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9 Destinations for Your Next Milestone Trip

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Santorini, Greece

Santorini, Greece

Weddings and milestones are always something to look forward to and our nine best destinations demonstrate how you can mark these occasions with a spectacular vacation.

Delve into the beauty of the Italian coastline with colorful architecture and views of the Mediterranean Sea. Embrace the charm of a secluded bay ringed with coral gardens. Bask in the splendor of an island sunset or sink into the powdery white sands of a remote beach. By understanding how you like to celebrate such events, you can indulge in your preferred experience.

Whether enjoying your honeymoon, celebrating a graduation, or extending the joys of an anniversary, we share our ideas on how to enjoy your milestone with a custom trip designed around your goals and interests.

  1. 1. Amalfi Coast, Italy
  2. 2. Bora Bora, French Polynesia
  3. 3. Santorini, Greece
  4. 4. The Islands, Thailand
  5. 5. Placencia, Belize
  6. 6. Masai Mara, Kenya
  7. 7. Lisbon, Portugal
  8. 8. El Calafate, Argentina
  9. 9. Cape Town, South Africa
  10. Start Planning Your Custom Milestone Trip

1. Amalfi Coast, Italy

Amalfi Coast, Italy

Amalfi Coast, Italy

“Italy has seen pent-up demand and a collective joy for travel,” says Robert, a Zicasso travel specialist on the country. Without question, popular destinations such as the Amalfi Coast continue to draw crowds with a combination of international renown, village charm, and natural beauty.

The towns share a dramatic coastline and an alluring aroma of citrus from lemon groves. Whether lounging on a traditional beach beneath an umbrella or basking in the panoramic views from a villa belvedere, the Amalfi Coast is an endless thrill for any celebratory occasion.

Should you be considering a trip to Italy, a Zicasso travel specialist can share the many regions of the country to consider. Puglia is an excellent option for second-time visitors looking to go beyond the popular sites or for any traveler looking for a less popular region. “[Puglia] is of classical Greek origin, with medieval towns, vineyards and farms, a beautiful coastline dotted with beaches and ancient villages, and a bit of the old Italy not found in those places more heavily visited,” says Robert.

Learn more: Italy Tours & VacationsItaly Travel Guide

2. Bora Bora, French Polynesia

Bungalows in Bora Bora

Bora Bora, French Polynesia

A volcanic island in French Polynesia, Bora Bora is an iconic destination for romance. With white-sand beaches, overwater bungalows, and top-notch service that provides privacy, luxury, relaxation, and adventure, Bora Bora is considered perfect for a honeymoon or anniversary celebration.

Beyond the white sands and hidden corners with views of crystal-clear water, Bora Bora offers adventure and relaxation. Embrace the possibility of a jungle trek in search of waterfalls or venture into the water to view colorful coral gardens brimming with marine life. The splendor of the island and the greater archipelago connect the welcoming ambiance of local culture with the unforgettable wonder of the natural scenery.

Learn more: Bora Bora VacationsTahiti Travel Guide

3. Santorini, Greece

Santorini, Greece

Santorini, Greece

Greece offers endless natural beauty, ancient wonders, magnificent food, and luxurious accommodations, so it is no surprise this country is a consideration for any traveler looking to plan the trip of a lifetime. With iconic sites abounding, the challenge can be deciding where to go.

Santorini is one of the most popular destinations and your Zicasso travel specialist can ensure you enjoy the island’s famous treasures and hidden charms according to your preferences. “You can watch the amazing sunset in Santorini, but you don't have to go to the spot where everybody gathers. Instead, you can discover the favorite spots on the islands that only locals know,” says Villy, a Greece expert for Zicasso.

No matter how you like to travel, Santorini is a destination for everyone, where a milestone can be coupled with a treasured memory of visiting the possible home of Atlantis or enjoying the breeze on a caldera cruise. “It is important to know and get advice from local travel experts who know the country very well,” says Villy, and Zicasso is here to help.

Learn more: Greece Vacations & Tours Greece Travel Guide

4. The Islands, Thailand

Infinity Pool at Six Senses Yao Noi, Thailand

Yao Noi, Thailand

Thailand has some of the most beautiful islands in the world. For those who wish to celebrate romance and appreciate a mix of culture, history, great food, and beaches, Thailand is a wonderful destination. We recommend an itinerary that ends at one of the islands for pure relaxation and rejuvenation.

While Phuket is a popular, well-known island, there are several other destinations with marvelous coastlines, such as Koh Samui and Krabi, with fewer people and luxury resorts. “One of our favorite hotels in the world is on the small island of Koh Yao Noi,” says Zicasso CEO Brian Tan, who took the photo above during his stay there. “The sea-view villas, each with their own plunge pools, offer stunning views of the bay and each morning we saw a spectacular sunrise behind the limestone karsts.”

Thailand is always an exceptional place to experience the pleasures of daily life found in the cuisine, culture, and views. Remarkable karsts, sensational massages, active discoveries, or endless options for relaxation place the luxuries of Thailand's islands within reach.

Learn more: Thailand Tours & VacationsThailand Travel Guide

5. Placencia, Belize

Strech of beach at Placencia, Belize

Placencia, Belize

Belize is much more than just a tropical getaway, which is why it’s a perfect destination for a milestone trip. Whether celebrating a birthday, anniversary, or graduation, the Placencia peninsula in Belize provides the perfect space in which to bask in views of the Caribbean Sea from the glint of golden sands or embrace a wildlife boating experience in search of monkeys and manatees.

Placencia provides central seclusion for travelers who wish to balance a remote ambiance beneath swaying palm trees with thrilling excursions and culture. “The archaeological history and world’s second-largest coral reef sets it apart from other places like Costa Rica,” says Catarina, a Belize travel specialist. “There is tons of nature and wildlife, like howler monkeys and wetland birds, and scarlet macaws. There are also guided hikes and plenty of kids activities.”

From an adventure searching for Mayan ruins to lounging in the comforts of a boutique lodge that highlights the surrounding natural beauty, Placencia in Belize is a marvelous destination for any kind of celebration for any kind of traveler.

Learn more: Belize Vacations & ToursBelize Travel Guide

6. Masai Mara, Kenya

Lion pride walking along jeep tracks in Masai Mara, Kenya

Masai Mara, Kenya

Kenya is a destination where iconic experiences and classic beauty help you celebrate any type of milestone. From a romantic escape to a festive family-friendly gathering, the Masai Mara immerses you in wildlife, wilderness, and seclusion.

The national park and protected area captures the ideal safari experience with sensational game drives that promise unique possibilities, from viewing lions lounging in the tall grasses to watching giraffes graze on the tall trees. Kenya travel specialist Kristy says: “Northern conservancy has more private conservancies, with great chances of viewing leopards, cheetahs, and lions. There are rhino sanctuaries travelers can visit and Lake Nakuru has lots of birding options, rhinos, and lions. There are lots of topography changes in Kenya to give visitors plenty of variety.”

While Mt Kilimanjaro lies in Tanzania, the best views of Africa’s tallest mountain are actually from Amboseli National Park. From visiting a local village to enjoying a private cooking class, taking a horseback safari to lounging by a pool with a panoramic view, the Masai Mara offers a celebration like nowhere else in the world.

Learn more: Kenya Safaris & ToursKenya Safari Guide

7. Lisbon, Portugal

Sao Jorge castle on the hilltop in Lisbon, Portugal

Lisbon, Portugal

Lisbon is a timeless collection of cobbled lanes, classic castles, and a rich connection between the locals and the cuisine for a stunning milestone trip. Let romance reign or enjoy a family travel experience as you capture the spirit of Portugal in the capital city’s relaxed ambiance, historical architecture, and vibrant artistic heritage.

Portugal travel specialist Seo says: “In Lisbon, we like a lot of time outside, are very emotional, and spend time with friends and family. We have a rich culture, rich history, where civilization goes back to the Romans, the Moorish kings and queens. Our heritage is reflected in the way we eat, drink, and dress. Portugal is full of diversity and everything is so close, yet everything is its own entity.”

Lisbon embodies this authenticity with warm locals and unique touches that only the mixture of preserved heritage and contemporary cosmopolitan culture can provide.

Learn more: Portugal Tours & Vacations Portugal Travel Guide

8. El Calafate, Argentina

Perito Morneno Glacier in Los Glaciares National Park, Argentina

Perito Morneno Glacier near El Calafate, Argentina

South of Buenos Aires and a passion for tango stands the great wilderness of Patagonia and the wonders that surround the charming town of El Calafate. Adventurers, nature-lovers, and romantics alike can embrace the unique destination during a milestone trip as you expand your celebration to include the marvels of Perito Moreno Glacier and the pink flamingos grazing in Laguna Nimez.

El Calafate is a town of artisans and chocolate, ice cream and panoramas, making every step a perfect introduction to Patagonia, a marvelous connection to the local cuisine, and a stunning example of untouched nature at its finest. Visiting El Calafate for any type of milestone adds to the memory of your experience.

Learn more: Argentina Travel GuideArgentina Tours & Vacations

9. Cape Town, South Africa

Table Mountain in Cape Town, South Africa

Cape Town, South Africa

Cape Town is the ultimate destination for a milestone trip, a city that combines cuisine, landscape, and beauty for a celebration worth remembering. Crowned by the sensational plateau of Table Mountain and its protected national park, the glistening water and lively neighborhoods only add to the charming ambiance.

While Cape Town is great for adventure and beaches, it also offers fantastic opportunities to nearby iconic experiences, from exploring the Winelands to visiting Aquila Game Reserve, viewing penguins in Simon’s Town to venturing to the scenic edge of the Cape of Good Hope.

“You can spend 15 to 18 days in South Africa and never run out of things to do,” says safari travel specialist Neil. From Robben Island, Table Mountain, horseback riding on the beach, or visiting Kirstenbosch National Botanical Gardens, “you might be surprised at what you can do”, he says.

Learn more: South Africa SafarisSouth Africa Travel Guide

Start Planning Your Custom Milestone Trip

Masai Mara, Kenya

Masai Mara, Kenya

How you wish to celebrate your milestone is personal and an intimate reflection of your wishes. Whether looking to accentuate romance or enjoy bringing the family together, a milestone trip is an occasion to remember.

Plan each day to perfection or give yourself sporadic goals to enjoy for a less structured itinerary. From adventure to relaxation, active exploration to cultural connections, you can find inspiration for your personalized trip with our sample itineraries at Zicasso.

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