Five Fabulous Dream Holiday Itineraries

It’s the dog days of summer. The air is thick, the breeze barely blows. Summer vacation has come and gone. For many, school is back in session.

It is during these days of limbo, precariously balanced between the waning summer and waxing autumn, when my travel dreams kick into full gear.

I blame the heat.

During these stifling afternoons, I like to fire up the computer and scour the search engines for deals on a dream holiday. My love for anticipation gets the better of me. I get a deep satisfaction seeing a calendar with days blocked off, a week held in October, or over the holidays, left for me to fill with adventure, a lovely hotel room, and lots and lots of food.

A whole week, on the distant but glittering horizon, for my next vacation.

If you are like me, itching to book your next flight, never fear. Here are five itineraries that I’ve been dreaming of – holidays that are on my personal short list.

Five Fabulous Dream Holiday Itineraries: The fun Key West

The Florida Keys

The Florida Keys are ideal for a holiday because they feel like the Caribbean, with its quirky villages and local characters, but you can travel the distance by car. The beauty of the Keys is that you can explore at a slow pace, and the total distance isn’t too far. Without stopping, the whole stretch can be covered in under 2.5 hours.

Given a full week, you’ll find me spending a night or two on each of the major keys: Key Largo, Islamorada, Marathon and Key West.

Start your journey in Key Largo, the easternmost key in the chain. There is an unwritten rule (say us) that having a daily piece of key lime pie is basically a requirement, and there are plenty of online resources to direct you to the best spots for your sugar fix. Other Keys highlights include the Turtle Hospital in Marathon which has been rescuing and rehabilitating sea turtles for decades and Ernest Hemingway’s house in Key West. Sprinkled up and down the Keys are funky outdoor restaurants and bars, lots of kitschy gift shops full of seashells and a plethora of ocean-front hotels to call home.

You’re guaranteed to leave the area refreshed and revitalized…and also with an extra few pounds thanks to all that pie.

Five Fabulous Dream Holiday Itineraries: Cartagena, Colombia

Cartagena & Bogota, Colombia

For US-based travelers, Colombia is one of those destinations that should be much more popular given its proximity to the States. Fly to Cartagena, a colonial walled city that is a great introduction to the country. Wander the Old Town, and sample the fabulous food (Carmen restaurant gets consistently great reviews). After a couple days soaking in the history of Cartagena, take a bus to Tayrona National Park, which is home to one of the highest coastal mountain ranges in the world, right on the sea.

You don’t see that combination too frequently!

Hike, explore and spend the night in the park (in a hammock!), or head to nearby Guachaca, home to lovely pristine beaches and small family-run inns. After you have had your fill of beach, travel back to Santa Marta where you can catch a short flight will take you south to Bogota, Colombia’s capital. In Bogota, be sure to visit the Paloquemao Market, where you’ll find exotic local fruits like feijoa, araza, guanabana, maracuya and lulo – many of which are seldom found outside of Colombia. The gold museum also comes highly recommended. For that quintessential panoramic photo, take a cable car up Montserrat to get a great view of the city.

Five Fabulous Dream Holiday Itineraries: Copenhagen, Denmark and Gothenburg, Sweden

Copenhagen, Denmark & Gothenberg, Sweden

For lovers of the European television show The Bridge, you already know that Copenhagen, Denmark and Malmo, Sweden are connected by the beautiful Øresund Bridge that rises out of the sea (via tunnel, very creepy). It’s easiest to fly in and out of Copenhagen for most visitors, and a few days exploring coastal Sweden by car will give you a taste of the country.

Copenhagen is well known in Europe as a food lover’s paradise. Noma, one of the world’s most famous restaurants, put Copenhagen on the map, and these days the city is speckled with restaurants run by former Noma chefs. When we spent the weekend there, we enjoyed long walking tours, the Tivoli Gardens, a visit to Carlsburg brewery, and the many museums.

Of course, we planned our entire visit to Copenhagen around the food – booking restaurants first and filling in the rest. It did not disappoint!

With a rental car, cross the famous bridge into Sweden and head north to the town of Gothenburg (about a three hour drive). It’s a city that is the perfect size for two or three days. Highlights include the Gothenburg Museum of Art, the gorgeous local opera house and Liseberg Amusement Park, Sweden’s most popular tourist attraction (3 million visitors per year!). For food, look no further than the Saluhallen Market Hall, home to 40 vendors and small restaurants, good for any time of day. When it’s time to return home, reverse your steps back to Copenhagen and depart.

Five Fabulous Dream Holiday Itineraries: The Garden Route road trip in South Africa

South Africa Road Trip

It is possible to see the highlights of Africa without an official tour, and a self-guided drive in South Africa is just one of those adventures. Start and end your journey in Cape Town. There, you can visit Table Mountain, take a swim with seals or sharks (or both, who are we to judge?), see Robben Island (where Nelson Mandela was jailed), or take a local cooking class.

After a couple of days in the city, pick up a rental car (we’ve seen rates as low as £20/$30 per day). The major scenic driving route in South Africa is called The Garden Route. A five-day round trip is sufficient to drink, eat and sight see comfortably. Drive east to Knysna during the first day. On day 2, take a day trip to Plettenberg Bay and Tsitsikamma National Park, returning to Knysna in the evening.

The next day, head inland via the scenic Outeniqua Pass to Oudtshoorn. Up here you can visit an ostrich farm, those crazy looking dinosaur birds that fascinate us. Take a long day to drive from Oudtshoorn to Karoo National Park, stopping at Cango Caves on the way for a walk around. On the way back to Cape Town the next day, stop at the Victorian village of Matjiesfontein and consider a winery visit (or two!) in Breede River Valley.

And don’t forget to pop a few bottles of some fabulous South African wine!

Five Fabulous Dream Holiday Itineraries: The islands of Thailand

Thailand Islands

Thailand is an amazing destination and many travelers’ favorite country. But Bangkok is insane. We loved it but after two days of soaking in the Bangkok culture in sweltering heat, we would have loved to hop on down to the coast to see another whole side of the country. For this holiday, arrive into Bangkok and give it a day or two of your time. There are lots of highlights here, from Wat Arun to Wat Pho to the Grand Palace.

After a few days of city life, take a sleeper train overnight to Surat Thani and wake up in paradise. Well, almost. A connecting bus will take you to Ao Nang, a lively beachside town where you will be stationed for a few relaxing days. From this point, there is a lot to do.

Scuba abounds here, as well as rock climbing, or you can rent a bicycle to ride around, or take a cooking class, or even take a boat trip out to one of the outlying islands. Or just relax some more.

Your next beach destination is Ko Yao Noi, about two hours south of Ao Nang. This island is off the well-trod tourist path and is home to stretches of empty beach, plenty of good snorkeling and the opportunity to hire a boat to explore even more islands offshore.

Finally, make your way to Phuket, the final destination of the holiday. Phuket is Thailand’s largest and most visited island (and home to a large airport!). Here, you can splurge out on a fabulous resort, or steer to more budget accommodation. Stop by the Khao Phra Thaeo Wildlife Sanctuary, or use your time to see a Thai boxing exhibition. The various beaches around the island have different vibes, so do some research and find your perfect final resting place. If this isn’t the definition of the ideal beach holiday, I don’t know what is!

Dream Holiday Itineraries

So, there you have it.

Five fantastic ideas for your next dream holiday. I’m leaning to the Florida Keys in winter, but the Thai Islands also sound amazing.

If these itineraries are the kind of dream-inducing snack you need to make your next vacation a reality, why not check out the other 47 itineraries that we have put together into a fabulous and free e-book? Subscribe to our monthly newsletter (at the bottom of this page) and we’ll send you 52 Vacation Itineraries, our free eBook that will keep your travel calendar full for a lifetime!

What’s your dream holiday trip? Share your thoughts below!

Dream Travel Itineraries!

  • August 11, 2016

    These trips look awesome- I particularly want to visit Copenhagen…
    sophie nadeau recently posted…BISE ETIQUETTE: COMMENT FAIRE LA BISE?My Profile

  • August 13, 2016

    I love all your suggestions, and would be happy to go on any of those trips. My favorite, though, is South Africa. We didn’t do a road trip but seeing all that breathtaking scenery and those gorgeous animals was amazing.
    Lois Alter Mark recently posted…life reimagined: my organization projectMy Profile

  • August 13, 2016

    Copenhagen, Denmark & Gothenberg, Sweden and Thailand are on my to-go-to-list…Thanks for sharing this post its motivating!!!

  • August 13, 2016

    I was just reading this alongside my bucket list… Cartagena we’re going next year during our trip to Colombia. Florida Keys is a large gay destination which we keep hearing a lot about, so saving that one for a big road trip across the States.

    • August 15, 2016

      Have fun in Cartagena! Well, I think you will have fun on your entire South American adventure for that matter! Enjoy your cruise too!

  • August 13, 2016

    That South African road trip looks absolutely epic! Table mountain, of course, is a must but taking in the landscape would be unforgettable. I’d also like to get back to Sweden. I was just in Stockholm and Lapland, so seeing the southern portion and Denmark would be great!
    Jackie Sills-Dellegrazie recently posted…United Changes Stopover Rules on Award FlightsMy Profile

    • August 15, 2016

      Denmark, especially Copenhagen, is fantastic. Highly recommended!

  • August 13, 2016

    With the horrible weather we’ve been getting here in Finland, I sure won’t mind a lovely trip somewhere nice!
    Evan Kristine recently posted…Hello past meet present. It is quite a wild introduction, is it?My Profile

    • August 15, 2016

      Bad summer in Finland? That’s too bad. I was there last July and lucked out with amazing weather. Sunny and 28C. I actually got a tan in Finland!

  • August 14, 2016

    Cartagena is on my radar but I can’t fund any decent flights!

    • August 15, 2016

      it’s the one downside about Cartagena. JetBlue and Spirit fly there and have deals from time to time, but certainly have to time it right

  • August 14, 2016

    Actually a driving tour of South Africa (the Wine trail) is very much on mine;)
    Fiona Maclean recently posted…#Giveaway Identicals DVD #WinMy Profile

  • August 14, 2016

    I would love to plan a food trip to Copenhagen and Sweden. Where did you eat? And, I’ve always wanted to visit the Thai islands. Thanks for reminding me!

    • August 15, 2016

      We loved Relae and Manfred and Vins in the Nørrebro area of Copenhagen. Same chef, with Relae being a little more upscale. Loved the hot dog stands too!

  • August 15, 2016

    I’ve been wanting to visit Bogota and Cartagena for ages now – we’re in Mexico City so really not very far away at all! I’d also love to go to Copenhagen….Actually, I’d like to go to all these places!
    Katja Gaskell recently posted…Sweden with Kids: De-stress (with your kids!) in a Family-Friendly SpaMy Profile

  • August 16, 2016

    Oh, I’m all in for the Carribean but my heart always falls for those lovely European towns and sights. That long road shot from South Africa’s just beautiful!