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dest 1- Caribbean
Trips by Accessorized Wanderer destinations


Warm seas, breezy, palm-fringed shores, an upbeat vibe, and fun-filled cultures; What isn’t there to love about the Caribbean? There are 26 different island nations, each with its own set of culinary specialties, style of music, historical sites, and unique geographical identity. The Caribbean is for newlyweds, for star-crossed lovers, for fun-loving friends, and anyone craving a dreamy tropical escape. From the crystalline waters of Dunns River Falls in Jamaica to hiking between the stunning pitons on the island of St. Lucia, to the charming cobblestoned streets of Old Town in Puerto Rico, whatever it is you’re seeking, you’ll find it in the Caribbean.

Best Time To Visit

The ideal time to head down to the Caribbean is between the middle of December to the middle of April. This is the driest period and conveniently, it also happens to be the worst weather window in the Midwest and Northeastern parts of the United States, so get packing! If you’re trying to avoid peak season, traveling in early December before Christmas will mean thinner crowds. And the end of March and early April will also be quieter. From June through to November, it’s hurricane season so you may want to avoid the Caribbean during that time.

Highly Recommended Experiences
  • Have a personal photoshoot amongst the beautiful Baths at Virgin Gorda on the British Virgin Islands - The massive granite boulders make for a fabulous backdrop

  • Go on a group tubing expedition down the Layou River on the Caribbean’s ‘nature island’, Dominica.

  • Laze on the beach, snorkel with exotic species and watch planes take off and land on Bonaire’s pristine Te Amo Beach

  • Shake what your Mama gave you at one of Jamaica’s iconic beach bars where reggae, soca, and dancehall will be your hip-winding soundtrack

  • Go night kayaking and be mesmerized by Puerto Rico’s bioluminescent cove on Vieques Island

  • Watch as vibrant flamingos prance, sip on champagne and enjoy exclusivity on Aruba’s private Renaissance Island

dest 2-Maldives
Trips by Accessorized Wanderer destinations
Best Time To Visit

You’ll be happy to hear that the best time to fly to the Maldives is between November and April. This window brings the most consistent weather, and you can expect average temperatures somewhere between 28°C to 32°C. The absolute driest and least humid months are between January and April. This period is also peak season for resort visitors, so keep that in mind before we start planning your trip.


Just saying the name instantly conjures up images of thatched overwater bungalows, turquoise waters, lapping up against private swimming platforms, and spectacular sunsets over the Indian Ocean. The Maldives are a collection of islands that have captured the imagination of travelers for decades, but they’re so much more than white-sandy jewels of paradise. The Maldives is home to a distinct culture - colorful, rich, warm, and inviting. If you love culinary fusion, Maldivian curries, fresh seafood, and coconut-infused everything await your adventurous palate. You could easily spend days on end lazing about the beach, but don’t forget, an underwater biosphere invites you to explore its exotic flora and fauna.

Highly Recommended Experiences
  • Enjoy some much-needed privacy on Fulhadhoo Beach located on the Maalhosmadulhu Atoll - Guests can take a speedboat from Male, and with only 250 people inhabiting the island, you’ll feel like you’re completely on your own

  • Have the complete Maldives experience and stay in an overwater bungalow

  • Spend some time on the water on a sailing trip, paddle-boarding excursion, kayaking session, or thrilling jet-ski tour

  • Go on a dolphin watching trip - The Maldives is world-famous for its dense population of spinner dolphins

  • Go island hopping, visit some fish markets, and mingle with the locals - the Maldives is full of charming villages, perfect for photography enthusiasts

  • Explore the local reefs on a diving or snorkeling expedition - You’ll find manta rays, turtles, moray eels, and whale sharks here.

dest 3-Greek Islands
Trips by Accessorized Wanderer destinations
Best Time To Visit

For the best weather, a trip to the Greek Islands should happen between October and Easter (mid to late April). You can of course visit any time of year, however, July and August can be unbearably hot, and know that late October through to March can be chilly, with some spots of rain. These winter months will also see the closure of some tourist attractions, hotels, and restaurants. For fewer crowds, the late spring (May) and early fall (September to October) may be ideal for you.

Greek Islands 


Did you know that it would take one year and almost seven months to explore the Greek Islands! Okay, to be fair, we’re counting the rocky outcrops and more than 5,700 islands that aren’t inhabited. If you decide to make the Greek Islands your next stop for a couples getaway or small group escape, we can’t recommend it enough. Greece is a choose-your-adventure type destination meaning if you want to spend your days wandering the iconic streets of Athens, dance the night away in one of Mykonos beautiful Cycladic (Bronze era) villages, or photograph wild horses race around Mount Aenos in Kefalonia on one of the Ionian islands, you’ll leave knowing you have so much more experience and explore.

Highly Recommended Experiences
  • Enjoy one or many of Greece’s world-famous and idyllic beaches - On Zakynthos Island, Shipwreck Beach is an absolute must

  • Take a winery tour - Greece is one of the world’s oldest wine producers and Santorini is a phenomenal island to experience this

  • Stay in a private villa on the laid back, chic island of Corfu

  • Spoil yourself with a spa day worthy of the ancient monarchs - Much like the Romans, the Greeks believed in opulent self-indulgence, and who doesn’t deserve a little self-care on holiday?

  • Go Island hopping to the Saronic Gulf Islands and the Cyclades - Experience rich folklore and beautifully preserved villages from the Byzantine era

  • Kick-off your Greek Island adventure on the mainland with a candlelit dinner on any number of famous rooftop patios in Athens

dest 4-Mayan Riviera
Trips by Accessorized Wanderer destinations
Best Time To Visit

If you’re looking for a winter escape, the Mayan Riviera is calling your name! The driest time to visit is between late November through to the end of February. The entire tourist season spans from November to May. If you’re thinking of sneaking down for a quick summer escape, you may be dealing with heavy rains and oppressive heat and humidity. For fewer crowds and quieter beaches you may want to skip going down on the major American holidays including Thanksgiving, Christmas, New Years and Spring Break.

Mayan Riviera

If you’ve never visited Mexico, or you’ve vacationed in other places like Puerto Vallarta, Cabo San Lucas or Cancun, it might be time to head to the Yucatan Peninsula and experience Mayan Riviera for a dash of culture, a dose of beach life and a pinch of adventure. The Mayan Riviera stretches 75 miles from the small fishing village of Puerto Morelos south to Punta Allen, a slice of paradise on earth with few visitors. In between those points you’ll find the bustling town of Playa Del Carmen, the exclusive resort community of Puerto Aventuras, the pristine region of Akumal and the jungle-lush region of Tulum. The Mayan Riviera is the perfect destination for newlyweds, couples looking to take a much-needed break from work, and for groups interested in experiencing a blend of thrills in nature, waterfun, incredible food and ancient cultural sites.

Highly Recommended Experiences
  • Visit Aktun-Chen, an incredible system of underground caverns that date back some 5 million years - This is one of the less-visited cenotes and one of the more spectacular

  • For nature enthusiasts, be sure to visit Sian Ka'an, a World Unesco Heritage site and 1.3 million acre nature reserve home to tropical rainforests, mangrove swamps and several hundred species of migratory birds, fish, plants and other animals.

  • Party, sip and dance the day away at one of Playa Del Carmen’s exclusive and private cabanas

  • Channel your inner Indiana Jones and take a walk around the ceremonial limestone paths of Cobá and enjoy 360 views of the thick jungle below

  • Leap into the crystalline waters of Cenote Azul just south of Playa Del Carmen 

  • Spend the day on the water in a catamaran and go snorkeling with sea turtles, diving, or just lounge in the sun and listen to the sounds of the sea

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