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.

Hudson is my top pick for a first visit. It has the best restaurant scene in the valley, a walkable main street (Warren Street) full of antique shops and galleries, and good hotel options. It's also centrally located for day trips.

Rhinebeck is charming and quieter — great for a romantic weekend. The Beekman Arms is the oldest continuously operating inn in America and worth staying at just for the experience.

Woodstock has the most character — artsy, a little eccentric, excellent for browsing. Don't expect the music festival; it was actually held in Bethel, 60 miles away. But the town itself is worth a half day.

Olana State Historic Site is one of the most beautiful places in New York State. The Hudson River School painter Frederic Church designed the house and the landscape himself. The views of the Catskills are extraordinary, especially in fall.

Dia:Beacon is a world-class contemporary art museum in a converted factory on the Hudson River. Even if you're not an art person, the building and the scale of the work are worth the trip.

The farm stands and orchards are part of the experience. Migliorelli Farm in Tivoli, Greig Farm in Red Hook, Fishkill Farms in Dutchess County. Pick your own apples in October — it's a cliché for a reason.

Swoon Kitchenbar in Hudson is my go-to for a proper dinner — farm-to-table, excellent wine list, consistently good. Book ahead on weekends.

The Pines in Hudson for a more casual dinner. Bread and Butter in Rhinebeck for breakfast. The Crimson Sparrow in Hudson for cocktails.

The farmers markets are worth planning around. Hudson Farmers Market on Saturdays, Rhinebeck Farmers Market on Sundays. Buy cheese, bread and fruit and have a picnic somewhere with a view.

Fall weekends book up fast. If you're coming in October, plan at least 6–8 weeks ahead for accommodations. The foliage peaks mid-October and everything fills up.

You really do need a car. The towns are spread out and there's no good public transit between them. The train gets you to Hudson or Rhinebeck from NYC, but you'll be limited without wheels.