From cruise excursions in Europe and Morocco to rainforest adventures, private boat experiences, and exploring destinations entirely on our own, here's how our family approaches travel beyond traditional sightseeing.
Not every memorable travel experience involves a museum, historic landmark, or private walking tour. Some of our favorite memories have come from exploring rainforests, cruising along beautiful coastlines, discovering new cultures during cruise stops, and simply having the freedom to explore a destination at our own pace.
Over the years, we've experienced several different styles of travel. We've taken organized cruise excursions, booked outdoor adventures with local operators, experienced traditional escorted tours, and planned entire family vacations ourselves. Each approach has its advantages and each has helped shape how we travel today.
In Part 1 of this series, I shared the private guides and tour companies we've used for museums, history, and cultural sightseeing around the world.
This second article focuses on a different side of our travels: cruises, outdoor adventures, special experiences, and the flexibility of exploring independently because sometimes the best travel experience is the one where you don't have a schedule at all.
Celebrity Cruises: Exploring New Destinations During Port Stops
Destinations we've experienced: Porto, Portugal; Tangier, Morocco; and Cádiz, Spain.
Cruising offers a unique way to visit several destinations within a relatively short period. You unpack once, travel between ports, and have the opportunity to experience different cities and cultures along the way, but cruise travel also presents a challenge. Your time in each destination is limited, and you need to make sure you're back at the ship before departure. That's where organized shore excursions can be particularly useful.
During our Celebrity Cruises travels, we booked several sightseeing excursions directly through the cruise line.
Porto, Portugal - Panoramic Porto
Porto is a beautiful city known for its historic architecture, hillside neighborhoods, and setting along the Douro River. Our panoramic sightseeing excursion provided an introduction to the city during our port visit. With limited time available, an organized tour was a practical way to experience some of Porto's major highlights without having to manage transportation independently.
Tangier, Morocco: A Taste of Tangier and Panoramic Tangier
Tangier was one of the most culturally distinctive destinations on our cruise itinerary. Located along the Strait of Gibraltar, the city has a fascinating history shaped by its position between Africa and Europe. We booked sightseeing experiences that included A Taste of Tangier and Panoramic Tangier.
These excursions introduced us to the city's architecture, culture, and history within the time available during our cruise stop. For a destination where we were less familiar with the local logistics, having an organized excursion made sense.
Cadiz, Spain: Panoramic Cadiz
Cadiz is one of Europe's oldest continuously inhabited cities, with a fascinating maritime history and a beautiful coastal setting. Our panoramic excursion offered an introduction to the city and its historic landmarks. As with Porto and Tangier, the organized format helped us make use of our limited time in port.
Our Take on Celebrity Cruises Excursions
Cruise line excursions aren't always the most personalized way to explore a destination. They typically follow fixed itineraries and may involve larger groups than a private tour, but they can offer valuable convenience. Transportation is arranged, the itinerary is designed around the ship's port schedule, and cruise-sponsored excursions generally have additional coordination with the ship if delays occur. That doesn't mean every cruise excursion is automatically the best option. For some ports, exploring independently or booking a private local guide may be a better fit. We decide based on the destination, transportation logistics, and how much time we have available.
Best for: Cruise passengers, limited port visits, and destinations where organized transportation and timing provide peace of mind.
Castillo Tours: Rainforest Adventures and Old San Juan
Destination we've experienced: Puerto Rico.
Puerto Rico offered a wonderful combination of natural beauty, history, and culture. We booked two experiences with Castillo Tours, each highlighting a different side of the island. These tours were booked through our hotel, the former St Regis Bahia Beach Resort, which is now a Four Seasons branded hotel.
Half-Day Rainforest Tour
Puerto Rico's tropical rainforest provides a completely different experience from the historic cities and museums we often explore. Our half-day rainforest excursion gave us an opportunity to experience the island's lush natural environment and learn more about its ecosystems. Outdoor experiences like this are an important part of how we travel.
While we enjoy museums and cultural landmarks, we also want our kids to experience the natural beauty of the destinations we visit.
Old San Juan Walking Tour
Old San Juan is one of the most beautiful historic districts in the Caribbean. Its colorful colonial buildings, cobblestone streets, historic fortifications, and waterfront setting make it a fascinating place to explore. We booked a walking tour to learn more about the city's history and the Spanish colonial influence that shaped it. This was a great example of combining two very different experiences within one destination. One focused on nature and the other focused on history and culture.
Our Take on Castillo Tours
Castillo Tours gave us a way to experience different sides of Puerto Rico through organized excursions.
It's the type of combination I particularly enjoy when planning a trip: balancing cultural sightseeing with outdoor adventures.
Best for: Puerto Rico sightseeing, rainforest experiences, and Old San Juan walking tours.
Papillon Yachts — A Private Boat Experience in Los Cabos
Destination we've experienced: Los Cabos, Mexico.
Not every memorable family experience needs to involve a full-day sightseeing itinerary. Sometimes the experience itself is the highlight.
During our stay at Solaz, a Luxury Collection Resort in Los Cabos, we arranged a private boat experience with Papillon Yachts through the hotel.
Los Cabos is known for its dramatic coastline, where the desert meets the Sea of Cortez and Pacific Ocean. Exploring the area from the water offered a different perspective from spending time at the resort or visiting the surrounding towns. For our family, having a private arrangement made the experience more personal. We could enjoy the scenery, spend time together, and experience the coastline without being part of a larger sightseeing group. This also reinforced something I've learned about staying at good hotels. A knowledgeable concierge can be an excellent resource for arranging local experiences. Not everything needs to be booked through a large online tour marketplace.
Our Take on Papillon Yachts
Private boat experiences can be a wonderful addition to a coastal vacation, particularly when traveling with family or a small group. They aren't something we book on every trip, but they're worth considering when the setting makes the experience special.
Best for: Private coastal excursions, family celebrations, and personalized experiences in Los Cabos.
GetYourGuide: An Evening Along the Seine in Paris
Destination we've experienced: Paris, France.
Paris is one of those cities that takes on a completely different atmosphere after sunset. The illuminated bridges, historic buildings along the Seine, and Eiffel Tower lighting up the skyline make evening sightseeing particularly memorable. During our family visit, we booked the Seine River Evening Cruise and Eiffel Tower Tour through GetYourGuide.
This experience complemented the private family walking tours and museum visits we had already planned in Paris. Rather than spending another day walking between landmarks, we wanted an opportunity to see the city from a different perspective. A Seine River cruise is particularly appealing because so many of Paris's famous landmarks are located along the waterfront. Combining the cruise with an Eiffel Tower experience made for a different kind of sightseeing outing.
Booking Through GetYourGuide
One thing worth understanding is that GetYourGuide is a booking marketplace. Like Viator, it offers experiences operated by a variety of local companies. That means the quality and format of the experience can depend on the actual operator. Before booking, I recommend reviewing the itinerary, meeting location, inclusions, cancellation terms, and recent reviews.
Our Take on GetYourGuide
GetYourGuide can be useful when you're looking for a specific activity to complement a larger itinerary. Our Paris booking is a good example of how we mix private guided tours with individual experiences rather than relying on one tour company for an entire trip.
Best for: River cruises, landmark experiences, evening sightseeing, and individual activities that complement independently planned trips.
Trafalgar: Exploring Croatia + Bosnia and Herzegovina
Destinations experienced: Zagreb, Split, Dubrovnik, Mostar, and Sarajevo.
Before we started designing most of our family itineraries independently, I also had opportunities to experience traditional escorted touring. One of those experiences was traveling through Croatia and Bosnia and Herzegovina with Trafalgar. This region is one of the most fascinating parts of Europe. It combines beautiful Adriatic coastlines, historic cities, medieval architecture, and a complex history that continues to shape the region today.
Exploring Croatia
Our travels included Zagreb, Split, and Dubrovnik. Each city offered something different.
Zagreb provided an introduction to Croatia's capital and its Central European influences.
Split combined historic architecture with its beautiful coastal setting.
Dubrovnik, with its famous Old Town and impressive city walls, was one of the most memorable destinations along the Adriatic.
Bosnia and Herzegovina
Our travels also included Mostar and Sarajevo. These are destinations where understanding the historical and cultural context is particularly important.
Mostar is known for its iconic Stari Most bridge and Ottoman-influenced old town.
Sarajevo has an extraordinary history shaped by different cultures, religions, and significant events.
Traveling through this region reinforced how valuable knowledgeable guides can be when visiting places with complicated histories.
What Escorted Touring Offers
One of the biggest advantages of an escorted tour is that many of the logistical details are handled for you. Transportation, accommodations, sightseeing, and the overall route are organized in advance. That can be especially appealing when traveling between several destinations in a relatively short amount of time, but escorted tours also come with trade-offs.
You're generally following a set schedule, traveling with a group, and spending a predetermined amount of time in each destination. For some travelers, that's ideal and for others, particularly families who prefer more flexibility, it may feel restrictive.
Our Take on Trafalgar
My experience with Trafalgar helped me appreciate the convenience and structure of escorted touring. It also reinforced the value of knowledgeable guides when exploring destinations with significant historical and cultural depth.
Best for: Multi-country itineraries, travelers who prefer organized logistics, and those who enjoy structured group travel.
Travel Impressions: Exploring Costa Rica's Natural Beauty
Destination experienced: Costa Rica.
Costa Rica is one of those destinations where the natural environment is the main attraction. From tropical rainforests and volcanoes to wildlife, waterfalls, and adventure activities, it's a country that offers an incredible range of outdoor experiences. I experienced organized travel in Costa Rica through Travel Impressions and the local companies they used. Our travels included the Arenal Volcano region, rainforest landscapes, hot springs, and wildlife-focused experiences.
Arenal Volcano and the Rainforest
The Arenal region is one of Costa Rica's most recognizable destinations. Its volcanic landscape, lush vegetation, and outdoor activities make it a wonderful place for travelers who enjoy nature and adventure. Experiencing the region reinforced how different travel can feel when the focus shifts from historic cities to the natural environment.
Wildlife and Outdoor Adventures
Other experiences included wildlife excursions around Palo Verde, Llanos del Cortes waterfall, and adventure activities. Costa Rica is a great example of a destination where having local knowledge can be particularly valuable. Experienced guides can help identify wildlife, explain the environment, and organize activities that might be more complicated to arrange independently.
Our Take on Travel Impressions
My Costa Rica experience helped shape how I think about incorporating outdoor adventures into our travels. It also reinforced that memorable experiences don't always need to involve famous landmarks. Sometimes the highlight is a rainforest, a waterfall, or seeing wildlife in its natural habitat.
Best for: Organized nature-focused travel, outdoor adventures, and travelers looking to explore Costa Rica's natural attractions.
The Family Travel Guy: Sometimes We're Our Own Tour Guides
Destinations we've explored independently: Hawaii, California, and many other places around the world.
After years of traveling with different tour operators, one of the biggest changes in how we travel is that I've increasingly taken on the role of planning our own adventures and honestly, I enjoy it. Researching destinations, finding interesting places to visit, choosing hotels, organizing transportation, and building itineraries are all part of the experience for me.
As a photographer, I also appreciate the freedom to explore at our own pace. Sometimes that means stopping at a scenic viewpoint. Other times it means spending longer in a neighborhood, finding a local restaurant, or changing plans because we discover something interesting along the way.
Hawaii: Exploring the Islands Our Way
We've spent time exploring Oahu, Maui, Kauai, Lanai, and Hawaii Island. Our trips have included scenic drives, beaches, hikes, cultural experiences, historic landmarks, and plenty of time enjoying the islands. Some experiences, such as organized adventure activities or cultural programs, are worth booking through local operators, but much of Hawaii is also perfectly suited to independent exploration. With a rental car and a thoughtfully planned itinerary, we can explore at our own pace and stop whenever something catches our attention. That flexibility is one of the things I enjoy most about traveling through the islands.
California: Adventures Close to Home
Living in Northern California gives us access to an extraordinary variety of destinations. We've explored Lake Tahoe, San Francisco, Monterey, Mendocino, Carmel, Los Angeles, San Diego, and many other places throughout the state. Some of our favorite experiences have been simple day trips or weekend getaways: Hiking along the Lake Tahoe shoreline, exploring Point Lobos and the Monterey coastline, visiting museums and attractions in San Francisco and spending time along Southern California's beaches. These are experiences we can organize ourselves without needing a tour guide.
Japan: Finding the Right Balance
Our March 2026 Japan trip is probably one of the best examples of how we travel today.
We combined private guided sightseeing in Osaka, Kyoto, and Tokyo with independent exploration, train travel, cultural activities, and a visit to Tokyo Disney Resort. The private tours helped us understand the destinations and navigate some of the more complicated sightseeing days, but we also left time to explore neighborhoods, enjoy local food, and experience Japan without a guide. We didn't need someone organizing every hour of the trip. We simply used local expertise where it added value.
Copenhagen and Dublin (Another Example)
Our summer 2026 trip to Copenhagen and Dublin followed a similar approach. We booked private walking tours to introduce us to each city, then planned other activities independently.
In Copenhagen, that included Tivoli Gardens, a canal cruise, and time exploring the city.
In Dublin, we combined sightseeing with experiences such as the Guinness Storehouse, Jameson Bow St., and a visit to the coastal village of Howth.
It was a good balance of guided experiences and time on our own.
Why We Prefer This Approach
The biggest advantage is flexibility. We can choose the hotels we want, visit the places that interest us, and organize each day around our family's preferences. We don't have to follow a group schedule or visit attractions simply because they're included in a tour package. We can also decide when paying for convenience is worthwhile and sometimes that means booking a private guide and sometimes it's arranging a private transfer, but it is also doing everything ourselves.
Best for: Families who enjoy planning, scenic road trips, independent sightseeing, and customized travel experiences.
How We Decide Between Organized Tours and Independent Travel
There's no single approach that works for every destination. Here's how I generally think about the different options.
For us, the decision usually comes down to three things:
Will this experience be better with a guide?
Will booking an organized tour save us meaningful time or logistical headaches?
Does the added cost provide enough value to justify it?
If the answer is yes, we'll consider booking the tour. If not, we're perfectly happy exploring independently.
The Luxury Is in How We Travel
Over the years, our travel style has evolved into something that combines the freedom of independent travel with the convenience of carefully selected guided experiences.
We generally prefer centrally located hotels, private transportation when it makes sense, knowledgeable local guides for selected activities, and enough flexibility to enjoy a destination without constantly watching the clock. We don't need every experience to be luxurious. We don't need every restaurant to be fine dining. And we certainly don't need to visit every attraction simply because it appears on a list of must-see sights.
For us, the luxury is in how we travel. It's having the freedom to build an itinerary around our family's interests. It's hiring a private guide when it makes a meaningful difference. It's choosing a convenient hotel that allows us to walk out the door and start exploring. And sometimes it's deciding that an afternoon at the pool or wandering through a neighborhood is more valuable than squeezing in one more attraction. We enjoy the process of creating our own trips and we've learned that paying for convenience selectively can make a family vacation much more enjoyable without needing to turn every experience into an expensive one.
Final Thoughts: Finding the Right Balance
Looking back at our travels, some of our favorite memories have come from organized tours and excursions: Exploring new destinations during a cruise, discovering the rainforests of Puerto Rico and Costa Rica, experiencing the coast of Los Cabos from a private boat, traveling through Croatia and Bosnia and Herzegovina, seeing Paris from the Seine in the evening, but just as many memorable experiences have come from the adventures we've planned ourselves like exploring Hawaii, driving along California's coastline, discovering neighborhoods in Japan or simply spending an afternoon somewhere without a detailed schedule.
Every experience has helped shape how we travel today. Perhaps the biggest lesson is that the best family travel doesn't come from following someone else's perfect itinerary. It often comes from creating your own., choosing the places that interest you, finding experiences that connect with your kids and knowing when a guide will add value; and when it's better to simply explore.
We still use tour operators, and I expect we always will, but today, they're one part of a much larger travel experience that we design around our family. At the end of the day, it's not about how many tours you book, how many landmarks you visit, or how much you spend. It's about the experiences you share, the places you discover, and the memories you make together.
And we're always planning the next adventure.
Read Part 1: Private Guides, Museums & City Tours
For more of our firsthand experiences with companies such as Family Twist, ToursByLocals, Context Travel, and local guides throughout Europe and Japan, read Part 1: Private Guides, Museums & City Tours.