This itinerary is inspired by my honeymoon trip to Lake Como in Italy, another dream destination that Jess has been to without me (starting to notice a pattern here) but given her love for the country and my strong desire to visit, deciding on Italy as our honeymoon destination was one of the easiest choices we’ve made. Since I have never been, I’d like to share with you our itinerary and how we plan to spend our 10 days there, hopefully giving you some inspiration!

As usual, let’s start with travel and getting to northern Italy. Milan, which is the most convenient, has 3 airports, Malpensa Airport, Linate Airport (mostly domestic and regional travel) and Caravaggio Orio al Serio Airport. From what I’ve researched, Malpensa Airport is the largest international airport in northern Italy and that’s where we’ll be flying into from JFK Airport in New York, about an 8 hour flight. I’ve mentioned it in a previous post, but be sure to check Skyscanner for possible deals. For our trip, I’m still debating if renting a car is worth it, tourists can rent a car and drive in Italy as long as they meet the following:

• At least 18 years old

• Have a driver’s license in your home country

• International Driving Permit

• Passport

• Car Insurance

As you see, it’s not that complicated to actually rent the car, but I’m more hesitant about the driving part. From what I’ve read and heard from people who have, there are a few things to be aware of:

• Tolls are much more expensive than the U.S.

• Gas (or petrol) is a lot more expensive, currently $5.96 a gallon

• Most cars are manual transmission and renting an automatic usually comes with a fee

• U.S. car seats are illegal, so keep that in mind if you are traveling with younger kids

Now I don’t want to discourage you, if you truly feel the need to rent one or want the convenience, I’m sure you could pull it off and make it work! Check out Discover Cars if you decide renting a car is the move.

Day 1 - (Milan Day Trip)

With so much to do and see I imagine it’s easy to get overwhelmed, so let’s start with the basics, The Duomo di Milano. Now don’t get me wrong, nothing about this magnificent icon is “basic”, but is definitely one of the most, if not the most, popular tourist attractions in Milan. We’ll take time to admire the stunning combination of Gothic and Renaissance style and the attention to detail of the over 2,000 statues. After gazing at the architectural genius of the exterior, we’ll step inside to marvel at the alters, patterned floors and stone columns. Eventually we can make our way to the rooftop terrace either by stairs or elevator and enjoy spectacular views of Piazza del Duomo, but disclaimer the stairs consist of 250 steps so choose wisely! Once we’re done exploring the cathedral and rooftop, we’ll make our way to the Duomo Museum and check out one of the 26 exhibition rooms.

Since there is simply so much art and history to absorb, we plan on doing a guided tour of the cathedral with an expert local, we’ll most likely purchase tickets in advance for the combo tour, which allows access to the cathedral and our next attraction!

Leonardo Da Vinci’s, “The Last Supper”, I can’t visit Milan and not see one of the most famous works of art in the history of history. I am by no means an art connoisseur, hell I can barely draw stick figures, but you don’t need to be an expert to enjoy this masterpiece. The painting is located in the Santa Maria Delle Grazie Church about a 10-15 minute walk from The Duomo so we plan to book our tour of The Duomo and “The Last Supper” back to back, as I mentioned above, tickets for both can be purchased together as part of a combo! I think it goes without saying but I’ll say it anyway, be sure to buy tickets well in advance, I’m talking like months in advance (which reminds me to book ours). There is a 15 minute observation period and pictures are allowed but no flash and videos are prohibited so follow the rules or else we’ll be sleepin with the fishes.

After our tours I’m sure we’ll be hungry which leads me to “Apertivo” or “Happy Hour”, to my understanding Italians love their happy hour! Apparently they start around 6pm and last until 8 or 9pm and consist of an absolute feast for a reasonable price of 10 euros or 11 dollars at the time I’m writing this, so 11 dollars for an assortment of meats, bread and cheeses along with an Aperol Spritz? How can I apply for citizenship? Because 11 dollars in New York gets you a bottle of water and gas station sandwich. After shamelessly stuffing our faces we’ll be hopping on a train to Varenna where we’ll spend the next 3 nights in Lake Como.

Days 2-4 (3 nights at Lake Como)

Varenna is a beautiful village on Lake Como about an hour train ride from Milan and we’ll be spending 3 nights and 4 days at The Villa Monti while we explore Lake Como and some of the other surrounding villages. Now truthfully, I’m most excited for this part of the trip, this region of Italy looks so majestic, like a kingdom in a Disney movie.

Just waking up here is enough entertainment and excitement for me but in the spirit of adventure here are some things we plan on doing while there:

Kayaking on Lake Como -

This is on my bucket list so an absolute must, I think this will be a great way to connect with the beauty of the lake and surrounding villages and get a real appreciation for the natural wonder. There’s so many options to rent all types of water sports, but these were some of the highest rated companies, these all offered kayaking, paddle boarding, etc.

• Boat2Go

• Water Experience Center

• Bellagio Water Sports

If watersports ain’t your thing and you want more of a boat tour vibe, here’s a link to private boat tours.

Visiting Villa Monastero -

Located in Varenna, this eclectic waterfront villa is a symbol of history and beauty. We plan on spending an afternoon roaming the museum and botanical garden. Villa Monastero is an ancient woman’s monastery dedicated to the Virgin Mary. In 2003 the museum was built, there are 14 rooms allowing visitors to commend the original decorations and furniture. The botanical garden stretches just a little over 1 mile and contains over 900 tree species. You can purchase tickets for access to both the museum and garden for $15 here, but keep in mind the villa is closed November 6th through March 2nd for renovations and maintenance.

A Day in Bellagio -

The internet says Bellagio is one of the most famous and picturesque villages in Lake Como so it must be true but I’d love to see for myself by spending a day there. Bellagio is apparently split into 2 sections, the lower section and upper section. I’d love to just wander around the staircases and alleyways aimlessly, checking out the shops and boutiques.

After browsing the streets I plan on hanging out at La Punta Spartivento, a park at the tip of the village which offers views of the lake with the Alps in the background, a great place to mellow out and take in the surroundings.

Eventually working up an appetite, I can’t wait to have pizza and a glass of wine while asking what’s the worst that can happen if I decide to just never return home. This restaurant looks out of this world, I’m sure you can’t go wrong wherever you eat, but the combination of views and the reviews caught my eye, Trattoria Baita Belvedere.

I also want to check out Villa Melzi, this compound was built in 1808 and allows visitors to stroll through beautiful gardens filled with exotic tress, bushes and flowers all while offering views of Lake Como. The villa is still privately owned so we’ll only be able to explore the grounds, but I’m sure it’ll be worth the $9 entry fee, the villa is closed to visitors from March-October, you can find more details to plan your visit here.

Night 4 into Day 5 - (One night in Milan)

Sadly, the day will come where I need to leave Lake Como and head back to Milan where we’ll spend one night there. We’ll be getting there in the evening so I’m excited to experience Milan’s nightlife. I’ve scouted some restaurants and have my eyes set on Langosteria, based on what I’ve read, this is one of the best restaurants in all of Milan, known for the fresh seafood, mixed drinks and intimate atmosphere.

After dinner I’d like to head over to a rooftop bar for some drinks while taking in the scenery and am between Radio Rooftop Bar and Ceresio 7. Both offer food, cocktails and views of Milan but I’m leaning towards Ceresio 7 as it has a pool, I’m not a fan of public pools but it adds to the ambiance at night and has slightly higher reviews.

After enjoying my lobster pasta and an espresso martini or 4, it’ll be time to head back to The Westin to shower, relax and watch some Love Island before waking up to catch the train to Santa Margherita.

Day 5-9 (4 nights in Santa Margherita Ligure)

Santa Margherita is in the province of Genoa, about a 2 and a half hour train ride from Milan located in the Italian riviera so I’m excited to explore the beautiful beaches and tropical climate, for this part of the trip we’ll be staying at Villa Gelsomino.

One of the first things I plan to do when there is stroll the promenade and soak in the colorful buildings, crystal blue water and admire the massive yachts that serve as a subtle reminder that I am poor.

Since I can’t afford my own boat, might as well opt for the next best thing, rent someone else’s boat for a tour! There are many boat rental services in the area but Albatros Boat Tour has a 5 star review so they must be doing something right. From what I’ve read, the tour stops at neighboring villages like Portofino, San Fruttoso and Camogli. I’m leaning towards booking a sunset tour as I think that will be more romantic and memorable, they also offer focaccia and wine so I’m sold.

Up next I’d like to see Cervara Abbey, this monastery was built in 1361 and for centuries served as a retreat for prominent military and religious leaders, it was turned into a hotel and event venue in 1990 and features an Italian garden that overlooks the Mediterranean, it looks like you have to call or email to schedule a guided tour.

This next excursion I don’t know how I feel about it yet but I’m debating booking a snorkeling tour in Paraggi Bay near Portofino. My hesitation stems from my fear of being submerged in open water, I’m not scared of swimming, I’m scared of drowning...oh and sharks, but this bay is known for crystal clear and calm waters, does not allow nautical traffic (boat traffic) in the area and from my research has an extremely low prevalence of sharks. With that being said I would like to conquer my fear of open water and explore the marine life it has to offer! It also might be my best shot of finding and playing with my favorite animal, an octopus. I think I’m going to give it a try and book here.

Returning to my natural habitat on land, before leaving Santa Margherita, I want to traverse the hike from Santa Margherita to Portofino. From what I’ve read it’s more of a walk than “hike” as over the years many sidewalks and boardwalks have been built and the route consists of gentle up and down hills, offering views of the sea, coastline and neighboring villages. It seems like it will take a little under 2 hours to complete and the total trip is 10 miles, 5 miles to Portofino and 5 miles back, but I’m sure you can bus, water taxi or find another method of public transit to get back if you chose not to walk back. I plan for us waking up early in the morning, walking to Portofino and getting brunch to treat ourselves!

Day 9-11 (2 nights in Milan)

I fully anticipate being heartbroken having to leave Santa Margherita and the Italian riviera as I’m sure I’ll quickly get use to the temporary paradise, the next and final stop on our trip is returning to Milan for 2 nights, staying at the Park Hyatt, which we booked using Chase points (40,000 a night), this hotel is way to boujee for my standards and I will undoubtedly be the poorest person to have stayed there, but hey, I’m here for a good time, not a long time.

At this point we’ll have already spent time in Milan and have done most of the touristy attractions so that combined with the fact that we both enjoy cooking (well Jess does, I enjoy eating, especially Italian food) we plan on signing up to take a cooking class. There’s so many options when looking for classes, but I think I’m going to sign up for The Secrets to Learn Fresh Pasta and Tiramisu. In this workshop, a Michelin trained chef teaches how to recreate tagliatelle, ravioli and tiramisu.

We plan on spending the last day in Milan shopping, checking out Via Torino and Via Monte Napoleone, two shopping streets/centers. From what I’ve gathered, Via Torino has more moderate shops like H&M, Zara and Bershka, while Via Monte hosts the elite fashion brands like Armani, Ferragamo and Versace. Now me personally I’m more of a TJ Maxx and Target kind of guy but I guess I’ll settle for Europe’s finest.

So there you have it folks, that is our itinerary for spending 10 epic days in Northern Italy. When we return from our trip I’ll be sure to write another post detailing our experience and providing more photos!