Perfect weather, Perfect Week!
At least once a year, we plan a vacation that’s just us—our family of seven. No sports, no schedules, no chaos—just time to reconnect, explore, laugh, and yes, argue a little too. This summer, we spent our one precious free week soaking up all that San Diego has to offer. And honestly? It might be our favorite trip yet.
If you’re looking for a family-friendly vacation destination that has something for everyone—beaches, wildlife, city vibes, and unforgettable experiences—this guide to our San Diego itinerary might be just what you need.
Getting There: Flights, Hotels, and First Impressions
We flew out of Chicago O’Hare, which isn’t our favorite (hello, 3-hour drive), but we scored amazing credit card point tickets and loved having a direct flight with our crew of seven. To make the early 7:00 AM departure manageable, we stayed the night before at Embassy Suites Rosemont—our go-to for:
- Spacious suites that sleep 6 (we squished in 7!)
- Evening cocktail reception (yes, please)
- Free breakfast (which we sadly missed)
- Airport parking and shuttle service
Once we landed in San Diego at 9:40 AM, we had pre-arranged a ride with La Costa Limousine. It was nice riding together, but Uber/Lyft turned out to be super easy and more budget-friendly for our group—even if we always needed two vehicles.
Where We Stayed: Catamaran Resort in Mission Bay
Our first few nights were spent at the beautiful Catamaran Resort Hotel & Spa, nestled between Mission Bay and Pacific Beach. It had a true tropical vibe—we kept saying it felt like we were in Hawaii!
We had two ground-floor rooms right next to each other, which was perfect. While waiting for check-in, we walked to lunch at World Famous, an oceanfront spot with gorgeous Pacific views.
Belmont Park Fun
That evening, we strolled less than a mile to Belmont Park, a lively boardwalk amusement area with:
- An ocean-view roller coaster
- Mini golf
- Carnival games
- Ropes course
- Classic rides
This spot was a hit with the whole family and perfect for burning off travel day energy.
Day 2: The San Diego Zoo + A Little Date Night
We spent the next day at the San Diego Zoo, and it did not disappoint. Highlights included:
- The bus tour (great overview!)
- Skyfari Aerial Tram
- Seeing giant pandas (wow!)
The older kids compared it to Disney’s Animal Kingdom, minus the rides. It’s hands-down the best zoo we’ve ever visited.
That evening, the kids swam while Dan and I had a little resort date night at Oceana Coastal Kitchen. I tried tofu for the first time in their Pad Thai—surprisingly amazing! Dan had scallops and loved them.
Day 3: Sailing, Swimming, and Sunset Views
We booked a private sailing charter with Sail San Diego, and it was one of our favorite experiences of the trip. On the two-hour morning sail, we spotted:
- Dolphins (one followed our boat!)
- Sea lions
- Naval ships and fighter jets
- Even a helicopter takeoff
Snacks and drinks were included, and the whole vibe was unforgettable.
That afternoon was spent relaxing at the pool, meeting new friends, and later dining at Waterbar, where we scored a table with a stunning sunset view. The salmon there was fantastic.
Day 4: Kayaking in La Jolla + Sea Lions
Next up: a morning of kayaking through the caves in La Jolla. Getting through the waves was tricky, and Dan, Em, and John tipped, so it ended up just me and the boys continuing the tour. It was adventurous—and a bit seasick-inducing for a couple of us!
Afterward, we explored La Jolla Cove, where we saw tons of sea lions lounging and barking—such a cool experience.
We wrapped up the day with dinner at PB AleHouse, enjoying rooftop views and Ahi Tuna Nachos that I’m still dreaming about.
Time to Explore Downtown San Diego
We moved hotels to Embassy Suites San Diego Bay Downtown, which was the perfect base for the rest of our trip. Highlights from our downtown days included:
USS Midway Museum
A huge hit with all five kids! We explored the sailor sleeping quarters, command centers, flight deck, and more. It was incredibly educational and moving.
SeaPort Village
Cute shops, an open-air food court-style setup, and a casual dinner where everyone got what they wanted. Em and I picked up matching San Diego sweatshirts—souvenirs are a must.
A Yacht Day, Little Italy, and a Top Gun Moment
Dan’s uncle (who lives in San Diego) arranged for us to take out his private yacht with a captain. We toured Coronado Island, cruised past the USS Midway, and even jumped in for a swim in the chilly bay. It was such a fun and unique way to see the city.
Later that night, we explored Little Italy and had dinner at Filippi’s Pizza Grotto—super family-friendly with hearty Italian favorites. We took bike carriages back to the hotel, which was such a fun way to end the night!
And yes—we also visited Kansas City Barbeque, aka The Top Gun bar, just a few minutes from our hotel. A must-stop for our Top Gun-loving teen!
Final Day: Baseball, Burgers, and Goodbyes
After checkout, we had some time to kill before our flight. Here’s how we wrapped up our adventure:
- A walk through Children’s Park
- A stop at Petco Park (there was a game!)
- Lunch at Harry’s Watch Bar—their back patio gave us a view into the stadium, with the game on the jumbotron and audio playing. A perfect, no-ticket-needed baseball experience.
Then it was back to grab our bags and head to the airport.
Things We Didn’t Get To (But Wanted To!)
Even with a packed itinerary, we didn’t make it to:
- Torrey Pines hiking trails
- San Diego Air & Space Museum
- Downtown Coronado
Definitely on our list for next time.
Final Thoughts on Our San Diego Family Trip
San Diego checked all the boxes: great weather, kid-friendly adventures, amazing food, and plenty of unforgettable memories. We laughed, explored, got salty and sandy, and enjoyed the rare chance to simply be together.
If you’re considering a family vacation to San Diego, DO IT. There’s truly something for everyone—from toddlers to teens to tired parents.
Got questions about where we stayed or what we did? Drop them in the comments or message me—happy to share more!
