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Your 2024 Travel Calendar: Where to Go & When to Book Your Trips

As we begin a new year, it’s time to start dreaming about where your travels will take you—whether it’s a romantic escape to the Italian coast, a family adventure at a luxury dude ranch or an African safari over the holidays. Though it may seem early to begin planning, advanced booking is essential in order to secure rooms at the top hotels, tables at the most popular restaurants and insider tours with the best guides. Here, Indagare maps out your 2024 travel calendar, including our travel tips and the best times to book each destination.

Contact Indagare to begin planning your next trip, or learn more about upcoming Indagare Journeys around the world.


Many of the world’s bucket-list destinations—and Indagare’s most beloved spots—can be visited throughout the year, but some require planning up to a year in advance.


Perfect for: Adventurers, Families, Romantics

Ideal Trip Length: 7 to 10 days. Note that the winter months experience very few hours of daylight, but this is also the best time to see the Northern Lights.

First-Time Musts: Exploring Reykjavik; soaking in the Blue Lagoon (currently closed due to volcanic activity); hiking through Thingvellir National Park; seeing a myriad of natural wonders, including waterfalls, glaciers, geysers, volcanoes and black sand beaches.

Indagare Tip: Though most first-time visitors stay near Reykjavik and the Golden Circle, adventurers should also head north to Deplar Farm, a one-of-a-kind resort with five-star service, ultra-posh lodgings and some of the best heli-skiing and fly-fishing in the world. Contact Indagare to book.

When to Book: 6 months in advance


Perfect for: Adventurers, Families, Romantics, Soul Searchers, Ultimate Indulgers

Ideal Trip Length: 10 days

First-Time Musts: Visiting the Ngorongoro Crater; seeing the Great Migration on the Serengeti; meeting local Maasai villagers

Indagare Tip: Avid climbers may wish to combine time on safari with a bucket-list summit of Mount Kilimanjaro (most treks take between six and ten days to complete). For this, it’s best to avoid the months of April, May and November, which are the rainiest.

When to Book: 1 year in advance

Parts of Tanzania are already sold out entirely for the Christmas to New Year’s window. To guarantee private vehicles, top lodges, and specific travel dates, I encourage people to book six to 10+ months in advance.”

Isabel Graubert, Trip Designer

New Zealand

Perfect for: Adventurers, Families, Romantics, Ultimate Indulgers

Ideal Trip Length: 9 to 14 days. Note that the winter months can be cold and rainy.

First-Time Musts: Enjoying first-rate golf courses and wineries near Hawke’s Bay; fly-fishing at Taupo; driving along the scenic coast track in Abel Tasman National Park; thrill-seeking in the “adventure capital” of Queenstown; viewing Milford Sound from above with a helicopter tour

Indagare Tip: For a pampering conclusion to an active trip, Fiji is an easy add-on after time in New Zealand (though not recommended during typhoon season from November through April).

When to Book: 1 year in advance. There is a backlog of trips booked in New Zealand, so reserving early with flexibility is key, even as we look ahead to 2023.

The Long Weekend

London Or Paris

Perfect for: Families, Romantics, Foodies, Intellectuals, Style Mavens, Art Lovers

Ideal Trip Length: 3 to 5 days

First-Time Musts: Visiting world-class museums and monuments; shopping in some of the world’s best boutiques; strolling classic neighborhoods; dining on Michelin-starred cuisine

Indagare Tip: Though both cities are easily navigated on your own, an expert guide can take you behind-the-scenes at popular sites and help you explore the city based on a particular passion, from history and art to fashion and food.

When to Book: 2 weeks to 1 month in advance, although busy periods, such as Paris Fashion Week, require additional lead time.

Related: Melissa Biggs Bradley’s Latest Paris Update

Join us for an art-focused Indagare Journey hosted by expert art historian Page Knox in Spring 2024. Celebrating French Impressionism runs May 1-5 in Paris.


Whether you’re escaping the chill with a Caribbean holiday or embracing the season with snowy adventures in Scandinavia, there are plenty of places to visit in the winter.


Perfect for: Romantics, Intellectuals, Families, Ultimate Indulgers, Soul Searchers

Why Go Then: The best time of year to visit is the fall and winter, when the weather is warm and dry (and you avoid the summer’s rainy season).

Ideal Trip Length: 8 to 10 days

First-Time Musts: Soaking in the history and nightlife of Bangkok; immersing yourself in the countryside and visiting a responsible elephant sanctuary in Chiang Mai or Chiang Rai; relaxing at a beach resort on a southern island

Indagare Tip: Both Phuket and Koh Samui offer luxury resorts with beautiful beaches, scuba diving and sea cave kayaking, but Phuket is best for scenesters looking to stay active, while Koh Samui is the more tranquil choice for wellness-seekers.

When to Book: 3 to 6 months in advance

Travel to Thailand has picked up in the years since the pandemic, and now everything is firing on all cylinders. This is Thailand's year—especially with the upcoming season of White Lotus filming here. The months of November through March are ideal.”

Sarah Minges, Associate Director, Industry Partnerships

South Africa

Perfect for: Adventurers, Families, Romantics, Foodies, Ultimate Indulgers

Why Go Then: Though South Africa is a year-round destination, the months of October through March are best for beach weather.

Ideal Trip Length: 10 to 16 days

First-Time Musts: Experiencing the rich and complex culture, history and culinary scene in Cape Town; soaking in the views from atop Table Mountain; tasting world-renowned wines in the scenic Cape Winelands; seeing the Big Five on safari in Kruger National Park

Indagare Tip: Don’t miss an excursion to the Cape Peninsula, including close-up encounters with African penguins and a scenic drive along the coastal mountain pass of Chapman's Peak.

When to Book: 6 months to 1 year in advance, although popular periods, such as the holidays, require additional lead time.

St. Barth's

Perfect for: Romantics, Style Mavens, Ultimate Indulgers, Foodies

Why Go Then: Though many hotels open in November, scenesters will want to wait until December, the beginning of the island’s peak season, when the weather is warm and comfortable, and the hotels, restaurants and bars are buzzing.

Ideal Trip Length: 5 to 7 days

First-Time Musts: Shopping at the chic boutiques in Gustavia and St. Jean; savoring fresh seafood at a trendy waterfront restaurant; enjoying a romantic picnic on a secluded beach

Indagare Tip: Book your rental car as soon as you book your hotel. Renting a car is a must for properly exploring, dining out and making the most of the fabulous shopping, but the island’s supply of vehicles is notably limited.

When to Book: 3 months in advance. The exception is the period between Christmas and the New Year, which books up as far as a year in advance and requires a minimum number of nights.

Sápmi, Sweden

Perfect for: Adventurers, Trailblazers, Families, Romantics

Why Go Then: The winter months offer the best opportunities for Northern Lights viewing, and outdoor enthusiasts will be thrilled by the myriad of snow-based activities.

Ideal Trip Length: 7 days

First-Time Musts: Seeing the Northern Lights; partaking in winter adventures such as ice-fishing, snowshoeing, Nordic skiing and snowmobiling; learning about the indigenous Sámi people

Indagare Tip: The food in the Lapland is nearly always locally sourced and delicious. Adventurous eaters should try the traditional dishes of reindeer and moose, though fresh fish, herbs, vegetables and berries are also common.

When to Book: 3 to 6 months in advance

Sweltering summers in the south of Europe have driven travelers north, up towards Scandinavia, where the weather remains cooler; empty, open landscapes roll on for miles; and the long (and light) days never seem to end. While summers in the north are enchanting, though, the winter months cannot be beat. A few years ago, if you had told someone that you’d be visiting Sweden or Finland in February, you’d likely be met with a skeptical glance, at best. However, travelers are more and more beginning to understand that the long and dark, starry nights serve as the perfect backdrop for magnificent northern lights sightings. The crisp, white snow cover is the ideal foundation for exhilarating sled-rides behind bounding huskies. And the sub-zero temperatures don’t feel nearly as cold when experienced from your steaming hot tub, a spiced glögg in hand. Many friends and members alike have come back, enamored, telling me that their trips to the north of Sweden in winter have been unlike anything they have ever experienced. That said, if this is a destination that’s found its way onto your bucket list, I would suggest going sooner rather than later as the charm of Swedish winters won’t remain a secret for much longer.”

Jenny Schroder, Indagare Trip Designer

The Long Weekend

Miami & Miami Beach

Perfect for: Families, Romantics, Art Lovers, Ultimate Indulgers

Why Go Then: The winter months in Miami promise warm weather and sunshine without the humidity of summer.

Ideal Trip Length: 3 to 5 days

First-Time Musts: Relaxing by the pool or on the beach; chartering a private boat for a day of water sports and fishing; exploring the top art galleries and shops in the Design District and Wynwood Art District; indulging in a treatment at one of the city’s top spas

Indagare Tip: Miami recently welcomed the reopening of an iconic property along a beautiful stretch of coastline just 20 minutes north of Miami Beach, which is perfect for both families and couples. Contact Indagare to book.

When to Book: 2 weeks to 1 month in advance

Related: Editors’ Picks: The Best Restaurants in Miami


The spring shoulder season brings beautiful weather to many destinations, without the masses of crowds seen during peak summer months.


Perfect for: Families, Romantics, Intellectuals, Foodies, Art Lovers

Why Go Then: Europe’s coolest country is currently finding its way into the spotlight, so it’s best to avoid the larger crowds of tourists that come in the summer.

Ideal Trip Length: 5 to 8 days

First-Time Musts: Touring Lisbon’s historic neighborhoods; taking a day trip to the resort towns of Sintra and Cascais; shopping the hidden gems of Porto; wine tasting in the Douro Valley

Indagare Tip: The Six Senses Douro Valley is a destination in itself, with delicious cuisine and a 24,000-square-foot spa that you’ll never want to leave. Contact Indagare to book.

When to Book: 3 to 6 months in advance

The Long Weekend

Harbour Island, Bahamas

Perfect for: Families, Romantics

Why Go Then: The island’s peak season runs from December through April, and hurricane season in the fall should be avoided.

Ideal Trip Length: 5 to 7 days

First-Time Musts: Traversing the tiny island by golf cart; getting up close to marine life with snorkeling, paddle boarding in the harbor and horseback riding on the beach; sampling island dishes like fresh conch ceviche and lobster quesadillas

Indagare Tip: For active travelers, Harbour Island is home to the first beach venture from Eleven Experience, which caters to high-end travelers with an intrepid attitude and passion for the outdoors. Contact Indagare to book.

When to Book: 3 to 6 months in advance. The exception is spring break, in March and April, which books up a year in advance.


A perennially popular time to travel, the summer is ideal for family getaways at home and abroad, from European cities to the Alaskan wilderness.


Perfect for: Adventurers, Families, Trailblazers

Why Go Then: Travelers can enjoy the best weather and maximum daylight hours in June and July.

Ideal Trip Length: 10 days

First-Time Musts: Viewing brown and black bears in their natural habitats; dog-sledding with Iditarod huskies; fishing for salmon, halibut and trout; trekking atop a majestic glacier; flying through remote, snow-covered peaks; searching for humpback and orca whales by private boat

Indagare Favorite: Though many travelers assume that a cruise is the best way to visit the 49th state, a land-based itinerary (which requires taking helicopters or small fixed-wing planes) provides even greater immersion in the Alaskan wilderness and unique access to untouched terrain.

When to Book: 1 year in advance


Perfect for: Adventurers, Trailblazers

Why Go Then: The dry season in Rwanda lasts from June to September, and again from mid-December to early February, offering less muddy hiking conditions and reduced malaria risk.

Ideal Trip Length: 3 to 5 days

First-Time Musts: Trekking to see the endangered mountain gorillas in the wild; tracking golden monkeys in the Virunga peaks; exploring local communities and learning about Rwanda’s complex history; visiting a premier gorilla research facility; searching for the Big Five in Akagera National Park (which will soon welcome new lodges from Wilderness Safaris and Singita)

Indagare Tip: Gorilla trekking permits in Rwanda are limited to only 96 per day, so it is important to secure your permits well in advance. Travelers must be 15 years of age or older to embark on a gorilla trek.

When to Book: 6 to 9 months in advance

American West

Perfect for: Families, Adventurers

Why Go Then: The warm summer months are ideal for living out your own Wild West fantasy packed with outdoor activities.

Ideal Trip Length: 4 to 7 days

First-Time Musts: Hiking; mountain biking; horseback riding; skeet shooting; archery; fishing; white-water rafting

Indagare Tip: From Jackson Hole to Montana, there are many five-star Western retreats to choose from, and an Indagare specialist can help match you with the best fit.

When to Book: 6 months in advance


Perfect for: Romantics, Intellectuals, Families, Ultimate Indulgers

Why Go Then: For an ideal beach vacation, head to Santorini and Mykonos in the summer, when the weather is warm and the clubs are lively.

Ideal Trip Length: 7 to 10 days

First-Time Musts: Touring ancient historical sites in Athens; hopping between beach clubs and experiencing the legendary nightlife in Mykonos; unwinding in white-washed Santorini; indulging at a serene resort in the Peloponnese

Indagare Tip: For travelers who love spending time on the water, a private cruise provides access to Greece’s unspoiled islands. Visit the culturally rich Paros and Antiparos, see the ancient ruins of Naxos, swim in the translucent waters of the Koufonisia islands and end on the beautiful beaches in Ios.

When to Book: 6 to 9 months in advance

British Columbia, Canada

Perfect for: Families, Adventurers, Foodies, Romantics

Why Go Then: Many of the top wilderness resorts are only open from June through September.

Ideal Trip Length: 5 to 7 nights

First-Time Musts: Eating at farm-to-table restaurants in Vancouver and biking in Stanley Park; hiking, kayaking and unplugging at a five-star wilderness lodge in a secluded coastal setting on Vancouver Island

Indagare Tip: Getting to the wilderness resorts in British Columbia is often complex and may require a combination of commercial flights, cars, sea planes and boats, so it’s best to rely on a trip designer to work out the logistics for you.

When to Book: 3 to 6 months in advance, although our favorite properties require at least 6 months.

The Long Weekend

New England

Perfect for: Romantics, Families, Foodies

Ideal Trip Length: 3 to 5 days

First-Time Musts: Touring historic mansions in Newport; biking along the water in Nantucket; shopping in Martha’s Vineyard; strolling the grounds at a beloved property in Vermont

Indagare Tip: There are lots of great options in New England, ranging from cozy inns with a homey feel to large resorts with pools, restaurants and spas. Contact Indagare to find the best match for you.

When to Book: 1 to 3 months in advance, although some of the top properties can book up 6 months in advance.


These months mark the beginning of the dry season in many African and Asian destinations, so travelers hoping to avoid rain and enjoy comfortable temperatures should take advantage. Plus: early fall is a great time to visit Europe after the summer crowds have left.


Perfect for: Families, Foodies, Romantics, Ultimate Indulgers, Art Lovers

Why Go Then: Rome is a year-round destination, but we recommend visiting summer hot-spots like the Amalfi Coast and Sicily in the fall shoulder season, when the water is still warm and some of the crowds have gone.

Ideal Trip Length: 7 to 10 days

First-Time Musts: Learning the history of Ancient Rome with behind-the-scenes monument tours; taking a day-trip to Pompeii; relaxing at the Amalfi Coast’s chicest beach clubs; savoring the world’s best pasta; taking a pizza- or gelato-making class

Indagare Tip: Chartering a boat in Amalfi is a must do. Swim in secluded grottos and calm inlets, visit local fishing villages along the way and arrive in style to a waterfront beach club for lunch.

When to Book: The Amalfi Coast books up 9 to 12 months in advance. Rome and Sicily require 3 to 6 months in advance.

I am a huge fan of Sicily in the fall, particularly September. The sea has had all summer to warm up, the crowds have dissipated, and the air temperature is lovely (in the 70s). You could do a few days at Grand Hotel Timeo, relax by the sea at Villa Sant'Andrea, then head down to Noto for some culture.”

Eliza Scott Harris, Indagare COO

Italy-lovers should consider our Indagare Journey to Slovenia & Istria–experience Europe’s best-kept secret destinations in the company of their most plugged-in tastemakers.


Perfect for: Adventurers, Families, Trailblazers

Why Go Then: These months usher in the Southern Hemisphere’s summertime, when the weather is warmer. The shoulder months of October and November are cooler (approximately 50 to 60 degrees Fahrenheit during the day) but also less windy than peak season from December through February.

Ideal Trip Length: 7 Days

First-Time Musts: Hiking some of the world’s most spectacular trails; visiting a local ranch on horseback; viewing glaciers up close on a boat trip

Indagare Tip: Combining a stay in Chilean Patagonia with time spent among the otherworldly landscapes of the Atacama Desert makes for the ultimate Chile itinerary. Alternatively, combining Argentine Patagonia with Buenos Aires makes for a fabulous city + adventure combo.

When to Book: 9 months to 1 year in advance. The holiday season requires at least one year of lead time.

Join our upcoming Indagare Journey to Patagonia by signing up here.


Perfect for: Adventurers, Art Lovers, Intellectuals, Families, Trailblazers, Soul Searchers

Why Go Then: Egypt's weather is best during the fall and winter months.

Ideal Trip Length: 10 days

First-Time Musts: Seeing King Tut's treasures in the Egyptian Museum in Cairo; gazing in awe at the Sphinx and Pyramids at Giza; cruising along the Nile River, with stops at temples and tombs along the way; visiting the Tomb of Nefertari, considered the most beautiful tomb in Luxor

When to Book: At least 4 months in advance, and up to 1 year in advance for popular periods, such as the holidays


Perfect for: Families, Art Lovers, Intellectuals, Style Mavens, Foodies

Why Go Then: Sakura season in Japan has become extremely crowded. We prefer the fall—outside of peak foliage season—when visiting popular destinations like Kyoto becomes more manageable.

Ideal Trip Length: 10 to 14 days

First-Time Musts: Visiting shrines, taking a sushi-making class and shopping in Tokyo; relaxing at a hot spring resort with views of Mount Fuji in Hakone; seeing temples and a geikko performance in Kyoto; exploring the “art island” of Naoshima Indagare Tip: In general, it is faster, easier and more comfortable to travel around the country by train than by plane. Japan’s train system is highly efficient and impressive, taking travelers from city center to city center.

When to Book: 6 months to 1 year in advance. (Peak cherry blossom and fall foliage weeks can book up a year in advance.)

Be the first to know about our fall Indagare Journey to Japan (hello foliage!) by signing up for preview access here.


Perfect for: Style Mavens, Intellectuals, Families, Romantics, Soul Searchers

Why Go Then: October through March is the best time to travel to most parts of India. This is the cool, dry season in Rajasthan, which is where first-time travelers are typically headed.

Ideal Trip Length: 10 days

First-Time Musts: Touring Old and New Delhi by rickshaw; seeing the sun rise over the Taj Mahal; tracking tigers in Ranthambore National Park; shopping for gems and textiles in the “Pink City” of Jaipur; sailing on the lake in Udaipur

Indagare Tip: A common saying in India is that all drivers need three things: a good horn, good brakes and good luck. Delhi, in particular, is known for its chaotic traffic, and hiring a professional driver is crucial.

When to Book: 6 months in advance


Perfect for: Romantics, Style Mavens, Families, Ultimate Indulgers, Trailblazers

Why Go Then: Due to Morocco’s Mediterranean climate, spring and fall are the best times to visit, when temperatures are pleasantly mild throughout the country. Travelers should avoid the summer, when days can get blisteringly hot.

Ideal Trip Length: 7 to 10 days

First-Time Musts: Shopping in the souks in Marrakech; learning about Berber culture in the Atlas Mountains; exploring the medieval city of Fez; relaxing at a sumptuous camp in the desert; meandering through hidden streets of Tangier

Indagare Tip: To make the most of Marrakech’s often-overwhelming marketplace, we recommend hiring a personal shopping guide who can help you navigate the maze of shops, find the highest-quality items and help negotiate the prices.

When to Book: 9 months in advance. Keep in mind that the peak travel times to Morocco are March, April, October and the holiday season.

While Morocco focuses their efforts on supporting and healing the communities impacted in the Atlas Mountains, Marrakech is even more glorious than ever, and despite some minor scaffolding around the Medina, the effects of the earthquake are practically undetectable. New shops and restaurants have opened since I visited last October, lush landscaping has been added along the promenades (a project started by His Majesty a few years ago), La Mamounia just celebrated 100 years and the completion of a multi-million dollar renovation and after enjoying cocktails on the El Fenn rooftop last night and finding inspiration in their boutique, I can confirm that Marrakech is thriving. Those who worry that it is insensitive to travel to Morocco while the communities in the High Atlas are suffering should know that the economic support from tourism is critical to recovery and regeneration efforts—by traveling and enjoying, you are helping.”

Elise Bronzo, VP of Sales

Dreaming of Morocco? We have Indagare Journey offerings to Morocco multiple times per year, led by expert hosts or our favorite local guides, with itineraries centered around passion points and insider access. Join us in Marrakech in February, Tangier in May and be sure to check out our Magical Morocco itinerary with trips in October and November.

The Long Weekend

American South

Perfect for: Families, Foodies, Art Lovers, Intellectuals, Romantics

Why Go Then: The autumn months down South bring reliably pleasant weather.

Ideal Trip Length: 3 to 5 days

First-Time Musts: Enjoying southern feasts and carriage rides in Charleston; attending country music shows in Nashville; touring historic homes in Savannah; sampling beignets and listening to jazz in New Orleans; hiking in the Smoky Mountains; golfing on Sea Island

Indagare Tip: Many Southern cities can be explored in a leisurely long weekend, or you can embark on a road trip to hit several spots in one go, making stops at classic roadside diners and historic mansions and gardens along the way.

When to Book: 1 to 3 months in advance

Updated onJanuary 1, 2024

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