Your 2023 Travel Calendar: Where to Go and 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 2023 travel calendar, including our travel tips and the best times to book each destination.


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; 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

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.

Long Weekend: Paris or London

Château de Bagatelle, Paris
Château de Bagatelle, Paris. Photo by Kathryn Nathanson, courtesy Indagare
Chalcot Crescent, where Paddington was filmed. Photo by Annie Fitzsimmons, courtesy Indagare

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


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

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.

– Nikki Erlick on February 15, 2023

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