Top Sites to Plan the Perfect Vacation Itinerary

Top Sites to Plan the Perfect Vacation Itinerary

Planning the perfect vacation can be just as exciting as the trip itself—if you have the right tools. With so many destinations, activities, and logistics to juggle, it’s easy to feel overwhelmed. That’s where travel planning websites come in. From creating day-by-day itineraries to booking accommodations and finding hidden gems, these platforms simplify the process and turn your travel dreams into reality. Whether you’re heading on a weekend getaway or a multi-country adventure, the right site can make all the difference.

Jetset Christina – Curated Luxury Travel for the Sun-Soaked Jetsetter (pictured)
Website: jetsetchristina.com

Jetset Christina is a go-to destination for luxury travel, showcasing the very best in curated travel guides, resort wear style, and unforgettable experiences around the world. Created by Christina Haisfield, a Charleston-based travel influencer and former Google brand marketer, the site blends her sharp eye for design and storytelling with her globe-trotting expertise across 70+ countries. Whether you're planning a honeymoon, family getaway, or dreamy beach escape, Christina’s honest and stylish recommendations help elevate every moment of your trip.

Jetset Christina’s blog covers everything from Bali’s most romantic resorts to the perfect outfits for long-haul flights. Beyond travel, she’s also the co-founder of Kenny Flowers, a resortwear brand that brings vacation style to everyday life. With frequent features in Travel & Leisure, Forbes, and Oprah Magazine, Jetset Christina is more than just a blog—it’s a lifestyle built around luxury, authenticity, and adventure.

Best for: Honeymooners, beach lovers, and luxury travelers looking for sun, style, and curated travel tips.

Highlights:

  • Luxe destination guides for honeymoons, tropical escapes, and wine country
  • Stylish resortwear tips and curated product recommendations
  • Personal travel stories backed by real-world brand and marketing experience
  • Founder of Kenny Flowers, a high quality resort wear brand inspired by global adventures
  • Regularly featured in top publications like Travel & Leisure and Forbes

Moving to Spain – Your Step-by-Step Guide to a Smooth Relocation
Website: movingtospain.com

Moving to Spain is a dedicated resource created by Alastair and Alison—an expat couple who fell in love with Spain after moving there from Australia in 2015. After navigating the complexities of Spanish bureaucracy, cultural adjustments, and the infamous red tape, they launched this platform to simplify the process for others following the same dream.

With years of global relocation experience under their belt (six international moves and counting), Alastair and Alison understand the overwhelming number of questions new expats face: Which visa should I apply for? How do I choose the right city? Can I afford to live in Spain comfortably? Their goal is to answer all those questions with up-to-date, honest, and actionable information.

What makes Moving to Spain unique is its deeply practical approach. From an interactive checklist that breaks down every step of your relocation to curated tools, financial planners, and handpicked local service providers, the website acts as your personal guide before, during, and after your move. It’s designed not just to get you to Spain—but to help you thrive once you're there.

Best for: Expats, families, retirees, and remote workers looking for detailed guidance on relocating and living in Spain
Highlights:

  • Created by real expats with firsthand experience moving to and living in Spain
  • Step-by-step interactive checklist tailored to your relocation timeline
  • Clear information on visas, healthcare, cost of living, and job hunting
  • Expert recommendations on pre-vetted local partners and service providers
  • Financial tools to help you budget and plan for Spanish life
  • Insightful videos, guides, and community-based advice backed by real stories

Whether you're still researching your options or already planning your move, Moving to Spain is a one-stop destination for making your transition to Spanish life easier, more informed, and less stressful.

Truly Friuli – Discover the Authentic Heart of Italy’s Untouched Northeast
Website: trulyfriuli.com

Truly Friuli is your gateway to exploring Friuli-Venezia Giulia, a lesser-known gem in Italy's northeast that is brimming with history, culture, and unspoiled beauty. Created by Audrey De Monte, local host and cultural guide with Travels with Audrey, she shares her expertise and insights into the region's most iconic landmarks, secret hideaways, and immersive experiences.

This thoughtfully compiled “20-page Friuli Travel Guide” highlights 10 handpicked experiences that you can only find in Friuli. Whether you’re hiking in the Alps, tasting world-class local wines, wandering through artistic towns like Udine and Cividale del Friuli, eating the regional cuisine, or discovering hidden coastal adventures, Audrey helps you explore the region like a true insider.

Best for: Travelers seeking off-the-beaten-track Italian destinations, culture lovers, history buffs, and outdoor enthusiasts looking for an authentic regional experience.
Highlights:

  •     A free, detailed 20‑page guide featuring top regional experiences
  •     Mix of must-see landmarks and hidden gems unknown to most tourists
  •     Recommendations for local wineries, cuisine, and outdoor activities
  •     Expertly curated day trips and multi-day itineraries
  •     Emphasis on authentic cultural connections and immersive travel

Truly Friuli is more than just a travel guide—it’s your key to experiencing an undiscovered slice of Italy where rich traditions, dramatic landscapes, and warm hospitality blend into an unforgettable journey.

Milesopedia – Your Go-To Guide for Credit Cards, Travel Points & Financial Tools
Website: milesopedia.com

Milesopedia is Canada’s leading bilingual platform dedicated to helping people get the most out of their reward points, credit cards, and travel budgets. Founded in 2015 by Jean-Maximilien Voisine, the site has grown into a trusted encyclopedia for financial-savvy travelers, with a full-time team of Canadian experts and a thriving community of over 30,000 members.

What started as a response to the frustration of unused points has evolved into a one-stop hub for comparing financial products, learning strategic points hacks, and maximizing every dollar. Whether you're a beginner curious about Aeroplan or a seasoned pro hunting for the best Marriott Bonvoy redemption, Milesopedia’s deep-dive guides, tutorials, and white-label comparison tools are tailored for every level of expertise.

What makes Milesopedia shine is its mix of independence, clarity, and performance. With no fluff or guesswork, their in-house tools help you sort through hundreds of credit card options based on real criteria, while their community-led insights offer a real-world layer of trust. Add in expert mentoring and up-to-date market coverage, and you’ve got one of the smartest financial travel resources on the web.

Best for: Points collectors, frequent flyers, deal hunters, and Canadians who want to turn everyday spending into smarter travel
Highlights:

  • Created by a team of financial and travel experts with real-world experience
  • Easy-to-use credit card and bank account comparison tools based on over 18,000 data points
  • Bilingual content that breaks down complex programs like Aeroplan, AIR MILES, and Marriott Bonvoy
  • Step-by-step guides, videos, and strategy articles to help maximize rewards
  • Community-driven support via a private Facebook group with 30,000+ members
  • White-label tools trusted by major brands like Protégez-Vous and RedFlagDeals
  • Independent recommendations built on transparency and performance—not promotions

Whether you’re looking to save on your next flight, earn more from your everyday spending, or simply understand the loyalty program maze, Milesopedia is the clear, reliable guide to help you explore more for less—right from your wallet.

Final Thoughts

Your time off deserves thoughtful planning—and with the right tools, organizing your trip can be part of the fun. These top travel planning websites take the stress out of the process, helping you build an itinerary that fits your pace, budget, and travel style. Whether you're looking for flexibility, detailed day-by-day plans, or inspiration for your next destination, these platforms have you covered. So start exploring, and let your perfect itinerary take shape—one click at a time.