Do you have one of the “0” birthdays coming up, perhaps a 30th or a 60th? Is your 50th wedding anniversary approaching? Perhaps you have a child or grandchild graduating college. How are you planning to celebrate? Is it time for a milestone trip?

What’s a milestone trip? Quite simply: a special vacation to commemorate a special occasion. Major birthdays are popular triggers for milestone trips. Of course, there are anniversaries, honeymoons and even the growing-in-popularity “babymoons.” Special religious occasions such as bar or bat mitzvahs, college reunions, family gatherings and “just because we want to” group trips are all reasons to explore the world.

No matter where you choose to go, often the best milestone trips are wrapped around memorable events. Abercrombie & Kent put together many of these, including such extravagant trips as a private tented safari for 11 members of the family of a Fortune 500 CEO. The luxury travel company arranged for a dinner on the maharani’s private barge on Lake Pichola in Udaipur, India, followed by fireworks for another group. But trips don’t have to be extravagant to be unforgettable. Maple Leaf Adventures’ expedition cruises in Alaska are a popular “bucket list” choice for anniversaries. Raft trips, such as running the Cataract Canyon out of Moab, Utah, make great adventures for families celebrating graduations.

Many a bucket list includes an Alaskan expedition. © Lawrence Weslowski Jr | Dreamstime.com

PICKING A LOCATION for a milestone trip may not be as easy as plucking a journey from your personal bucket list. While that’s a tempting option, if the trip will celebrate your spouse’s 60th birthday, his bucket may be filled with other countries and activities. Maybe you want to ski in Colorado, but he dreams of hiking the whiskey trail in Ireland. Even though you’d love to sit on a beach in Hawai’i, if he likes lots of activity during a vacation, keep in mind this trip is for him.

“It takes away the element of surprise perhaps, but the most successful trips are when everyone is on board. You can then have fun with the travel counselor working out all of the surprises during the trip,” says Richard Harris, senior vice president, product development and operations, Abercrombie & Kent.

There are lots of choices. Perhaps bring the entire family or your best friends on a cruise in the Galapagos Islands. Isolated from the mainland, this is a perfect milestone locale. Up-close encounters with unique species are just one of the many special experiences that await milestone memory makers. Or take one of those “fly around the world on a private jet” trips. Take a package trip to a country you’ve always wanted to visit or a river cruise. Spend a few days on your own in a special setting and plan a special celebratory meal.

The sheer logistical aspects of timing the trip can be daunting, especially if there’s a large group involved. “If you want to bring extended family along, you should plan it at least a year in advance,” says Maureen Gordon, Maple Leaf Adventures. Adults will need to book vacation time. If the children are in school, you might have to plan the trip during their vacations. If you’re planning a milestone vacation with friends, make sure in advance that everyone gets along well and will do so while traveling since you’ll be spending so much time together.

Once you’ve zeroed in on a location, find a travel advisor or consultant who knows the location well. The first question to ask: How well does he or she know the country and how often has he or she been there? Does the company have operators on the ground in the country you want to visit? If you want to go on a safari, for example, work with an African specialist, whether it’s a company that only does safaris or a major company that employs safari specialists. If you want to take a bike trip through the vineyards in France, work with a company such as DuVine Cycling, which only handles bike trips. If it’s a country that’s new on travelers’ radar, consider contacting Zicasso Handcrafted Travel. You’ll fill out a brief form online and get responses from specialists who really know the destination well.

Milestone trips come in an intriguing number of styles, costs and locations. Some require hours of working with skilled travel consultants, while others are totally planned on the Internet. Others require just a phone call or two. Decide which approach works best for you, then act on it.

RESORTS ARE A POPULAR CHOICE for large gatherings because you never have to leave the property. Personal concierges at resorts and high-end hotels excel at creating special experiences. At The Broadmoor in Colorado, for example, a couple celebrating an anniversary flew by helicopter to a private location on a golf course and enjoyed a gourmet dinner on an elegantly set table. For a college reunion, the resort once redecorated one of its luxury cottages with furniture reminiscent of the year friends graduated.

Denverite Dan Leeth and his wife, Diane, decided to celebrate multiple major events with friends on a yacht. He was turning 65 and she was turning 60 and retiring from a 30-year nursing career. They asked two couples they’d traveled with before, who also had major birthdays, to join them. Skilled in researching online, they scouted for companies renting yachts and picked The Moorings, a choice backed up by recommendations from several people who had used the company. They’ll cruise in the Caribbean for a week on a four-bedroom catamaran with a crew. “It’s close quarters,” Leeth says, “but we all get along with each other.”

Hiking the Grand Canyon is a popular milestone trip. © Designpicssub | Dreamstime.com

Seeking more active adventures? Biking through French vineyards, skiing in Switzerland and hiking are popular choices. Coloradan Mona Mesereau wanted to do something physical for her 50th birthday, so she and her husband collected a group of friends to hike in the Grand Canyon. After hiking to Phantom Ranch at the base of the canyon and staying for two nights, then hiking back up, she says, “We all had a real sense of accomplishment.”

Guest ranches are a good choice for multigenerational trips centered around special celebrations, such as the grandparents’ major anniversary, because you’ll find activities for varying age levels and degrees of athleticism. At the Vista Verde Guest Ranch in Colorado, for example, some guests can go horseback riding while others go fishing, hiking or on photo tours with photographers while the kids are in camp.

Hotels are coming up with creative packages for milestone events. At the beginning of a marriage, have your wedding at a Ritz-Carlton anywhere in the world and you’ll get special rates on a honeymoon package at The Ritz-Carlton, Kapalua. The wedding coordinator will work with the Kapalua hotel to set up your Hawai’ian honeymoon. If the romance is over, Thailand’s Aleenta Hua Hin has a break-up offer for any traveler who wants to get over an ex.

Cruises work for people who wish to explore parts of the world but don’t want to move from lodging to lodging during the trip. For that special celebration, choose a more luxurious cabin or suite on the ship, or pick a more upscale cruise line.

For faith-based trips, work with companies who specialize in this type of travel. For example, several companies arrange trips to Israel to celebrate bar and bat mitzvahs that could include a service at the Western Wall in Old Jerusalem and activities such as participating in an archaeological dig. The Israel Ministry of Tourism lists companies on its website.

People who travel for a living may want to stay close to home. The fiancé of Sharon Lieb, a writer who has traveled to more than 40 countries, simply booked a suite at Charleston Place, a luxury Orient-Express property in her hometown, Charleston, S.C. The next morning, a dozen of her best friends showed up for a surprise brunch for her 60th birthday.

Let your imagination run wild when deciding where you want to go and what you want to do. But always keep in mind careful planning is a key to creating a successful milestone trip. “You really need to get the basics right before you set out to impress,” says Abercrombie & Kent’s Harris.

Ann Alba, reservations manager, The Broadmoor, sums it up: “Some of the most special milestone trips are ones that people have waited a lifetime for. You can’t afford to make a mistake on these special occasions because you can’t redo them!”