Travel Advisor

Jacob Roland

Expertise

Group Travel,
Luxury,
Caribbean,
Bahamas,
Mediterranean,
Europe

Based in

The Port City! Oswego, NY

Languages spoken

English

Travel Advisor

Jacob Roland

Profile details

About

As a travel advisor with over a decade of experience exploring the Caribbean and Mediterranean, I specialize in curating unforgettable experiences tailored to discerning travelers. My mission is to transform your travel dreams into reality, ensuring every detail is meticulously planned to inspire wanderlust and provide unparalleled service.

Follow Jacob

Travel style

Hi, my name is Jacob, and for over 10 years, I've been exploring the stunning Caribbean and Mediterranean! My travel style embraces luxury, allowing me to indulge in the finest experiences while enjoying breathtaking views. I thrive on adventure, whether it's diving into crystal-clear waters or discovering hidden gems in vibrant local cultures. My purpose is to bring my passion for travel to you and inspire the wanderlust within! Every trip is a chance to immerse yourself in new experiences and create unforgettable memories!

Jacob's travel guides & trip reports

A view of blue water near a rocky shoreline and bridge during the daytime.

Guide

Eleuthera, Bahamas — Island of Freedom

With more than 130 beaches, Eleuthera offers seclusion, peace and adventure all wrapped into an authentic Bahamian cultural experience. Made up of Harbor Island, the island of Spanish Wells, a few...

Favorite hotels

Hotel Xcaret Arte – Adults Only

An hour south of Cancun, this mammoth adults-only resort is a true all-inclusive, with 900 rooms, nine restaurants and access to all the adventures at eight nearby activity parks.

Fora Perks

★
$100 resort / hotel credit.
★
Welcome amenity.
★
Breakfast daily.
★
Upgrade & extended check-in/out whenever possible.

The Cove Eleuthera

A paradisical enclave in a tranquil cove in the Bahamas offering spa-style accommodations, organic garden and water activities.

Fora Perks

★
$100 hotel / resort credit.
★
Breakfast daily.
★
Upgrade & extended check-in/out whenever possible.

Barcelo Maya Beach Resort

A beachfront paradise where all-inclusive luxury meets turquoise waters and endless Riviera Maya adventure.

Sandals Royal Bahamian - ALL INCLUSIVE Couples Only

Set on Delaport Bay in the Bahamas, this all-inclusive, couples-only resort has it all: ten restaurants, eight bars, seven pools and a spa — oh, and a private island!

Jacob's travel photos

Picture of Jacob swimming with scuba goggles on underwater

Picture of Glass Window Bridge surrounded by two different bodies of water against the blue sky and clouds

Picture of people on a boat ready to dive into water with scuba gear on

Picture of Jacob swimming in crystal clear water with the beach and trees in the background

Picture of a yacht on crystal clear water near a white sand beach

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Jacob's reviews

This was my third time booking with Jacob, & once again — he went above & beyond to make our trip perfect!!!! My friend and I were planning a vacation to Mexico, and Jacob ensured every detail was taken care of. From suggesting local fun attractions to see / do, to booking an on-site transfer for added convenience and safety. He truly thought of everything. He made the entire process smooth and stress-free. Jacob is incredibly easy to work with, attentive, and is genuinely passionate about creating a great travel experience custom to YOU! I highly recommend his services to anyone planning a trip. You won’t be disappointed!!

Kayla D.
Booked travel to Playa del Carmen
March 2025

Get in touch with Jacob

Reach out to customize and book your own experience. Or, just to chat about travel in general.

You can expect a response from Jacob within 1–2 business days. You’ll also be subscribed to our traveler newsletter (you can unsubscribe at any time).