Trip to Anywhere

Epic Dream Trips and How to Make Them Happen

St. Regis Bora Bora


Some experiences really are dreams come true, and they don’t have to feel like a gargantuan chore to plan. The first step is deciding what your idea of a dream trip is. For some people, the idea of a dream trip is really just a time out. Requests for bucket-list type experiences are fewer and farther between than they once were.

While there are still travelers looking to summit Kilimanjaro and go on safaris in East Africa, the idea of a dream trip is changing, it's more about getting the family together. Many families are choosing to travel with young children, often turning vacations into educational experiences.

Whether it's a relaxing escape, a family walk through history, an escape into nature or something you seek, we’ve got an itinerary for you. Here are five dream trips and what you need to know about planning them.

Relax in an over-water bungalow

St. Regis Bora Bora


If your idea of a dream trip is an escape to a quiet corner of paradise, Bora Bora has an over-water bungalow for you.

The St. Regis Bora Bora Resort offers nearly 50 acres of French Polynesian paradise, featuring the largest over water villas and suites in the South Pacific. Expect to spend your days enjoying crystal blue waters, lounging on white sand beaches and taking in view of picturesque Mount Otemanu, with its rich vegetation.

Bungalows range in size from 1,500 to 3,500 square feet, many with pools, whirlpools, and decks for outdoor dining. Each comes with viewing panels to give you a glimpse of the turquoise water below.

When you’re ready to leave your bungalow, consider visiting a Tahitian pearl farm or taking an excursion lagoon cruise to see sharks and feed sting rays. Don’t try to make this one a last-minute dream trip, though. The St. Regis recommends booking over-water bungalows at least a couple of months ahead.

Experience la dolce vita in Italy

Ischia, Italy


If your idea of a dream trip involves beach time, fresh Italian food, celeb-spotting and maybe a yacht, fly into Naples and head toward Italy’s Amalfi Coast.

Exploring this region known for its cliff-side towns, epic views, limoncello and fresh seafood. From Sorrento, you can hire a yacht or catch a ferry to Ischia, an island known for its thermal baths and fine wines, or to Capri, known for its colorful lagoons. Sorrento is near both Mt. Vesuvius and Pompeii, the ancient city destroyed when Mt. Vesuvius erupted in AD 79, making it easy to delve deep into history when you’re ready to take a break from island hopping, sipping limoncello, and sampling gelato.

From Sorrento, you can also rent a car, hire a car and driver, or rent a yacht to explore a half dozen picturesque towns including Amalfi, Ravello, and Positano.

Wake up to the Taj Mahal

Taj Mahal


If your idea of a dream trip is checking out a wonder of the world, pack your bags and head to northern India. Fly into New Delhi to embark on your journey through India’s Golden Triangle.

Hire a car and driver to explore the city’s sights, making time to wander around the Red Fort, Qutub Minar, and old Delhi. Pay your respects to Mahatma Gandhi at Raj Ghat, and when you’re ready, catch an express train to Agra. Express trains will take you from Delhi to Agra in under two hours. When you’re ready to explore the Taj Mahal, plan to spend several hours there and hire a guide to help you spot architectural secrets you might otherwise miss.

After two nights in Agra, you’ll likely be ready for something new. Head to Jaipur, India’s famed pink city to complete your Golden Triangle experience.

Fall asleep to the Northern Lights

Northern lights in Iceland


If you’re looking to experience a natural phenomenon on your dream trip, catch a flight to Reykjavik. Iceland is located at 65 degrees North, at the edge of the Arctic Circle, and offers one of your best chances to see the Northern Lights without the extremely cold temperatures you would have to endure in other parts of Scandinavia.

Start your journey toward the Northern Lights with a dip in the Blue Lagoon, a thermal spa complex located not far from Keflavik International Airport, to shake off any jet lag you may have.

If you choose to stay in Reykjavik, several companies offer Northern Lights tours. If you’d prefer to drive, renting a car is also an option — just beware of the Icelandic roads in winter.

Go on safari in South Africa

Kruger National Park safari


If your idea of a dream trip is a crossing a safari off your bucket list, head to South Africa. The country is especially good for first safari experiences as it offers so much more than just safaris. An easy first safari could start with a flight into Johannesburg and then a road trip to Kruger National Park in the eastern part of the country. South Africa is home not only to Kruger National Park, but also has beaches, mountains and wine country in addition to bustling cities like Cape Town.

Contact Olsen-O’Leary to Start Planning Your Dream Trip ✨

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