Boats in the harbor below the town of Amalfi

Destination guides

Where to go, when to go, and where to stay

I plan trips all over the world. Here are a few favorites, with the basics I share on a first call. If you have somewhere else in mind, I’d love to plan that too.

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Garden terrace of Villa Monastero overlooking Lake Como in Varenna

la dolce vita

Italy

Long lunches, beautiful hotels, and a pace that’s easy to fall into. Italy works for honeymoons, family trips, and everything in between.

The essentials
Best time to go
May to June and September to early October. July and August are hot and busy, especially on the coast.
Where to stay
The Amalfi Coast (Positano or Ravello), Lake Como (Bellagio or Tremezzo), Rome, Florence, and the Tuscan countryside.
Don’t miss
A private boat day along the Amalfi Coast, a cooking class in Tuscany, and an evening stroll through Rome.
Waterfront tables in Little Venice, Mykonos

island hopping

Greece

Whitewashed villages, impossibly blue water, and sunsets worth planning a whole day around.

The essentials
Best time to go
Late May to June and September. July and August are the busiest months, and the island winds pick up.
Where to stay
Santorini for the views, Mykonos for the energy, Paros or Milos for a quieter pace, and Athens for a night or two.
Don’t miss
Sunset in Oia, a catamaran day around Milos, and a long taverna lunch right by the water.
Aerial view of turquoise water and reef in the Turks and Caicos Islands

easy escapes

Caribbean

Short flights, white-sand beaches, and resorts that work just as well for families as they do for couples.

The essentials
Best time to go
December to April for the driest weather. Hurricane season runs June through November.
Where to stay
Turks and Caicos for the beaches, St. Barts for chic and glamorous, and Grand Cayman or Anguilla for an easy, relaxed trip.
Don’t miss
Grace Bay at sunrise, Stingray City in Grand Cayman, and a long beach lunch in St. Barts.
Aerial view of the green cliffs of the Na Pali Coast on Kauai

aloha

Hawaii

No passport needed, and one of my family’s favorite places in the world. Each island has its own personality.

The essentials
Best time to go
Any time of year. April, May, September, and October tend to be quieter, and winter brings whale season.
Where to stay
Maui (Wailea is great for families), Kauai for nature, the Big Island for adventure, and Oahu for a little of everything.
Don’t miss
Sunrise on Haleakalā (book ahead), a boat trip along the Na Pali Coast, and whale watching in the winter.
The Arch of Cabo San Lucas rising from the sea at sunset

close to home

Mexico

Incredible food, warm hospitality, and some of the best resorts in the world, often just a short flight away.

The essentials
Best time to go
November to April for dry, sunny weather.
Where to stay
Los Cabos for desert-meets-ocean resorts, Punta Mita for families, the Riviera Maya for beaches and cenotes, and Mexico City for food and culture.
Don’t miss
Sunset at the Arch in Cabo, a swim in a cenote, and a food tour in Mexico City.
Leopard resting on a rock in Kruger National Park, South Africa

africa

Safari

A true once-in-a-lifetime trip, and it’s wonderful with older kids. The right camps and guides make all the difference.

The essentials
Best time to go
June to October, the dry season in most safari areas. In Kenya, the Great Migration river crossings usually happen July through September.
Where to stay
Kenya and Tanzania for the Great Migration, South Africa for an easy safari plus Cape Town and the Winelands, and Botswana for remote, intimate camps.
Don’t miss
Sundowners in the bush, a hot-air balloon ride over the Mara or Serengeti, and a few beach days in Zanzibar or Mauritius at the end.
Red temple beside the water in Kyoto, Japan

wanderlust

Asia

From Japan’s temples and tea houses to the beaches of Bali and the Maldives, Asia is beautiful, welcoming, and easier than most people think.

The essentials
Best time to go
Japan is lovely in spring and fall. Bali is driest from April to October, and Thailand and the Maldives are best from November to April.
Where to stay
Tokyo and Kyoto in Japan, Ubud and the coast in Bali, Phuket or Koh Samui in Thailand, and an overwater villa in the Maldives.
Don’t miss
An early-morning walk through Kyoto’s temples, a night in a traditional ryokan, and a private villa with your own pool in Bali.
Two llamas on a grassy hill overlooking the ruins of Machu Picchu

south america

Peru

Machu Picchu, the Sacred Valley, and one of the best food scenes in the world. A real adventure that feels easy with the right plan.

The essentials
Best time to go
April to October, the dry season in the Andes. The Inca Trail closes every February.
Where to stay
Lima for a night or two of incredible restaurants, the Sacred Valley to adjust to the altitude, Cusco, and a lodge near Machu Picchu.
Don’t miss
Sunrise at Machu Picchu (book ahead), a tasting menu in Lima, and the scenic train ride through the Sacred Valley.
Arenal Volcano reflected in a lake surrounded by rainforest in Costa Rica

pura vida

Costa Rica

One of my favorite places in the world. Rainforest, volcanoes, and beaches in one easy trip, and it’s wonderful for families and couples alike.

The essentials
My favorite way to do it
A split stay: a few nights at Nayara in the rainforest near Arenal Volcano, then the beach at Four Seasons Peninsula Papagayo. To keep the budget lighter, Andaz Peninsula Papagayo is a beautiful beach option.
Best time to go
December to April is the dry season. May to November is the green season, with lush landscapes and afternoon rain.
Don’t miss
Soaking in the natural hot springs near Arenal, a hanging bridges walk through the rainforest canopy, and a sunset catamaran along the Guanacaste coast.

Also planning: cruises, more of Europe, Australia and New Zealand, and milestone trips for groups. If it’s on your list, I can plan it.

where to next?

Have somewhere in mind?

Tell me where you’re dreaming of and I’ll take it from there.

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