My wife and I just got back from another epic trip.
We went to Rome, Santorini and Mykonos in a 10 day trip, and flew there on Singapore’s Suite Class ($18,000 per ticket) for FREE with points and had an absolute blast. We had such a great time, I wanted to share with you how you can follow in our footsteps and relive this trip with us.
We flew on Singapore Airlines’ Suites Class
We flew from JFK to FRA on Singapore’s super first class “Suites”, and were sipping Krug on the tarmac.
We went to Rome and ate the best pizza
We sipped on negronis, and toured the Colosseum in Rome.
And stayed in the most beautiful place on earth: Santorini, Greece
We did absolutely nothing at Andronis Boutique Hotel in Santorini, Greece.
and finally to Mykonos where we had an epic infinity pool
We got hot stone massages at spa in the Myconian Villa Collection in Mykonos, Greece.
Follow us on our exclusive travel Instagram: @LifeTailoredTravel
We’ve also launched a new travel focused Instagram @LifeTailoredTravel to get your excited about where you should go on your next trip.
What to pack for your European vacation
Clothes for Europe
- Orlebar Brown setter length navy swim shorts
- Orlebar Brown FELIX White Amalfi Polo Shirt
- Orlebar Brown cotton terry polo shirt in navy
- Orlebar Brown BULLDOG mid-length printed swim shorts in navy zig zag
- Orlebar Brown BULLDOG Roc Pool Photographic Mid-Length Swim Short
Shoes for Europe
Dopp kit for Europe
I brought along the essentials to keep my hair in place, and ready for adventure.
- Creed’s Green Irish Tweed Cologne
- Mr. Natty Willie Mack’s All-Over Wax
- American Crew Forming Cream
- Hanz de Fuko Claymation
How to take the best flight from New York to Europe
Our tickets cost $18,000 to Europe, but we got them for $1,000.
To get to Europe, we took our preferred flight on Singapore Air’s Private Suites. The tickets cost almost $9,000 for each roundtrip ticket, but by the magic of frequent flyer miles, I got them for just $500 per ticket.
How to Book Singapore Suites Class
To get the tickets at this bargain rate, I transferred 297,500 points from AMEX to Singapore Airlines to book 2 round trip tickets. Read our previous guide on how you can book first class flights for free for more information.
The Suites Class is truly remarkable (we flew on them last year when we went to Barcelona and Mallorca).
The Suites flights are available on Singapore’s A380 from JFK to FRA (Frankfurt) and continuing onto SIN (Singapore). They also fly from SFO, and a couple other US locations, but JFK is obviously the most convenient for us.
JFK Virgin Atlantic Clubhouse Review
We got complimentary access to the Virgin Atlantic Clubhouse lounge.
Our flight was at 9pm on a Thursday, and since we got to the airport early, we got to use the Virgin America Lounge which offers free drinks and food. The cocktail menu is just okay, with the majority of the drinks being vodka based or containing a lot of fruit juices. They did offer a class champagne cocktail (champagne, sugar cube, and bitters), which I sipped on while waiting for our flight.
The food itself is nothing special, the only dish I would recommend is perhaps the cheese plate (because it’s really hard to mess up serving cheese). It is all free, so make sure to tip your server, they’re very nice and accommodating.
The one great aspect of the lounge is they have haircuts and showers. So if you have a long layover, you should definitely try to try this out. I’m not sure if it’s complimentary, but either way it’s a great amenity in an airport lounge.
Singapore Suites Review
Once our flight was boarding, we hurried to the gate to get on the flight. Unfortunately JFK has one line for everyone, so since they had already started boarding, we had to shimmy to the front of the line to take advantage of our priority boarding with Suites.
Suites is on the first floor of the plane.
Walking to the plane, we started to see the Suites experience. The top of the plane is devoted to business class, and the bottom is Suites and Economy. So unlike a typical plane, where everyone boards together, we headed down the stairs to enter the lower door. This made is a lot less congested, and once we got to the plane, we were guided to our seats by the Suites staff.
Within minutes of being seated, I was sipping Krug on the tarmac.
Once we were seated, the staff came to ask us if we’d like anything to drink. This being my 3rd flight on Suites, I knew to ask for Krug (my favorite, which I discovered after double-fisting on our previous flight; they let me taste the Dom Perignon and the Krug at the same time so I could find out which one I liked better).
They gave us a set of Givenchy pajamas
Once we had our drinks, they came to give us our slippers, and pajama set (by Givenchy).
So after we were in the air, we decided to checkout the in-seat entertainment. There is a built-in 23″ TV directly ahead of your seat, loaded full of movies and tv shows. With our movies streaming, the staff came by to confirm our meals.
We had pre-booked our meals with Singapore’s Book the Cook, which offers high-end fare on the plane.
This being a $9,000 ticket, the meal service wasn’t limited to just Book the Cook.
First, we started with the caviar plate. I had never eaten caviar before, but thought it was excellent, and most likely very expensive. So based on that, the next time I’ll probably have caviar is on our next Suites flight, but anyway…
Caviar with vodka, so good…
With the caviar, I opted to pair it with the chilled vodka. I was careful this time, and didn’t allow the staff to keep refilling my vodka (last year I had maybe 3-4 refills, and after sleeping for only 3 hours on the flight, I was really banged up trying to navigate my way through the airport and customs).
After our caviar, we had some bread (garlic with butter), and were ready to move onto our Book the Cook.
Roasted Sea Bass
With wilted spinach and glazed crab-mashed potato in white wine sauce infused chive & lemon.
I really liked my sea bass. It was light, fluffy, and had plenty of flavor. Also, unlike most airline meals that are really heavy, this was light enough not to leave me stuffed and make it hard to fall asleep.
Grilled Shrimps and Scallops
Grilled shrimps and scallops in tarragon mustard sauce with leeks, carrots, and linguini.
The dessert was da bomb.
For dessert, we had ice cream with chocolate sauce, a chocolate crisp and some nuts of some sort (the really fancy kind).
The staff is super talented.
To me, it really is remarkable how intricate the presentation is on all of the meals, especially this dessert. The expertise of the staff is really showcased when you look at the drizzle, the placement of the crisp, all while considering you’re in an airplane 5,000 miles in the sky that’s bumping around, and your prep space is about 30 square feet (all the prep is done in the galley where flight attendants normally just serve drinks).
After dessert, it’s time for bed.
After the staff clears our plate, they kindly ask us to go into the bathroom to change into our pajamas and they make up our seats into a twin size bed.
Here we are in our Givenchy pajamas enjoying more Krug while we wait for our beds to be ready.
Our bed had a featherbed, a blanket, a top sheet, and 3 different pillows. It’s super comfortable and arguably more comfortable than some of the hotel beds I slept on in Europe. If I hadn’t had 7-8 drinks, I could have slept a full 8 hours on these beds.
Singapore Suite’s entertainment options are awesome.
On our flight, we ended up watching Spy, Mad Max, a couple episodes of American Family, and didn’t get to finish Escobar: Paradise Lost. I was really impressed with the library — they will have the latest Mission Impossible movie and Southpaw. Watching the movies really made the 8 1/2 hour flight ‘fly’ by.
Rome City Guide
This guide is mainly contained to the areas we went, and we stuck to everything right near the Tiber since we only had 3 days in Rome.
Centro Storico / Spanish Steps
This neighborhood is touristy, but does have their equivalent of SOHO and 5th Avenue, with high end retailers (Gucci, Prada, Chanel, etc.) running directly off the Spanish Steps. Our favorite fast food pasta joint, Pastaficio was located here.
This is the Williamsburg of Rome, and it’s great. A lot of hip bars and restaurants, with nightlife that runs well past 2am. We grabbed pizza at Dar Poeta, the best pizza in Rome. There are also a lot of bars down here that offer free food during happy hour.
We stayed in the Centro Historic District, which is east of the Tiber, and close to all the major sights (Spanish Steps, Colosseum, Pantheon, etc.).
Campo De Fioro
This was a great area with a lot of small boutiques, food retailers, and plazas for dining. We grabbed a Negroni and a Spritz in one of the plazas, and just enjoyed doing nothing. You need to check out this charcuterie “restaurant”, Prosciutteria, that serves fresh meat and cheese only a couple paces away from the Trevi Fountain.
Rome’s First Luxury Art Hotel Review
Our hotel was very close to Spanish Steps, about a 10 minute walk away, but I wish it was a bit further South near Campo De Fioro, just so we could be a bit further away from the tourists and closer to the more authentic restaurants.
Art from wall to wall
The hotel is known for its art, and it has tons of artwork all over the hotel. Both pictures, as well as sculptures, and pretty much all of it is available for purchase. I didn’t inquire about the price for fear of a high number, but it was all beautiful and added to the charm of the place.
One Michelen Starred Restaurant
Our hotel had a restaurant with one Michelen star, All’Oro, which we didn’t have a chance to dine. Also, on the rooftop there was a Japanese restaurant, which made no sense to me, but happened to have a great rooftop with views of the city.
The hotel itself was a great price, at around $350 per night, and had an awesome bathroom. It was entirely covered in marble, and was the size of some New York apartments.
Caffe Grecco Review
This is the oldest cafe in Rome, dating back to the 1700s. It’s a quaint little spot perfect for people watching. They also bring you complimentary meats, cheese, and little sandwiches, so make sure not to order too much food (we did, and the Romans always asked us if someone was wrong when we left food at the table).
Visit the Spanish Steps, but from far away…
The Spanish Steps are equivalent to our Times Sqaure. A ton of tourists, but unlike New York, there are also awesome old school shops near the steps.
Caffe Grecco is just steps away from the steps, as is Pastificio, the best pasta shop in Rome.
When in Rome, Dulce Far Niente
“The sweetness of nothing.”
In Rome, the Romans live differently than we do. They appreciate idleness.
Instead of taking their coffee to go, they sip it at the caffe, and then once they’re done with their coffee, they leave.
My favorite part of Rome was sipping a Negroni at Baccano, and getting their free appetizers. The fried tuna (farthest), was fantastic as was the meatball (closest).
Walking just down the street from the Spanish Steps, we shopped in a number of great boutiques: Valentino Red, Tiffany. The street itself was well insulated from the steps, and didn’t feel touristy at all. Most stores had almost nobody in them, which is a huge departure from SOHO in New York.
Open container …What’s that?
In Rome, like most European cities, you can drink on the streets. We stopped by the dive bar near Piazza de Popolo to pickup some Negronis to go.
Nothing better than taking in the sights while sipping a Negroni.
Wherever you look, there is a masterpiece. Here we peered into the window of Rosscioli.
Oia, Santorini Review
This was our first time in Greece, and we spoke no words of Greek, so we were a bit worried about being able to get around, but luckily everyone spoke English, and didn’t mind at all we didn’t speak Greek.
Compared to Italian, Greek is much more difficult to pickup.
To say thank you in Italian is grazie.
To say thank you in Greek is Efharisto’. (I had to Google that, and good luck trying to read that phonetically).
Our first stop in Greece was Oia, Santorini. Santorini itself has a remarkable geographic story. The island used to be a complete circle of land, until its volcano erupted 2,000 years ago, and caused the circle to be cut in half so the island now resembles a croissant.
The inner area of the island is all mountains, and looks in on the caldera (A caldera is a cauldron-like volcanic feature usually formed by the collapse of land, following a volcanic eruption).
So back in the 1950s, only the poor people lived in the mountains because it is really hard to get to (you need to ride a donkey to get to the top), and nothing grows up there. Fast forward to the 1970s, and the poor people have been kicked out, and luxury boutique hotels have opened up in the mountainous area.
The view from the top of the mountains is simply breathtaking. It’s the most beautiful thing we have ever seen, and we almost cried when we had to leave, because it was such a beautiful place.
Our hotel, Andronis Boutique Hotel was located, in the town of Oia, which is on the North end of the island and at the top of the mountains.
Santorini City Guide
So a quick crash course about the cities in Santorini, and where you should stay.
Oia (pronounced ee-ahh; ignore the “O” in the name)
This is the most touristy town, but also the most pretty and accessible on foot. Every night, tourists pile into the North end of the town to see the sunset. The sunset was amazing, best sunset we’ve ever seen. All these tourists, however, really clog the streets before and after sunset. And this being an ancient town, the walkways only accommodate at their most narrow two people to walk side by side.
Oia has the most expensive hotels, and the hotels that are further down the mountains that Fira. There are a good number of tourist trap restaurants in Oia, and a handful of really great authentic Greek restaurants and some options for fine dining.
This is the city we initially looked at for our hotel. The hotels are cheaper, and look just as nice as Oia. The city, however, is a lot more rundown. The area at the top of the mountain is nice, but down from the top of the mountain, there are a lot more gas stations, and general shops you would find in any island town.
Imerovigli & Akrotiri
I would recommend staying in Oia if you’re looking for a city experience, and look to Imerovigli or Akrotiri if you want a beautiful hotel that is more secluded (and you’d have to take a taxi to get to a restaurant).
Andronis Boutique Hotel Review
In my short time on this Earth, this is the most beautiful hotel I’ve ever stayed.
To get to our hotel, we took a cab from the airport to Oia. Our cab driver called ahead to the hotel to have them pickup our bags. I thought this was nice of him, but didn’t really see the necessity.
Once we arrived, I quickly learned why he called ahead.
We were dropped off in the parking lot, which was a good 30 feet lower in elevation than the hotel’s entrance. Luckily, our bellboy carried both of our bags (my luggage was the extra large Rimowa and weighed ~40lbs). He carried our bags to the top of the mountain, then again down 50 steps to our suite.
I gave him a 5 euro tip, which I realized as soon as he left was not enough. (On our way home, when he carried our bags back up those 50 steps, I gave him 20 euros ).
In Europe, they don’t expect you to tip.
So if you do want to tip, which you should, cut your tip in half of what you would do in the US.
Our room was unreal.
I upgraded us to the private pool and jacuzzi, and this is the best money spent. Our nightly rate was $1,000, compared to a typical room which is around $500. If you’re staying in Santorini, upgrade your room. It’ll be the best upgrade you’ve ever done.
Our private pool looked right into the caldera, and appeared to just fall into the sea. It was hard not to spend the entire day just enjoying our room.
Best Restaurants in Oia
We were in Oia in 3 days, so we had to make it last, so I consulted TripAdvisor for Oia. TripAdvisor has a great feature that allows you download all the data and make it available offline, which was essential as we were navigating the streets san wifi.
Melitini has the amazing Santorinian salad
Melitini is located down a side street in the heart of Oia. The salad contains one of the few vegetables that actually grow on Santorini: cherry tomatoes that actually taste like cherries. They have a sweetness and flavor that you won’t find in typical cherry tomatoes here in the states (or most likely Mexican grown).
Pitogyros has the best gyros in Santorini
Pitogyros was a little hole in the wall literally 20 feet away from our hotel in Oia. They have a simple menu of gyros with beef, chicken, pork, and greek salad (in or out of a pita). It was epic. For around 5 euros, you get a super fresh chicken souvlaki gyro with fries stuffed in it. Plus, it’s open till 2am so you can have dinner, then fourth meal here.
If you visit Santorini you gotta checkout Pitogyros
We went here 4 times, and once on the way out (the parking lot is just beyond in the photo).
The views from the room were epic. You look forward you see the caldera. You look up, left or right, and you see nothing but whitewashed buildings.
This place was beautiful, in case you don’t get the point.
There were so many random side streets that were perfect for capturing a Santorini moment, with everything soaked in blue and white.
In Greece, they see white as a symbol of purity, that’s why the government requires everyone to paint their buildings white.
Also, since the water is so salty, it causes paint to quickly erode, which requires monthly paintings.
In Greece, everyone wore blue and white (at least the hotel staff), so I did my best to live the motto, when in Greece, do as the Greeks.
Great views from the breakfast table.
Excellent free breakfast buffet, with great views. The breakfast buffet consisted of pretty much anything you wanted, I didn’t partake because I wanted to save room for lunch and dinner, but what looked particularly good: greek yogurt, croissants and pastries, cheese plate, charcuterie plate, dessert cups, and complimentary orange juice and peach juice.
For breakfast, instead I opted for a cappuccino, which I ate the last bit of which with a spoon.
Santorini Sailing Review
On our second day in Santorini, we wanted to get a glimpse of everything the island has to offer, so we booked a catamaran cruise with Santorini Sailing.
We booked via their website, and it wasn’t the most intuitive. You couldn’t pay online, but rather had to email them a PDF with your credit card information.
When we arrived in Santorini, we checked with our concierge, George, who informed us Santorini Sailing didn’t have our reservation. Luckily, George helped us call them up and book a reservation. We initially chose the group tour on the Dreamcatcher, which was $107 per person for a catamaran with 40 people.
We sailed on Santorini Sailing’s Triton
After speaking to the Santorini Sailing team, they suggested we upgrade to the Triton tour, for $124 per person, for a more luxurious boat with just 10 people. It was well worth the upgrade.
The Triton picked us up in Ammoudi Bay, down a super steep hill at the northern end of Santorini. From the boat pickup point you could see the beautiful restaurants right on the waterfront and all the local fishermen boats.
The Triton was fast, smooth, and had plenty of space for laying out.
When we went to the South of Santorini, to near Akrotiri, we could see the remnants of an old riverbed (the white rock in the background, which sharply contrasts with the red and black rock on the rest of the island).
My Orlebar Brown trunks blended right in with Small Santorini.
On the tour, they took us to Thirasia, “Small Santorini”, which was accessible only by boat, and apparently is occupied by 4 or 5 families. Everyone seems to marry someone from another family and continue to live on the island.
We had a nice spread of calamari, greek salad, pasta, and shrimp. The food, while not the greatest, was more than I expected considering it was all prepared right on the ship.
Sadly, we had to leave Santorini, and head onto Mykonos.
Seastreak Ferry Review: Santorini to Mykonos
To get from Santorini to Mykonos, there are a number of high speed ferries that operate. We took the Seastreak Jet II, and it cost $60 per ticket, for one-way. The ferry itself was one of the newer ones in their fleet and it was much better than I expected.
View from the ferry of Naxos, Greece.
There were two food stations on the ferry, one serving freddo cappuccino (ice whipped cappuccino with cream), and a couple sandwiches and various yogurts. For beverages, they had Alfa beer (from Athens), as well as, curiously, Smirnoff Ice. I actually saw quite a few people buying Smirnoff Ices, so if you feel the urged to get iced on the ferry, that’s definitely doable.
The seating was excellent, big wide seats equivalent to business class flights in the US, and we got window views, which were really nice. We sailed past Naxos (the only stop on the way to Mykonos), as well as a couple other smaller islands.
I’ve heard the ferry can get a little rough if the seas are brewing, but for us it was smooth as ice.
Myconian Villa Collection Hotel Review
Getting to the hotel was a breeze since we called ahead to the concierge. They have a bus that picked us up from the ferry terminal. We also took this same bus to the airport on the island.
The view from the front door was heaven
Once we walked in the door, I immediately tuned around and snapped this pic. When you want to have a good day, this is the view you want to see as you walk out your front door.
The hotel lobby is stunning
When you walk in the hotel, you’re greeted by multiple seating areas all in chabby chic washed in white. Regardless of this being a beautiful location, it immediately takes you away to Greece and the white buildings.
Sit here, pretend to read that book while waiting to check in
There was one super comfy seating area after another.
The hotel grounds were beautiful
Everywhere you walked, you had beautiful backdrops for pictures. We wandered around and snapped a lot of great shots.
We even saw sheep grazing on the hotel grounds
The hotel is one of the newest in the Myconian Collection, and the decorator did a great job. These sheep (or are they lambs?) grazing next to the windmills reminds you of an idyllic Greek countryside.
Wow… Epic pool
While Santorini was beautiful, they didn’t have a pool like this. Infinity edge pool that was at least 60 feet long, and looked over Elia Beach.
We spent every day at Myconian Villas by the pool and loved it.
Order the Polite Negroni
We ordered cocktails from the bar menu (also the restaurant Cabbanes) and they were actually very good. My favorite was the Polite Negroni. For those of you who want to participate at home, it consisted of:
- 1 part gin
- 1 part sweet vermouth
- 1 part aperol
- 2 dashes Peychaud’s bitters
- Slice of orange
Get taken back to Mykonos’ seafaring past
Since Mykonos is in the Cyclades, the islands around in the South Aegean sea, lighthouses are an essential part of life. Prior to planes, the only way to get to Mykonos was by boat, and the lighthouse was a savior. This restored piece was plopped in the middle of the lobby and fit right in.
Get the hot stone massage at the spa
At the spa, we went for the hot stone massage, which was 150 Euros per person, and lasted for 1 hour. I had never had the hot stones before, so when the masseuese originally put them on me, I thought she was applying some white hot liquid to my back.
It felt good, but I had no idea what it felt like. Once I got used to it, it was great. I don’t think particularly rough massages, so using the hot stones allowed my muscles to relax, get looser, and feel better after the massage as opposed to a typical massage.
We had a room with a …pool
We opted for the plunge pool in our room and while it was beautiful, it wasn’t ideal. The pool itself didn’t get a lot of great sun, and since the hotel had such a great pool, we barely got to use this one.
For future hotels, whenever there is a massive pool, we’re going to not opt for the in-room pool, and possibly just go for a jacuzzi as this makes more sense to use at night.
I’m rocking my Orlebar Brown trunks again here.
It did make for fun photoshoots though.
Take Your Best European Vacation
We hope you enjoyed our trip, and if you plan to follow in our footsteps, let us know so we can share you even mode tips/tricks that didn’t make it into the article.
If you want to learn how to fly on Singapore Suites, we covered this in more detail on a post that also shares with you how to get Singapore Suites Class for free to the Maldives.
Here’s the links to book the hotels we stayed:
- The First Luxury Art Hotel, Rome
- Andronis Boutique Hotel, Santorini
- Myconian Villa Collection, Mykonos
Where Are We Headed Next?
Our top destinations for the next year:
- St. Barths
- Turks & Caicos
We are already in touch with the next hotels on our list to determine who will be featured on our next trip. Let us know where you’d like to see us visit in the comments or on Instagram.
Get your property featured on Life, Tailored
If you would like to see your property on Life, Tailored, send us a note, we’d be happy to work with you.