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.

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!

5 Things Anthony Bourdain Taught Me About Traveling

1.       Get off the beaten path. Sure, the Eiffel Tour is beautiful, and you’d certainly be remiss if you didn’t acknowledge that the tourist traps are famous for a reason, but don’t make the mistake of hitting only the highlights. The real beauty of a place comes in the unexpected surprises that come with a little risk taking—crawling to the bottom of an Egyptian tomb, an evening of Bohemian Rhapsody under the stars with local Mykonians, playing in a local jazz club in the Parisian underground, rolling cigars with a German-speaking Cuban national, and scurrying through hidden passageways in Dubai to buy knock-off watches and handbags aren’t exactly what you had in mind when you were planning your trip, but these are grout that cement and shape your experience into place. Sure, these moments aren’t instagrammable, and your watch might say Bowflex instead of Rolex, but they aren’t cookie-cutter prefabricated dime a dozen experiences. No, these are the raw revelations that can show both a city’s charm and underbelly in ways that are hard to forget.

2.       People are generally the same. Sure, they may look different, speak different languages, and god-forbid, vote for a different political party than you, but deep down we all want the same things—to live peacefully, to provide for our families, to be proud of where we come from, and to belong to something. The more people you meet, the more undeniable it is that the barriers that separate us are figments of our imagination.

3.       Ask the hard questions. It was over a vegetarian meal in Munich, with a friend of a friend, and coincidentally a Green Party Politician, that we found ourselves tiptoeing around political correctness and thanking our hosts for the amazing meal when her husband blurts out, “Well, I didn’t really want you to come if we are being honest.” What followed was a surprisingly refreshing, albeit straightforward, discussion about misconceptions we all had of each other as Americans and Germans. We left with an incredibly different understanding of one another than we would’ve had without such an incredibly German conversation starter.

4.       Home is where the heart is, and no, not your own home. Anthony Bourdain taught us the importance of sharing a meal in someone’s home. When you’re home, your guard is down—conversation flows more naturally in a safe space. If you stick to restaurants, you miss spontaneous living room concerts, Icelandic local handicrafts, and cute little granddaughters teaching you “the floss.” Go out of your way to find opportunities to organically connect. You never know what you’ll uncover. I wouldn’t have found out about the award winning French film “Three Colors: Blue” if it hadn’t been for the movie poster hanging in Giampaolo’s tiny half-bath—I also wouldn’t have met the winner of Top Chef Sweden if it weren’t for taking a risk on an invitation to dinner with a new acquaintance in Milan. When an opportunity presents itself to meet people where they are their most comfortable—jump on it.

5.       Travel is not a luxury. There was a time that travel felt like a privilege for the elite. Maybe it feels that way for you still. But the truth the way I see it is, travel is a responsibility and a constant opportunity to learn. It’s an eye-opening lesson in empathy to be the foreigner for a change—to be required to cover your tattoos in a mosque or your shoulders in a cathedral, and to discover just how handicapping it feels to have to have the menu read to you like a child because not everyone caters to English speakers, are all humbling experiences—experiences that make you much more tolerant. Collect the beautiful things you see, learn from the struggles, and bring them all back home and put them into practice.  

Tips and Tricks for Italy + Greece

If you’ve always dreamed of heading to Italy + Greece, you’re not alone! Both are magical destinations that leave your eyes wide and your mouth watering. The people, the landscape and the food in both regions are second to none. It’s no wonder people flock in hoards to the beautiful shores of the Aegean!

You know what they say? When in Rome, do as the Romans do. But how do you go about that exactly? If you’re heading to Italy and Greece and are feeling completely overwhelmed with all of the cultural nuances and ways to prepare, we are here to help!

So without further ado.. Here are my tips and tricks for navigating Italy + Greece like a pro!

SET REALISTIC EXPECTATIONS

Cities like Rome and Athens are rich in history and architecture, but some uncomfortable realities that accompany that are smaller rooms, and no central heating and air, to name a few.  Unlike America, A/C is not a standard in Europe. It will unlikely be in many of the shops you frequent, or in the hotels. Adjust your expectations accordingly. Drink plenty of water and wear sunscreen and heat protection to counteract the effects of the heat. Also, wear layers so that you can add and remove clothing as necessary.

DRESS CODE CONSIDERATIONS

Understand that when visiting many religious sites, you will be expected to cover up. A general guideline to follow would be to keep your shoulders and knee caps covered if planning to visit a church in Italy. Due to the heat, it may not be practical to fully cover up during the day, but have a scarf or coverup handy for your visit to religious sites. Some churches will provide a coverup, but many do not, and you will be denied entry if you don’t meet the dress code requirements. Take care to plan your clothing in advance to avoid missing out on seeing certain sites.

PICKPOCKETS

Unlike America, pickpockets run rampant in most of Europe. Again, you are unlikely to find yourself in any physical harm, but understand, your pockets WILL be picked if you aren’t on high alert. High traffic areas like the bus and the metro are a feeding frenzy for “little fingers.” Also keep your eyes peeled at large tourist sites such as the Colosseum, Vatican, and the Parthenon. Where the tourists flock, so do the pick pockets. A good under-your-shirt money belt will definitely help lower your chances of becoming an easy target. Another interesting note: keep your cell-phone close. Leaving it on the edge of a table while eating or next to you on the metro is inviting theft. I once saw a poor sap get his phone snatched off a table in a restaurant while the waiter was explaining the specials. You can never be too careful. If you care about an item, don’t advertise it. Keep any valuables out of sight and secured if you want to hang on to them.

ELECTRICITY

If you plan to charge your phone, dry your hair, or use small appliances on your trip, you’ll need to be aware that Europe has a few major electrical differences with America. For example, the outlet plug shape varies from our standard two prong outlet. Though there are a variety of outlet types acceptable in both Italy and Greece, they both use the F and C type, with two small round prongs. You can find images and details on this outlet type here.  You can pick up a small pack of outlet converters rather inexpensively at Target or Amazon like these here. Another crucial thing to bear in mind is voltage. In America, we use 120 V of power in our outlets. In Italy, the standard is 220V and in Greece it’s even higher at 230V. Small items like cell phone chargers are okay with just a wall adapter that changes the shape of your outlet plug, but if you plan to use bigger items like blow dryers and straighteners, you’re going to want to equip yourself differently.  Purchasing a wattage converter before you leave will allow you to use your home appliances without overpowering them with European voltage and spares them from a sad burned out death. You can pick one up on Amazon like this one here.  

MONEY

We already mentioned that keeping a money belt below your clothing is a good idea, but that is just one aspect of being money conscious in Italy and Greece. While credit cards are widely accepted in Europe, Greece is more of a cash-based country so plan accordingly by hitting up an ATM or converting Euros before your trip. Italy, on the other hand, is very credit card friendly, but if you are using your normal credit card from home, be aware that there can be fees for every swipe if you aren’t careful that can add up quick. Not only does your bank charge a fee, you will face foreign transaction fees per swipe as well. If you’re dead set on using plastic for the majority of your purchases, it would be a good idea to invest in a card that has zero foreign transaction fees. My go to cards for international travel are the Capital One Venture Card, and the Chase Business Ink. Make sure that you also report international travel dates to your bank before you leave to avoid having your card frozen while abroad. I also suggest changing foreign currency at your home bank a few weeks before you depart. Take anywhere from $60-150 with you in local currency. Once you are in Italy and Greece, you can easily access ATMs for any additional cash you might need. Be aware, both your bank and local ATMs will charge you an exchange fee, so you will want to budget what you need and keep your ATM transactions to a minimum to avoid those unnecessary fees. The worst place to convert money is the airport, so plan on exchanging money before you leave, or at an ATM once while in Europe.

TIPPING

If you have a tour guide during any part of your trip, just know that it is customary to tip 1-2 euros after any guided tours. Similarly, you’ll want to tip any bus drivers (particularly ones who handle your luggage) for their services. We usually suggest $3 per driver per day of service. If you have a helpful waiter, they will certainly appreciate a few euros for good service as well. Some restaurant receipts will include a cover charge (coperto). This is a fee for setting your table. You may also see a service charge (servizio) usually around 10% already included on your ticket. Some restaurants will not have a fee at all and choose rather to include these fees in the menu prices. In the case that service has not been included, 1-2 euros per person is perfectly acceptable. Be aware that waiters aren’t reliant on tips as their sole source of income the way American waiters are. However, a tip for good service is always appreciated and for some services, the tourism industry for example, it’s expected.

PHONE USAGE

If you plan to use your phone abroad, make sure you call your phone carrier prior to leaving. The major ones like Sprint, ATT and Verizon have very reasonable international plans, however, you must add them before you leave to avoid paying exorbitant roaming fees. ATT, for example lets you use your phone as normal for $10 per day. If you don’t plan to stay connected, you can connect to Wi-Fi in the hotels. Just be aware the Wi-Fi can be spotty and often slower than at home, but hey, you’re in Europe. Enjoy the scenery and get your nose out of your phone 😊

FERRIES

If you plan to take a ferry at any point during your journey, there are some things you should know before you go. Ferry services are often behind schedule, so understand that you can be waiting for the ferry to arrive, sometimes much longer than you anticipated. They are affected by wind, waves and all other sorts of uncontrollable factors. The larger the ferry, the slower, but also the most likely not to cancel or delay. Be patient, and understand how it works. You will want to be at the dock at least 30 minutes before your boat leaves. Most locals won’t line up until right before, but getting there early will ensure a better seat and streamline the boarding process. Ferry’s take longer than flying, but they are really relaxing, beautiful experience. On big, slow ferries, you can sit outside and walk along the deck taking in the seascape. Most ferries allow you to stow your luggage on a rack on the boarding level of the boat. You are free to haul it up to the passenger deck and keep an eye on it yourself if you prefer. Most ferries have bathrooms, charging outlets and Wi-Fi, usually for a fee. They also have food and drinks for purchase.

Obviously, there is so much more to traveling in Italy and Greece than can be explored in this blog, but hopefully this will at least give you a leg up and keep you from looking like a total noob while visiting the ancient world. If you are looking for fun things to do while in Italy and Greece, feel free to take a look at our itinerary. These are only just some of the highlights, but it will give you an idea of how much time to allot at each location and how to pace yourself.

Happy travels!

What to Pack (Italy + Greece: Summer Edition)

Headed to Italy + Greece? Good news, you are about to be BLOWN away by history and breathtaking scenery. Italy and Greece are crowd pleasers for a reason. They are both unbelievably beautiful, historically rich, and incredibly inviting. BUT you may find yourself at a loss for what to pack. After all, air conditioning isn’t a standard, and there are specific dress codes for certain sites. Not to worry though, we’ve got your back. Here is your ultimate packing guide for this trip-of-a-lifetime!

The first key is to pack light! Since you’ll be carrying your luggage on and off the plane, the bus, hotels, and winding staircases (think Oia, Santorini), you should try to condense what you need into one small suitcase and a carry-on.

Packing essential items into a carry-on has other advantages too! You will basically eliminate the risk of your bag getting lost or delayed. Win! Just make sure your bag meets the dimensions required for the airline you're flying. 

If you're traveling with Land + See, you can check out Delta’s carry-on baggage weight and dimension requirements by clicking here. 

Here is a list of essential items you won’t want to forget to pack.

Travel Aids

·         Chewing gum

·         Meds for motion sickness and sleep

·         Travel Pillow

·         (The airplane will likely supply earplugs, headphones, and a sleep mask so you can leave those at home unless you are partial to your own).

Clothing and Accessories

·         Comfortable walking shoes

·         Shirts (Have a few with sleeves in order to meet Italian church dresscode: shoulders and knees covered)

·         Socks and underwear/bras

·         Watch

·         Jewelry

·         Pants/jeans/shorts (again, a few with covered knees)

·         Pajamas

·         Glasses/contacts

·         Sunglasses

·         Belts

·         Bathing suit (Be aware, in Santorini the water can stain your suit so plan accordingly)

·         Dressier outfit

·         Raincoat and/or umbrella 

·         Scarf or coverup (for Italian Churches)

·         Hat or other sun protection

·         Collapsible tote/duffel bag for dirty clothes, souvenirs (if only using a carry-on)

·         Luggage tags

·         Journal (if planning to document your trip)

·         Backpack or daybag

Toiletries

·         Toothbrush

·         Toothpaste

·         Floss

·         Mouthwash

·         Shampoo/conditioner

·         Soap

·         Deodorant

·         Hairbrush/comb

·         Hand sanitizer

·         Straightener/curling iron (If you have wattage converter)

·         Hair styling products

·         Hair accessories

·         Cleanser

·         Moisturizer/Sunscreen

·         Shaving Cream

·         Razor

·         Perfume/Cologne

·         Makeup

·         Makeup Remover

·         Feminine Hygiene Products (if applicable)

·         Nail clippers

·         Nail File

·         Hand wipes

·         Tweezers

·         Cotton swabs

·         Tissues

·         Lint Roller

·         First Aid Kit/Band Aids

·         Lip Balm

·         Washcloths (not standard in European hotels)

·         Any medications (in addition to a copy of any prescription)

·         Spare set of contact lenses/glasses (if applicable)

·         Saline Solution (if applicable)

Money

·         ATM card (Call your bank prior to departure to alert them of the trip; foreign purchases sometimes result in a hold on bank accounts.)

·         Personal credit card

·         At least $50 converted to the currency of the first country that you’re visiting

·         Pouch for storing money and passport under clothing

Electronics/Technology

·         An alarm clock (Many hotel rooms won't have one.)

·         An adaptor/converter (details for Italy + Greece plug types found here)

·         Camera with extra batteries or charger

·         Cell phone and charger

·         Portable charger (my personal favorite travel item)

Documents

·         Passport—(Remember to leave one copy of it at home and bring a couple more copies on tour, in case your passport gets lost.)

·         Emergency contact information

·         A copy of your medical insurance card (and trip insurance if you’ve purchased it)

·         A copy of the tour itinerary

·         A list of important phone numbers 

·         Addresses to send postcards home

·         Copy of any prescriptions (Customs officials may want to verify that a container's contents match its label, so all medication should be carried in its original container.)

·         List of medications/prescriptions

Carry-on bag

Here’s a short list of things travelers might need on the first day of the trip. These should be packed in your carry-on in case your checked luggage is delayed:

·         Passport

·         Money

·         Money Belt

·         Airline boarding pass

·         Toothbrush and toothpaste (Check tsa.gov for current security requirements.)

·         Hairbrush

·         Contact lens case/glasses (to sleep comfortably on the plane)

·         A change of clothes (in case luggage is delayed)

·         Medication

·         Any valuables

Hopefully this helps ease the burden of knowing exactly what to pack. You know yourself and what you need so if you see something on the list you know you just won't need, skip it!

Now that you're done packing, let's get back to our countdown! If you're like me, you've got this itinerary pinned already and you check it daily, but I'll throw it on here anyway so you can get back to daydreaming about the Aegean!

Let the countdown begin!

Italy + Greece Itinerary