
BAY2BAY TOURS invite you to experience the HIGHLIGHT of your visit to Anna Maria Island, cruising stunning waters on a private and fully customizable boating excursion for up to 6 guests. Enjoy 4 fun-filled hours with friends or family, while on vacation or celebrating a special event!
WHY PRIVATE?
Just your group - no strangers, no crowds, no lines, no set plan. We lay out all options and customize your experience based on what you and your group prefers to do; whether spending more time swimming and snorkeling, cruising by waterfront homes and looking for dolphins & manatees or even stopping at a bar/restaurant for food or refreshments…our captain, your plan!
WHAT'S INCLUDED?
Always included at no extra cost: snorkeling gear, paddleboard, extra-large inflatable mat, nets, beach balls, pool noodles, water, soda, ice, and more!
WHY BAY2BAY TOURS?
*Flawless 5-star reviews across multiple booking platforms
*Flexible schedules and meeting locations based on availability
*Custom routes and stops to maximize your fun on the water
*Expert local captains who know the best spots
*Comfortable and clean boat with lots of interior space
*Bluetooth sound system to sync up your favorite playlist
THERE'S MORE!
You can add a charcuterie board or sandwich sliders meal to your experience - order by phone after booking. Charges apply.
LOOKING FOR A LONGER EXPERIENCE?
Ask us about extending your adventure based on availability.
CELEBRATING AND ANNIVERSARY, BIRTHDAY OR OTHER SPECIAL EVENT?
Contact us - we may have just what you need to make any occasion extra special.
BOOK NOW for a fun, personalized, and unforgettable adventure!
*Captain tips are discretionary – 15% to 20% is customary for excellent service and a great experience offered. Cash, Venmo or Zelle are preferred tipping methods.
Rating summary
Photos & videos by reviewers (27)
Customer rating
Customers claimed
Good experience
100%
Appropriate for children
93%
Friendly captain
100%
Satisfied with the boat
100%
Recommend this charter
92%
Mar 8, 2026
The charter operator canceled 1 days prior to the trip date. This is an automated posting.
Jul 22, 2025
Sandbar & Dolphins 4hr (PM)
My family of 5 (3 kids from 12-16) had an amazing afternoon with Captain Santiago yesterday. From the moment we stepped on the boat, he made us feel at ease, safe and the day was ours to enjoy. He went out of his way to make sure we did everything we wanted and remained safe, away from pending storms. My kids loved the sand bars, collecting sand dollars and shells, throwing the football, floating on pool noodle and wresting on the air track. Santiago had plenty of water and soda for us. The best part was spotting a manta ray jumping out of the water and following a dolphin swimming in the bay. Perfect relaxing afternoon on the water. Thank you!
My family of 5 (3 kids from 12-16) had an amazing afternoon with Captain Santiago yesterday. From the moment we stepped on the...
Jun 13, 2025
3 Hr – Dolphins & Sandbars (AM)
Santiago is the best! This was our first time visiting Anna Maria Island, and we had a blast, definitely the highlight of our trip! He is very knowledgeable and shared so much information, he was fun, and had a lot of fun stuff for use to use while we got to swim at the sandbar (snorkel gear, nets, raft, etc). He made sure we got to see dolphins before leaving which was absolutely beautiful! He was so accommodating and so great with my kids, we were all so happy! All boxes were checked and he exceeded our expectations. We will definitely be returning and booking again with Santiago and Bay2Bay Boat Tours again! Thank you!!
Santiago is the best! This was our first time visiting Anna Maria Island, and we had a blast, definitely the highlight of our...
May 27, 2025
2 Hr – Stunning Sunset Cruise
⭐️⭐️⭐️⭐️⭐️ We had such a wonderful time on our sunset boat trip last night! The boat was spotless and comfortable, and our captain, Islander, was absolutely fantastic. He was warm, personable, and made us feel completely at ease the whole time. My aunt and I were both very fond of him—he truly made the experience special. We even docked for a drink at a bar along the way, and Islander was nothing but friendly and professional. Highly recommend this trip if you’re looking for a relaxing, scenic evening on the water with great company!
⭐️⭐️⭐️⭐️⭐️ We had such a wonderful time on our sunset boat trip last night! The boat was spotless and comfortable, and our captain,...

Nov 8, 2025
Sandbar & Dolphins 4hr (PM)
Santiago was wonderful! He catered the afternoon perfetlctly for our family. We saw manatees and dolphins, searched for sand dollars, and ended the day playing on the lilly pad as the sun set. It was a great day making core memories with our group. He even recommended a great local restaurant that we all enjoyed. 10/10 recommend for family fun in the sun!
Santiago was wonderful! He catered the afternoon perfetlctly for our family. We saw manatees and dolphins, searched for sand...
| Su | Mo | Tu | We | Th | Fr | Sa | |
|---|---|---|---|---|---|---|---|
Rating summary
Photos & videos by reviewers (27)
Customer rating
Customers claimed
Good experience
100%
Appropriate for children
93%
Friendly captain
100%
Satisfied with the boat
100%
Recommend this charter
92%
Trip was supposed to happen on March 8, 2026
The charter operator canceled 1 days prior to the trip date. This is an automated posting.
Experience:
Equipment
Crew
Overall
Sandbar & Dolphins 4hr (PM) on July 22, 2025
My family of 5 (3 kids from 12-16) had an amazing afternoon with Captain Santiago yesterday. From the moment we stepped on the boat, he made us feel at ease, safe and the day was ours to enjoy. He went out of his way to make sure we did everything we wanted and remained safe, away from pending storms. My kids loved the sand bars, collecting sand dollars and shells, throwing the football, floating on pool noodle and wresting on the air track. Santiago had plenty of water and soda for us. The best part was spotting a manta ray jumping out of the water and following a dolphin swimming in the bay. Perfect relaxing afternoon on the water. Thank you!
My family of 5 (3 kids from 12-16) had an amazing afternoon with Captain Santiago yesterday. From the moment we stepped on the boat, he made us feel at ease, safe and the day was ours to enjoy. He went out of his way to make sure we did everything we wanted and remained safe, away from pending storms. My kids loved the sand bars, collecting sand dollars and shells, throwing the football, floating on pool noodle and wresting on the air track. Santiago had plenty of water and soda for us. The...
Experience:
Equipment
Crew
Overall
3 Hr – Dolphins & Sandbars (AM) on June 13, 2025
Santiago is the best! This was our first time visiting Anna Maria Island, and we had a blast, definitely the highlight of our trip! He is very knowledgeable and shared so much information, he was fun, and had a lot of fun stuff for use to use while we got to swim at the sandbar (snorkel gear, nets, raft, etc). He made sure we got to see dolphins before leaving which was absolutely beautiful! He was so accommodating and so great with my kids, we were all so happy! All boxes were checked and he exceeded our expectations. We will definitely be returning and booking again with Santiago and Bay2Bay Boat Tours again! Thank you!!
Santiago is the best! This was our first time visiting Anna Maria Island, and we had a blast, definitely the highlight of our trip! He is very knowledgeable and shared so much information, he was fun, and had a lot of fun stuff for use to use while we got to swim at the sandbar (snorkel gear, nets, raft, etc). He made sure we got to see dolphins before leaving which was absolutely beautiful! He was so accommodating and so great with my kids, we were all so happy! All boxes were checked and he...
Experience:
Equipment
Crew
Overall
2 Hr – Stunning Sunset Cruise on May 27, 2025
⭐️⭐️⭐️⭐️⭐️ We had such a wonderful time on our sunset boat trip last night! The boat was spotless and comfortable, and our captain, Islander, was absolutely fantastic. He was warm, personable, and made us feel completely at ease the whole time. My aunt and I were both very fond of him—he truly made the experience special. We even docked for a drink at a bar along the way, and Islander was nothing but friendly and professional. Highly recommend this trip if you’re looking for a relaxing, scenic evening on the water with great company!
⭐️⭐️⭐️⭐️⭐️ We had such a wonderful time on our sunset boat trip last night! The boat was spotless and comfortable, and our captain, Islander, was absolutely fantastic. He was warm, personable, and made us feel completely at ease the whole time. My aunt and I were both very fond of him—he truly made the experience special. We even docked for a drink at a bar along the way, and Islander was nothing but friendly and professional. Highly recommend this trip if you’re looking for a relaxing, scenic...

Experience:
Equipment
Crew
Overall
Sandbar & Dolphins 4hr (PM) on November 8, 2025
Santiago was wonderful! He catered the afternoon perfetlctly for our family. We saw manatees and dolphins, searched for sand dollars, and ended the day playing on the lilly pad as the sun set. It was a great day making core memories with our group. He even recommended a great local restaurant that we all enjoyed. 10/10 recommend for family fun in the sun!
Santiago was wonderful! He catered the afternoon perfetlctly for our family. We saw manatees and dolphins, searched for sand dollars, and ended the day playing on the lilly pad as the sun set. It was a great day making core memories with our group. He even recommended a great local restaurant that we all enjoyed. 10/10 recommend for family fun in the sun!