Fly from Indianapolis International Airport to San Diego International Airport; depending on your connection, plan on roughly 4–6 hours in the air, plus airport time. Once you land, allow a little breathing room for baggage and check-in. Downtown is close: a rideshare typically takes about 10–20 minutes, while the San Diego Flyer shuttle connects the airport with the Old Town Transit Center, where you can continue by trolley or bus. If you’re renting a car, check your hotel’s parking fee before deciding whether to keep it downtown.
Head to Waterfront Park for an easy 45-minute leg stretch and bay views. It’s open daily, and the broad paths and fountains make this a comfortable first stop after a travel day. From downtown hotels, it’s an easy walk; from the airport, a short rideshare is simplest if you have luggage.
Make Little Italy Food Hall your low-key first dinner: several casual vendors let everyone choose their own meal, with about $20–$35 per person a reasonable budget. Then wander over to Piazza della Famiglia for a relaxed half-hour among the restaurants and cafés on India Street. The food hall’s vendor hours can vary, so check before heading over; Little Italy is compact and easy to explore on foot, and a rideshare back to your hotel saves the effort if you’re ready to call it a night.
Start with brunch at The Prado at Balboa Park—a lovely way to ease into reunion day amid the park’s Spanish Colonial architecture. Weekend brunch typically begins at 10 a.m.; allow about an hour and budget roughly $20–$40 per person. From there, stroll across the park to the Balboa Park Botanical Building for a 45-minute visit. It’s generally free, but access and hours can change, so check before you go. Keep an eye on the time: with the reunion starting at noon and its venue unspecified, leave Balboa Park by around 11 a.m. and allow generous time for the drive, parking, and finding the event.
Your reunion runs 12–4 p.m. Treat that window as fixed, and confirm the venue and parking arrangements in advance; San Diego traffic and event parking can add time. Afterward, head to Juniper & Ivy in Little Italy for a celebratory dinner. Make a reservation, especially for Saturday night, and expect about $60–$100 per person before drinks and tip; the meal is best enjoyed at an unhurried pace, around 1½–2 hours.
This is a long day, so leave San Diego around 5:30–6 a.m. for the drive to the Catalina Flyer terminal at Balboa Pavilion in Newport Beach. Allow 1½–2 hours in light traffic, but Sunday traffic can add time; budget for parking and arrive by the operator’s required check-in time. Important: the Catalina Flyer sails from Newport Beach, while Catalina Express sails from San Pedro and Long Beach. They are different operators and terminals, so book the Newport Beach round trip specifically and confirm that both sailings run on October 11 before setting out.
The crossing takes about 1 hour 15 minutes. From Avalon’s waterfront, walk to the Catalina Island Museum for an hour among island history and art; check its Sunday hours and admission price before you go. Then have lunch at Bluewater Grill, right on the harbor, with seafood and waterfront views—figure $25–$50 per person and about 1–1½ hours.
Walk to Descanso Beach Club to unwind by the water, then leave ample time to stroll back to the ferry terminal and board. The return sailing is the make-or-break detail: check the actual October timetable before booking, since the gap between arrivals and the return boat may leave only a short island visit. If the schedule doesn’t allow time for the museum, lunch, and beach stop in that order, this same-day plan won’t work as written—don’t count on a later boat. After the roughly 1¼-hour crossing, drive back to San Diego; allow 1½–2 hours or more, plus time to retrieve the car.
Take a morning Catalina Express ferry from Avalon to its mainland terminal, then allow roughly 2–2½ hours to drive back to San Diego. Confirm the October 12 sailing and terminal when booking, and check the drive time before you leave; traffic can stretch the return. This plan is most comfortable with an evening flight, so keep an eye on the clock as you go.
Head to Liberty Public Market in Liberty Station for a relaxed lunch from the food stalls—budget about $15–$30 per person and check Monday hours before setting out, as vendors may vary. Give yourself about an hour to browse, then take an easy 45-minute walk through nearby Liberty Station NTC Park, where the old naval-training grounds meet the waterfront.
Drive to Harbor Island Park for a brief 30–45-minute bayfront walk and a last look across the water toward downtown. From there, continue to San Diego International Airport; allow extra time for rental-car return or rideshare drop-off, airline check-in, and security. For your flight back to Indianapolis, work backward from the airline’s recommended airport arrival time—and leave a generous buffer if your ferry or drive runs late.
No packing list attached yet.