5 Day Cabo San Lucas Itinerary
Westin Resort Villas & Spa, Cabo (Baja California Sur, Mexico)
Cabo San Lucas, just on the tip of Baja California Sur, is an easy and extremely popular beach getaway for many Californians. Whether it’s escaping the cold winters or chasing the high surf in summer, Cabo is a high adrenaline destination to enjoy the holidays. It’s has been on our bucket list for years. Well, we finally made our trip which was largely driven by the fabulous villas and resort at the Westin. Great design and architecture It’s close by, yet away from the twin cities of Cabo and San Jose Del Cabo. If you are there with family & kids, a 4-5 day trip is ideal and make this resort your base and enjoy the resort and Cabo!
Trip Highlights
Duration - 5 Days
Places - Cabo San Lucas, BCS, Mexico
Best for - Family Vacation, Small Friends Group Travel, Outdoor Adventure
Travel Pace - Relaxed
Season - Mid-Winter (February)
Experiences - Organic Farm tour and lunch; Beach, Spa and Sunset Sailing
Trip Cost - $350 to $400 / person / day (includes Rt airfare, hotel stay, food and tours
Trip Route
Day 1 Arrive and Check-in at Westin Los Cabos
Day 2 Full day at the resort beach + swim
Day 3 Half day trip to Flora Farms + explore the town
Day 4 Sunset Sailing in the Sea of Cortez
Day 5 Departure to San Francisco
Itinerary
Day 1 Travel to Cabo San Lucas (Baja California Sur, Mexico)
Arrive at SJD Airport, Drive to Hotel, Check-in at The Westin Resort Villas & Spa
You will likely arrive at SJD around early afternoon if coming from San Francisco. If it’s your first time (like us), suggest getting the resort’s limo airport transfer. The drive from the airport is about 1 hour and honestly, our chauffeur gave us a fantastic intro to Cabo’s history and culture and we practiced our Spanish language skills with him too! By mid-afternoon, arrive at the beautiful, airy lobby of the Westin Los Cabos Resort Villas & Spa, Check-in to your ocean-front villa rooms, and enjoy the rest of the day at the resort - lunch, swim in the lagoon pools, and wrap up with dinner and evening cocktails! Also, read my full review on Tripadvisor
Tip: Rent a car from the hotel only for the days you need to drive for day trips. Super convenient!Duration: 2.5 hours flying (SFO-SJD) + 1-hour airport transfer
Good To Know: The West Tower 2 bedroom Villa @ the Westin has stunning views of the Sea of Cortez. The location and the large villas-style rooms at this Westin were important criteria for the Cabo trip.
Afternoon
Pool side Lunch @ The Coralline (in the resort)
After check-in head down to the lagoon pools and beach area and grab delicious lunch - can't go wrong with mouth-watering fresh caught fish tacos + fresh guac, chips and ice-cold Corona Beer!
60 - 90 Minutes
Game of Basketball & Swim Lagoon Pools
No better way to enjoy the sunny afternoon with a 1:1 basketball (yes they have an outdoor court!)
..and enjoy a nice swim in the lagoon pools
Tip: Enjoy the lagoon pools, beach can be rough and cold (especially in Feb) Evening
Drinks & Dinner @ La Cantina Sports Bar
Hang out at the resort and make La Cantina Sports Bar your daily Happy Hour (6-7) base. Great margaritas for $4, pool tables and the like...and a great atmosphere for families to hang out.
~ 2 hours
then head back to your ocean-front villa and enjoy the sea breeze before getting a good night’s sleep!
Day 2 Day at the Westin’s Resort Beach and Pool
Full day at beach, swim in the infinity pool + yoga!
On your second day , suggest enjoying the beautiful resort area. Start the morning with yoga in their fabulous outdoor studio. Then grab some coffee and breakfast treats at the Mercadito (in resort market) and head to the infinity pool on the beach. Plan to spend most of the day here. Mix it up with some nap at the beach or back in your villa room. In the evening head to town for dinner at Edith’s to enjoy fine Baja fare, drinks, and lively atmosphere.
Duration: Full Day
Activity Level: Relaxed
Good To Know: Make sure to ask the concierge to make dinner reservations at Edith’s as it’s very popular with travelers and locals alike!
Morning
Yoga @ Outdoor Studio at the Westin Resort
Freshen up in the morning with some yoga stretches - join a class or take a private lesson from your own family member (yes we had an in-house certified yoga instructor!)
45 min
Afternoon
Swim and Poolside Lunch
After yoga, grab some coffee and muffin from Mercadito and head to the beautiful pool at the beach. Plan to spend most of the afternoon at the pool and the beach. Grab lunch (tacos of course) and a beer (adults) at the poolside Cantina and take a nap!
2 - 3 hours
Evening
Dinner @ Edith’s
In the evening head to the lively, al fresco fine Baja dining at Edith’s, a popular Mexican restaurant in town. Order the traditional margarita and fish tacos. For vegetarians, you cannot go wrong with a salad and cheese enchiladas.
Note: Make sure to to get dinner reservations in the morning. 
Day 3 Half Day Trip to Flora Farms and Town
Flora Farms and Kitchen
Field-to-Table Foodie & Culture Experience
Today, plan to spend most of the afternoon enjoying Flora Farms and exploring the town of Cabo San Lucas. Rent a car for the day from the hotel and drive to beautiful Flora Farms. First, grab a great al fresco field-to-table lunch and margaritas. Then explore the farm grounds and boutique shops, a wine cellar, and finally some coffee and ice cream! Plan to spend 3 hours here. Then head to town to explore the cobbled streets of old town Cabo. Get some souvenirs (we loved the colorful woven blankets!) before heading back to the hotel. Spend the evening at the resort for dinner, playing pool, and hanging out with the family!
Duration: Full Day
Activity Level: Relaxed
Good To Know: Flora Farms is closed Mondays and closes for lunch by 2:30 PM and reopens from 5-9 for dinner. Make sure you have a cell connection for GPS, as some turns into the farm can get tricky.
How to get there: Rent a car and drive on Mexico Hwy 1 for 25 minutes. Directions here.
Afternoon
Explore Flora Farms and Al Fresco Lunch
Flora Farms is a very popular and family-friendly place to spend the afternoon. Get a farm tour to explore on your own. Get a table at the Flora Field Kitchen, rustic and lively al fresco setting. Order “Hibiscus infused” margaritas at the Farm Bar and super fresh pizzas.
Tip: For list of additional exciting experiences from the spa, cooking classes to movie night!, visit Flora Farms website 
Evening
After a long day out and about, it’s nice to relax at the resort. Grab dinner right back at The La Cantina Sports Bar and enjoy a game of pool and foosball and then take an evening walk on the beach and enjoy the warm breeze
Day 4 Sunset Sailing in the Sea to Cortez
Experience sunset sailing against the back-drop of Land’s End Arch
Today, it’s all about the experience of the Sea of Cortez, famously referred to as the “World’s Aquarium” by Jacques Cousteau. Start with a run or walk on the resort beach, get a massage and relax in the Spa, and take a light lunch and nap before heading to the downtown marina to experience a spectacular sunset sailing with Cabo Adventures company. The sailboat is spacious, comfortable, and allows 12 (max) guests. It was perfect for our family of 3. Drinks (beer and wine) and hors d'oeuvres are included. Plan for 2 hours of sailing (could vary by season and weather conditions)
Duration: Half Day
Activity Level: Relaxed
Good To Know: It can get cold in the winter months, so take a jacket. Blankets are provided by the tour company. Trust me it was super cozy - you will need it.
How to get there: Book a round-trip air-conditioned transportation from the hotel itself for just $5 /person. Super convenient!
Morning
Walk on the Beach & Massage
Grab a fresh cup of coffee and muffin from the Mercadito and walk along the beach. There are some nice high points that you can climb to get a nice view. Then head to the Spa for a nice relaxing massage and then lunch by the pool!
Tip: The water is often cold and rough in most of Cabo, so not ideal for swimming.
Sunset Luxury Sailing with Cabo Adventures
After a nice massage and afternoon siesta, jump into your van to be transported to the Marina in downtown Cabo and to board your Sunset Yacht. Once you check in, you will get the wrist tags and welcome drinks aboard.
Relax and soak in the beautiful sunset, especially as you turn around the famous arch Rock (land’s end). This is a must-have experience for the first-timers for sure!
Tip: Remember to take a jacket as it gets cold on the yacht at Sunset, even though they provide blankets!3 - 4 Hours
Take your pre-paid hotel transfer shuttle and unwind and get some nice sleep as the next day is travel back home!
Day 5 Departure to San Francisco
Say goodbye to the exotic Cabo San Lucas. Grab quick-to-go breakfast and take your airport transfer limo for a 45 min to 1Hour drive. If flying to San Francisco, then likely your flight is around 2 PM. Before you know you will be home. It’s a short 2.5Hr flight back, with no time zone change!
Before You Go
This itinerary was based on a family trip during February (Mid-Winter break). So plan for slightly cooler evenings and cold ocean water!
Check Passport expiration and post 2020, the status on openings/restrictions due to COVID-19.
Book early as Westin and similar luxury resorts are hard to get during major holidays.
Map It!
This map is a day-by-day list of places to stay, eat, and experience on this itinerary. Also indicated are recommended alternatives to help personalize this itinerary.
Download and use it for your trip. Have fun!
Recommended Alternatives
Here are some helpful alternatives to add /swap on this itinerary.
Stay - Consider renting an Airbnb Villa with a pool or for lux retreat if in a large group, Zuden (A Ritz Reserve). Nobu Hotel or Viceroy, Los Cabos
Experiences - From Airbnb, I found Paddleboard and Snorkeling Experience and a Local Foodie Tour - or Baja Outback (Camel ride, ATV and Eco-farm tour) from Cabo Adventures or some golf or Sand-boarding!
Note: These recommendations are on my Cabo bucket list. Yet to experience them but have seen good trusted reviews.
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Plan Your Trip
Take this itinerary as is or if you like to make some tweaks you can cherry-pick from this itinerary to create a 3, 5, or 7-day trip as well. If you have questions about planning your trip, leave us a comment below.
