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What to Pack: Italy (Shoulder Season)

What to Pack: Italy (Shoulder Season)

Packing light for Italy in the shoulder season (spring or fall) is a great choice, as the weather is usually mild with occasional rain. Here’s a practical list for a carry-on-only trip, focused on versatile clothing that can be layered to adjust to varying temperatures.

Clothing

  1. Tops:

    • 3–4 versatile tops in breathable fabrics (a mix of short- and long-sleeved)

    • 1 lightweight sweater or cardigan for layering

    • 1–2 nicer tops for dinners out

  2. Bottoms:

    • 2 pairs of pants (one lighter and one darker pair)

    • 1 pair of comfortable jeans or stylish pants

    • 1 skirt or casual dress (optional but nice for going out)

  3. Outerwear:

    • 1 lightweight, water-resistant jacket

    • 1 scarf (adds warmth and style, especially for cooler evenings)

    • Compact umbrella (optional but helpful for rainy days)

  4. Shoes:

    • 1 pair of comfortable walking shoes (water-resistant if possible)

    • 1 pair of dressier flats or loafers for evenings

    • Optional: 1 pair of sandals if you’re expecting warmer weather

  5. Sleepwear and Undergarments:

    • Pajamas or sleepwear

    • Enough undergarments for the trip (or plan to hand-wash)

    • 3–4 pairs of socks

Accessories and Essentials

  • Crossbody bag or small backpack (safe and hands-free option for sightseeing)

  • Sunglasses and a sun hat (for warmer days)

  • Compact toiletries (under 3.4 ounces/100 mL each for TSA, or buy essentials in Italy to save space)

  • Minimal makeup and personal care items (consider multi-use products like tinted moisturizer with SPF)

  • Travel-size laundry detergent (hand-washing essentials as needed)

Electronics

  • Phone and charger

  • Plug adapter (Italy uses the type C, F, and L plugs; ensure compatibility)

  • Portable power bank (helpful for long sightseeing days)

Documents and Extras

  • Passport and travel documents

  • Printed or digital copies of important reservations

  • Travel journal or guidebook

Tips for Shoulder Season

  • Layering is key: Italian weather can be warm during the day but cooler in the mornings and evenings.

  • Pack versatile clothing that can mix and match to create multiple outfits.

  • Pack light: Italians tend to dress stylishly yet simply, so you can blend in without bringing too much.

  • Cover Up: If your plans involve visiting churches or religious sites, plan to have both your knees and shoulders covered out of respect.

This list will keep you prepared and comfortable while enjoying Italy’s beauty without the hassle of heavy luggage.

Photo Blog: Girls Trip Spain + Portugal

Photo Blog: Girls Trip Spain + Portugal

As a traveler, I often get sucked into the dark vortex of obsessing about pictures. Sometimes I spend more time looking at my phone than at my surroundings. Hours of editing, applying filters and timing when to post eat away at time I could be eating, drinking, and experiencing a place.

As convenient as it is to have a tiny camera in your pocket at all times, there’s something nostalgic about simpler times when we could travel and just soak in the moments, candidly laugh with our friends without worrying if we are capturing it correctly, and instantly flocking to social media to share.

Don’t get me wrong. I do all those things.. and often. But I find it tedious and wasteful and it definitely takes away from the joy of travel (for me anyway).

Thankfully, this trip was a game changer, thanks to our resident travel photographer and friend, Brooke. She dreamed up the idea of having a photographer capture the moments, allowing the rest of us to simply be present—no strings attached.

While I’m sure this trip would’ve been magical no matter what, thanks to Brooke, we were able to really immerse ourselves in the experience. Many of the girls in these photos will tell you they didn’t even know the camera was rolling, giving us a rare glimpse into the candid side of our Girls Trip—the laughs, the scenery, the newly formed friendships, and all the beautiful memories we made together.


Seville, Spain


We started our adventure in Seville, Spain. Our hotel straddled the banks of the Guadalquivir River and we went on a locally guided walking tour of the old town. Our guide Alba showed us the many juxtapositions of Seville—the Moorish architecture, the Jewish history, and the Catholic influence that remains today. We learned about many impressive women that played a role in making this city what it is today. We enjoyed a live flamenco show and ended most evenings on a picturesque rooftop somewhere—dancing, sipping sangria, and planting seeds in the soil of new friendships.


The Algarve, Portugal


From Spain, we made our way west to Portugal, to the Algarve coast. Along the way, we stopped at Cabrita Winery, a locally-owned and operated Vineyard. At Cabrita, it’s not about speed or mass production, it’s a slow, savory experience from start to finish, and one that can’t be rushed. Here, there are no shortcuts. Only the freshest locally-sourced products will suffice. Similar to the relaxed pace one experiences elsewhere in the Algarve, the grapes are in no hurry to mature. They take their time in the rich, arid soil, soaking in the Portuguese sun until they reach perfection. Much like the evolution of the vineyard itself, the wine is cared for delicately and intentionally—recipes and techniques that have been handed down for generations. Our host, Duarte took us on a tour of the vineyard, followed by a master class in the maturation and fermentation process. Finally, we enjoyed locally sourced charcuterie and a sampling of their four most famous wines. Needless to say, many of us came home with cases to enjoy later.

Our hotel was in Carvoeiro along the coast and it had the most beautiful uninterrupted cliffside that guests could hike. One direction took you into town where you could souvenir shop and eat at the most amazing restaurants, and the other direction took you to the beach. Many of us opted to stay at the hotel and enjoy the facilities because they were so relaxing. As you can see, we had the most amazing views you could ask for.

One of the funniest memories from this trip came on Wednesday. We had a boat tour planned to see the coastline and Portugal’s renown cliffside caves. When our driver dropped us off we had a little trouble finding the specific dock we were supposed to depart from as it wasn’t clearly marked and there were so many docks. The captain called and said if you aren’t here in one minute we are leaving without you. We took off in a mad sprint to the dock that wasn’t very funny at the time, but we all shared a good laugh at after-the-fact.

The tour itself was beautiful. There were so many amazing cliffs, each with unique features. The boat ride itself was really entertaining. We passed a nude beach, one of our travelers got pretend engaged, a few of us got a little seasick, while others took a dip in the beautiful water.

The town of Benagil was one of a kind. It’s vibrant buildings were so colorful and interesting even if they wreaked of the 1990s and Saved By The Bell reruns.


Lisbon, Portugal


From the coast, we headed north to the capital of Lisbon. I’ll be honest, I expected this to be my least favorite of all our stops, but I couldn’t have been more wrong. Lisbon has so much charm and character and it absolutely stole our hearts. We met our guide, Angela, and promptly tasted Portugal’s most prized treasure, the pastel de nata pastries. These suckers are addictive. From there we took a walking tour through Lisbon’s winding streets and neighborhoods. We definitely put some miles on our feet this day, but we were rewarded with amazing views and delicious Ginjinha, a cherry liquor that is best enjoyed from an edible chocolate shot glass.

We spent the following day exploring the fairy tale town of Sintra. We took TukTuk rides up to the top of the mountain. Our first stop was Pena Palace, where our guide Angela gave us a first hand look at what life was like for the royals. Our visit coincided with the anniversary of their execution, making it a somewhat somber day to visit and walk in their footsteps. We spent the remainder of the day exploring the town of Sintra, shopping, eating, and of course enjoying more Ginjinha!

On our final day in Lisbon we took a walking tour of Belem where we saw preparations underway for a royal wedding. We walked along the water and marveled at some of the beautiful street art in the area. In the evening we went on a food tour where we sampled many local favorites like ham sandwiches and sardines! We ended the evening by honoring three very special travelers, Tammy, Yasmine, and Angela, who combined have traveled to 19 countries with Land + See Tours.


All in all it was a fantastic trip, and one that none of us will ever forget. It’s true what they say—girls really do run the world :)

Top 5 Ways You Benefit From Group Travel

Top 5 Ways You Benefit From Group Travel

Group travel often gets a bad wrap. There are so many misunderstandings surrounding it.

I often hear reservations like, “I value my freedom too much to travel with a group,” or “I would, but it costs too much!” I was a huge skeptic myself before I dipped my toe in the group travel world, but let me tell you, it was a GAME CHANGER.. And in all the best ways. I found myself questioning how it had taken me so long to discover the wonderful world of group travel. 

I’m here bust a few myths surrounding group travel and let you know some of the top ways it will actually enhance and benefit your travels to travel as a group.


Reason #1: Shared Experience

Group travel provides an opportunity for people to connect and bond with one another. Shared experiences create memories that are unique to the group, fostering a sense of camaraderie and friendship among the travelers, many of whom start out as strangers.

I’ll never forget returning from my very first trip abroad and beaming through my jetlag to recount every single magical moment I had experienced on my adventures in Eastern Europe. By the second -or third shepherd reference, my well-meaning, but totally-disconnected-from-my-experience mother’s eyes sort of glazed over into a polite, but impersonal gesture of thats-nice-but-I-couldn’t-really-care-less. Nothing is quite as defeating as coming home from a life-altering experience, willing and eager to share the magic that you learned, only to find a not-so-enthusiastic audience. They weren’t there with you and they simply don’t get it. It can feel very isolating.

With group travel, you have the bond of sharing your life-altering experiences with several people. You can reminisce and connect over your memories together for years to come. 


Reason #2: Enhanced Safety

Traveling in a group can increase your safety in several ways. A group of people is less vulnerable to potential threats compared to an individual. Criminals are less likely to target a larger group, as they tend to look for easier targets. Additionally, when you're part of a group, you have people you can rely on in case of emergencies or unexpected situations.

I know with Land + See, one of the unspoken perks of our groups is we often have many medical professionals that tour with us. I’ll never forget seeing a man collapse on a ferry to Santorini and watching Dr. Tony spring into action! We have been so lucky than none of the medical mishaps have happened to our travelers, but there have been more than one occasion where our heroes have saved the day. It definitely gives me peace of mind knowing we are in such good hands.

Whether it's a medical issue, getting lost, or running into difficulties, having others with you means there are people to help and support you.

And lastly, traveling with others can provide emotional support and reduce feelings of vulnerability, especially in unfamiliar or challenging environments.

I’ll never forget a particularly tearful, but supportive afternoon in Austria where a female traveler and I completely bonded over our past. I haven’t seen her for years, but I am confident if I picked up the phone tomorrow she would be by my side in an instant, and vice versa.


Reason #3: Cost Savings

Group travel allows you to have a custom-tailored travel experience at a fraction of the cost of solo travel. When you travel with others, you can split the costs of various expenses, such as accommodation, transportation, and food. Sharing these costs can significantly reduce your individual financial burden without compromising on quality.

I’ll never forget my first group travel experience as an adult. Jordan and I had traveled to Paris with his family just the year before so I naively assumed I’d already “seen what there was to see” on the re-visit a year later. How wrong I was. Because we were with a group we had the means to have a private driver on call for us and hire private local guides to show us the city through their eyes. Our Parisian guide, Mario, made the city come alive for me—as if I was seeing it for the very first time. The history, the art and the culture started to feel like it was a part of my own narrative. I simply hadn’t experienced anything like that when I was visiting on my own. While I was a tourist, my experience wasn’t just that of a tourist—I had someone showing me their personal favorite places off-the-beaten-path, translating what certain looks or gestures meant to true Parisians, sharing anecdotes and stories of his family and personal meaningful details of the places we would go—sometimes exposing unflattering or comical aspects and leaving me with a plethora of inside jokes and fond memories. This magic didn’t just “happen,” we were able to afford a much richer experience because we were splitting the cost with so many other participants. Hiring Mario would’ve been intangible on a single traveler’s budget.

Group bookings often come with bulk discounts for things like flights, hotels, guides and tours, and the reasons make sense. Travel providers are more likely to offer better deals when they know they have a large group of customers. Additionally, by sharing a hotel room or vacation rental with others in the group, you can split the cost of the room, leading to substantial savings compared to booking a single room for yourself, helping you keep costs low or allowing you the wiggle room to indulge in something a little fancier than you might be able to afford on your own.

Whether you’re hiring a guide or renting a vehicle or bus, splitting the costs among group members can make these services more affordable for everyone and they definitely make a tangible difference in the quality of your travel experience.


Reason #4: Diverse Perspectives

Traveling with people who have diverse perspectives can be immensely beneficial in several ways. For instance, interacting with people from different cultural backgrounds allows you to gain a deeper understanding of their customs, traditions, and ways of life. This exposure can help break down stereotypes and promote empathy and respect for cultural diversity. You may encounter a variety of perspectives, not only with the locals you interact with, but within the dynamics of the group itself. Traveling with individuals who see the world differently than you do can open your mind to new ideas and ways of thinking.

I’ll never forget this amazing dinner we had in the home of Albert and Bergthor in Reykjavik, Iceland. Albert is a world-reknown opera singer, and Bergthor is a chef. Together we spent an incredible evening learning about Iceland, equality, naked grandpas and how to do the coolest new dance moves. I hesitate to admit this, but had we known ahead of time that Albert and Bergthor were a same-sex couple, it’s possible we would’ve had some preconceived ideas about what we would experience, but by allowing that wall to come down and meet them on a human level first, it challenged our bias and taught us valuable lessons in humanity.

Diverse perspectives challenge your assumptions and encourage you to question your beliefs, leading to personal growth and intellectual enrichment. By experiencing diverse perspectives firsthand, you are more likely to develop a sense of tolerance and acceptance for people who are different from you. This fosters a more inclusive and harmonious society and quite simply makes the world a better place.


Reason #5: Stress Reduction

Traveling with a group and having a full-time group leader can indeed reduce stress in several ways. The most obvious way, is with the addition of a group leader.

With a group leader in charge, you don't have to worry about planning the itinerary, booking accommodations, arranging transportation, or managing logistics. The group leader takes care of these tasks, ensuring a smoother travel experience for everyone. A group leader can be experienced in handling various travel situations, including emergencies. Their knowledge of the destination and local customs can enhance safety and security for all group members, reducing individual stress related to unfamiliar environments. And lastly, in regions where language or cultural differences may be a challenge, having a group leader who is familiar with the local language or customs can facilitate communication and create a more enriching travel experience.

When you travel, things happen—it’s just the nature of travel. Don’t let the stress of the unknown fall on you to figure out. Join a group that has a knowledgeable and competent group leader that knows what their doing and has a proven track record.

No one wants to spend their vacation time putting out fires. When you envisioned this trip, you saw yourself lounging by the sea, eating gelato, and exploring to your hearts content. Group tours allow you the freedom and flexibility to enjoy your vacation, so you don’t come home needing a vacation from the vacation.


Obviously this isn’t an exhaustive list of all the benefits to group travel, but it at least gives you a small taste of the some of the top ways that group travel can enhance and even improve your travel experience.

I know there are a lot of misconceptions circling about the realities of group travel, but chances are, if you ask someone who’s tried it, you will learn that the benefits far outweigh the risks.

Take it from me, the biggest former skeptic of them all–take a sip of the group travel Kool-Aid. Not only does it stand a great chance of whetting your travel appetite, you may just find that fully immersing yourself in the culture without the stress and worry of coordinating it all, is your new “thing.”

Happy travels, friends!