Trip Planning

I Used ChatGPT to Plan Trip to Door County, Wisconsin. It Saved Me Hours

Published

3 weeks ago

July 19, 2025

Sarah Gray

Before I plan a trip, I have a straightforward goal: Learn everything there is to know about the place I’m visiting.

I know, I know. That sounds time-consuming. And truthfully, for me it is.

But for ChatGPT?

I stumbled upon this AI use case when starting to plan a relatively uncomplicated trip to Door County, Wisconsin, for later this summer. Rather than doing the hours of background reading that I usually do to get the lay of the land in a new destination, I let OpenAI‘s chatbot do it for me.

For context, I travel frequently in my personal life and cover travel for Business Insider, but until now, I’d yet to find a use case for AI that I felt really made my trip planning process more efficient.

I’d experimented with AI-powered trip planning tools but had never found them particularly useful. I’d also tried using ChatGPT as a glorified Google, describing to it vaguely what my interests were and asking it to recommend restaurants or attractions. The results were less than promising. From what I could tell, our individual tastes are still too personalized — and chatbot answers too universal — for specific recommendations to be helpful.

But for replacing all my pre-planning background reading? It was great.

AI does all my background reading for me

Let me give you a sense of my usual process.

Once I know I am visiting a place, I will Google the most generic things a tourist could think to ask: Top attractions. Must-do activities. Neighborhood guide. Best restaurants. One-day itinerary. Three-day itinerary. Weeklong itinerary.

I will do all of these searches, open more tabs than any browser should be reasonably expected to host, and then, I read.

I read the top 10 or so results for every search. Then I do more niche searches like best neighborhoods to live in or best vintage shopping, and do the process all over again, this time also rifling through countless Reddit threads where locals discuss the goings-on in their own neighborhoods.

Next, I move to social media — often TikTok — to scroll all the videos I can find about the destination to get some visual context and, most importantly, to learn which restaurants or attractions are viral so that I can avoid them.

It takes hours, and it’s arguably more information than a tourist technically ever needs. But by the time I am done, I feel I have a shockingly full understanding of a place, as both a tourist destination and even as a place where real people live. I feel I could recommend to my friends which neighborhood would be uniquely right for them, which highly-rated restaurants are overrated, and which niche museum is actually a lot cooler than the one ranked first on TripAdvisor.

The process is excessive, but it gives me confidence that when I get to the hard planning stage — selecting a neighborhood, narrowing down hotels or Airbnbs, booking restaurant reservations — that my hard-earned PTO is being put to its best possible use.

Luckily for me, it turns out ChatGPT is pretty good at doing this.

ChatGPT helped me plan my trip to Door County, Wisconsin

I was recently planning a trip to Door County, which is a small peninsula in northeast Wisconsin situated between Lake Michigan and Green Bay that’s known for being one of the prettier natural places in this part of the Midwest. I wanted to book a house on the water for a busy travel weekend, so I knew I needed to do it quickly.

So, instead of embarking on my usual trip planning odyssey, I did something that I had previously been very skeptical about: I turned to AI.

The kind of comprehensive overview that I get from reading all the top Google results, ChatGPT was able to give me with just a few prompts. I asked which popular attractions are frequently called overrated and which ones people say are worth weathering the crowds. I asked it to include any tips or tricks on the best times to visit certain places, and to provide several sample itineraries that were varied so I could get a complete picture of my options.

I even described my vague travel preferences — good food, good drinks, nature, away from crowds, vintage shops, where locals actually go — and asked it what town I should stay in. It gave me a quick summary of what each of the towns were best known for and which were most likely up my alley.

I also asked follow-up questions and played devil’s advocate, as AI can tend to repeat marketing-speak or be overly optimistic.

In about half an hour I felt like I understood visiting Door County almost as much as I would’ve if I had spent those hours consuming everything myself. It’s able to summarize the 90% of recommendations that pop up on every list and then also include the more unique ones.

The responses were not perfect. It recommended at least two restaurants that closed several years ago. And to be clear, I doubt that I know Door County as well as I would if I had done all that reading myself.

But I felt like I knew it enough to be confident in my choices while planning — enough so to book a rental home that same night, a decision that would generally take me a lot more time.

And yeah, I’m still going to do a bit of excessive reading for the hidden gems. What can I say? Old habits die hard.

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Trip Planning

Must-See Ports On A Mediterranean Cruise, And Those To Skip

Published

12 hours ago

August 10, 2025

David Nikel

The Old Port of Marseille is a pleasant place to spend a day on a Mediterranean cruise itinerary.

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A typical Mediterranean cruise is packed with iconic destinations, which is exactly why so many cruise lines build itineraries around the same handful of ports.

According to MedCruise, more than 35 million cruise passengers passed through the region in 2024. That’s more than ever before, and an increase of almost 10% on 2023.

Some of the most famous ports in the region offer truly unforgettable experiences. Others, while historically significant or logistically important, can feel overcrowded or underwhelming.

If you’re planning a Mediterranean cruise or choosing between itineraries, it helps to know which ports truly deliver and which are best swapped for something more rewarding. First of all, here are the top five cruise ports in the region.

Barcelona, Spain

Barcelona continues to be Europe’s top cruise port for good reason. The city offers a rare combination of world-class architecture, walkable neighborhoods, vibrant culture and access to golden beaches.

Whether it’s your first or fifth visit, the surreal designs of Gaudi, several bustling food markets and the buzzing tapas bars never lose their appeal. Landmarks like the Sagrada Familia and Gaudi’s Park Guell remain must-sees, while the Gothic Quarter rewards those who wander beyond the main sights of La Rambla.

But timing matters. With more than 3.5 million cruise passengers visiting each year, summer crowds can feel overwhelming in the city’s most popular areas.

If possible, look for spring or fall sailings when the weather is mild and the streets, and cruise ports, are less congested. If arriving in peak season, join an organized excursion, make a plan to visit major attractions early in the day or venture into quieter neighborhoods like Gracia or Poble-sec for a more authentic, relaxed experience.

Verdict: Go. Barcelona is almost unavoidable on a Mediterranean cruise itinerary, and for good reason. Whether you’re embarking here or stopping in for the day, it’s a vibrant, iconic city that earns its place as the region’s most popular cruise port. Just be smart about when and how you explore it.

Civitavecchia (Rome), Italy

Civitavecchia is the cruise port for Rome, but few passengers linger here. The appeal of the Colosseum, the Vatican and the Trevi Fountain is undeniable but are more than an hour away from the industrial port by coach or train.

For first-time visitors eager to see Rome’s ancient wonders, the long transfer is often worth it. But between the early departures, tight schedule and Rome’s tourist crowds, a day trip from the port can feel exhausting.

The Colosseum is one of major tourist attractions in Rome, but getting there from the Port of Civitavecchia requires some planning and patience.

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Travelers who have already “done Rome” may want to consider staying local or booking a less intense excursion. The Lazio coast has its own charms, from medieval Tarquinia to the laid-back beaches of Santa Marinella.

Verdict: It depends. Rome is bucket-list territory, but a day trip via Civitavecchia demands stamina and smart planning. If you’ve never been to Rome, only pick an itinerary featuring Civitavecchia if it’s a long port call. Otherwise, consider other itineraries for your trip.

Marseille, France

Marseille is one of France’s most misunderstood cities. As a port, it ranks among the busiest in the Mediterranean, serving more than 2.5 million cruise passengers a year. It’s the gateway to Provence, with shore excursions heading inland to lavender fields and hilltop villages.

But Marseille itself is worth a closer look. The Old Port is lively, the North African-influenced food scene is excellent, and neighborhoods like Le Panier are filled with character. That said, the cruise terminal is located far from the center, and public transport isn’t especially intuitive for newcomers. Shuttle buses can be crowded.

Some travelers report a gritty, unwelcoming first impression, especially when venturing out on their own. But those who dig a little deeper often leave with a new appreciation for France’s second city.

Verdict: Go, with context. Marseille rewards curious travelers who are open to a different kind of French experience. If in doubt, consider a guided tour into the countryside or take a taxi to the Old Port with an open mind.

Palma de Mallorca, Balearic Islands (Spain)

Palma is the capital of Mallorca, the largest of Spain’s Balearic Islands. It’s a popular cruise stop for Western Mediterranean itineraries, with more than 2.5 million passengers passing through in 2023 alone.

The gothic cathedral and palm-lined promenade make an immediate impression, and there’s no shortage of shopping, tapas, or sea views.

But on busy summer cruise days, the charm can fade. The streets near the port fill up quickly, and the historical center becomes a bottleneck for tours. While Palma is still enjoyable, some visitors leave feeling they’ve seen a city curated for mass tourism rather than one that lives at its own pace.

Mallorca is also a hotspot for mass tourism protests against the cruise industry, so guests should be wary.

Verdict: Avoid. Palma absolutely has its moments, but on a crowded cruise day, it can feel more performative than authentic. Unless you’re venturing into the island’s quieter interior, there are many other ports offering a genuine Mediterranean experience without the crowds and potential protests.

Genoa–Savona, Italy

These twin ports in northern Italy serve as embarkation points for many Western Med cruises, particularly those run by Italian lines. Genoa is a historic city with grand palaces, narrow alleys, and an impressive maritime past. Savona is smaller and less known but has its own coastal charm.

Despite their heritage, neither port is especially beloved among cruise passengers. The terminals can feel crowded and chaotic on embarkation day, and some areas around the ports lack visual appeal.

Many passengers see these cities only as logistical starting points and skip the chance to explore them properly.

Still, Genoa has much to offer if you give it time. Art, architecture and one of Europe’s largest aquariums are among the highlights. Alternatively, both ports offer access to the Italian Riviera, including Portofino and Cinque Terre, via train or excursion.

Verdict: Skip unless you’re curious. Genoa and Savona function best as embarkation points rather than sightseeing stops. While they offer access to the Italian Riviera, they’re rarely highlights in themselves. If your itinerary begins, no problem. But if it’s a port call on your itinerary, it might be best to consider alternative itineraries.

Other Mediterranean Cruise Port Highlights

Beyond the most popular ports, a Mediterranean cruise could include a wide variety of destinations. Here are several worth seeking out on itineraries.

Valetta, Malta, makes for a striking arrival or sailaway on a Mediterranean cruise itinerary.

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Valetta, Malta: Few ports in the world rival the visual impact of sailing into Valletta. Malta’s capital is compact, albeit hilly, and steeped in history, with golden sandstone streets and panoramic views. It’s a frequent favorite among seasoned cruisers.

Naples, Italy: Naples is gritty, intense and entirely unforgettable. It offers access to Pompeii, Capri, and the Amalfi Coast, but also rewards those who explore its historic center. Pizza, churches and local flavor abound, all within easy reach of the port.

Kotor, Montenegro: Tucked into a fjord-like bay, Kotor offers one of the most dramatic arrivals in the region. The medieval old town is atmospheric and easy to explore on foot and the hike up to the fortress offers spectacular views with minimal crowds compared to more famous ports.

Santorini, Greece: Despite its popularity, Santorini remains a highlight for many cruisers. The island’s whitewashed villages, blue-domed churches and caldera views are undeniably photogenic. Just be prepared for tendering, steep climbs and crowds.