How to Plan a Multi-Stop Vacation Without Losing Your Mind

Dreaming of a European adventure with multiple cities? Or a tropical escape that hops between islands? Multi-stop trips can be magical—but they also come with layers of logistics most people underestimate.

Here’s your guide to planning a smooth, unforgettable multi-stop vacation—without the stress.

1. Start With the Big Picture
Choose a region that makes sense for the amount of time you have. For example: Italy + Greece is doable in 10–12 days. Mexico + Belize? Easy with a week and a half. I’ll help you map out a realistic route that doesn’t leave you airport-hopping every day.

2. Know the Best Transportation Methods
Trains, ferries, domestic flights—every destination is different. I help you figure out what’s most efficient (and cost-effective) between each leg of your journey.

3. Factor in Travel Recovery Time
Don’t underestimate how tiring it can be to hop from city to city. I help build in chill days or shorter stays in relaxing locations so your trip still feels like a vacation.

4. Choose the Right Accommodations
Different cities, different vibes. Want boutique in one city, beachfront in another, and a luxury hotel to wrap it all up? Done. I help you layer your stay to match your energy as the trip progresses.

5. Let Me Handle the Itinerary Building
From transfers to excursions to timing airport check-ins—I’ve got you. You focus on the fun part, I’ll handle the puzzle.

A multi-stop trip doesn’t have to mean multi-level stress. Let me piece it together so you get the absolute most out of your vacation.