Our First Trip Together- Need recommendations

Question

My girlfriend and I will be taking our first trip together. We’re in our early 50s and have been dating 4 months. We arrive just before noon on Thursday this week and fly out around 2:30 on Sunday. We will be staying at the Pentai Inn in La Jolla. For Friday I have rented a convertible and plan to drive the 59 mile Scenic Drive that day. I’m looking for recommendations on what to do on Saturday? We are both in good physical shape and cost is not a concern. Just looking to do something memorable during our short stay. We like food, we like drinks, we like music and are really open to just about anything. Thanks for your help!

Answer

Hi! It sounds like you have a wonderful first trip planned in San Diego, and staying in La Jolla is perfect for combining scenic beauty with food, drinks, and activities. Since Friday is covered with the scenic drive in your convertible, here’s a detailed plan for Saturday to make it memorable.

Morning:

Start with breakfast or brunch at a highly-rated La Jolla café or bistro, such as The Cottage or Brockton Villa, which offer great ocean views and hearty options.
After brunch, consider a guided kayak or paddleboard tour of La Jolla Cove. You can see sea lions, caves, and marine life up close. Many tours also include snorkeling opportunities if you’re interested.

Midday / Afternoon:

Drive or stroll through Torrey Pines State Natural Reserve for a moderate hike along the bluff trails. The views of the coastline are spectacular and make for great photo opportunities.
Alternatively, if you want something more relaxed, take a private sailing cruise or a harbor tour from San Diego Bay, which can include lunch or champagne for a romantic touch.

Evening:

Enjoy early evening cocktails at a rooftop bar in downtown San Diego or La Jolla, such as Altitude Sky Lounge or M Lounge, for panoramic sunset views.
Dinner at a memorable restaurant—options include George’s at the Cove in La Jolla for fine dining with ocean views, or Born and Raised in Little Italy for a trendy steakhouse experience. Book a reservation to ensure a prime table.
Post-dinner live music: Consider catching a jazz or blues set at a venue like Humphreys Concerts by the Bay, or a smaller intimate live music bar in Little Italy or Gaslamp Quarter.

Optional Special Experiences:

Private wine or craft cocktail tasting tour in downtown San Diego.
Hot air balloon ride over Del Mar or Temecula (about 1–2 hours from La Jolla) for a truly unforgettable experience if you’re willing to travel a bit.
Couples spa treatment in La Jolla at a luxury spa such as La Costa or The Lodge at Torrey Pines, for relaxation after your active Friday.

With this plan, you’ll have a balance of adventure, stunning scenery, great food and drinks, and a touch of romance for a truly memorable Saturday in San Diego.

Our First Trip Together- Need recommendations

More San Diego Travel Questions

The attractions mentioned in this question

Popular Destinations

Popular Travel Questions