One of the questions we get asked all the time is, “Where should we travel next?”
Our answer is almost always the same: it depends on when you’re planning on going!
The best destinations change throughout the year – weather, crowds, wildlife, seasonal events, and even airfare can all influence whether a place feels magical or disappointing.
If you’re looking for inspiration, here’s where we’d travel each month of the year, along with some of our favorite experiences in each destination!
January
Costa Rica
January is one of our favorite months to visit Costa Rica. The dry season is in full swing, making it perfect for both beach days and rainforest adventures.
We especially love the Papagayo Peninsula, Las Catalinas, and Tamarindo!
Must-do experiences:
- Catamaran charter with Manta Ray Sailing
- ATV / UTV tour with Flamingo Adventures
- Deep sea fishing charter with Ocean Life
For adventure, go ziplining through the rainforest or hike around Arenal Volcano before relaxing in nearby hot springs!
February
The Caribbean
February is one of the best times to escape winter, and the Caribbean offers beautiful weather without the extreme summer heat.
Our favorite islands include:
- USVIs (especially St John!)
- BVIs (especially Jost Van Dyke!)
- Anguilla
- St. Barth
- St Kitts & Nevis
Must-do experiences:
- Spend a day on Trunk Bay Beach in St John
- Charter a private boat with Midnight Sun and zip around the USVIs or BVIs for the day!
- Book a daybed at Nikki Beach in St Barth
For something active, paddle boarding through calm, turquoise water or taking a guided snorkeling excursion to explore marine life are always great options!
March
Japan
March marks the beginning of cherry blossom season in many parts of Japan, making it one of the most beautiful times to visit.
We recommend splitting most of your time between Tokyo and Kyoto (though there are SO many other destinations throughout the country to visit as well)!
Must-do experiences:
- Visit Senso-ji Temple
- Wander through Tsukiji Fish Market
- Eat ALL the amazing food – wagyu beef, fresh sushi, ramen … the list goes on & on!
For more adventure, hike through the thousands of torii gates at Fushimi Inari Shrine or explore the bamboo forest in Arashiyama!
April
The Netherlands
April is one of the most beautiful times to visit the Netherlands. Tulip season is in full bloom, the days are getting longer, and the weather is usually mild enough for plenty of outdoor exploring.
We recommend spending time in Amsterdam, then taking a day trip into the countryside to see a quieter side of the country.
Must-do experiences:
- Visit Keukenhof Gardens while the tulips are in bloom
- Take a canal cruise through Amsterdam
- Explore the windmills and traditional Dutch houses in Zaanse Schans
For something more active, rent a bike and ride through the countryside. It is one of the best ways to enjoy the tulip fields and experience the Netherlands like a local!
May
Greece and the Greek Islands
May is one of our favorite times to visit Greece. The weather is warm, the islands are coming back to life, and you can enjoy popular destinations before the busiest summer crowds arrive!
We especially recommend Santorini, Paros, and Naxos. We visited Santorini in May, and it was a beautiful time to experience the island!
Must-do experiences:
- Spend the day at Wet Stories Beach Club in Santorini
- Book a sunset catamaran charter with Sunset Oia
- Enjoy fresh seafood and traditional Greek dishes at a waterfront taverna (we loved Sunset Ammoudi in Ammoudi Bay!)
For something more active, hike from Fira to Oia for incredible views of Santorini’s coastline and caldera!
June
Scotland
June is a beautiful time to visit Scotland. The countryside is lush and green, the days are especially long, and the mild temperatures are perfect for road trips and outdoor adventures!
We visited Scotland in September and fell in love with its dramatic landscapes, historic castles, and charming towns. For longer days and slightly warmer weather, we recommend planning your trip in June!
Must-do experiences:
- Explore Edinburgh Castle and walk the Royal Mile
- Take a boat ride across Loch Ness and visit Urquhart Castle
- Spend a day on the Isle of Skye exploring its rugged coastline and small villages
For something more active, hike through the Scottish Highlands or walk to the Old Man of Storr for incredible views!
July
Alaska
July is one of the best months to visit Alaska. The days are long, temperatures are generally mild, and there are excellent opportunities to spot whales, bears, eagles, and other wildlife!
We have visited Alaska before and are returning next July for our group cruise on Explora Journeys! A cruise is one of our favorite ways to experience the state because it allows you to see remote ports, dramatic glaciers, and incredible scenery in one trip.
Must-do experiences:
- Cruise through a glacier-filled area like Glacier Bay or Hubbard Glacier
- Go whale watching in Juneau
- Ride the White Pass & Yukon Route Railway from Skagway
For something more adventurous, kayak near a glacier or book a helicopter tour that lands directly on one!
August
The Canadian Rockies
August is a beautiful time to visit the Canadian Rockies. The lakes are typically their famous turquoise color, the mountain roads are open, and most hiking trails are accessible.
We have not made it to the Canadian Rockies yet, but it is very high on our bucket list! Banff and Jasper look like the perfect combination of dramatic scenery, outdoor adventure, and charming mountain towns.
Must-do experiences from friends:
- See the turquoise water and mountain views at Moraine Lake
- Spend time at Lake Louise and rent a canoe
- Drive the Icefields Parkway between Banff and Jasper
For something more active, hike to the Lake Agnes Tea House for beautiful views and a well-earned treat at the top!
September
The Western Mediterranean
September might just be our favorite time to visit the Western Mediterranean! The weather is still warm, but the intense summer heat begins to ease and crowds often start to thin as the month continues.
This region includes incredible destinations throughout Italy, the South of France, and Spain, along with islands like Capri, Sardinia, Corsica, and the Balearic Islands. We always recommend a Mediterranean cruise as a “sampler platter” for your first visit. You can experience several destinations in one trip, discover your favorites, and return for a longer stay later!
Must-do experiences:
- Explore the colorful towns and dramatic coastline of the Amalfi Coast
- Visit the seaside villages and glamorous ports of the French Riviera
- Experience Barcelona’s architecture, food, and lively neighborhoods
For something more active, hike the Path of the Gods along the Amalfi Coast, bike through the Tuscan countryside, or kayak along Spain’s beautiful coastline!
October
New England
October transforms New England into one of the most beautiful places in North America. The fall foliage brings brilliant shades of red, orange, and gold, while the crisp weather is perfect for scenic drives and charming small-town stops!
The timing of peak color varies each year and by location, so we recommend checking foliage reports as your trip gets closer. A road trip through Vermont, New Hampshire, and Maine is one of the best ways to experience the region.
Must-do experiences:
- Drive Vermont’s scenic roads and visit towns like Stowe and Woodstock
- Travel along the Kancamagus Highway in New Hampshire
- Explore Maine’s rocky coastline and spend time in Bar Harbor
For something more active, hike through Acadia National Park or rent bikes and ride along its scenic carriage roads!
November
French Polynesia
November is a wonderful time to visit French Polynesia before the holiday crowds arrive. The weather is warm, the water is beautiful, and the islands feel relaxed and peaceful.
We visited Bora Bora, Tahiti, and Raiatea during a cruise and loved seeing how different each island felt! Bora Bora may receive most of the attention, but French Polynesia has so much more to explore. We have also heard incredible things about Moorea!
Must-do experiences:
- Take a shark and ray snorkeling excursion
- Explore Tahiti’s waterfalls, markets, and black-sand beaches
- Discover Raiatea’s lush landscapes and important Polynesian history
For something more active, take a jet ski tour around Bora Bora, paddleboard across a calm lagoon, hike through Moorea’s dramatic landscape, or join a responsible guided excursion to swim with humpback whales in Moorea!
Whale season generally runs through November, although sightings and in-water encounters are never guaranteed, especially later in the month.
Final Thoughts
One of the easiest ways to improve any trip is simply traveling at the right time of year.
Matching your destination to the season often means better weather, fewer crowds, and more memorable experiences!
Whether you’re snorkeling in the Caribbean, hiking through the Canadian Rockies, sailing around the Greek Islands, or wandering Christmas Markets in Europe, every month offers somewhere incredible to explore.
If you’re planning your next trip and aren’t sure where to go based on your travel dates, we’d love to help you find the destination that’s at its absolute best when you’re ready to travel. Fill out the form below for our travel planning assistance!
