(18 Reviews)
100% Recommended

Tabitha Callesen

Cleveland, OH

US and Caribbean Travel Agent Specialist

As a dedicated Travel Advisor, I specialize in crafting unforgettable journeys tailored to each client's unique preferences. From luxury cruises and private jet charters to honeymoons and adventure travel, I focus on delivering personalized, high-end experiences that go beyond the ordinary. With an eye for detail and a passion for creating seamless travel experiences, I offer concierge-level service, ensuring that every trip is planned with care and expertise. Whether it's a romantic getaway, a family vacation, or a business trip, my goal is to exceed expectations and turn dreams into reality. I stay updated on the latest travel trends and maintain exclusive partnerships with top resorts, hotels, and travel services worldwide. Let me guide you to your next destination, providing expert insight and exceptional service to ensure your journey is truly memorable.

My Travel Specialties

Key West Travel Agent Expert

As a Key West Travel Agent Expert, I specialize in crafting unforgettable experiences in this iconic Florida destination. Whether you're looking for a romantic sunset sail, exciting water sports, or a peaceful beach getaway, I know all the best-kept secrets that make Key West a unique paradise.

I’ll...
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Bahamas Travel Agent Specialist

With extensive knowledge of the Bahamas, I am your go-to Travel Agent Specialist for this stunning tropical destination. I know the best islands for snorkeling, diving, and beachfront relaxation, and I can recommend luxurious resorts as well as budget-friendly hidden gems.

Whether you're interested...
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Jamaica Travel Expert

From the vibrant reggae culture to stunning beaches and waterfalls, Jamaica is an island with heart. I’ll curate a personalized experience, whether you're looking to relax at an all-inclusive resort in Montego Bay or explore the rich landscapes and culture of Negril and Ocho Rios. With my expertise,...
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Dominican Republic Travel Expert

With its beautiful beaches, vibrant culture, and luxury resorts, the Dominican Republic is a versatile destination. I can help plan your ideal getaway, whether you’re interested in a relaxing Punta Cana beach vacation or a cultural exploration of Santo Domingo. Let me handle the details to ensure...
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Puerto Rico Travel Expert

Experience the vibrant culture, historic charm, and beautiful beaches of Puerto Rico. Whether you’re interested in exploring Old San Juan, hiking in El Yunque, or relaxing at a luxury resort, I’ll create an itinerary that captures the island’s unique blend of history and natural beauty. Discover the...
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Barbados Travel Expert

Known for its incredible beaches, historic charm, and lively festivals, Barbados is an ideal Caribbean destination for both relaxation and exploration. I can guide you to the best local spots, from hidden beaches to vibrant markets and dining experiences. Let me help you discover the magic of Barbados...
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Aruba Travel Expert

Experience the 'One Happy Island' of Aruba, known for its pristine beaches, friendly locals, and vibrant culture. With my insider knowledge, I can tailor your trip to include everything from serene beach resorts to exciting excursions like off-road island tours and water sports. Let’s make your Aruba...
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Turks & Caicos Travel Expert

Discover the breathtaking turquoise waters and luxurious resorts of Turks and Caicos with my expert guidance. From arranging secluded beachside accommodations to planning exclusive snorkeling and diving experiences, I’ll create a tropical getaway that’s both relaxing and unforgettable. Let me help...
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U.S. Virgin Islands Travel Expert

With three unique islands to explore, the U.S. Virgin Islands offers a variety of experiences from luxury resorts to vibrant nightlife and natural beauty. I’ll help you explore St. Thomas, St. John, or St. Croix with a customized itinerary that captures the essence of each island. Your Caribbean escape...
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British Virgin Islands Travel Expert

Famous for its sailing culture, pristine beaches, and unspoiled beauty, the British Virgin Islands are an ideal destination for a luxurious and tranquil escape. I’ll tailor your experience to include private boat charters, secluded beaches, and the best local cuisine. Let me take care of every detail...
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Cayman Islands Travel Expert

Dive into the Cayman Islands’ crystal-clear waters and luxurious island lifestyle with a customized travel experience. Known for world-class diving, stunning beaches, and upscale dining, this destination offers something for everyone. I’ll craft your itinerary to include the best of Grand Cayman’s...
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New York City Travel Expert

New York City dazzles with its iconic skyline, world-class arts, and endless entertainment options. From exclusive restaurant reservations and private shopping tours to curated itineraries for Broadway shows and famous landmarks, I’ll make sure your experience in the Big Apple is both luxurious and...
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New York City Travel Expert

New York City dazzles with its iconic skyline, world-class arts, and endless entertainment options. From exclusive restaurant reservations and private shopping tours to curated itineraries for Broadway shows and famous landmarks, I’ll make sure your experience in the Big Apple is both luxurious and...
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Niagara Falls Travel Expert

Niagara Falls offers a unique blend of natural wonder and romance, making it ideal for couples and thrill-seekers alike. I’ll plan your adventure to include unforgettable views from boat tours, charming nearby towns, and intimate dining experiences, ensuring your trip to Niagara is filled with both...
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Atlanta Georgia Travel Expert

Atlanta is a city of contrasts, offering everything from lush parks and gardens to dynamic nightlife and cultural landmarks. I’ll plan your visit to include must-see attractions, vibrant dining spots, and local entertainment options, ensuring you experience the best of what this bustling city has...
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Charleston SC Travel Expert

Charleston enchants visitors with its storied past, beautiful architecture, and celebrated culinary scene. I’ll design an itinerary that showcases the best of Charleston. From historical tours and scenic walks through the city’s iconic streets to exclusive reservations at award-winning restaurants....
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Myrtle Beach Vacation Expert

Myrtle Beach is the ultimate family-friendly destination with endless entertainment, sandy beaches, and kid-approved activities. From arranging accommodations to tickets for live shows and amusement parks, I’ll handle all the details so you can focus on creating joyful memories with your loved ones....
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Hilton Head Island Travel Expert

Hilton Head is an oasis of beautiful beaches, championship golf courses, and an inviting coastal atmosphere. I’ll design a relaxing stay that balances days on the beach with rounds of golf, local shopping, and waterfront dining. With my expertise, you’ll discover the serene charm of Hilton Head and...
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Tampa Beach Getaway Expert

Tampa offers a perfect mix of sunny beaches, thrilling water sports, and vibrant city life. I’ll help you make the most of this coastal paradise with a carefully crafted itinerary that includes relaxing beach days, sunset cruises, and unforgettable waterfront dining experiences.

With the charm...
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Napels & Marco Island Travel Expert

Experience the tranquil beauty and elegance of Naples and Marco Island. Known for its serene beaches, luxurious resorts, and exceptional golf courses, this slice of Florida’s paradise coast is ideal for relaxation and refinement. I’ll create a unique itinerary that balances peaceful beach time, world-class...
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Fort Lauderdale Travel Expert

Fort Lauderdale is where beach relaxation meets cruise adventure, offering beautiful shorelines and easy access to the Caribbean. I’ll arrange a seamless pre-cruise experience or help you make the most of your stay with personalized beachfront accommodations, lively dining, and local exploration....
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Miami Travel Expert

Miami embodies glamour and excitement with its world-famous beaches, upscale dining, and vibrant nightlife. From chic rooftop lounges and private yacht charters to exclusive beach clubs, I create travel experiences that highlight Miami’s luxurious side.

Whether you’re a couple seeking a romantic...
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Orlando Vacation Expert

Orlando offers endless adventures for families, thrill-seekers, and relaxation lovers alike. From navigating the wonders of Disney and Universal to uncovering hidden gems in nearby areas. I specialize in creating fun, seamless vacations filled with magic and ease.

Whether it’s VIP tours, character...
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Cruise Vacation Expert

Set sail on your dream cruise vacation with guidance from an experienced Cruise Vacation Expert. Whether you’re a first-time cruiser or a seasoned sailor, I’ll help you find the perfect cruise line, itinerary, and excursions that match your preferences.

From the Caribbean and Mediterranean...
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Family Vacation Travel Expert

As a Family Vacation Specialist, I understand the unique needs of families when it comes to travel. I specialize in creating fun, memorable, and stress-free family vacations, from theme parks like Disney World to beach resorts that cater to kids and adults alike to cruises that are designed with family...
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My Reviews

Stress-Free Trip!
Our trip to the British Virgin Islands was stress-free and fun! Tabitha had great recommendations for sailing and local cuisine. Looking forward to traveling again!
By  Michelle  from  Cuyahoga Falls, OH
Traveled to  Virgin Gorda ~ Virgin Islands ~ Caribbean
I would recommend this agent to my family and friends
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Smooth Family Vacation!
Our family vacation to the Dominican Republic went so smooth! Thanks to Tabitha's thorough planning, we loved every minute!
By  Tina  from  Hudson, OH
Traveled to  Dominican Republic ~ Caribbean
I would recommend this agent to my family and friends
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Blast in Jamaica
Tabitha arranged a dream trip to Jamaica for us. From the all-inclusive resort to the guided tours, everything was just perfect. Highly recommend her services!
By  Andrew  from  North Olmsted, OH
Traveled to  Jamaica ~ Caribbean
I would recommend this agent to my family and friends
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Best trip to Charleston
Thanks to Tabitha, out trip to Charleston was amazing! Her tips on dining and ours made all the difference. We loved every moment!
By  Jessica  from  Sandusky, Ohio
Traveled to  Charleston ~ South Carolina ~ USA
I would recommend this agent to my family and friends
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Dream Trip to New York
My trip to New York City was a dream come true! Tabitha's recommendations for dining and entertainment were spot on. I'll definitely be traveling with her again!
By  Jordan  from  Beachwood, Ohio
Traveled to  New York City ~ New York ~ USA
I would recommend this agent to my family and friends
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Destination Expert:

  • Aruba
  • Bahamas
  • Barbados
  • Cayman Islands
  • Turks and Caicos Islands
  • Alaska
  • Culebrita
  • Cruz Bay
  • Virgin Gorda
  • Fort Lauderdale
  • Key West
  • Marco Island
  • Miami
  • Orlando
  • Tampa
  • Universal Orlando
  • Atlanta
  • New York City
  • Niagara Falls
  • Charleston
  • Hilton Head Island
  • Myrtle Beach
  • Palm Beach
  • Nassau
  • Bridgetown
  • Little Cayman
  • Fajardo
  • Grand Turk
  • St. Croix
  • Tortola Island
  • Clearwater
  • Key Largo
  • Miami Springs
  • Naples
  • Port Everglades
  • Walt Disney World
  • Athens
  • Bronx
  • Buffalo
  • North Charleston
  • Pawleys Island
  • New York
  • Eagle Beach
  • Castaway Cay
  • St. Lawrence
  • Georgetown
  • Pine Cay
  • Road Town
  • St. Thomas
  • Cape Coral
  • Clearwater Beach
  • Coral Gables
  • Marathon
  • Marietta
  • Brooklyn
  • Kiawah Island
  • Litchfield Beach
  • Puerto Rico
  • Oranjestad
  • Paradise Island
  • St. Phillip
  • Cayman Brac
  • Grace Bay
  • Scrub Island
  • St. John Island
  • Coconut Grove
  • Duck Key
  • Fort Myers
  • Hollywood
  • Kissimmee
  • St. Petersburg
  • Alpharetta
  • Queens
  • Jamaica
  • Virgin Islands
  • Georgia
  • Grand Bahama Island
  • Holetown
  • Grand Cayman
  • South Caicos
  • Peter Island
  • Key Biscayne
  • Palm Beach
  • Palm Beach Gardens
  • Port Canaveral
  • Savannah
  • Lancaster

Travel Specialist:

  • Adventure
  • All Inclusive
  • Architecture
  • Arts & Culture
  • Bachelorette Parties & Girlfriend Getaways
  • Beach Vacations
  • Business Travel
  • Disney Vacations
  • Family Vacations
  • Golf
  • Luxury Cruises
  • Sailing & Boating
  • Couples & Romance
  • Cruises
  • Culinary & Foodie
  • Entertainment
  • Luxury
  • Nature
  • Small Ship Cruises
  • Theatre & Music
  • Bucket List
  • Adult Only
  • Destination Weddings
  • Groups
  • Historical Sites
  • Scuba
  • Universal Parks & Resort Vacations
  • Expedition Cruises
  • Festival Tours
  • Holiday Travel
  • Nightlife
  • Outdoor Activities & Sports
  • Photography
  • Shopping
  • Theme Parks
  • Water Sports
  • Celebration Travel
  • City Breaks
  • LGBTQ+ Travel
  • Parks & Gardens
  • World Cruises

Industry Affiliations:

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