ostuni, One Week in Puglia

ROUND-UP: My Top 10 Travel Moments from 2021

Ten highlights from an unprecedented year

I make it a yearly tradition to hunker down during the last week or two of the year to reflect on milestone moments, my โ€˜winsโ€™ (which I often neglect to celebrate), lessons learned, and my favorite travel experiences. The past couple of years, despite a great amount of travel, have been a tougher exercise though. I found myself constantly hitting a roadblock. 2021 has felt like a dozen years wrapped into one, but also simultaneously seemed fleeting. And while I have a ton to be grateful for and so much to look forward to in 2022, there’s also a hearty dose of uncertainty that’s in the air that’s left most of us feeling unsettled. I’ve stayed optimistic, though, and what gives me hope is seeing the state of the world when we arrive somewhere new. For all of the fear that’s shown in the media, that’s not the truth that I’ve come to know during my 2020 and 2021 travels. What I’ve seen on the ground are people trying to live ‘normal’ lives within the parameters of an unprecedented time, and other travelers who are thankful and excited to explore the world again. If anything, we’ve learned not to take our ability to travel for granted and it makes each trip and each newfound experience that much more vibrant.

By the Numbers

Countries Visited: 8 (9 if you include Vatican City!)
Airplane Legs Flown: 24
New Passports Earned: 1 ๐ŸŽ‰

2021 took us through Europe, back and forth to the Caribbean, and to East Africa, including a healthy dose of family time that felt long-awaited after a difficult 2020. I’m thankful for our adventures – big and small – and grateful to have a new appreciation for my island home. In rough order, I’m sharing my top 10 trips of the year. โ‡ฃ

Wine Tasting our Way through Napa

Napa Valley, The Wanderlust Effect

10Lest I discount our time in the US, we spent two weeks in California exploring from Napa and Sonoma down to Huntington Beach and Temecula. Our foray into wine education made Napa a must for us to gain a deeper understanding of a world-famous region that we’d long taken for granted as California natives. Major success on sipping lots of great wines and enjoying some great family time in Northern CA.

Wine Tasting through Bordeaux

Two Days in Bordeaux

9What wine lover doesn’t have Bordeaux on their bucket list? Burgundy and Bordeaux were two outstanding French wine regions for us so when I had the opportunity to spend two days in Bordeaux and then cruise the waterways with Scenic for a week, I jumped on it last minute. The town of Bordeaux itself exceeded my expectations and touring St. Emilion and the right bank was a fabulous final send-off for us. Now that we’re spending more time in Italy going forward, it’s a place that we hope to return to. โœจ

Exploring Italy During Its Reawakening

Venice Italy

8After our three weeks in Kenya earlier this year, we jetted off to Italy for three additional weeks… which turned into seven given our home island’s lockdown. We were on the search for a property that would fit into our wine-focused hotel concept and were granted entry for work purposes during Italy’s red zone. It was simultaneously eerie and magical to be there as Italy moved from the red zone to yellow and began its slow reawakening. We walked through Venice sans tourists (we were quite literally the only people in St. Mark’s Square one evening) and bounced around to take advantage of exploring Italy’s hot spots as they began to reopen after an all-too-long slumber.

๐Ÿ‘‰๐Ÿผ Read more about traveling to Italy during COVID,ย my take on Cinque Terre vs the Amalfi Coas,ย and how to spend two days in Portofino.

Experiencing Southern Italian Culture in Puglia

One Week in Puglia

7With five months in Italy this year, it’s no wonder that Italy is featured so prominently on this round-up list. With border crossings being a bit more complicated than usual this year, we made it a mission to dive deeper into Italian history and culture. Puglia ticked all the boxes for us: a contrast to the Amalfi Coast’s glitzy edge, with charming towns and a bit of an Italy-meets-Malta vibe. We spent one week in Puglia and adored our last few days of the summer sun.

Settling Back into Anguilla

COVAC Insurance

6Anguilla has been our home for nearly a decade so it’s often excluded from this list. This year, having spent nearly half of it off-island, we appreciated our returns to Anguilla more than ever before. Our house here, more than anywhere in the world, has unequivocally felt like our true home, and we now have the Anguillian passports to show for it! Our new half-and-half lifestyle split between Anguilla and Italy is allowing us to appreciate the island more than ever.

Seaside Lifestyles in Ibiza

Ibiza, Spain

5Ibiza challenged my preconceptions. The island had long been on my wishlist and when we had the opportunity to spend a week there with Scott’s family, we couldn’t pass it up. My focus on the Mediterranean for Compass & Vine has encouraged me to explore more of the region and assess it a bit more deeply. Ibiza’s party kid rep is only part of the reality; the wellness scene, boating opportunities, and stunning landscapes are another part of the story that often goes untold.

A Heritage Trip through Malta

10 Things to Do in Malta

4It had been over a decade since I had last visited the Maltese islands so when I had the opportunity to share my family’s homeland with my husband on a heritage trip through Malta, it was a no-brainer. I was impressed with Valletta’s renaissance, a city completely reborn in the past ten years, bringing a sexy-cool nightlife scene amidst a city of antiquity. We adored our brief day exploring Gozo, only wishing that we’d had more time to dedicate to enjoying Malta’s little sister island, and spent days visiting family, exploring age-old towns and fortresses, and exploring the islands by boat.

๐Ÿ‘‰๐Ÿผ Read up on 10 things to do in Malta.

Birthday Celebrations on the Amalfi Coast + Capri

Cinque Terre or the Amalfi Coast

3I’ll shoot it to you straight: I don’t care how touristy or overrun the Amalfi Coast and Capri can be, they’re a draw for a reason. Positano is charm embodied and Capri is a gem amongst gems with its stunning views, quaint piazzetta, fabulous shopping, and excellent dining. A decade ago when I first set eyes on the Amalfi Coast, I vowed that I’d return to what I was sure was one of the prettiest places on earth. When we made it back in May 2021, it was an easy pact for us to make when we decided that we’d continue to make the coast part of our regular travel circuit.

Read up on our itinerary for three days in Capri.

Friendsgiving in Morocco

Scarabeo Camp, Agafay Desert, One Week in Morocco

2There are trips that just hit right. They’re the right trip with the right people at the right moment in life. That was Morocco for us as we celebrated Friendsgiving with our besties in Marrakech, the Atlas Mountains and the Agafay Desert. I was zapped from weeks of long days, Zoom calls, and meetings, and needed a mental break in a major way. Perhaps it was the company as well, but our time in Morocco exceeded our expectations in a major way – a true North African gem.

Get our itinerary for one week in Morocco.

Going on Safari with Family in Kenya

Africa Travel Questions, Africa Travel Planning1And finally, because you simply cannot beat a trip to East Africa and also cannot beat spending time with family: Kenya.ย Our first (perhaps only) family trip to Africa was a major success. My parents fell in love with the pace, the culture, and the experiences, and left as major Africa advocates. It’s no secret that Africa is my zenned out happy place, and making it part of our annual tradition has been one of the most rewarding choices we’ve made when it comes to spending money on travel.

๐Ÿ‘‰๐Ÿผ Read about our experience hot air ballooning in the Masai Mara.


I’m looking forward to an exciting 2022, despite the undoubted challenges we’re facing as we start the new year. My parents and grandmother are slated to join us in Italy for New Year as we kick off 2022 in Venice! Wherever you’re closing out your year and welcoming the next, I wish you the absolute best for a year filled with love, laughter, and amazing memories.

Shannon Kircher, The Wanderlust Effect

More about Shannon Kircher

Shannon Kircher is the founder and editor of The Wanderlust Effect. Founded in 2009, she has continued to document her international escapes as an expat in Europe and the Caribbean. Additionally, Shannon is the founder of Compass & Vine, a luxury boutique travel design firm, and is the Director of Marketing for the Frangipani Beach Resort. Shannon holds an MSc in Social Policy and Development from the London School of Economics and is a current candidate for WSET Level 3 in Wines & Spirits.