You’re headed to beautiful San Diego! It’s one of the nation’s top convention destinations for a reason. Extend your trip by a couple of days, if possible, to get the most of your time here. Once you’ve booked your tickets and finalized your schedule—here’s how to make the most of your time away.
Workcations and bleisure travel—the blend of work and vacation—are a popular trend among business travelers. A 2024 American Express Travel Survey found more than 50% of employees will take a workcation in the next year. They said combining work and travel improved their work-life balance and increased creativity.
Why fly in for only the event? Extend your stay, explore a new city, and still get work done.
Here’s how to transform your next San Diego convention trip into a rejuvenating workcation.
What You’ll Learn:
- How to balance work and leisure during your trip
- Research-backed strategies for maintaining productivity
- Actionable tips for finding the best co-working spaces and accommodations
1. Extend Your Trip Strategically
The first step? Give yourself extra time.
Add an extra day or two before and after the convention if possible. It gives you to time to enjoy the destination without feeling rushed.
Why it matters: Extending business trips by a day or two around the event can reduce travel fatigue. It increases overall satisfaction with the trip.
Pro tip: Many hotels offer discounted rates for extended stays, especially over weekends. If you’re staying a full week, ask the hotel if they offer “bleisure” (business + leisure) packages. It’s a funny word, but longer stays often include perks like free breakfast or late check-out.
Search for San Diego Hotel Deals on Booking.com
2. Choose Work-Friendly Accommodations
Not all hotels are equally suited for remote work. Finding the right accommodations can make or break your workcation.
What to look for:
- Reliable Wi-Fi: Read recent reviews specifically mentioning Wi-Fi speed and reliability.
- Dedicated Workspace: A desk in your room is ideal, but communal business centers can also work.
- Amenities for Downtime: Pools, fitness centers, and nearby attractions can help you unwind.
Pro tip: Check platforms like Workfrom or Workspaces that rate hotels and cafés based on Wi-Fi speed and work-friendliness. Or, consider booking an Airbnb with a dedicated home office setup for extra privacy and space.
3. Plan a Flexible Work Schedule
Balancing work and leisure is the cornerstone of a workcation. It takes a little planning if you’re going to get work done when you’re not at the conference.
Sample Workcation Schedule:
- Morning (8 AM – 11 AM): Focused work (emails, deadlines)
- Late Morning (11 AM – 1 PM): Conference sessions or client calls
- Afternoon (1 PM – 4 PM): Explore the city or relax at a café
- Late Afternoon (4 PM – 6 PM): Wrap up work, check emails
- Evening: Local dining, events, or networking opportunities
Pro tip: Have a plan for tasks and deadlines while you’re on the go. Set clear expectations with your team by scheduling “out-of-office” hours in your calendar.
4. Use Local Coworking Spaces
Even if your hotel has solid Wi-Fi, coworking spaces can offer a more professional and focused environment. Most offer day passes, and they’re an opportunity to chat with local professionals. San Diego has a ton of coworking spaces across the city, so you’ll have plenty to choose from.
Why use co-working spaces?
- Consistent high-speed Wi-Fi
- Quiet areas for calls and virtual meetings
- Opportunities to network with local entrepreneurs and freelancers
How to find them:
- Apps like Workfrom or LiquidSpace list top-rated coworking spaces by city.
- Many places offer day passes, so you’re not tied into long-term memberships.
Top San Diego Co-Working Spaces:
- Downtown Works – Located near the convention center, offers open spaces and private rooms.
- Deskpass – Check current listings across the city.
5. Maximize Downtime Between Conference Sessions
What about maximizing your downtime during the conference? Even short breaks can be great opportunities to explore sunny San Diego.
Ideas for Short Breaks:
- 30-Minute Break: If you’re near landmarks like Seaport Village or Gaslamp Quarter, take a quick walk around.
- 1-Hour Lunch: Visit a local café or food truck near the conference center (ask convention center or hotel staff for recommendations)
- Afternoon Break: Enjoy fresh air at Embarcadero Marina Park
Pro tip: Sign up for conference-sponsored field trips and day tours. Conference planners organize tours and networking events for attendees, and they’ll take care of transportation and scheduling. There’s usually a nominal fee on top of registration, but it’s a great way to connect with other conference attendees.
6. Combine Networking with Local Experiences
Step away from the convention hall to make memorable connections. Most conferences are packed with sponsored networking events at local restaurants. Some of the best business conversations happen at these happy hours and sightseeing events.
Creative Networking Ideas:
- Host a casual meetup with colleagues at a local brewery like Ballast Point Brewing.
- Organize a “walk and talk” with potential collaborators through Balboa Park.
- Attend city events or mixers (find them on Meetup or Eventbrite).
Pro tip: Use the official conference app or LinkedIn Events to coordinate off-site meetups with other attendees.
7. Pack for Work and Play
Packing for a workcation can be a balancing act. You’ll need a mix of professional and casual clothes, and don’t forget your tech essentials.
Workcation Packing List:
- Work Essentials: Laptop, chargers, headphones, portable Wi-Fi hotspot (if you want to make sure you have coverage!)
- Professional Attire: Bring comfortable walking shoes and business casual attire for conference sessions and networking events
- Casual Clothes: Keep it simple and easy for exploring the city
- Health & Safety: Don’t forget hand sanitizer and immune boosting supplements like Airborne
- Extras: Portable power charger, day pack, reusable water bottle
Pro tip: Use packing cubes to stay organized. Separate work attire from leisure clothing for easy access.
8. Practice Self-Care During Your Trip
Traveling for work can be draining. Make sure to schedule self-care time during your workcation to recharge.
Self-Care Ideas:
- Morning Yoga: Some San Diego hotels offer fitness classes like yoga, or use YouTube Yoga for in-room sessions
- Nature Breaks: Visit local parks like Sunset Cliffs Natural Park
- Mindfulness apps: Use Calm or Headspace for quick meditation sessions to start or end your day
Pro tip: Don’t overbook your schedule. Leave time to relax and enjoy the experience.
Turning a San Diego convention trip into a workcation is a chance to experience a beautiful city while boosting creativity. Use these tips to make the most of your time away from home … and enjoy all the city has to offer.
Work Travel Getaways 