I’ve Vacationed In 15 Different Places — These Are The 8 I’d Book Again And The 7 I’d Skip (Even If The Trip Was Fun)

After years of exploring different corners of the world, I’ve developed strong opinions about which vacation spots truly deserve a return visit. Some destinations exceeded my expectations with unforgettable experiences, while others left me feeling that once was enough.

My travels have taught me that the perfect vacation isn’t just about famous landmarks or luxury hotels—it’s about how a place makes you feel and the memories you create there.

1. Book Again: Kyoto, Japan – A Cultural Paradise

Walking through Kyoto’s ancient streets felt like stepping into another time. The city balances traditional temples with modern conveniences perfectly, making exploration easy even for first-timers.

My morning visits to Arashiyama Bamboo Grove before the crowds arrived created moments of pure tranquility. The food scene surprised me most—from casual ramen shops to elegant kaiseki dining, every meal became an adventure.

If you love history, beautiful gardens, and authentic cultural experiences without overwhelming crowds, Kyoto delivers in ways Tokyo cannot. I’d return in a heartbeat, especially during fall when the maple leaves turn fiery red.

2. Skip: Cancun, Mexico – Overpriced Resort Bubble

My week in Cancun taught me that beautiful beaches can’t compensate for an artificial vacation experience. The all-inclusive resort felt disconnected from authentic Mexican culture, with prices rivaling major European cities.

Venturing outside the hotel zone became frustrating with persistent tourist traps and inflated rates for basic services. Though the Caribbean waters sparkled with postcard perfection, the crowded beaches and rowdy spring break atmosphere diminished the natural beauty.

Despite some delicious meals and friendly staff encounters, Cancun left me craving a more genuine connection to the destination. Mexico has far more rewarding coastal spots with similar beaches but greater cultural richness.

3. Book Again: Lisbon, Portugal – Affordable European Charm

My heart still skips when remembering Lisbon’s sun-drenched hills and colorful buildings. This underrated European gem offers incredible value—I enjoyed museum visits, fantastic meals, and charming accommodations at half the price of Paris or London.

Locals welcomed questions and conversations despite my laughable Portuguese attempts. The city’s melancholy fado music performances in tiny Alfama district venues created evenings I’ll never forget.

Lisbon’s walkable neighborhoods reward curious travelers with hidden viewpoints, family-run pastry shops, and stunning tile work around every corner. I’d return not just for the affordability but for the genuine warmth that permeates this seaside capital.

4. Skip: Dubai, UAE – Impressive But Soulless

Dubai wowed me initially with architectural marvels and luxury shopping beyond imagination. The Burj Khalifa view impressed everyone on my Instagram feed, and desert safari adventures provided genuine thrills.

Yet after three days, the city’s artificial atmosphere became increasingly apparent. Moving between climate-controlled spaces while barely interacting with actual Emirati culture left me feeling disconnected from any authentic experience.

Though service standards reached perfection everywhere, the lack of historical depth and walking-friendly neighborhoods made Dubai feel more like an elaborate theme park than a living city. For the considerable expense, other destinations offer more meaningful cultural exchanges and natural beauty.

5. Book Again: Quebec City, Canada – European Vibes Without Flying Overseas

Wandering Quebec City’s cobblestone streets made me question whether I’d accidentally teleported to France. The walled Old Town transported me to another century with its preserved architecture and French-speaking locals.

Winter transformed the city into a magical snow globe during Carnaval, complete with ice sculptures and maple taffy pulled fresh onto snow. Summer brought outdoor cafés and street performers that kept the historic district lively until late evening.

My budget stretched surprisingly far despite the charming surroundings, with affordable boutique hotels and reasonably priced restaurants serving incredible poutine and local specialties. This accessible slice of Europe right in North America deserves multiple visits across different seasons.

6. Skip: Venice, Italy – Beautiful But Overwhelmed

Venice stunned me with its impossible beauty—waterways replacing streets and centuries-old palazzos defying the lagoon. Morning explorations before cruise ships arrived revealed the magical city I’d always imagined.

Yet by midday, narrow alleys became human traffic jams, with selfie sticks creating hazards at every turn. Restaurant prices tripled for mediocre tourist-trap meals, while authentic eateries required advance reservations or insider knowledge.

The constant struggle against overwhelming crowds diminished what should have been a romantic experience. While I’m glad to have seen this floating marvel once, other Italian cities offer similar historical richness with more breathing room and authentic interactions. Venice deserves better than what mass tourism has created.

7. Book Again: Costa Rica – Eco-Paradise Worth Every Penny

My Costa Rican adventure reset my understanding of what vacation relaxation truly means. Waking to howler monkeys instead of alarm clocks while staying in a sustainable jungle lodge created immediate perspective shifts.

The country’s commitment to conservation shows everywhere—from plastic-free initiatives to protected wildlife corridors. Though transportation between regions took longer than expected, each new destination rewarded patience with incredible biodiversity and genuinely friendly locals.

Whether hiking cloud forests, soaking in volcanic hot springs, or surfing Pacific waves, Costa Rica’s “pura vida” philosophy infused every experience with mindfulness. I’d gladly return to explore more national parks and continue supporting their environmental leadership through tourism dollars.

8. Skip: Bali, Indonesia – Instagram vs. Reality Disappointment

Social media promised serene rice terraces and empty beaches, but my Bali reality included traffic jams and influencers staging photoshoots at sacred temples. The disconnect between expectations and experience created constant disappointment.

Plastic pollution marred otherwise beautiful beaches, while development sprawl transformed once-quiet villages into noisy tourist corridors. Finding authentic cultural experiences required escaping popular areas entirely, which consumed precious vacation time.

Though I encountered genuine Balinese hospitality and stunning natural landscapes occasionally, the overwhelming commercialization and environmental challenges made Bali feel like a paradise lost. Indonesia offers many less-developed islands with similar natural beauty but fewer crowds and more cultural integrity.

9. Book Again: New Zealand’s South Island – Nature at Its Finest

Driving New Zealand’s South Island highways delivered a new breathtaking vista around literally every curve. The landscape diversity stunned me daily—from glacier-carved fjords to rolling vineyard hills, often within hours of each other.

Friendly Kiwis shared local secrets that enhanced my journey, suggesting hidden hiking trails and uncrowded viewpoints. The well-maintained camping infrastructure made outdoor immersion easy even for someone not typically drawn to roughing it.

Despite the long flight from home, New Zealand’s combination of accessibility, safety, and unspoiled natural wonders justified every travel hour and dollar spent. I’d return specifically for multi-day treks through national parks that I only sampled briefly on my first visit.

10. Skip: Paris, France – Overrated Romance

My Paris expectations crashed against reality within hours of arrival. The city’s beauty remains undeniable, but persistent scams, indifferent service, and astronomical prices for basic accommodations created constant stress.

Famous landmarks disappointed with multi-hour queues and selfie-stick armies blocking every view. Finding authentic French dining experiences required leaving tourist zones entirely, though these neighborhood discoveries provided trip highlights.

While I appreciate having seen iconic sites firsthand, Paris demanded too much effort for too little reward compared to equally beautiful European cities. France has numerous charming regions offering similar architectural beauty, superior culinary experiences, and warmer welcomes without the capital’s exhausting intensity.

11. Book Again: Sedona, Arizona – Desert Magic Worth Experiencing

Red rock formations glowing at sunset created natural cathedral spaces unlike anywhere else I’ve visited. Sedona’s energy feels special regardless of whether you believe in vortexes—something about this landscape inspires immediate presence.

Hiking trails offered options for every fitness level, each rewarding with spectacular views and surprising solitude despite the destination’s popularity. The town itself balanced touristy gift shops with genuinely excellent restaurants and wellness offerings.

Though accommodation prices ran higher than expected, waking up surrounded by crimson cliffs justified the splurge. Sedona works equally well as a romantic getaway, family vacation with older kids, or solo wellness retreat—I’d return for any of these purposes.

12. Skip: Santorini, Greece – Beautiful but Brutally Overcrowded

Those famous blue-domed churches against whitewashed buildings lived up to their photographic promise. Watching sunset from Oia created a legitimately breathtaking moment that almost justified the entire trip’s expense.

Almost—because beyond these postcard scenes, Santorini struggled under tourism weight that transformed narrow village pathways into human gridlock. Finding authentic Greek experiences became nearly impossible in main towns, where restaurants served mediocre international food at premium prices.

My hotel overlooking the caldera provided stunning views but required climbing hundreds of steps multiple times daily. While I cherish certain Santorini memories, dozens of less-famous Greek islands offer similar Aegean beauty with authentic village life and beaches not overrun by cruise ship crowds.

13. Book Again: Mexico City – Cultural Metropolis That Exceeds Expectations

Mexico City shattered my preconceptions within hours of arrival. This sophisticated metropolis blends world-class museums, ancient ruins, and innovative dining scenes into an intoxicating cultural cocktail.

Safety concerns proved largely unwarranted in tourist and residential districts, where I wandered freely day and night. The affordability shocked me most—michelin-caliber meals cost a fraction of US prices, while beautiful boutique hotels offered luxury experiences at mid-range rates.

Moving between neighborhoods revealed distinct mini-cities with unique characters, from historic Centro to trendy Roma Norte. I’d return specifically for deeper exploration of specific areas, art galleries I missed, and the seemingly endless street food adventures that await around every corner.

14. Skip: Las Vegas, Nevada – Exhausting Sensory Overload

Vegas delivered exactly what it promised—sensory overload, 24/7 entertainment options, and over-the-top everything. The sheer spectacle impressed me initially, from dancing fountains to recreated world landmarks.

By day three, the constant casino noise, artificial environments, and relentless consumerism created a strange exhaustion unlike any other vacation. Finding authentic experiences or moments of tranquility required escaping the Strip entirely.

While I enjoyed certain aspects—excellent restaurants, professional entertainment shows, and nearby natural wonders like Red Rock Canyon—the overall experience left me feeling drained rather than refreshed. Las Vegas works better as a weekend splurge than a proper vacation destination, especially considering the hidden costs beyond initial bargain room rates.

15. Book Again: Montana’s Glacier National Park – America’s Wild Heart

Morning mist rising off alpine lakes while mountain goats watched from nearby ridges made me feel like I’d discovered America’s best-kept secret. Glacier National Park’s raw wilderness creates perspective shifts impossible in more developed destinations.

Hiking trails for every ability level led to jaw-dropping vistas that required no filters or photography skills to capture beautifully. The park’s limited cell service forced a digital detox that quickly transformed from inconvenience to blessing.

Though summer crowds required some strategic planning, finding solitude remained possible with early starts and less-traveled trails. I’d return specifically during September when visitor numbers drop but weather typically remains favorable—and to see remaining glaciers before climate change claims them entirely.