Jaco is the easiest base if you want beach access without a long drive from San José. It's not the prettiest town, but it's convenient and has good restaurants. I stayed at a small boutique hotel just off the main strip — nothing fancy, but the pool was perfect and the staff were genuinely helpful.

If you want something more remote, Manuel Antonio is worth the extra hour south. The national park is right there, the beaches are stunning, and there are some excellent mid-range hotels with jungle views. Book early — it fills up.

The Manuel Antonio National Park is non-negotiable. Go early (it opens at 7am), hire a guide for the first two hours — you'll see sloths, monkeys and birds you'd walk right past on your own — then spend the afternoon on the beach inside the park.

I did a sunset sailing trip out of Jaco that I'd recommend to anyone. Two hours on the water, snorkeling, open bar, dolphins if you're lucky. It's touristy, yes, but it's touristy for a reason.

What I skipped: the zip lines. I know everyone does them. I just didn't want to, and I don't regret it. Costa Rica is worth visiting even if you never leave the ground.

Eat at the sodas — the small, family-run local restaurants. Gallo pinto for breakfast every morning. Fresh ceviche wherever you can find it. The seafood is excellent and cheap if you stay away from the resort restaurants.

In Jaco, El Hicaco is worth a visit for a nicer dinner. In Manuel Antonio, La Luna at Gaia Hotel has a beautiful terrace and the food matches the view.

The roads are rough. A 4WD isn't always necessary but it helps, especially in the rainy season. Don't underestimate drive times — what looks like an hour on Google Maps can be two.

Tipping is appreciated but not always expected. 10% is standard at restaurants. Guides work hard — tip them well.

Don't skip Athens. I know everyone treats it as a layover city on the way to the islands, but it deserves two full days minimum. The Acropolis is as impressive as advertised. The Monastiraki neighborhood is excellent for wandering. The food scene in Psiri is genuinely great.

Stay in Plaka or Monastiraki if you want to walk everywhere. The boutique hotels in these neighborhoods are charming and reasonably priced compared to the islands.

Santorini is worth it — once. The sunsets in Oia are genuinely spectacular. But it's expensive, crowded in July and August, and the beaches are volcanic black sand (not everyone's thing). Go in May or October.

Naxos is my favorite. Bigger than most people expect, with excellent beaches, a charming old town, and a fraction of the Santorini crowds. You can rent a car and drive the whole island in a day.

Paros is a good middle ground — livelier than Naxos, less overwhelming than Santorini. The village of Naoussa is beautiful and has some of the best restaurants in the Cyclades.

Order the grilled octopus everywhere. Fresh feta with everything. The Greek salad is a cliché because it's perfect. Loukoumades (honey donuts) for dessert.

Eat at the tavernas away from the waterfront — the ones with handwritten menus and plastic chairs. They're almost always better and half the price.

July and August are brutally hot and crowded. If you have flexibility, May, June, September and October are dramatically better experiences.

Ferry schedules change. Build buffer days into your itinerary, especially if you're island-hopping. Missing a ferry because you were too tight on time is a very avoidable stress.

La Jolla is my favorite base — beautiful cliffs, great restaurants, walkable, and only 20 minutes from downtown. It's a bit more expensive but worth it for the setting.

Little Italy is excellent if you want to be in the middle of the food and nightlife scene. Walkable to the waterfront, great coffee shops, and some of the best restaurants in the city.

Coronado is worth considering if you want a beach resort feel — the Hotel del Coronado is iconic, and the island has a lovely small-town energy.

The La Jolla Cove is non-negotiable. Walk the cliffs, watch the sea lions, have lunch at one of the restaurants overlooking the water. It's one of the most beautiful spots in California.

Balboa Park is worth a half day — the museums, the gardens, the architecture. The San Diego Museum of Art is genuinely good. The botanical garden is free.

Yes, the San Diego Zoo is excellent. If you have kids or just love animals, it's worth the price. Go early, leave by noon before it gets crowded and hot.

Little Italy has the best restaurant density in the city. Ironside Fish & Oyster for seafood, Juniper & Ivy for a special dinner, Breakfast Republic for the morning.

The fish tacos are a San Diego institution. Rubio's is the famous chain but the best ones are at the small spots in Ocean Beach and Pacific Beach. Order them grilled, not fried.

North Park is worth a dinner trip for the independent restaurant scene — more local, less touristy, excellent cocktail bars.

June Gloom is real. The marine layer keeps mornings overcast in June, sometimes into July. It burns off by noon most days, but if you're going for beach weather, July through October is more reliable.

Parking is annoying in La Jolla and Little Italy. Build in time for it or just use rideshare for evenings out.