Cruising Southeast Asia & The Philippines With Windstar Cruises

There are two people who love luxury travel even more than I do, and that’s my parents. So when they wanted to come over to Bali this year to visit me, we all decided that we would be fun to explore a new area of Southeast Asia together instead (since they’ve already visited Bali)! – and we all agreed we wanted it to be The Philippines. So I started researching how to travel around the Philippines…..

Crazy flights, long ferries, 10 hour bus rides, and a whole lot of travel time to get ANYWHERE you wanted. It was crazy. 

It’s not that I didn’t understand why – the beautiful Philippines is an archipelago made up of more than 7,000 islands. The islands are not nearly as close to one another as you’d think (So, say, if you wanted to go to Manila, Borocay, El Nido, Cebu, Puerto Princessa, Siargao and Coron all in one trip… you’d need many weeks off work and a big affinity for long ferries & bus rides) So I found myself almost giving up on this beautiful area of the world altogether…

until I found Windstar Cruises’  Philippines and Best of Borneo Cruise! A 14 day luxury cruise taking off from Singapore and ending in Hong Kong – exploring many of the best Philippine islands along the way… It seemed too good to be true.

When it comes to areas of the world like Southeast Asia, there is (in my opinion) no better way to explore than on a luxury cruise ship. Why? Well, first of all, you only have to unpack once (!!!!) and your ship becomes your “home” on your vacation, as you get transported to destination after destination every day. You have all the luxuries of a fancy resort, and all of your meals are included in the price of the cruise (plus you can get a drink package for around $50 a day to include alcohol as well), you also have a super friendly staff that knows your name by the first day, takes care of you (in my case, always bringing me avocado from the back of the kitchen each breakfast because they knew I loved it!), and cleans your room every day (!!!), and… not only all that but you get to wake up to the view of the ocean outside your window. I MEAN DOES IT GET ANY BETTER?!

I first fell in love with cruising on Semester at Sea – a study abroad program I did in college where we lived on a ship for a semester while circumnavigating the globe (you can read more about that here). I quickly learned that if you wanted to see A LOT in a little amount of time (in Semester at Sea’s case, 12 countries in 4 months, or in my parents’ case, 4 countries in 2 weeks off of work), there’s no better way to do it than on a ship.

Windstar Cruises operates a fleet of small luxury cruise ships. Its six yachts carry just 148 to 310 guests and cruise to more than 150 ports throughout Europe, Asia, the South Pacific, the Caribbean, and Central America. Windstar’s small cruise ships take on an extremely personalized approach – so they feel more like your private yacht than a big ship. Half of the fleet is sailing ships, which are drop-dead-gorgeous, and the other half are yachts (like the one I was on – The Star Legend) They are WONDERFUL.

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The Ship Experience on Windstar

First of all, the rooms on Windstar ships are HUGE. This is one of the biggest differentiators of Windstar vs. other cruise lines. I cruised on the Star Legend – which actually just went into dry dock to get a multi-million-dollar renovation before next year. Even before its renovation, it was flawless. An all-suite ship that truly felt like your own. The food was incredible (the chefs on Windstar are some of the very best in cruising). You always have gorgeous dinners and a big breakfast buffet, but one of my favorite parts of Windstar was the sundeck barbecue that happened during lunch (and once for dinner!). They switch up the offering by what’s fresh, but it was anything from a build-your-own poke bowl bar (SO GOOD) to a fried noodles bar, to barbecued surf and turf.

I definitely regularly had to hit up the gym on board to work off all the amazing food on the cruise, but Windstar’s food was noticeably VERY high quality and definitely health-conscious, so I felt good about what I was eating – even when I was on my third poke bowl and second glass of chard.

Also, I feel like it’s such a misconception that on cruises you gain weight. Maybe if you’re going on a cheap lower-end cruise, but I find myself SO active on Windstar’s cruises. When I’m in port, I’m staying active by walking so much and exploring, and they even have a watersports platform that Windstar puts out when the weather and port is righ – where you can paddleboard, kayak, or just hang on an inflatable right off of the ship’s deck. SO much fun. 

The Windstar Clientele – and What it Was like Cruising With My Parents

While I usually travel with my fiance Kenny, he stayed back in Bali to work with his factory on his Spring launch (he founded the brand Kenny Flowers – a tropical shirts and swimwear brand made in Bali), so this trip was just me and my mom and dad. I was excited to get to spend such good quality time with them, since I’m usually traveling so much I don’t see them as often as I’d like! I had also just gotten engaged, so my mom and I were VERY excited to plan the wedding over champagne and canapes in our Windstar suites.

The Windstar clientele is definitely younger than most cruise lines (maybe around an average age of 40-60 vs over 60 on a lot of cruise lines) – especially on its summer routes. But, that being said cruising is definitely still an older crowd. I don’t mind at all personally – those are the people who get the most time off to travel! But I think that trend is changing rapidly – millennials are hearing more and more about cruising and, with new luxury cruise brands popping up like Virgin Voyages and the Ritz-Carlton Yacht Collection trying to capitalize on this market, I think we’re going to see a much more younger audience on cruises.

I’ve been asked if I was bored on a cruise as a younger person, and the answer is definitely not! There is so much to do on Windstar – it’s impossible to get bored (especially if you have some good books for sunny sea days). I loved cruising with my parents – a cruise makes for a great multi-generational getaway (like we did!) if you have older kids you want to travel with, or a great multi-couples trip because you can all do your own thing during the day (or do an excursion together) and every night meet up for dinner and cocktails. It’s the perfect balance between together time and feeling like you have your own space, as well. I can also totally imagine a Windstar cruise being the ultimate honeymoon, especially on one of their French Polynesia routes!

Cruising Asia versus traveling on your own: Why cruising is a better value, and a better experience

Aside from just the time, effort, and hassle it takes to try and navigate a place like the Philippines (or anywhere in Southeast Asia really) on your own, let’s think about the cost of that for a second. Even on a luxury cruise, the price for everything included can be around $3-4000 per person for a 12-night cruise, or only about $300 per night, INCLUDING all of your food, accommodation and transportation. Now I don’t know about you guys but this, for everything that Windstar gives you (five star food, five star accomodation, AND transportation from island to island and port to port), is such a huge value. And, as someone who loves luxury things (but also loves to find ways to get them for a fraction of the price!), cruises are the ultimate way to travel.

Highlights of our Windstar cruise and recommendations!
Singapore -> Philippines -> Hong Kong


The cruise guide to Singapore: What to see in one day in Singapore

Must-sees for one day in Singapore:

Marina Bay Sands

Only guests are allowed to swim in the MBS breathtaking pool – so if your cruise is leaving out of Singapore like ours did, make sure you book a night before your cruise in the beautiful hotel!

The Gardens By the Bay : You may recognize these gorgeous skytrees from the Crazy Rich Asians movie – they are located just outside of the Marina Bay Sands are BREATHTAKING! The gardens are open 5am-2am but if you’re there for a night – make sure you time it right for “Garden Rhapsody” an incredible FREE light and sound show at 7:45pm and 8:45pm daily.

Garden Rhapsody

Eat some chili crab at a hawker stall!

Head to Gluttons Bay hawker stand for some of the best food in all of Asia. It’s not too far from the MBS, and a perfect spot. My favorite Singaporean dish is their famous “chili crab” – it’s SO good.

Borocay : The cruise guide to Borocay Island

Shop JetsetChristina’s bikini here!

One day in Borocay: Must-sees:

White Beach

Borcoay puts a limit on the number of tourists and people allowed on their island, which helps to keep it SUPER clean and beautiful. The beaches here are even better than the caribbean and the water is to die for. White Beach is the main beach on the ilsnad

Shop what I’m wearing: Juliet Dunn

Puka Beach

You’ll feel like you’ve been dropped on a deserted island on Puka Beach (only about $25 private boat ride away from White Beach). But, don’t worry, there’s plenty of tuktuks to take you from Puka to wherever else you need to go on the island (or back home) so even though it feels remote, you’ve still got some fun shops and society right nearby.

Sunset cocktails at the Shangri-La Borocay

I can’t recommend ANYWHERE in Boracay as highly as the Shangri-La. I mean, just look at this sunset set-up. It’s gorgeous and I was also SUPER impressed by the food and cocktails.

Bird's-eye View

The beautiful Shangri-La Borocay

Coron, Palawan

Shop my look: Koy Resort Buzios Skirt & Top 

Coron was easily my highlight of our Philippines cruise. It was named “Coron” by Prince Philip (who named the Philippines), and it is truly the crown jewel of the country. When it comes to the best islands in the Philippines, I think it tops every list. Coron has the most incredible landscape I’ve ever seen (think, jagged, majestic limestone cliffs leading to unbelievably blue lagoons) and it makes for the perfect honeymoon, romantic trip, or family getaway. It’s also a part of Palawan island, so a quick flight away from the other part of Palawan where El Nido is!


Further south on Palawan is Puerto Princesa, home to one of the seven natural wonders of the world – the Unesco Heritage site the Puerto Princesa Underground River . This excursion through Windstar was definitely a huge highlight as we got a tour of the underground river and meandered through the majestic caves.

Manila, Philippines

The one-day guide to Manila

We chose to do a Windstar excursion for our day in Manila that took us outside of the city to the beautiful Pagsanjan Falls. It was a long bus ride (Manila can be trafficky!!!) but it was worth it. We took a long canoe up-river (don’t worry, a very strong Filipino rows the boat for you) and ended up at this drop-dead-gorgeous waterfall. Then, once you get there, you get to go UNDER it, as one of the guides paddles you into the falls. It’s like a natural theme park, and so much fun.

Hong Kong

What to do with one day in Hong Kong

If your flight is later that day and your cruise ends in Hong Kong: Get off the ship, check in your bags at one of the ULTRA convenient downtown check in counters (yes, you can actually check your bag up to 24 hours before your flight downtown, long before you take the train to the airport), and head straight into town to explore.

Depending on how much time you have, try to do any of the following

Get some Dim Sum at Lin Heung Tea House. 

Hailed as the best dim sum by locals, Lin Heung Tea House is a gem in HK, and a must before leaving the city

Head up to Victoria Peak

Soak up some of the best views in the city at Victoria Peak – accessible by tram.

Grab drinks in Hong Kong’s famous LKF

Lan Kwai Fong is a district of more than 300+ bars and restaurants lining its streets. It’s super fun at night, or just for a casual afternoon cocktail. My favorite bar there is The Woods!

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Have more questions about my cruise with Windstar in southeast Asia? Ask them in the comments below or reach out to me on Instagram!






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Christina is a leading luxury lifestyle and travel blogger with over 2 million readers. Follow her on instagram @jetsetchristina.

  • Mary Zaxou

    Amazing pics! I want to book a Windstar Cruise now! Thanks for sharing!!

    April 23, 2019