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Destination Weddings
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Stephanie
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Recommended by 100% of couples

About this vendor

Located in Bolingbrook, Illinois, Pleasant Point Travel is a full-service travel agency specializing in destination weddings, honeymoons, and romantic travel experiences around the world. We work with couples who want more than just a beautiful wedding location. They want a seamless planning experience and a trusted travel professional to guide them every step of the way.

We know that planning a destination wedding comes with a lot of moving pieces, especially when family and friends are traveling from different locations. That's where we come in. We help with everything from choosing the right destination and resort to coordinating guest accommodations, flights, airport transfers, payment plans, and travel protection. Our goal is to make travel planning as easy as possible so you can focus on enjoying your engagement and celebrating your wedding day.

Every couple has a unique vision, and we believe your wedding should reflect your style, your story, and what matters most to you. We take the time to get to know you before making recommendations, ensuring every destination and resort we suggest is a great fit for your celebration.

Whether you're dreaming of saying "I do" on a tropical beach, in a European villa, at a luxury safari lodge, or somewhere unique, we're here to help make it happen. From your first consultation to the day you return home, we're committed to providing personalized service, honest advice, and support you can count on.

At Pleasant Point Travel, we don't just book trips. We help create unforgettable experiences and memories that last a lifetime.

We'll Help You Discover the World!

Features

Woman-owned

Small team (2-10 members)

Experience

  • 10 years in business

  • We speak English and Spanish

Links

Visit website

FAQ

What types of travel do you specialize in?

Cruises
Destination Weddings
Family Trips
Group Travel / Tours
Honeymoons
Luxury Trips

What destinations do you specialize in?

Africa
Alaska
Asia
Caribbean
Central America
Dominican Republic
East Europe
Hawaii
Mexico
Pacific Islands
South America
West Europe

What travel services do you provide?

Emergency Assistance
Travel Insurance
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Reviews of Pleasant Point Travel

This AI-generated summary gives you a snapshot of the overall ratings and feedback from the reviews this vendor has received.

Review summary

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Pleasant Point Travel streamlined destination-wedding travel, making planning and on-trip logistics smooth and stress-free. Their agent was professional, responsive, organized, and went above and beyond—handling hotels, excursions, and vendor coordination. Highly recommended.

Review summary

Powered by AI
This AI-generated summary gives you a snapshot of the overall ratings and feedback from the reviews this vendor has received.

Pleasant Point Travel streamlined destination-wedding travel, making planning and on-trip logistics smooth and stress-free. Their agent was professional, responsive, organized, and went above and beyond—handling hotels, excursions, and vendor coordination. Highly recommended.

Stephanie
Stephanie Sent on 08/19/2026
5 out of 5 rating

Used as a travel agent for destination wedding

Choosing Pleasant Point Travel helped streamline our destination wedding and took the pressure off trying to manage everyone’s travel arrangements. They worked directly with our venue, allowing us more time to focus on the actual wedding. They were helpful even while on our trip, answering questions for first time travelers and assisting with any unexpected delays that came up. Would definitely recommend them and would use them again!
Pamela
Pamela Sent on 08/19/2026
5 out of 5 rating

Amazing Experience w/ Pleasant Point Travel

We had a wonderful experience working with Pleasant Point Travel! TSheeka arranged travel for my husband, our guest, and me for our destination wedding in beautiful Santorini, Greece. From beginning to end, she made the entire process smooth and stress-free.

She selected an absolutely amazing hotel that was perfect for our stay and made sure all of our travel arrangements came together seamlessly. Having someone handle the details and make sure everything went smoothly allowed us to truly enjoy such a special time in our lives.

TSheeka was professional, attentive, responsive, and simply wonderful to work with. We truly appreciated the care she put into planning our trip.

Job well done, TSheeka! I highly recommend Pleasant Point Travel for your travel needs, especially for a special occasion or destination wedding!
C
Cherlonda Sent on 08/12/2026
5 out of 5 rating

Amazing Experience Tsheeka was our travel agent for our destination wedding in 2018, and she was absolutely amazing! She went above and beyond, helping with everything from excursions to finding our DJ, MC, photographer, and even an additional wedding coordinator. She made what could have been a stressful experience feel seamless and truly unforgettable. I honestly don’t know what I would have done without her. Eight years later, I’m still incredibly grateful for everything she did to make our wedding so special. I highly recommend her! ❤️

Tsheeka was our travel agent for our destination wedding in 2018, and she was absolutely amazing! She went above and beyond, helping with everything from excursions to finding our DJ, MC, photographer, and even an additional wedding coordinator. She made what could have been a stressful experience feel seamless and truly unforgettable. I honestly don’t know what I would have done without her. Eight years later, I’m still incredibly grateful for everything she did to make our wedding so special. I highly recommend her!
J
Jason Sent on 08/12/2026
5 out of 5 rating

Destination Wedding

We had an amazing experience working with Pleasant Point Travel to plan our destination wedding in the Dominican Republic! The customer service was excellent from start to finish, and Tsheeka was incredibly helpful, professional, and easy to work with. She made the planning process feel smooth and stress-free, was responsive to our questions, and helped ensure that everything came together beautifully. Our wedding was a wonderful and memorable experience, and we truly appreciate all of the support and care we received. We highly recommend Pleasant Point Travel—and especially Tsheeka—to anyone planning a destination wedding!
Khaaliyah
Khaaliyah Sent on 08/11/2026
5 out of 5 rating

Above and Beyond Services!!

Tsheeka was absolutely amazing! I attended a destination wedding in July, and she made the entire travel process so smooth and stress-free. She was extremely helpful, responsive, organized, and always available whenever we had questions or needed assistance. Traveling for a destination wedding can be overwhelming, but Tsheeka made everything feel easy and well coordinated from beginning to end. Her professionalism, communication, and willingness to help truly stood out. I had such a great experience working with her and would absolutely recommend Tsheeka to anyone planning a destination wedding, group trip, or vacation. She truly went above and beyond!
Regine
Regine Sent on 08/11/2026
5 out of 5 rating

Dream destination wedding

T’Sheeka was awesome! 10/10 recommended :)
She went above and beyond and my wedding was amazing!
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Team

TSheeka Ruffin
TSheeka Ruffin
Travel Advisor

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