As an Amazon Associate I earn from qualifying purchases. This post may have Amazon and/or other affiliate links, which means I may receive commissions if you choose to purchase through the links I provide (at no extra cost to you). Please read my Disclosure Policy for more information. Thank you for supporting the work I put into this site!
How to Plan Your Travel Calendar: When, Where, How
Have you ever found yourself with four days off in a row and thought, I should go somewhere? You started to think about where you would want to go, got flustered, and decided to forget it. Then your four-day holiday comes up and you find yourself curled up on the couch binging Netflix and wishing you were on a beach sipping rum punch. I can relate. Many of us say we want to travel more, and we really do, but life gets in the way. Work gets crazy, family commitments increase, the house floods and you have to deal with mold. You know, the normal stuff. Years go by watching our friends take amazing vacations and we continue to say next year will be different. Let’s make next year different! Use this guide to create a travel calendar and be prepared for the next four-day weekend.
When is the Best Time to Travel
What are your travel goals? How often would you like to travel? In a perfect world do you want to travel internationally for several weeks at a time? Or do you prefer a couple week-long domestic vacations? Maybe you want a combination of international travel mixed in with a few weekend getaways.
The first step to traveling more often is figuring out when you can take time off and how many days you have available. There’s a good chance you haven’t been using your vacation days and you have quite a few built up. Now that you know how many days of PTO you have available, sit down with a calendar, and block off ideal times for a trip.
If you burn through your vacation time caring for sick kids or waiting on repairmen to fix that mold problem, don’t give up. Check out these tips for planning a vacation with a full-time job. Now go back to that calendar and apply what you learned.
Where is the Best Location for Travel
The second step to traveling more often is figuring out where to go. This step is equally overwhelming. It’s a big world. There’s a lot to see and do. It’s hard to know where to start and no one has time to sit down and search the internet for the best time to visit every major city in the world, not to mention all the festivals and seasonal activities.
Jump to the season and/or month you identified for vacation and browse the notes. The advantages of travel during the shoulder season are lower prices, mild weather, and fewer crowds. Pay special events and festivals. Now is the time to dream. Fill possibilities into your calendar and ask friends or family for recommendations. Do a Pinterest and Instagram search. Google the destination + travel blog for other people’s experiences.
Winter Travel Calendar
For most people, a winter break involves escaping the cold weather and relaxing on a beach with an umbrella drink. There are many travel experiences you can only have in the winter. What’s on your winter bucket list? Would you like to see the northern lights, explore an ice cave in Iceland, dog sled in Alaska, kayak with penguins in Patagonia, ski the Alps, or browse the European Christmas markets? If your budget doesn’t allow for a European vacation, traveling off-peak season in the winter may be a solution. You will discover flights and accommodations cost less and there are fewer crowds during your visit. It is common to receive amazing customer service and upgrades during this time as well. Unfortunately, it can be grey and dreary without a dusting of snow days, many businesses are closed, and daylight hours are much shorter.
Where to Travel in December
It is the shoulder season in Costa Rica. Laos, Bangladesh, Thailand, the Philippines, Mexico, and the Caribbean typically have good weather. It is the beginning of the monsoon season in Northern Australia and Northern Brazil. Malaysia, Indonesia, and Papua New Guinea.
Christmas Markets [Europe, UK]
Hogmanay Street Festival [Edinburgh Scotland]
Junkanoo [Nassau Bahamas]
New Years Eve [Times Square NYC]
Where to Travel in January
It is the shoulder season in Egypt and Morocco. South Africa, Australia, and New Zealand are experiencing summer. It is the rainy season in Indonesia, Papua New Guinea, East Timor, and Polynesia. It is cyclone season in Madagascar, Reunion, Seychelles, and Mauritius.
Festival of Lights [Ghent Belgium]
Chinese New Year [Hong Kong China]
Up Helly Aa [Shetland Scotland]
Harbin Ice and Snow Festival [Harbin China]
Jaipur Kite Festival [Jaipur India]
Storyland Music Festival [Cartagena Colombia]
Where to Travel in February
South Africa, Egypt, Chile, and Argentina typically have good weather. It is the rainy season in Costa Rica, Indonesia, Papua New Guinea, East Timor, and Polynesia. It is the cyclone season in Madagascar, Reunion, and Mauritius.
Venice Carnival [Italy]
Rio Carnival [Rio De Janeiro Brazil]
Barcelona Carnival [Barcelona Spain]
Mardi Gras [New Orleans Louisiana]
Art Deco [Miami Florida]
Chinese New Year [Bejing, Singapore]
Ice and Snow Festival [Harbin China]Yuki Matsuri Snow Festival [Sapporo Japan]
Yanshuei (Yanshui) Beehive Fireworks [Tainan Taiwan]
Pingxi Sky Lantern Festival [Taipei Taiwan]
Busójárás Winter Scare away Festival [Mohács Hungary]
Spring Travel Calendar
Spring travel is difficult. There’s a good chance of snow through April and rain through May. Cities look grey without green trees and grass. Yet, it is a shoulder season with lower prices and fewer crowds. If you find yourself with time off in the spring consider walking under the Spanish moss in Savannah Georgia, attending a cherry blossom festival, visiting a tulip field, or finding out for yourself why people rave about springtime in Paris.
Where to Travel in March
It is the shoulder season in Hawaii, Brazil, and India. Columbia, the Middle East, and Egypt typically have good weather. It is the rainy season in Kenya, Tanzania, and Uganda.
Desert in Bloom [Petra, Egypt]
Holi Colour Festival [Bharatpur India]
St Patrick’s Day Festival [Dublin Ireland]
Las Fallas [Valencia Spain]
Where to Travel in April
It is the shoulder season in Australia, and Western Europe. The Caribbean, Mediterranean, Crete, Cyprus, and Malta typically have good weather. It is very hot in Southeast Asia and humid in South America. It is the beginning of the monsoon season in Sri Lanka.
Keukenhof Garden Tulip Bloom [Lisse Holland]
Cherry Blossoms Bloom [Washington DC]
Cherry Blossom Festival [Tokyo, Kyoto Japan]
Rouketopolemos [Vrontados Greece]
Songkran [Thailand]
Where to Travel in May
It is the shoulder season in Bali, Croatia, and Japan. China and Peru typically have good weather. Egypt and the Middle East are becoming very hot. It is the beginning of the monsoon season in Thailand, Maldives, Vietnam, Cambodia, Taiwan, and Southeast China.
Floating Lanterns Festival [Honolulu Hawaii]
New Orleans Jazz Festival [New Orleans Louisiana]
Puffin Viewing [Iceland]
Battle of the Flowers [Cordoba Spain]
Cinco de Mayo [Mexico]
Fuji Shibazakura Festival [Lake Motosuko Japan]
Vivid Sydney [Sydney Australia]
Ramadan [Egypt, Indonesia, Malaysia, Morocco, and Turkey]
Green Rice Terraces [Philippines]
Monaco Grand Prix [Monaco]
Electric Daisy Carnival Music Festival [Las Vegas NV]
Summer Travel Calendar
Summer is the high tourism season with many families traveling. Days are long and typically full of sunshine. There are many bucket list festivals scheduled throughout the summer months. Beach vacations and adventure travel is also in high demand during the summer.
Where to Travel in June
It is the shoulder season in Baja Mexico. Europe, the UK, Scandinavia, Toronto, Brazil, and Thailand typically have good weather. It is the beginning of the hurricane season in Florida, the Caribbean Islands, and the Gulf of Mexico. India and Sri Lanka are in the monsoon season and Sub-Saharan Africa and the Middle East often have heat waves.
White Nights Festival [St Petersburg Russia].
Scarlet Sails [St Petersburg Russia]
Electric Forest Music Festival [Rothbury Michigan]
Scottish Highland Games
Glastonbury Music Festival [Worthy Farm UK]
Batalla del Vino [La Rioja Spain]
Where to Travel in July
It is the shoulder season in the Northern Caribbean. Canada, the United States, Europe, Seychelles, and Indonesia typically have good weather. It is monsoon season in India, Sri Lanka, and Southeast Asia. The Middle East, North Africa, and Sub-Saharan Africa often have heat waves.
African Wildlife Migration [Tanzania, Kenya]
Pflasterspektakel [Linz Austria]
Calgary Stampede [Calgary Canada]
Bastille Day [Paris France]
Spice Mas Carnival [Grenada]
Carnival [Saint Lucia]
Umbrella Sky Project [Agueda Portugal]
Lavender Fields in bloom [Provence France]
Tour de France [France]
Boryeong Mud Festival [South Korea]
Burning Man [Black Rock City NV]
Where to Travel in August
The Mediterranean typically has good weather. The Caribbean and Central America are in hurricane season and Cuba is typically hot and humid.
Fringe Festival [Edinburgh Scotland]
Military Tattoo [Edinburgh Scotland]
Grand Place Carpet of Flowers [Brussels Belgium]
Obon Lantern Festival [Tokyo Japan]
La Tomatina Festival [Valencia Spain]
Fall Travel Calendar
Fall is a great time to travel. Days are warm and there is plenty of sunlight. Fall travel items to tick off the bucket list are visiting Oktoberfest, Salem at Halloween, seeing the Fall colors in New England, attending the International Balloon Fiesta, or participating in a lantern festival.
Where to Travel in September
It is the shoulder season in Northern Europe, South Africa, and India. The UK, Hawaii, Toronto, Croatia, Greece, and Portugal typically have good weather. Madagascar, North Africa, the Middle East, and Central Asia also typically have good weather. Monsoon and hurricane season continues in Southeast Asia, the Caribbean, and Central America.
Oktoberfest [Munich Germany]
Where to Travel in October
It is the shoulder season in Southern Europe. The Mediterranean, Maldives, Argentina, Chile, Turkey, and Cyprys typically have good weather. It is the beginning of the monsoon season in Indonesia. It is typhoon season in the South Pacific and Southeast Asia and hurricane season in Mexico, Central America, and the Caribbean.
Fall Colors [Blue Ridge Parkway, Canadian Rockies]
International Balloon Fiesta [Albuquerque New Mexico]
Fantasy Fest [Key West Florida]
Halloween [Romania Transylvania]
Halloween Festival of the Dead [Salem Massachusetts]
Festival of Lights [Berlin Germany]
International Sand Sculpture Festival [Pêra Portugal]
Coachella Music Festival [Indio CA]
Where to Travel in November
It is the shoulder season in the Caribbean and South Pacific. North America, Europe, and East Asia are in the low season; Northern Africa is in the high season. Thailand, Cambodia, Vietnam, Bali, Singapore, and Malaysia. Tahiti, Fiji, South Pacific, Caribbean, Hong Kong, and Morocco typically have good weather.
Yi Peng Lantern Festival [Chiang Mai]
Day of the Dead Festival [Mexico City, Oaxaca]
Diwali Festival of Lights [India]
Monkey Buffet Festival [Lopburi Thailand]
Bookmark and Pin Travel Planning