
September Vacation Ideas
September vacation ideas take you around the world with fantastic weather to discover adventurous destinations, captivating cultures or cities steeped in heritage. From European grandeur to the rugged terrain of Patagonia, elegant resorts in Southeast Asia to the wonderful wilderness of an African safari, embrace the exceptional with a personalized custom trip. Find inspiration for your September vacation using our sample itineraries, and plan with a travel specialist when you are ready.
Explore Our Trip Ideas
Let these itineraries inspire your personalized travel experience

10 Day Trip IdeaFrom $3,300
September Nights in Spain: Off the Beaten Path Tour of Spain

12 Day Trip IdeaFrom $10,200
Zimbabwe Dry Season Safari: June to September

8 Day Trip IdeaFrom $5,600
Frozen Inspired Autumn Family Tour of Norway

14 Day Trip IdeaFrom $5,100
Best of Italy in Autumn: 14-Day Romantic Tour

13 Day Trip IdeaFrom $13,200
Signature Okavango Wetland Safari: June to September

12 Day Trip IdeaFrom $5,100
Amazing Aegean Highlights: 12-Day Greece Tour
How Zicasso Works
Here's how we create life-enriching, luxury travel experiences
1.Share Your Travel Dreams
Zicasso specializes in custom tours, vacations, and safaris tailored to your interests and preferences. From private African safaris to culinary experiences in Europe, submit a trip request to share your ideas and travel style.
2.Meet Your Travel Specialists
To ensure a personalized experience, we'll carefully handpick and introduce you to two of our top travel specialists, each with unsurpassed destination knowledge and local insight aligned to your luxury travel dreams.
3.Design Your Perfect Journey
Compare the expertise of two specialists with itineraries crafted exclusively for you. You can refine these further and choose your preferred proposal. Our unique process ensures a more creative, personalized, and expertly crafted trip.
Reviews of Zicasso's September Vacation Ideas
Based on 696 verified traveler reviews.
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We visited Madrid, Toledo, San Sebastián, Bayonne, Biarritz, Saint-Jean-de-Luz, Hondarribia, La Rioja, Barcelona, Montserrat, and the Penedes (Cava) region.
We loved our private guides, private wine tastings, and day trips outside of the big cities.
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My husband and I returned from a 19-day trip to Spain and Portugal on September 22nd and would highly recommend our travel agency, arranged through Zicasso Travel.
Our travel agent customized a trip, taking into account our budget and incorporating visits to Barcelona, Madrid, Toledo, Málaga, Granada, Seville, and Ronda in Spain, and the Algarve coast, Évora, and Lisbon in Portugal.
We easily communicated via emails, phone calls and zoom, and after four drafts we agreed to a final itinerary that met out interests, along with his excellent recommendations. Our agent was always gracious and understanding to the changes we wanted to make. He also included some down time on a few half days of tours to do some sightseeing on our own along with his recommendations.
Having planned two trips abroad ourselves in the past, and being older, it was so reassuring to have a competent and knowledgeable travel agent to take care of all train reservations, tickets, hotels, private drivers and tour guides. It was also reassuring to know if we encountered any problem during the course of our trip we could contact someone at a 24/7 emergency number. The train transportation arranged between a few cities went smoothly in the comfort of first class, our private drivers were pleasant, professional and informative and our individual tour guides that were arranged to meet us were prompt and so knowledgeable which made each tour all the more memorable. Lastly, our agent was able to provide the resources for us to meet some personal needs at each hotel where we stayed.
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This was a dream vacation made reality–five stars!
We just returned from the most unforgettable two-week adventure through Greece, all thanks to the exceptional planning and care of Zicasso's travel operator and her team! From the moment we landed until our final farewell in Athens, every detail was flawlessly executed.
Our journey began in Crete, where we were welcomed by a warm, knowledgeable guide who brought Chania's rich history to life during all of our many activities. From touring the many villages to hiking Imbros Gorge to the Palace of Knossos, we felt immersed in the true spirit of Crete.
Next was Santorini, where the sunsets were just as magical as we’d hoped. Our stay was filled with stunning cliffside views, wine tastings, and personalized recommendations that made it feel like we were exploring the island with a local friend.
Naxos was an unexpected gem—less touristy, but bursting with charm. The tour guide here was particularly fantastic, taking us to authentic villages, ancient ruins, and serene beaches that felt like our own private paradise.
Our final days in Athens were the perfect ending to this epic journey. The historical sites were breathtaking and our guide’s passion for Greek history made every moment at the Acropolis and the museums feel deeply meaningful.
What truly set this experience apart was how responsive and supportive our agent and her team were throughout the trip. Any time we had a question—whether about transportation, recommendations, or small changes in plans—they replied quickly and helpfully, making us feel completely at ease and well cared for.
Throughout the trip, the logistics were seamless—beautiful accommodations, smooth transfers, and thoughtfully curated excursions. Every guide was not only professional and knowledgeable, but also incredibly kind and engaging. It felt like we were traveling with friends who truly cared about our experience.
We can’t thank our agent enough for crafting such a memorable and enriching vacation. Greece was always on our bucket list and now we’re already dreaming of our return!
Highly, highly recommended!
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The travel fairy at Zicasso's tour operator, as she called herself (and I felt it fit her well), certainly put together a magical trip to Greece for our group of four. We all had a fantastic vacation in Greece and were super-impressed and pleased with the staff at the travel company.
The connections for flights and ferries, as well as all of the transfers to and from our hotels and excursions, were seamless, which made for a stress-free vacation. The hotels they arranged for us ranged from old Venetian buildings in older parts of Athens and Heraklion to an upscale small resort in Naxos, as well as a fantastic hotel in Chania that overlooked the harbor. My husband and I loved every one, especially the resort in Naxos.
I highly suggest this travel company because they listened to our group's likes and dislikes to plan the perfect trip. Our trip consisted of Athens, Naxos, and two places on Crete, filled with two food tours, a boat trip, historical excursions to the Parthenon and Knossos, as well as excursions in nature to Imbros Gorge and Balos Beach. Any guide during these excursions was very knowledgeable.
We would change only the following two things. Naxos was so beautiful and we were all sad to leave and wish we could have added an extra day to just relax on the beach for a full day. So, my suggestion to anyone traveling to Greece would be to save at least one full day at one of the beautiful islands without an excursion.
The other thing we would change is to take a boat to Balos Beach instead of walking down to the beach. My husband is 80 years old and although he is in good shape, the hike was very steep and scary in some parts. As we were walking down to the beach, we loved the incredible vistas, but were also concerned about having to walk back up the equivalent of 66 flights of stairs. I say this just as a cautionary tale to really look into this walk before your trip. The views were hard to beat, but the walk was not easy.
Highlights of this trip included the hotel in Naxos (our resort on Plaka in Naxos), with super-friendly and helpful staff, private tour of Knossos and the museum, and the charming city of Chania. Greece is truly a beautiful country, with stunning vistas, beaches, historical sites, museums, and cute narrow streets filled with shops and restaurants.
Thank you for a vacation that will stay in our hearts forever.
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We traveled to Greece in September 2025 for an 18-day trip to five locations. We went through Zicasso and were paired with the primary travel company and the local partner. I cannot express how wonderful our trip was. It was apparent that every detail was carefully tailored to meet all of our wants and needs. From the transfers to the tours, and the hotel accommodations and locations, everything about it was just perfect! Highly recommended if you want a worry-free trip.
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