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12 Destinations for Your Next Milestone Trip

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Santorini, Greece

Santorini, Greece

Weddings, anniversaries, birthdays, graduations, and other milestones are always something to look forward to. Our 12 best destinations will help you 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 want to celebrate, you can savor your personalized 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. Maasai Mara, Kenya
  7. 7. Lisbon, Portugal
  8. 8. El Calafate, Argentina
  9. 9. Cape Town, South Africa
  10. 10. Tokyo, Japan
  11. 11. Machu Picchu, Peru
  12. 12. Sydney, Australia
  13. Explore the Best Destinations for a Milestone Trip

1. Amalfi Coast, Italy

Amalfi Coast, Italy

Amalfi Coast, Italy

“Italy is always a collective joy for travelers,” 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 beach beneath an umbrella or basking in the panoramic views from the historic Villa Cimbrone clinging to the cliffside, the Amalfi Coast is an endless thrill for any celebratory occasion.

Should you be considering a trip to the Amalfi Coast, a Zicasso travel specialist can expand your experience by sharing the many areas of the coastline to consider. “Unexpected Greek origins, with medieval towns, vineyards and farms, a beautiful coastline dotted with beaches and ancient villages, and a bit of the old Italy,” 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 romantic destination. With white-sand beaches, overwater bungalows, and top-notch service providing privacy, luxury, relaxation, and adventure, Bora Bora is 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 VacationsTop Things to Do in Bora Bora

3. Santorini, Greece

Santorini, Greece

Santorini, Greece

Santorini offers endless natural beauty, ancient wonders, magnificent food, and luxurious accommodations, so it is no surprise this island is a consideration for any traveler looking to plan the trip of a lifetime around the Mediterranean. 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 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 & ToursGreece Travel Guide

4. The Islands, Thailand

Koh Yao Noi Island in Thailand

Koh Yao Noi Island in Thailand

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

While Phuket is a famous, 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 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 its 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

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 ideal space 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 celebration for any kind of traveler.

Learn more: Belize Vacations & ToursBelize Travel Guide

6. Maasai Mara, Kenya

Maasai Mara, Kenya

Maasai Mara, Kenya

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

The national park and protected area capture 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. It is easy to connect Maasai Mara to other popular places in the country, and there is much to see with a variety of topography to explore.

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 Maasai Mara offers a celebration like nowhere else.

Learn more: Kenya Safaris & ToursKenya Safari Guide

7. Lisbon, Portugal

Sao Jorge castle on the hilltop in Lisbon, Portugal

Lisbon, Portugal

Lisbon offers 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 Sao 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 & VacationsPortugal Travel Guide

8. El Calafate, Argentina

Perito Morneno Glacier in Los Glaciares National Park, Argentina

Perito Morneno Glacier near El Calafate, Argentina

The charming town of El Calafate is south of Buenos Aires and lies deep in the heart of the great wilderness of Patagonia. 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. Visiting El Calafate for any milestone adds to the memory of your experience, whether celebrating a milestone with family or as a couple.

Learn more: Argentina Tours & VacationsArgentina Travel Guide

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 a wildlife safari on the 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 all there is to do.

Learn more: Cape Town VacationsSouth Africa Travel Guide

10. Tokyo, Japan

Rainbow bridge in Tokyo, Japan

Rainbow bridge in Tokyo, Japan

Tokyo is a surprisingly seductive city, perfect for lovers of fashion, anime, exquisite cuisine, and an overall fascination with metropolitan life. The city is too simply described as unique, and you can quickly dig beneath the surface to find how 26 separate cities, towns, and villages create the broader metropolis of Tokyo.

Each ward has its own distinct identity in which you can find family-run restaurants serving exquisite dishes from fresh sushi to luscious ramen broths. Experience the traditional of hamami, a picnic in one of the best places to see cherry blossoms, or visit one of the specialty coffee shops in the desirable Kichoji neighborhood on your way to a stroll through Inokashira Park.

Seamlessly blend the old and new in Tokyo as you celebrate with a visit to Shinto shrines and protected gardens, a pristine view of Mount Fuji when riding the bullet train, or when wandering through the romantic city lights. No matter how you prefer to experience Tokyo, it can feel like an unforgettable celebration around your milestone.

Learn more: Japan ToursJapan Travel Guide

11. Machu Picchu, Peru

Machu Picchu, Peru

Machu Picchu, Peru

Machu Picchu is an iconic wonder of ancient history befitting of a milestone event. The journey itself rewards travelers with views into a kingdom cloaked in mystery. The soaring structure high in the Andes can take you on a whirlwind adventure perfect for elaborate birthday celebrations, graduations, a spirited retirement party, or a whimsical friendiversary.

Trek along the awe-inspiring trails once walked by Incas to reach the Sun Gate known for its impressive view over the ruins. Wander the tiered levels lined with exquisitely carved stones untouched by mortar and in harmony with nature. Enjoy farm-to-table cuisine using indigenous ingredients. No matter your reason for the trip, the time to visit Peru, or when traveling through Peru with kids, Machu Picchu never disappoints and is always an impressive site,

From stargazing excursions to spiritual ceremonies with a shaman, relaxing in nearly natural thermal baths to trekking along the multi-day path of the Inca Trail, Machu Picchu offers unique ways to reconnect with Mother Earth, engage with history, and connect with local culture.

Learn more: Peru Tours & VacationsPeru Travel Guide

12. Sydney, Australia

Sydney, Australia

Sydney, Australia

From the country’s best sun-soaked beaches to vibrant multicultural districts, Sydney captivates retirees, couples, and those celebrating birthdays with its easygoing spirit and captivating ambiance.

Enjoy a unique view of the Harbour Bridge during a special dinner. Stand atop the Sydney Tower Eye taking in the magnificent city sights. Wander beneath the shimmering sails of the iconic Opera House. Venture beyond the harbor to the nearby Blue Mountains to stroll along trails among ancient rainforests and waterfalls or visit one of the best wine regions in Australia at Hunter Valley for leisurely tastings at award-winning vineyards.

From cosmopolitan cafes to the famous golden sands of Bondi Beach, Sydney will tempt you whether celebrating retirement freedom, romantic anniversaries, or milestone birthdays by offering something for everyone.

Learn more: Australia ToursAustralia Travel Guide

Explore the Best Destinations for a Milestone Trip

Positano at sunset on the Amalfi Coast, Italy

Positano at sunset on the Amalfi Coast, Italy

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, explore new ideas with our milestone experiences of a lifetime, or find inspiration for your personalized trip with our itineraries at Zicasso.

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