20th Anniversary Trip 2021: Reader Asks Where to Go

20th Anniversary Trip 2021: Reader Asks Where to Go

Where is Ideal to Celebrate a 20th Anniversary in 2021, Using Frequent Flyer Miles for Flights and Staying in a Luxury Resort? TravelSort Reader Harry writes: “I currently have about 825K miles across Amex, United and Capital One. Its my 20 year anniversary this year and my wife would like to go to Japan, Africa, Maldives or Fiji. I would not fly economy but not first class either unless it made sense. I would use miles and I would pay for the lodging if I can fly better than economy (like business). Doesn’t have to be first class. What would you suggest?”

In a non-pandemic year it would be harder to decide among options, but in 2021, given the recent surge of COVID-19 cases in Japan and the distinct possibility that Japan may continue to restrict the entry of non–Japanese citizens/residents, I'd recommend not attempting a Japan trip in 2021. Similarly, Fiji is currently not permitting leisure visitors to enter the country. If going all the way to Africa for a safari, we'd normally recommend including some resort time in the Seychelles at the end, but that will entail additional COVID-19 testing (even for those who have been vaccinated) so it may be best to wait on this destination as well. We'd recommend the Maldives, since, as a highly tourism dependent destination, it's open (with a negative COVID-19 test) to visitors, and the nature of the Maldives helps make it safer, since generally each resort is on its own private island, with plenty of outdoor space and the ocean in which to social distance. The Maldives also has some of our favorite luxury resorts anywhere–we'll get to our specific recommendations soon.


Getting to the Maldives with Frequent Flyer Miles

Given that Harry has AMEX Membership Rewards points, United MileagePlus miles and Capital One rewards points, which should he use to get to the Maldives?

We'd recommend flying Emirates Business Class, using Emirates Skywards miles, as that would enable a one stop itinerary (connection in Dubai DXB) from U.S. gateways such as New York JFK, Los Angeles LAX, Chicago ORD, Boston BOS, Washington Dulles IAD, Dallas DFW, Houston IAH, and Orlando MCO. Emirates Business Class roundtrip would be ~200,000-250,000 Skywards miles = AMEX Membership Rewards points + ~$530 in taxes per person, depending on which U.S. airport one departs from.

United miles won't be able to book Emirates, and Capital One points only transfer 2:1 to Emirates (so worth half as much as AMEX Membership Rewards points), hence AMEX points are the best ones to use. If Harry had any Chase Ultimate Rewards points, those transfer 1:1 to Emirates Skywards as well.


Best Maldives Luxury Hotels and Resorts

We've personally stayed at 8 of the top Maldivian luxury resorts, and our clients have stayed at additional ones. Our top recommendations are as follows. TravelSort Clients enjoy special Virtuoso or preferred partner benefits:

Cheval Blanc Randheli

Cheval Blanc is the luxury hotel brand of LVMH, and the Maldivian property is the jewel in the crown. There are just 46 stand alone villas, and yet the resort manages to have arguably the top fine dining restaurant in the entire Maldives, Le 1947. There's also a separate spa island and separate tennis island, making it an ideal haven for both spa enthusiasts and avid tennis players.

Cheval Blanc Randheli Virtuoso benefits

  • Upgrade on arrival, subject to availability
  • Full Breakfast daily for two guests per bedroom
  • $150 USD Food & Beverage credit to be utilized during stay in any of the resort's restaurants, bars or for room service, i.e. “Carte Blanche” (not combinable, no cash value if not redeemed in full)
  • Early check-in/late check-out, subject to availability
  • Complimentary Wi-Fi


Velaa Private Island

Velaa Private Island isn't as new as Cheval Blanc Randheli or Joali, so we didn't find the villas quite as impressive, but it is the island to be on if you want more land based activity options. It has the Maldives' only private island golf course, and is one of the few to offer basketball, volleyball, and a climbing wall in addition to a covered tennis court (no more sunburn while playing!) There's also a pool table, places to enjoy a drink with ones feet in a pool, and an extensive wine cellar with tasting room in a tower that also features Japanese cuisine at the top. There are also a host of fun water toys to rent, for adrenaline junkies.

Velaa Virtuoso Benefits

  • Upgrade at time of arrival, subject to availability
  • Daily Full breakfast for two guests per bedroom served in Athiri restaurant
  • $150 USD Food & Beverage credit to be utilised during stay in any of the resort's restaurants, bars or for room service. (not combinable, no cash value if not redeemed in full)
  • Early check-in/late check-out, subject to availability
  • Complimentary Wi-Fi



Joali's villas seem inspired by Cheval Blanc Randheli's, which in our book is a good thing–we love the soaring ceilings and the luxury of all that space. We also really enjoyed Saoke, the Japanese restaurant, and excellent breakfasts. My scuba dive was good, although I've had better dives–the dive shop is not Joali's own team, but a third party dive operation.

Joali Virtuoso Benefits

  • Upgrade on arrival, subject to availability
  • Complimentary A la Carte breakfast for two, per bedroom daily for duration of the stay
  • $150 USD equivalent Food & Beverage credit to be utilized during stay
  • Early check-in/late check-out, subject to availability
  • Complimentary Wi-Fi

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