Marking a Milestone

Fill your milestone vacation with activities like horseback riding on the beach.

Celebratory getaways ensure that special occasions are one of a kind.

By Katherine Duncan

Life is filled with special events that call for celebration. Whether it’s an anniversary, birthday or another occasion, these exciting moments present unique travel opportunities. Couples can escape on romantic getaways to reminisce about their wedding day and the years that they have since enjoyed. Friends and family can come together to commemorate a loved one’s milestone birthday, and tailor the trip to his or her favorite activities. A graduation vacation can honor a loved one’s accomplishments while retirement trips can toast to newfound freedom. On the opposite end of the spectrum, a pre-wedding escape gives the bride or groom a chance to connect with friends for one last hurrah before the big day. In all of these cases, the key is to select an unforgettable destination with customizable activities and dining options that are equal to the occasion which inspired the trip in the first place.

Plan Like a Pro

Jim Augerinos, who is president and luxury travel consultant at Perfect Honeymoons & Holidays, says that when it comes to any successful celebratory vacation, planning ahead is absolutely essential. The further out, the better—especially when working around dates that hold special significance, like birthdays and anniversaries. For larger groups, everyone will need ample time to coordinate schedules and, for couples, plenty of advance notice means better chances of being able to secure that coveted suite or extra-special dinner reservation.

Sometimes, it’s best if one traveler takes it upon him or herself to take on the bulk of the research responsibilities. If too many people are involved, it can get confusing for everyone. Appoint one person to look into the best dining options, activities and more, then present them to the group to make a final plan.

Sea Island Cottages are the ideal spot for birthdays, anniversaries and more.

Personalization is especially important when crafting a milestone getaway in order to ensure that the experience is a memorable, one-of-a-kind celebration. Augerinos begins the planning process by learning about his clients’ prior travel experiences and unique preferences—for example, where they have traveled in the past, what their hobbies are and what type of atmosphere they have in mind. “Once I get a better sense of what they enjoy and if they have a vision for the trip, then I help refine that vision and bring out the special options,” he says.

Those special options are often determined by the destination; these are the activities that are unique to the area or particularly iconic there. At Sea Island, it could be enjoying an evening playing bingo, a longtime and especially popular tradition on the Island, or taking part in some of the best fishing on the Atlantic coast. Ultimately, determining which specific experiences will be most memorable depend on the particular occasion and who will be joining the festivities.

“If it is a couple celebrating a birthday or anniversary, it’s much easier to pick something that makes everyone happy,” says Laura Epstein, a luxury travel adviser at full-service travel company SmartFlyer. “If it’s a group of couples or [a] large family traveling together, it can be challenging to find something that makes everyone happy. People of different ages travel at different paces: some people may like museums, some may want to sit by a pool, some want to walk and explore, some want to be chauffeured. Finding a common ground to accommodate everyone is important.”

At Sea Island, accommodating the whole group is easy. From bowling, horseback riding, golfing and kayaking through local marshes to enjoying historical tours, wildlife walks and more, there is something for all interests—and plenty of them are ideal for bringing your crew together, whether friends or family.

Birthday Getaway

To celebrate the guest of honor, personalization is invaluable during a milestone birthday getaway. “It would be a good idea to take all of their preferences, hobbies and special interests and incorporate [them] into a special getaway,” Epstein says. “For a golf and hunting trip for [a] man, perhaps set up a few tee times, shooting courses, bourbon tastings or a steak dinner.”

The individualized touches can extend to smaller components, too. “The small details add up and make a huge impression,” Augerinos says. For example, he suggests arranging for a custom welcome amenity to be in the room for the birthday girl or boy when they arrive, which might include some of his or her favorite drinks and snacks.

Groups of guys can gather together on the golf course.

While the focus is naturally on the guest of honor, it takes a group to make a true party. However, arranging convenient accommodations for large groups can prove to be challenging. “In our experience, if you’re coming here to celebrate a milestone birthday or anniversary, you want to share that experience with the ones you love,” says Lauren Carter, owner and guest services manager at Sea Island Cottage Rentals. With 140 cottages to choose from, it’s easy to find the right fit for your group. Large sitting areas and kitchens provide all the space you’ll need while more intimate options are ideal for couples or smaller groups. It’s easy to tailor the experience with amenities like pools, home theaters or game rooms. Carter also says that some of the premium, oceanfront options offer the best views of the beaches anywhere on the Island. Still others present relaxing marsh scenes.

When booked through Cottage Rentals, cottages come with all of the same amenities that guests would enjoy at The Cloister (minus daily housekeeping, which can be arranged for an additional fee), while allowing the group to enjoy being together in a single, private space. For unforgettable celebrations, there are special options available, such as private chef dinners, in which a resort chef will come into the home to cook a meal for the group. This can be organized by the cottage rental concierge, who is also available to assist with pre-arrival itinerary planning, dining and spa reservations, tee times, grocery shopping and delivery, babysitting needs and activity suggestions, including exclusive private events outside of the cottage as well.

Some choose to celebrate with family. | Photo: LightField Studios/

A private special event can take the place of a more traditional birthday party for a truly one-of-a-kind celebration during a birthday trip. In addition to commemorating the occasion, Augerinos says that this type of festivity is often hosted by the person who arranged the birthday getaway as a thank-you to the group for coming. At Sea Island, Carter suggests a wine cellar dinner at The Cloister or The Lodge, which can accommodate up to 20 people. An elegant, multicourse meal is paired with award-winning wines for a “very special, very unique” experience. Another notable setting for a birthday bash is the Sea Island Explorer, the resort’s 71-foot, multilevel yacht, which can be reserved for groups of up to 49. Light bites and drinks are served during a scenic, leisurely cruise along local waterways.

While anniversaries are often limited to romantic getaways for couples or epic adventures celebrating the family tree, birthdays are an excuse to gather anyone and everyone you hold dear for a vacation that will be remembered for years to come.

Anniversary Trip

One trend that Augerinos has noticed in anniversary trips is the desire to return to the destination where the couple was married or where they honeymooned. Going back to that meaningful place provides plenty of opportunities to reminisce, and perhaps to revisit some of the same activities and restaurants. It’s so popular with members and guests at Sea Island that the resort offers an anniversary rate for returning honeymooners: For a stay of three nights or more at The Cloister or The Lodge, couples can bring their receipt from their honeymoon to receive one night at the rate that they paid originally.

Some couples are opting to invite more people along for the nostalgic vacation. However, while “the more the merrier” might be the approach for a birthday getaway, anniversary trips usually call for a smaller group—for example, couples might bring their children along so that the entire family can enjoy an activity that the couple first did together during their honeymoon. “Sometimes those activities are even better when you’re sharing them with more people rather than just doing them yourselves,” Augerinos says. Having the children present can make the experience extra-special in other ways, too: “Imagine being able to share renewing your vows with your kids,” he says. For another fun way to mark the occasion, Augerinos suggests re-creating a photo from the couple’s prior visit that incorporates the whole family.

The Sea Island Explorer allows guests to enjoy light bites or cocktail cruises on the water.

Sea Island member Lynne Byrd, who lives a few hours away in Thomasville, Georgia, was married at The Cloister Chapel in January 2010, complete with a rehearsal dinner in the Wine Cellar and an evening cocktail cruise on a yacht. Although they typically venture to the Island a few times per month, Byrd and her husband Jeff wanted to be sure to plan a trip for their 10th anniversary earlier this year. In January, the couple re-created much of the magic from their wedding.

“We booked an evening cruise with 17 of our family and friends,” she says. “Then, the next night, we had a fabulous five-course dinner in the Wine Cellar. All but two people present for the anniversary weekend were present at our wedding, so it was really fun to reproduce those events.”

Byrd says that the flowers, wine and food were memorable during their anniversary trip, but what really stood out was the service at Sea Island. “Elizabeth Killgallon was fantastic to work with—she even managed to locate the big leather-bound book … we all signed at our rehearsal dinner so that we could read that again, but also sign a new page for the anniversary,” Byrd explains. “Years from now, our children and grandchildren can go and see that book and read the comments made by everyone.”

Sea Island member Lynne Byrd and her husband Jeff, who planned a trip for their 10th anniversary earlier this year.

“Taking into account both guests’ interests is key,” Epstein says. “While a couple could be celebrating 50 years of marriage, that doesn’t mean they both like to travel the same way. It’s good to incorporate elements of both peoples’ wish lists. Perhaps for a couple … [on] an anniversary trip with a husband who likes to hike and a wife who likes to spa, front-load the days with activities like big hikes and then allow enough free time in the afternoon for wine tastings and spa treatments.”

For those celebrating at Sea Island, Carter recommends a couple’s treatment at The Spa at Sea Island, which features two couple’s suites with private balconies. When it comes to a one-of-a-kind dining experience, she suggests making a reservation for the Chef’s Table at the Georgian Room: “A table is set up in the kitchen where the world-renowned chefs prepare the meal right in front of the guests,” she says. The interactive, customized meal offers a unique and significant way to commemorate the special date.

With so many ways to celebrate, from intimate dinners to family-friendly outdoor activities, it’s a matter of selecting the options that can be tailored to honor the unique occasion, and adding personal touches to ensure that every moment is one of a kind.


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