The hit BBC programme Race Across the World was the talk of the office here at Flying Colours and what overland travel route we would all take. If you haven’t seen it before, five pairs must race from one location to another – this time it was across Canada – hitting checkpoints along the way. The catch is, they can’t take any flights and they have a limited budget to travel with. Some teams are eliminated along the way and the first team to reach the finish receives a cash prize. Every week, it was a hot debate in the Flying Colours office about who would take the win.
The show also got us thinking about our travel plans, because even the teams that didn’t win the cash still got to experience a unique trip across Canada. They were able to see things that they otherwise would have missed if they had just jumped on a plane from one side of the country to the other.
There’s a lot to be said for travelling through places instead of flying. So, if you’re thinking about your travel plans in retirement or just planning your next family holiday, here are five of the best overland travel routes in the world.
Explore These 5 Incredible Overland Travel Routes
1. Central America – The overland travel route
Central America, the bridge between North and South America, is a very culturally rich region with lots of small countries to visit. The Central America overland route is one of the best ways to hit all the highlights and get a good sense of the whole area.
Mexico is an excellent place to start because you can spend a few days in vibrant Mexico City before heading south towards some of the more rural areas on the trip. The most common 24-day route then moves through Belize, Guatemala, Honduras, Nicaragua, and finally to Costa Rica.
The amazing thing about this route is the diversity of cultures and natural landscapes. You’ll see everything from white sandy beaches and barrier reefs to jungles and ancient Mayan temples.
If you want to get out of your comfort zone and experience a true adventure, this is the ideal trip.
Top 5 Things to Do When Traveling Through Central America in Retirement
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Live like a local for a stretch
Don’t just hop between tourist spots, spend several weeks (or months, if possible) in small towns or in more rural areas. This gives you a feel for daily life: food, customs, neighbours, healthcare access, cost, infrastructure. It also helps you to decide what kind of pace and setting suits you (coastal beach, mountain cool, jungle humid etc.) while giving time for things like learning basic Spanish/Kriol/local dialect, discovering travel logistics. However some areas can be remote, have less reliable services (electricity, water, internet). Homesickness or culture shock can be bigger long-term in less tourist-oriented places. -
Explore natural landscapes & biodiversity
Central America is rich in volcanoes, rainforests, cloud forests, beaches, coral reefs. Things to try: night wildlife tours, birdwatching, hiking volcanoes (if fitness permits), snorkelling or scuba in reefs, exploring national parks. Costa Rica, Panama, Belize, Guatemala all offer excellent nature-oriented experiences. e.g. Tortuguero in Costa Rica for rainforests and turtle-nesting. We recommend this because the natural beauty is one of Central America’s biggest draws. As retired travellers you may have time to go off the beaten path. However it does have caveats that you should consider, such as the need to consider physical ability and safety; some trails or eco-parks can be more adventurous than comfortable. Wet or rainy seasons can make some places less accessible. Insects, tropical diseases etc. need preparation. -
Cultural immersion & history
Visiting indigenous communities, colonial towns, local crafts, markets, ancient ruins. For example, Guatemala has rich Mayan heritage & markets; Belize has Mayan ruins and local culture; walking tours of colonial Antigua etc. These kinds of experiences often are the most memorable; helps you understand more than just “holiday version” of the place. Sometimes language barriers, tourism commercialisation (some “authentic” experiences are very staged), infrastructure or accessibility in remote cultural sites. Also, cultural sensitivity is key: be respectful. -
Check out retiree / expat hubs & retirement systems
Even if not retiring immediately, visiting places where many retirees live can show you what works (and doesn’t). See how healthcare, cost of living, safety, amenities compare. Explore local visa/retiree programmes. Panama, for example, is often considered top destination. You’ll want to know where services are good, what legal/residency issues are, how easy travel to/from your home country is. In some areas expat enclaves are comfortable but can be expensive; you may miss out on authentic local life. Also not all services are consistent in rural or smaller towns. -
Travel slowly & seasonally
Plan itineraries to avoid extremes (too rainy, too hurricane-prone, too hot etc.), allow enough time to recover from travel, take rest days. Use slower transport where possible (bus, boat) to really see landscapes, rather than always flying. Mix active days with easy days. At this stage of life many travellers prefer comfort & meaning over rushing. Also reduces risk of burnout or health mishaps. However, take into account that slower transport can be uncomfortable or unreliable; some seasons bring storms or heavy rains that might disrupt plans.
2. The Baltics – A Hidden European Gem
“The Baltic States” is a collective term for three countries: Estonia, Latvia, and Lithuania. This area of Europe has become more popular with travellers in the last few years because of its unique history and incredible medieval architecture.
It’s also very affordable, which is good news if you are planning a long road trip through all three countries.
The city of Kaunas in Lithuania is a brilliant starting point as it’s centrally located and has plenty going on. It was European Capital of Culture in 2022, so you’ll find all kinds of great museums and historical buildings to explore.
From here, you can travel through Lithuania, visiting the coastal town of Klaipeda and the capital city of Vilnius along the way. In Latvia, highlights include Daugavpils – a less touristy city where you can get a real sense of life in the country.
Most people then choose to end their trip in Tallin in Estonia. This is perhaps the most modernised city in the region, but it is still steeped in history and culture, so you get the best of both worlds.
This is a great overland trip that can be as short or long as you want it to be, and you can easily do it by train too.
Top 5 Things to Do in the Baltics in Retirement
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Stroll through the medieval old towns
Explore Tallinn, Riga, and Vilnius. Each has a beautifully preserved historic centre, cobblestone streets, ancient churches, atmospheric squares, and a mix of Gothic, Renaissance, and Baroque architecture. Tallinn’s Old Town, for example, is one of the best surviving medieval walled towns in Europe. It’s great in retirement for the walkable, rich in history, good cafés and people-watching. The pace tends to be gentler. You should however, watch out for some streets being uneven cobblestones, which can be hard on joints. In winter, snow/ice can make walking more difficult. Also, on tourist high-days the narrow streets get crowded. -
Visit unique natural landscapes & parks
Get out of the cities. Some must-see natural wonders: Lahemaa National Park in Estonia, the Curonian Spit in Lithuania (with its dunes, forests, and beaches), and Kemeri in Latvia. There are bogs, forests, coastline, lagoons, very different from city-scapes. We love the peace, beautiful light, nature to explore at your own pace; good for outdoor lovers. However, access can be slower or more complex (buses less frequent, roads less maintained), weather can shift fast (rain, cold), and some places are remote so medical/help services may be farther away. -
Immerse in regional history & charred pasts
The Baltics have been under various rulers and empires: Teutonic Knights, Swedish, Russian, Soviet, etc. Museums of occupation, fortresses, castles (like Narva’s Hermann Castle in Estonia) give insight into struggles, resilience, identity. Also sites like the Hill of Crosses in Lithuania are evocative. It adds depth to your journey. Helps understand how history shaped today’s culture, values, languages. It’s important to consider that some of the stories/experiences are emotionally intense. Some museums might have less English translation. Physically climbing fortress walls or ruins can be harder. -
Experience local culture, crafts & food markets
Seek out local markets (e.g. Riga Central Market), crafts, textile-arts, folk music & song festivals (Baltic Song & Dance Festival happens across the three countries), local food tastes (rye breads, smoked fish, berry jams, foraged mushrooms etc.). Eating locally gives you flavour beyond tourist menus. Why it’s great if your looking for immersion, a slower pace, opportunities to meet locals, and low costs. You will have something new every day. Watch out for seasonality, some markets are more active only certain months; festival schedules vary; small towns may have fewer restaurant options or English menus. -
Discover off-the-beaten-path towns & hidden gems
Don’t just stick to capitals. Communities like Cēsis in Latvia, places like Sigulda (with Gutman’s Cave), or Alatskivi Castle in Estonia, or the dunes of Vecekrugas on the Curonian Spit are quieter, less crowded, and often more authentic. We love them because they are more relaxed, cheaper, you often feel you’re discovering rather than following. Lots of charm.
Challenges: Infrastructure might be more basic (slower transport, fewer amenities), signage or services in English can be less common, lodging might be simpler.
3. The Silk Road – A Journey Through History
The Silk Road is a network of trade routes that connected China with the Far East and Europe and changed the course of history forever.
Now, it’s a superb way to explore vast swathes of the world on some amazing overland routes. It would take years to explore every single route, but there are some well-established shorter journeys you can take.
The “five stans” is a popular trip that takes you through Turkmenistan, Uzbekistan, Tajikistan, Kyrgyzstan, and Kazakhstan. Or perhaps you’d prefer a highlights tour of China, Tibet, and Nepal in a month-long trip?
There are also some extended trips available if you want a true adventure. You can travel all the way from Istanbul to Beijing in three months, for example, hitting 11 different countries along the way.
Top 5 Things to Do When Travelling the Silk Road
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Walk the ancient cities of Central Asia
Visit places like Samarkand, Bukhara, Khiva in Uzbekistan, cities where stunning mausoleums, madrasas (Islamic schools), old caravanserais, and ornate bazaars still stand as they did centuries ago. The Registan in Samarkand is a highlight: three madrasas with beautiful tile-work, shaded courtyards, and a sense of grandeur. -
Stay among the landscapes — lakes, mountains, deserts
Go beyond the cities. For example, spend time by Issyk Kul in Kyrgyzstan, trek or relax in the Tien Shan mountains; cross deserts and oases, or stay in yurts. These quieter, scenic areas give you space to breathe, reflect, and take things at a slower pace. -
Explore off-grid archaeological ruins & UNESCO sites
Some gems are less visited but deeply rewarding: the ruined city of Navekat (Nevkat) in Kyrgyzstan, the Rawak Stupa in China’s Xinjiang, old fortresses and caravanserais along desert routes, ancient Buddhist grottoes. These show you the Silk Road’s layered history — religions, trade, changing empires. -
Engage with local culture, crafts & cuisine
Spend time in bazaars, try local food (plov, breads, fermented dairy, regional spices), attend traditional music or folk events. Visit artisans (pottery, tile-making, carpets) to see how old crafts survive today. Meet local people — stay in family-run guesthouses. This gives the journey richness beyond just photo stops. -
Plan with comfort, pacing & seasonality in mind
Because many Silk Road areas are harsh: deserts get extreme heat, mountains get cold, remote places have minimal amenities. Pick times of year when temperatures are moderate (spring, early autumn). Build in rest days. Use comfortable transport (trains, good-quality buses, private cars) rather than trying to push every link. Doubling up nights in one place so you can recover after long travel days.
4. Scotland North Coast 500 – The UK’s Ultimate Overland Route
You don’t necessarily have to travel halfway across the world to find a great overland route to enjoy. If you are looking for something closer to home, the Scotland North Coast 500 (NC500) is perfect.
This 500-mile route follows the north coast of Scotland, taking in the amazing scenery of the highlands, with plenty of places to stop off along the way.
The great thing about this route is that you can customise it to your tastes. The journey starts and ends at Inverness Castle and you’ll probably want to visit spots like Loch Ness along the way, but beyond that, it’s up to you.
You could explore some of the best places for local food and drink, find some famous whisky distilleries, go hiking, or tour some of the top golf courses in the world.
Top 5 Things to Do on the Scotland North Coast in Retirement
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Drive or take stretches of the NC500 at a relaxed pace
The North Coast 500 is one of the premier routes in Scotland — over 500 miles of coastline, remote single-track roads, rugged scenery, quiet villages, beaches, lochs, mountains. You can stop when you like, linger in a place with good views, and avoid trying to “do it all in one go.” The route gives you an intimate feel for Highland life, the coast, and nature. -
Walk or hike some gentler trails & viewpoints
There are many accessible walks: Glas Leitir trail at Loch Maree, short woodland walks in Beinn Eighe Nature Reserve, viewpoints such as at Kylesku Bridge, or the easier heights like Cnoc an Fhreiceadain for coastal views. -
Visit isolated beaches and coastal bays
Some of the most magical spots are the beaches like Achmelvich Bay, Oldshoremore Beach, and Durness coastline. White sands, sea air, dramatic shorelines. Perfect for strolls, wild swimming (if you’re brave), picnics, reading by the water. -
Discover small historic ruins & castles in dramatic settings
Scotland’s North Coast is full of atmospheric history: Ardvreck Castle on Loch Assynt, old fishing villages, ruined castles, ancient structures, etc. These sites often don’t require intense exertion to enjoy, are photogenic, and invite contemplation. -
Get off the beaten path for peace & wildlife
Islands like Handa, remote peninsulas, bird-reserves, cliff walks, spotting eagles or other wildlife, enjoying the quiet nights. There’s something restoring about being somewhere where the sky is big, the air is fresh, and the “noise” of traffic and crowds is rarely heard.
5. The Hippie Trail – A Classic Overland Travel Route
The Hippie Trail was a cultural phenomenon in the 1960s and 1970s, which saw thousands of westerners travelling overland from London all the way to Delhi, India.
While the 6,000-mile trek is not as popular as it once was, it’s an outstanding route that takes you through Europe to Istanbul and then through the Middle East all the way to India. In the past, travellers completed much of the journey on buses or by hitchhiking, but that’s all changed now.
These days, you can do the trip in a few months with a combination of flying, driving, and trains. Splitting it up and following smaller sections of the journey is a good option too.
Top 5 Things to Do on the Hippie Trail
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Start in Istanbul & soak in the meeting of East & West
Begin your overland journey in Istanbul. Wander the old streets of Sultanahmet, take ferry rides across the Bosphorus, explore bazaars like the Grand Bazaar and Spice Market, enjoy Turkish tea in neighbourhoods like Kadıköy and Üsküdar. The feeling of stepping from Europe into Asia begins here, architecture, food, history all interlaced. This sets the tone before things get more remote. -
Traverse Anatolia & the historic sites in Turkey
As you move east, explore places like Cappadocia (fairy chimneys, cave homes, hot air balloons), the Lycian Coast, ancient ruins like Ephesus, Troy, Pergamon. These places offer combinations of scenery, culture, history — typically easier to access, more comfortable lodging and services, which is good for easing into the more adventurous legs of the trail. TravelTwins’ modern version of the Hippie Trail emphasises this stretch through Turkey and northern Iran as rich and rewarding. -
Experience the cultural depth of Iran
If geopolitics and safety permit, Iran offers enormous rewards: the medinas of Tehran, Isfahan, Shiraz, gardens, Persian architecture, poetic history, hospitable people. Towns like Tabriz, Yazd, Kashan, and the old caravan routes or villages give insight into traditional life. The landscapes (mountains, deserts) are striking and varied, giving both beauty and contemplation away from urban energy. (The TravelTwins route includes Azerbaijan/Iran-villages and Alborz Mountains before Tehran.) -
Cross into South Asia—Pakistan, India & Nepal — for contrast
Once you pass Iran (or its eastern border), entering Pakistan (Lahore, Peshawar) then moving on into India and possibly Nepal, you get sharp contrasts: in chaos, in colour, in density of people, in sounds, smells, cuisines. Visiting places like the old bazaars, historic temples and mosques, sacred rivers, mountain landscapes (Himalayas) makes the latter part of the trail deeply memorable. The trail’s end in Kathmandu (or further into Nepal/South India/Sri Lanka) is often where people pause longest. -
Stay off-beat, connect with locals & build rest days
This isn’t a “fly-in, check-off, fly out” route. Some of the richest moments come from slower transit, staying in family-run guesthouses, spending nights in small towns or villages, tea with locals, hearing stories in bazaars, maybe even volunteering or helping locally. Also, plan rest days — after long border crossings, mountain drives, or days when travel has been rough. Use quieter places to recover, reflect, not just push ahead.
Get in touch
As you start thinking about retirement, you may be planning a big trip like this. We can help you ensure that you have the income that you need to achieve it.
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Please note
This blog is for general information only and does not constitute advice. The information is aimed at retail clients only.
Written: 31 July 2023
Updated: September 17th 2025