About Us

Corporate travel services
Bermuda romantic getaway
Cruise to Bermuda
Snorkel Park, Bermuda

As a travel company we wanted to differentiate from the noise of ‘everyone going everywhere’. That is why we specialize in one place. Since the founder grew up in Bermuda, we only help you travel to Bermuda. We have created memories for every occasion on the island since starting up in 2013, and we continue to plan to do so. Creating perfect memories every year.

By calling us 7 days a week, from 9:00 am – 10:00 pm, you are able to speak with a Bermuda travel expert and get great deals on Bermuda cruises, hotels and flights, and vacation packages.

Our wedding planners, yacht charters, tour guides, and everything else that is needed for visitors to the island, are all one phone call or email away when you work with us. Our travel specialists are also available by phone to book cruises hotels, and flights.

We have relationships with some of the best vendors on the island. All you need to do is get into contact with us at Thinking of Bermuda and every hotel, activity, cruise- and anything else you can think of in Bermuda – is at your disposal. It is the full Bermuda experience. No headaches, no stress – just the Bermuda experience.

Meet Our Team:

John Gallo
  is a certified Bermuda Travel Specialist, certified through the Bermuda Department of Tourism and he has been helping to plan weddings, vacations, and other events in Bermuda since 2012. He was raised on the island and has extensive knowledge of the local vendors and things to do. His ability to point visitors in the right direction has led to many lasting memories for our clients.

Since leaving Bermuda, John has traveled to many places and lived in Barcelona, Spain; Costa Rica; and Miami, FL. Yet even after traveling Europe, the Caribbean, and the United States, John still believes Bermuda is one of his favorite places to be.

Email: john.gallo@thinkingofbermuda.com
Office Line: +1 786-250-6841

Siairah Milano, a true island girl, was born and raised in Bermuda. She can tell you there is nothing like Bermuda’s surrounding turquoise blue ocean and relaxing environment on the island. She is able to guide all of Thinking of Bermuda’s clients to a memorable time on the island, with the ultimate experience. Whether it is organizing an entire travel itinerary, hotel and cruise included, or simple excursions on the island, she is able to offer fast and immediate advice.

Happily engaged herself, Siairah knows all the excitement of planning a wedding and all the stress that comes along with it too! She is delighted to put your mind at ease and turn your vision into a reality. More importantly she is happy to make this an easy, fun, and memorable experience for you and all involved!

Siairah looks forward to helping you plan your island experience.

Email: siairah@thinkingofbermuda.com
Cell: +1-441-516-2228 (Bermuda)
US/Canada Toll Free: 855-777-2038




NO Hotel Booking Fees
We price match all cruise and hotel prices with the cruise lines and hotel chains. We also organize all the deals specifically for Bermuda, and we are constantly offering our own promotions. Call or email us to organize group bookings, as these are separate from the online booking engine and may have more promotions that apply.

NO Cruise Booking Fees & Lowest Price Guarantee
We guarantee you the lowest price when you purchase your prepaid Cruise or Vacation Package, accessible via the “Cruises” or “Vacations” tab. If you find the same cruise or package for less on another website within 24 hours of purchasing one of our prepaid cruise or vacation packages, you could get a credit equal to the difference in price, plus 10% of the difference in price, between our cruise or package and the cruise or package on the other website. This applies up to a maximum claim amount of $100 per Package purchased. See the full terms and conditions and FAQs here.

Yacht charters, tours, and introducing you to our wedding and event planners, all have zero fees. We have partnerships with all of the vendors on our website and by booking with us, there is no additional cost to you.

Our Only Fees
Weddings and organized events have fees transparently outlined in our digital proposals.


We deliver creative travel plans and remain available 7 days a week.
Email us and request a unique travel plan and itinerary. We can provide a complete request for proposal within 24-48 hours.

Our Services

     Anniversary Trips
     Foreign Language Tour Guides – Spanish, French
     Water Tours and Activities
     Tour Guides
     Large groups and events
     Activities Surrounding Bermudian Holidays
          Kite-Flying (Easter)
          Cup Match and Non-Mariners Race


Our News Feed

We regularly write in our news feed about the hidden gems in Bermuda. We want to give you ideas about what to do, but from a local’s perspective. We will keep you up to date on the various special events you can take part in throughout the year and other tips to make your vacation more organized. Bermuda is an intriguing and beautiful place so expect there to be a lot of photos as well.
We want this to be your go to guide for Bermuda. If you look at the Main Menu above this post, you will see the Things To Do and Excursions tabs. If you want to just look for things to do and explore Bermuda, click through the pages on our site where you will find a lot of information on ideas. If you would like us to organize an excursion for you, just click the excursions tab and you will be directed to a page full of activities you can choose from. Give us a call, send us an email, or fill in your information on our contact us page and we will make sure an experienced Bermudian will get in touch with you. Thinking of Bermuda will organize your trip and take care of the details. Anyone can book a trip and go on a vacation; but the ultimate experience is when you go to a country with a friend that grew up there. We are that friend. We are your guide. So go ahead, explore the site. See what Bermuda has to offer and why we have been thinking about Bermuda all this time.