenic walk into town will bring you to the breakfast pop-up called Friends With Benedicts, located inside Mayes Oyster House, the oldest seafood restaurant in San Francisco. Friends With Benedicts is run by a former magician and staffed by local stand-up comedians, and it features unique themed brunch menus: “Star Wars” (with a Death Star croque), “The Simpsons” (with the Don’t Have a Cow, Man turkey burger), an entire cereal menu (with Lucky Charms marshmallow waffle) – the creativity is endless.

Ultimately, Friends With Benefits has featured more than 120 menus. And the food won’t disappoint. Like Cajun fried chicken french toast, which puts chicken and waffles to shame. Oh, and while you down your crab benedict with herb hollandaise, the owner’s father – a former street musician – visits guests performing tableside magic tricks. Only in San Francisco. 

Day 3: Sausalito

A scenic drive over the Golden Gate Bridge will bring you to Sausalito, where you can see San Fran from another perspective: across the bay. That’s where a hidden gem awaits: Cavallo Point, luxury lodging with a storied history, located within more than 75,000 acres of national parkland.

It’s easy to miss Cavallo Point, at the foot of the Golden Gate Bridge, as you drive past – and it feels like its own magical bubble isolated from the fast pace of San Francisco. Award-winning Cavallo Point, built in the Golden Gate National Recreation Area, offers some of the best service on the Pacific Coast Highway, complete with wine upon check-in, turn-down service, complimentary yoga and guided walks, an on-site spa, and interactive cooking classes. 

Choose between a historic or contemporary room. The 24 historic buildings used to belong to the U.S. Army: Fort Baker, until the land became a national recreational area in the ’70s. Then, the 91st Division was stationed here until the ’90s. The last soldiers left in 2000. Even farther back, this land (Horseshoe Cove) used to be home to the Miwok tribes. It’s a Historic District on the National Register of Historic Places. 

When the historic buildings were restored, they retained authentic turn-of-the-century details, including oversized windows that open to the bay. 

Then there are the new, contemporary rooms, perched on a hillside above the white historic buildings to assure the best possible views. Floor-to-ceiling windows provide a jaw-dropping panorama of the bay, the bridge, and the city across the water.

Cavallo Point provides free shuttle service and Lexus vehicles to wander the hilly downtown of Sausalito, where you can find delicious seafood restaurants (like the Barrel House), although the best service-taste combo in the area remains at Cavallo Point’s on-site restaurant, Murray Circle. Fresh, local ingredients make up a small but impressive menu with service to match. Enjoy brunch (try housemade warm popovers with strawberry butter and powdered sugar) by the crackling fireplace. 

Day 4 and 5: Slo Cal

Slo Cal (short for San Luis Obispo) is ideally located between San Francisco and Los Angeles. While it still remains a bit under the radar, this lesser-known gem is the real crown jewel of the Pacific Coast Highway. That’s why you need at least two days to explore Slo Cal. 

For the first day, acquaint yourself with Slo Cal by lounging on Avila Beach – the warmest beach on the Central Coast – and walking the long pier. Book a spacious room at the family-friendly Avila Lighthouse Suites, located right on the beach.

This freshly renovated, oceanfront hotel is all suites, some bigger than 1,000 square feet and all with great views, a private patio or balcony, and access to the heated pool and hot tub. It’ll be hard to pry your toes from the sand, but if you want, the hotel provides ping pong, life-sized checkers, and a putting green.  

While the Lighthouse Suites offers complimentary breakfast, it’s worth a short drive to eat at Hidden Kitchen Cayucos for its hand-pressed, gluten-free, blue corn waffles served in creative ways. The Monte Cristo puts ham, cheese, jam and powdered sugar on the waffle. The Weirdos Waffle is fried banana, peanut butter and bacon ends.

The Hidden Kitchen is truly epic and unexpected; you’d never know the delicious awaiting you inside, except for the endless, long line out front that starts well before the doors open. Spoon an ultra-thick superfood smoothie on the beach to fuel you for the next adventure: a tour through the famous Hearst Castle. 

This is a must-do in Slo Cal, especially for luxury and architecture lovers. The former home of newspaper tycoon William Randolph Hearst is filled with stunning design and entertaining, celebrity stories, all spread across 127 acres of gardens, fountains, pools and buildings. Celebrate Hearst Castle’s 100 years (ish) with the hour-long, guided Grand Rooms Tour, which takes you through the stunning social rooms, dining hall and theater.

Then head to bustling and charming downtown Slo Cal for a wood-fired pizza dinner at Bear and the Wren. 

Locals love this joint, so make a reservation well in advance. Bear and the Wren started as a mobile catering biz in an old Chevy truck equipped with a wood-fired oven and draft beer system. It was so beloved, it expanded into a permanent location, serving up unique pizzas with locally sourced ingredients. Try the sweet potato pizza, with mozzarella, cream, kale, bacon, onion and balsamic, or the mushroom and sausage, with fontina, cream, fennel pollen, calabrian chile oil and pecorino. Tip: The gluten-free crust rivals the best regular crust you’ve ever had. 

With a full belly, stop at the Sycamore Mineral Springs on your way back to Avila Beach.  

Book a private hot tub on the side of the mountain. Twenty-four open-air tubs are filled with naturally heated mineral water, and they’re surrounded by a private fence and scattered far apart throughout stunning, elaborate gardens and trees. Simply walking to your tub is a transcendent experience. This serene oasis also offers award-winning spa treatments, a secret garden, restaurant and yoga in the Yoga Dome, Tai Chi, Pilates and more. 

For day two in Slo Cal, immerse yourself in the downtown area at the hip, new, contemporary Hotel Cerro – a totally different vibe than Avila Beach.

Hotel Cerro is boutique luxury (the best blend) located in the heart of downtown. It features cool amenities like an edible garden (wander the garden and pick fruit and veggies off the vine), but the best part is the rooftop pool terrace. Look out over Slo Cal and its hillsides from a cozy cabana or lounge chair. 

Pair relaxing on the rooftop with the luxurious Hotel Cerro Spa. Start your treatment with a steam bath and a fireside tea in the otherworldly relaxation room, where the walls are made out of swirling, blue water features. Spa Cerro offers the full menu of treatments, from facials to wraps, as well as unique offerings like foot baths and Chromotherapy cascade water treatments–all inspired by the region.  

In the middle of a road trip, your body will thank you for a deep-tissue massage, and the therapists here are among the best. Try a Himalayan Salt Stone massage, which mixes in warmed stones to the bodywork. The antimicrobial salt stones, containing 84 essential minerals, are said to help improve circulation, lower your blood pressure, relieve anxiety and insomnia, promote healthy breathing and sinuses, and more.

After a morning massage, you’ll be ready for brunch. When in Slo Cal, it’s a bucket-list must to check out the famous Madonna Inn, known for its pink lavish decor and 110 uniquely themed rooms – and its indulgent pink champagne cake to match.

Madonna Inn, right of Highway 101, includes a restaurant, bakery, shops, rooms, and gardens decorated in pink roses, twinkle lights, leaded glass, a massive gold tree, gold angel statues and hammered copper with some Western accents. Every detail is over-the-top, from the pink trash cans, chairs, lamp posts, and booths to the pink floral carpet. There’s even a rock waterfall urinal in the men’s restroom. 

The menu here is classic American and surprisingly fresh and filling. Grab a sandwich and mimosa, served in an ornate glass, and finish with a massive slide of cake. Luckily, the pink champagne cake is light and fluffy.

Now that your stomach is full, it’s time to explore Slo Cal’s growing wine region: Paso Robles. Niner Wine Estates is a family-run winery with a tasting room and restaurant. Wine flights are seasonally tailored.

Then, make sure to set aside several hours to immerse yourself in Slo Cal’s greatest gem, Daou Vineyards. This is another family-run winery that epitomizes the American dream, opened by two brothers originally from Lebanon. It’s inspiring to learn the story of how they transformed their lives from war-torn and poor, by taking a massive leap to start a vineyard in a region that was, at the time, unchartered and off the wine map.

Today, you can enjoy wine tastings and food pairing atop the impressive Daou Mountain, with jaw-dropping, panoramic views. Relax in a private cabana with a charcuterie board (with Middle Eastern taste influences) and look out over the hills that ultimately led to Daou’s flagship cabernet sauvignon, the Soul of a Lion. 

You won’t want to leave Daou, but it’s worth the drive back into downtown for dinner outside on the patio at Brasserie Slo. This restaurant, inside Hotel Cerro, leans heavily on local ingredients and the on-site edible garden but gives them an international spin, the perfect extension of your time at Daou. Start with the roasted spring carrot and coconut soup with crystalized ginger. Follow that with beef bourguignon with spring carrots and mashed potatoes, and you’ll end day five with a happy belly.

Day 6: Santa Barbara

An hour and a half drive south will bring you to Santa Barbara, with its Spanish architecture and charm. Stay at the ideally located Hotel Milo, just steps across from stunning West Beach. 

Hotel Milo feels like home, with Spanish-style architecture, lush gardens and fire pits, beach views from bed, multiple heated pools with cabanas and an easy walk to the pier, museums and some of the city’s best restaurants. Borrow a complimentary beach cruiser to journey to the nearby Presidio Neighborhood, built around what used to be Spanish fortresses. 

For dinner, keep the Spanish feeling going with the absolute best bet in Santa Barbara, Loquita. This charming, authentic restaurant feels like you’ve really been transported to Spain, with tapas, wood-fired seafood and the star of the menu, various types of paella.

Sip on Spanish wines, sangria or the Spanish-style, colorful and playful gin tonicas, like La Reina, made with lavender. The dishes here are meant to be shared family-style, so you can try a variety of flavors, like local yellowtail crudo perfectly prepared with smoked pimenton, mint, pepper aioli and aji amarillo. And you gotta try the churros for dessert. They come with three different, indulgent dips: dulce de leche, raspberry vanilla and chocolate. 

Day 8: Redondo Beach

Break up today’s drive to Redondo Beach with a totally-worth-it stop for lunch at Killer Shrimp in Los Angeles/Marina Del Rey. This family-run seafood joint right on the marina is known for its “secret” Killer Shrimp recipe since 1988 – making this one of the oldest restaurants in the area. 

This is another business with a fun story. The recipe was created by ’60s rocker Lee Michaels; he made it for his family. It takes 10 hours of simmering to make the sauce. The dish was such a hit, Michaels began making it for neighbors. It grew from a tiny restaurant to the popular hot spot it is today. You can get your Killer Shrimp (or add lobster) with French bread or rice. Tip: Order it shelled.

After the tasty and scenic lunch, finish the short drive to Redondo Beach, where you will stay at the Portofino Hotel and Marina. Rooms in this relaxed, waterside hotel feature floor-to-ceiling windows and private balconies – but the best feature is all of the wildlife outside your window. You can hear and see sea lions from your room. Fall asleep to the crooning of sea lions and wake up to the chattering of birds. 

Portofino was founded in the ’60s by a race car enthusiast and welcomed various racers – even appearing in the final race scene of “The Cannonball Run.” Since then, it experienced a mega renovation, including a revamp of the lobby, which now features elegant chandeliers, cozy hangout nooks and couches, all revolving around a fireplace. The hotel also has a secluded, outdoor pool with ocean views. 

Day 8: Del Mar

There are so many charming beaches worth a stop as you get into the southern stretch of California. But the pristine beaches in Del Mar stand out. The small community of Del Mar is quiet, sophisticated, and yet welcoming. That goes for the luxurious L’Auberge Del Mar hotel, as well. This stylish, seaside spot overlooks the ocean, just a few-minute walk away. Just follow the hotel’s scenic pathway to the park and Del Mar Beach.

Award-winning L’Auberge greets you with champagne upon check-in and treats you with a full-service spa, pool and hot tub, tennis courts and bright white rooms. The hotel is in the heart of Del Mar and an easy walk to shopping and excellent dining, like Monarch. This casual eatery features an entire wall of windows open to the ocean, and the entire restaurant joins in a toast as the sun sets over the water each night. 

Not far from Del Mar: stunning Solana Beach, where dramatic cliffs meet the beach and surfers gather to ride the waves. A bit farther south: the relaxed, beach town of Ocean Beach, with its VW Bus-lined streets, sand volleyball and tasty local beer. 

Day 9: San Diego

Beach-hop your way down to San Diego. In the bustling city with seemingly endless options, it’s hard to decide where to eat. So save yourself the menu hunting and straight to the best brunch in San Diego: at the popular Garage Kitchen + Bar, located in a former garage built in 1890. 

Today, Garage Kitchen + Bar is known for having the best happy hour in town, live music and an Instagram-worthy menu. Where else can you order S’mores French toast or a flight of pancakes (French toast, an Oreo pancake, blueberry pancake and banana pancake) with a side of breakfast shots? These are alcoholic shots inspired by cereal, like Froot Loops (Rumchata, 3 Olives Loopy Vodka, topped with Fruit Loops cereal) or Cocoa Puffs (Rumchata and Creme de Cacao finished with the cereal on top). 

Not up for the sweet Cinnamon Toast Crunch shot? The most popular item on the menu is the Butcher’s Burger: a bison, wild boar and Wagyu blend with bacon jam and crispy shallots on a brioche bun. 

Although downtown San Diego is exciting, stay just outside of the baseball traffic and bar hopping at the nearby Mission Bay Resort. This large resort feels like it’s on an isolated island, with a private, quiet beach on the bay – the only beach of its kind in San Diego.

Mission Bay has everything you need on property, including multiple restaurants, a spa, pool (tip: book a cabana the night before you want to lay out), poolside dining service, outdoor activities like beach volleyball and spacious, newly redecorated rooms with balconies or patios. Mission Bay is especially ideal for families, although you can find peaceful nooks for a romantic evening, or go for a walk along the water. 

While Mission Bay’s main restaurant, Covewood, is truly delicious, if you’re looking for something extra special, head back into the city for a memorable dinner at Water Grill. Seafood is king here, with an ever-rotating menu and impressive raw bar.  

In fact, Water Grill boasts one of (if not the) biggest oyster selections in downtown. The list changes daily based on the catch; Water Grill has its own seafood distribution company. But you can always expect to see a selection of sweet, fruity Japanese kumamoto oysters. 

Water Grill has it all, including sea urchin, bay scallops, hard-to-find Santa Barbara spot prawns and squid ink pasta with calamari. Ask about the hidden menu item: the pink bream fish served as ceviche.  

If you’re lucky, maybe you’ll get a glimpse of the live king crabs in the tank in the kitchen. With its own seafood fishers and living crabs in the restaurant, it can’t get much fresher than Water Grill – the perfect way to end the ultimate Pacific Coast Highway trip.