California isn’t easy to love on paper, with its high taxes and frustrating politics giving residents plenty to complain about, but as soon as you step outside, you remember why people put up with it. The beauty here is outrageous, and living in San Diego feels especially lucky because within two hours, you can escape and explore plenty of magical towns. Desert landscapes, mountain hubs, and coastal hideaways are all close enough for a spontaneous staycation. Dana Point has that quiet, effortless charm; it’s the kind of place you’ll find yourself lingering longer than planned. Towns like these, and the memories made in them, make California’s compromises feel absolutely worth it.
We booked our stay in Dana Point while a major rainstorm was heading over. Despite the grey clouds and some rain, we had a wonderful time exploring the nearby towns and trails, dining at the many high-quality restaurants, and relaxing at the five-star Waldorf Astoria Monarch Beach. Below is a four-day itinerary in Dana Point which I hope you will find as fun and full as we did!
Check in to the Waldorf Astoria Monarch Beach Resort. For American Express Platinum cardholders, the Waldorf Astoria Monarch is a premier Fine Hotels + Resorts property offering exceptional value and luxury benefits when booked through Amex Travel. Guests can enjoy early check-in when available, a complimentary room upgrade upon arrival, and a generous daily breakfast credit of up to $90 for two guests. The stay is further enhanced with a welcome amenity that often includes two glasses of complimentary wine, along with a $100 resort credit that can be used toward eligible on-property dining, spa treatments, or activities. One of the most valuable perks is the guaranteed 4:00 p.m. late check-out, allowing for a more relaxed departure and full use of the resort on the final day. You’ll fall in love with the expansive, luxurious property where no detail is overlooked. The staff service is exceptional throughout – expect daily texts from the staff checking in to make sure you are satisfied with your stay. With a designer retail shop, elegant spa, top-notch restaurants, stunning views, endless paths to roam, and many nooks to relax in, this property offers the ultimate staycation experience!
Stroll the Many Trails that Hug the Coast and the Golf Course
Just walk and walk, and you’ll continuously be surprised by the breathtaking landscape. Pedestrians passing by will give you a cheerful welcome, whiffs of the flora will hit you in the best ways, and the views will keep you saying “wow”.
Savor a Delicious, Waterview Lunch
Lunch at Raya, located at the Ritz-Carlton, offers an outstanding experience with stunning vistas and interesting pan-Latin flavors. Our window table had a view like no other. Perched on top of the cliffs, we had a bird’s-eye view of the many surfers and pedestrians below us. The food served was equally tantalizing from start to finish. The achiote salmon, cooked to perfection, had me dreaming about it for days. The mezcal cocktail is masterfully well-balanced, making the smokiness of the tequila and the slight sweetness of the fresh passion fruit puree come together brilliantly. Lunch here was one of the best I have had in a while.
After an epic lunch, take a leisurely, scenic stroll back to the Waldorf‘s lobby bar, 33 North, and grab a seat by a firepit while sipping on a glass of wine and noshing on bar snacks.
The tower was built as a private staircase to the beach by castle-inspired homeowners who lived on the cliff. While the tower is locked to the public and inaccessible during high tide, it’s a pretty cool structure to look for and photograph. The walk from the tower to the Montage Laguna Beach is equally striking, and there’s no better time to explore that stretch of sun than during sunset.
Don’t Dress for Disappointing Fine Dining at The Loft
Although the Montage Laguna is one of Southern California’s most luxurious properties, our meal at The Loft was deeply disappointing. I rarely write about restaurants after a negative experience, but at this price point (think $22 for four small florets of cold cauliflower), I feel compelled to warn my readers. The service was unbearably slow, the dishes were uninspired and lacked creativity, and the final bill was shockingly high. Those who know me know I have no issue paying a premium when it’s matched with top-notch service and truly delicious food. However, that was not the case here.
Catch the Lights at Dana Point Wharf
Dana Point Harbor sparkles after dark as 700,000 LED festival lights dance along the water, illuminating the harbor and wharf in a warm, twinkling glow. Boats bob beneath strands of light, reflections shimmering across the bay and instantly setting a festive mood. The lights shine bright from mid-November to early-January.
Begin Your Day with a Breakfast Burrito at Aveo
Our Amex benefits include a daily breakfast credit of $45 per person. Aveo’s low reviews had me not-so-excited about my first meal of the day, but the coffee was brewed just right, and the burrito was stuffed with all the yummy things like tender steak, eggs, cheese, hashbrowns, and sour cream. No complaints from this diner!
One of my favorite features of the Waldorf Astoria Monarch is the many trails and endless paths accessible right outside the property’s doors. Countless parks and promenades, access to the sand or paved pathways, gorgeous golf course views, and coastal ones, too. Long, daily walks on the trails are highly encouraged to reconnect, reenergize, and rejuvenate.
We were in awe of the breathtaking grounds of the Waldorf Monarch. Every inch of the property is immaculate and beautifully decorated for the holiday season. From fountains to ocean views and Adirondack chairs on the lawns, and even a small botanical garden, every turn made captured the essence of a five-star resort at its finest.
Tram to Golf Club for Snacks at Club 19
The Waldorf Monarch offers rides in adorable trams that transport guests throughout the sprawling property, with rides to the Club House and the exclusive guest-only Monarch Bay Beach Club. For a mid-day snack, head over to Club 19 for a delicious plate of nachos; make sure to ask for a side of the homemade salsa and pickled jalapenos.
Soak in the San Clemente Sights
Just fifteen minutes away from Dana Point is the charming, coastal town of San Clemente, where you can easily spend an entire day soaking in the sights and sea. The pier is an iconic landmark, and walking to its end, perched way into the Pacific Ocean, as you inhale the saltwater air and get lost in the vast sea ahead, is a must!
Take a Walk Through History at Casa Romantica Cultural Center and Gardens
Casa Romantica Cultural Center and Gardens in San Clemente is a stunning historic estate perched above the Pacific, offering beautifully landscaped gardens, inspiring art exhibitions, and breathtaking ocean views. The home of the Founder of San Clemente, Ole Hanson, is now a vibrant cultural hub where history, music, and creativity come together to enrich the community and spark the imagination.
Slowly Stroll Avenida del Mar
Avenida del Mar is a long, lively stretch of stores and restaurants in San Clemente, blending high-end boutiques with delightfully wacky, surf-town shops. Framed by charming Spanish-style architecture, it captures the city’s relaxed yet upscale coastal character in one walkable avenue that captures all your shopping and dining desires.
Discover San Juan Capistrano
Founded in 1776, San Juan Capistrano is one of California’s oldest towns, where history runs deep, and the cowboy spirit still rides strong. With its rustic charm, equestrian roots, and western flair woven through historic adobes and rolling hills, the town feels like a step back into Old California. You’re guaranteed to love a visit to this small, historic town that has a deep history and lots of charm.
Get Lost in Los Rios, Old Historic District
Tucked just behind the Mission, Los Rios Historic District in San Juan Capistrano feels like Southern California’s answer to Woodstock, New York; an off-the-beaten-path enclave of quirky cottages, hidden gardens, and character-filled cafés. Founded in the late 1700s, it’s the oldest continuously occupied neighborhood in California, where adobe homes now double as art studios, shops, and cozy eateries. Fun fact: peacocks, chickens, and resident cats often roam the lanes, adding to the free-spirited, artsy vibe that makes wandering Los Rios feel like discovering a secret.
Make Your Way to Mission San Juan Capistrano
Perched in the heart of San Juan Capistrano, the Mission San Juan Capistrano is a breathtaking journey through California’s past. Founded in 1776, this historic gem enchants visitors with its beautifully restored adobe buildings, lush gardens, and iconic stone church ruins, all framed by the stunning Southern California sun. Wander the serene courtyards, marvel at centuries-old murals, and witness the legendary lighting of the mission during the holiday season.
Rosewood Social in San Juan Capistrano offers a laid-back yet sophisticated Thai-inspired menu that perfectly balances comfort with culinary creativity. Standouts like the Wagyu wonton dumplings and melt-in-your-mouth short ribs are simply divine. Sipping on cocktails while people-watching from the upstairs patio was a bonus!
Head Back to Mission for a Spectacular Light Show
During the holiday light show, Mission San Juan Capistrano transforms into a dazzling winter wonderland, with twinkling lights draping the historic adobe walls and gardens in a magical glow. The iconic stone church ruins and historic courtyards are brought to life in a blast of colors, casting reflections on pathways and fountains, creating an unforgettable, almost storybook atmosphere that enchants visitors of all ages.
Start your day slowly with a fireside coffee on the terrace, draped in your lush robe and warm slippers. Once you muster the will to pull away and get dressed, head over to Aveo for another scrumptous breakfast. Their chilaquilles are soooo good….
We didn’t let the rain stop us from enjoying our staycation. Instead, we headed over to Cineoplis for a wonderful movie experience. Although full-service theaters with reclining seats are quite common these days, Cineoplis stands out because you can order your food and drinks online, eliminating the disruptions that come with ordering once the movie begins. TIP: The upstairs restrooms are much larger.
The Monarch Bay Beach Club is an exclusive, waterfront restaurant for hotel guests that perfectly captures coastal vibes. Our window seat made us feel like we were sitting on the sand. Everything was perfectly prepared from the Bee Sting Cocktail (mezcal, jalapeño, and honey) to the roasted brussels sprouts, truffle fries, poke bowl, and short rib pappardelle.
All the sightseeing and non-stop eating may call you to rest in your fully appointed room. Take advantage of the spacious, well-thought-out space and linger for a while. Perhaps order some warm chocolate chip cookies and milk to help you ease into the evening.
Savor one last yummy breakfast, this time at Bourbon Steak, for a different setting. I devoured my salmon bagel – kitchens rarely get my request for an “extra well-toasted bagel” right, and this kitchen did! This last meal at the Waldorf Astoria Monarch sent me off with a really good taste in my mouth!
Our time in Dana Point was the perfect reminder of how special this stretch of Southern California truly is, lined with nearby towns full of character to explore, a stunning coastal hotel as home base, and memorable dining experiences at every turn. And the irony wasn’t lost on us when nearly every Uber driver asked if we’d been to La Jolla, where we live, a gentle reminder that San Diego itself is a vacation destination, and that we’re incredibly lucky that although an hour’s drive can deliver a whole new experience and escape, home isn’t too shabby.
