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Cruises Calling at Old Saybrook

25 upcoming cruises that stop at Old Saybrook, Connecticut, USA. Updated regularly; always confirm with the cruise line.

ACL American Eagle
American Cruise Lines Cruises
New York → Boston
⚓ Calls 02 Jul 20267 nights10 portsDeparts 2026 Jun 30
View itinerary · 10 ports
7 days, one-way from New York to Boston
  1. 30 JunDeparting from New York, NYC Manhattan-Brooklyn
  2. 30 JunNew York, NYC Manhattan-Brooklyn
  3. 01 JulLong Island New York, Sag Harbor, Port Jefferson
  4. 02 JulOld Saybrook CT, Connecticut
  5. 02 JulOld Saybrook CT, Connecticut
  6. 02 JulOld Saybrook CT, Connecticut
  7. 03 JulNew London CT, Connecticut, Mystic Seaport
  8. 04 JulNewport RI, Rhode Island
  9. 06 JulPlymouth MA, Massachusetts
  10. 07 JulArriving in Boston, Massachusetts
Find this cruise to book →
$6350from / pp
ACL American Eagle
American Cruise Lines Cruises
Boston → New York
⚓ Calls 12 Jul 20266 nights11 portsDeparts 2026 Jul 07
View itinerary · 11 ports
6 days, one-way from Boston to New York
  1. 07 JulDeparting from Boston, Massachusetts
  2. 07 JulBoston, Massachusetts
  3. 08 JulPlymouth MA, Massachusetts
  4. 08 JulCape Cod Canal, Massachusetts
  5. 09 JulNewport RI, Rhode Island
  6. 10 JulNew London CT, Connecticut, Mystic Seaport
  7. 11 JulLong Island New York, Sag Harbor, Port Jefferson
  8. 12 JulOld Saybrook CT, Connecticut
  9. 12 JulOld Saybrook CT, Connecticut
  10. 12 JulOld Saybrook CT, Connecticut
  11. 13 JulArriving in New York, NYC Manhattan-Brooklyn
Find this cruise to book →
$6350from / pp
ACL American Eagle
American Cruise Lines Cruises
New York → Boston
⚓ Calls 10 Sep 20267 nights10 portsDeparts 2026 Sep 08
View itinerary · 10 ports
7 days, one-way from New York to Boston
  1. 08 SepDeparting from New York, NYC Manhattan-Brooklyn
  2. 08 SepNew York, NYC Manhattan-Brooklyn
  3. 09 SepLong Island New York, Sag Harbor, Port Jefferson
  4. 10 SepOld Saybrook CT, Connecticut
  5. 10 SepOld Saybrook CT, Connecticut
  6. 10 SepOld Saybrook CT, Connecticut
  7. 11 SepNew London CT, Connecticut, Mystic Seaport
  8. 12 SepNewport RI, Rhode Island
  9. 14 SepPlymouth MA, Massachusetts
  10. 15 SepArriving in Boston, Massachusetts
Find this cruise to book →
$7190from / pp
ACL American Eagle
American Cruise Lines Cruises
Boston → New York
⚓ Calls 20 Sep 20266 nights11 portsDeparts 2026 Sep 15
View itinerary · 11 ports
6 days, one-way from Boston to New York
  1. 15 SepDeparting from Boston, Massachusetts
  2. 15 SepBoston, Massachusetts
  3. 16 SepPlymouth MA, Massachusetts
  4. 16 SepCape Cod Canal, Massachusetts
  5. 17 SepNewport RI, Rhode Island
  6. 18 SepNew London CT, Connecticut, Mystic Seaport
  7. 19 SepLong Island New York, Sag Harbor, Port Jefferson
  8. 20 SepOld Saybrook CT, Connecticut
  9. 20 SepOld Saybrook CT, Connecticut
  10. 20 SepOld Saybrook CT, Connecticut
  11. 21 SepArriving in New York, NYC Manhattan-Brooklyn
Find this cruise to book →
$7190from / pp
ACL American Legend
American Cruise Lines Cruises
Boston → New York
⚓ Calls 30 Sep 20266 nights11 portsDeparts 2026 Sep 25
View itinerary · 11 ports
6 days, one-way from Boston to New York
  1. 25 SepDeparting from Boston, Massachusetts
  2. 25 SepBoston, Massachusetts
  3. 26 SepPlymouth MA, Massachusetts
  4. 26 SepCape Cod Canal, Massachusetts
  5. 27 SepNewport RI, Rhode Island
  6. 28 SepNew London CT, Connecticut, Mystic Seaport
  7. 29 SepLong Island New York, Sag Harbor, Port Jefferson
  8. 30 SepOld Saybrook CT, Connecticut
  9. 30 SepOld Saybrook CT, Connecticut
  10. 30 SepOld Saybrook CT, Connecticut
  11. 01 OctArriving in New York, NYC Manhattan-Brooklyn
Find this cruise to book →
$8395from / pp
ACL American Glory
American Cruise Lines Cruises
Boston → New York
⚓ Calls 03 Oct 20266 nights11 portsDeparts 2026 Sep 28
View itinerary · 11 ports
6 days, one-way from Boston to New York
  1. 28 SepDeparting from Boston, Massachusetts
  2. 28 SepBoston, Massachusetts
  3. 29 SepPlymouth MA, Massachusetts
  4. 29 SepCape Cod Canal, Massachusetts
  5. 30 SepNewport RI, Rhode Island
  6. 01 OctNew London CT, Connecticut, Mystic Seaport
  7. 02 OctLong Island New York, Sag Harbor, Port Jefferson
  8. 03 OctOld Saybrook CT, Connecticut
  9. 03 OctOld Saybrook CT, Connecticut
  10. 03 OctOld Saybrook CT, Connecticut
  11. 04 OctArriving in New York, NYC Manhattan-Brooklyn
Find this cruise to book →
$7190from / pp
ACL American Maverick
American Cruise Lines Cruises
Boston → New York
⚓ Calls 14 Oct 20266 nights11 portsDeparts 2026 Oct 09
View itinerary · 11 ports
6 days, one-way from Boston to New York
  1. 09 OctDeparting from Boston, Massachusetts
  2. 09 OctBoston, Massachusetts
  3. 10 OctPlymouth MA, Massachusetts
  4. 10 OctCape Cod Canal, Massachusetts
  5. 11 OctNewport RI, Rhode Island
  6. 12 OctNew London CT, Connecticut, Mystic Seaport
  7. 13 OctLong Island New York, Sag Harbor, Port Jefferson
  8. 14 OctOld Saybrook CT, Connecticut
  9. 14 OctOld Saybrook CT, Connecticut
  10. 14 OctOld Saybrook CT, Connecticut
  11. 15 OctArriving in New York, NYC Manhattan-Brooklyn
Find this cruise to book →
$7835from / pp
ACL American Glory
American Cruise Lines Cruises
New York → Boston
⚓ Calls 24 May 20277 nights10 portsDeparts 2027 May 22
View itinerary · 10 ports
7 days, one-way from New York to Boston
  1. 22 MayDeparting from New York, NYC Manhattan-Brooklyn
  2. 22 MayNew York, NYC Manhattan-Brooklyn
  3. 23 MayLong Island New York, Sag Harbor, Port Jefferson
  4. 24 MayOld Saybrook CT, Connecticut
  5. 24 MayOld Saybrook CT, Connecticut
  6. 24 MayOld Saybrook CT, Connecticut
  7. 25 MayNew London CT, Connecticut, Mystic Seaport
  8. 26 MayNewport RI, Rhode Island
  9. 28 MayPlymouth MA, Massachusetts
  10. 29 MayArriving in Boston, Massachusetts
Find this cruise to book →
$6350from / pp
ACL American Legend
American Cruise Lines Cruises
New York → Boston
⚓ Calls 01 Jun 20277 nights10 portsDeparts 2027 May 30
View itinerary · 10 ports
7 days, one-way from New York to Boston
  1. 30 MayDeparting from New York, NYC Manhattan-Brooklyn
  2. 30 MayNew York, NYC Manhattan-Brooklyn
  3. 31 MayLong Island New York, Sag Harbor, Port Jefferson
  4. 01 JunOld Saybrook CT, Connecticut
  5. 01 JunOld Saybrook CT, Connecticut
  6. 01 JunOld Saybrook CT, Connecticut
  7. 02 JunNew London CT, Connecticut, Mystic Seaport
  8. 03 JunNewport RI, Rhode Island
  9. 05 JunPlymouth MA, Massachusetts
  10. 06 JunArriving in Boston, Massachusetts
Find this cruise to book →
$7415from / pp
ACL American Glory
American Cruise Lines Cruises
Boston → New York
⚓ Calls 03 Jun 20276 nights11 portsDeparts 2027 May 29
View itinerary · 11 ports
6 days, one-way from Boston to New York
  1. 29 MayDeparting from Boston, Massachusetts
  2. 29 MayBoston, Massachusetts
  3. 30 MayPlymouth MA, Massachusetts
  4. 30 MayCape Cod Canal, Massachusetts
  5. 31 MayNewport RI, Rhode Island
  6. 01 JunNew London CT, Connecticut, Mystic Seaport
  7. 02 JunLong Island New York, Sag Harbor, Port Jefferson
  8. 03 JunOld Saybrook CT, Connecticut
  9. 03 JunOld Saybrook CT, Connecticut
  10. 03 JunOld Saybrook CT, Connecticut
  11. 04 JunArriving in New York, NYC Manhattan-Brooklyn
Find this cruise to book →
$6350from / pp
ACL American Glory
American Cruise Lines Cruises
New York → Boston
⚓ Calls 07 Jun 20277 nights10 portsDeparts 2027 Jun 05
View itinerary · 10 ports
7 days, one-way from New York to Boston
  1. 05 JunDeparting from New York, NYC Manhattan-Brooklyn
  2. 05 JunNew York, NYC Manhattan-Brooklyn
  3. 06 JunLong Island New York, Sag Harbor, Port Jefferson
  4. 07 JunOld Saybrook CT, Connecticut
  5. 07 JunOld Saybrook CT, Connecticut
  6. 07 JunOld Saybrook CT, Connecticut
  7. 08 JunNew London CT, Connecticut, Mystic Seaport
  8. 09 JunNewport RI, Rhode Island
  9. 11 JunPlymouth MA, Massachusetts
  10. 12 JunArriving in Boston, Massachusetts
Find this cruise to book →
$6350from / pp
ACL American Legend
American Cruise Lines Cruises
Boston → New York
⚓ Calls 11 Jun 20276 nights11 portsDeparts 2027 Jun 06
View itinerary · 11 ports
6 days, one-way from Boston to New York
  1. 06 JunDeparting from Boston, Massachusetts
  2. 06 JunBoston, Massachusetts
  3. 07 JunPlymouth MA, Massachusetts
  4. 07 JunCape Cod Canal, Massachusetts
  5. 08 JunNewport RI, Rhode Island
  6. 09 JunNew London CT, Connecticut, Mystic Seaport
  7. 10 JunLong Island New York, Sag Harbor, Port Jefferson
  8. 11 JunOld Saybrook CT, Connecticut
  9. 11 JunOld Saybrook CT, Connecticut
  10. 11 JunOld Saybrook CT, Connecticut
  11. 12 JunArriving in New York, NYC Manhattan-Brooklyn
Find this cruise to book →
$7415from / pp
ACL American Legend
American Cruise Lines Cruises
New York → Boston
⚓ Calls 15 Jun 20277 nights10 portsDeparts 2027 Jun 13
View itinerary · 10 ports
7 days, one-way from New York to Boston
  1. 13 JunDeparting from New York, NYC Manhattan-Brooklyn
  2. 13 JunNew York, NYC Manhattan-Brooklyn
  3. 14 JunLong Island New York, Sag Harbor, Port Jefferson
  4. 15 JunOld Saybrook CT, Connecticut
  5. 15 JunOld Saybrook CT, Connecticut
  6. 15 JunOld Saybrook CT, Connecticut
  7. 16 JunNew London CT, Connecticut, Mystic Seaport
  8. 17 JunNewport RI, Rhode Island
  9. 19 JunPlymouth MA, Massachusetts
  10. 20 JunArriving in Boston, Massachusetts
Find this cruise to book →
$7415from / pp
ACL American Legend
American Cruise Lines Cruises
Boston → New York
⚓ Calls 23 Jul 20276 nights11 portsDeparts 2027 Jul 18
View itinerary · 11 ports
6 days, one-way from Boston to New York
  1. 18 JulDeparting from Boston, Massachusetts
  2. 18 JulBoston, Massachusetts
  3. 19 JulPlymouth MA, Massachusetts
  4. 19 JulCape Cod Canal, Massachusetts
  5. 20 JulNewport RI, Rhode Island
  6. 21 JulNew London CT, Connecticut, Mystic Seaport
  7. 22 JulLong Island New York, Sag Harbor, Port Jefferson
  8. 23 JulOld Saybrook CT, Connecticut
  9. 23 JulOld Saybrook CT, Connecticut
  10. 23 JulOld Saybrook CT, Connecticut
  11. 24 JulArriving in New York, NYC Manhattan-Brooklyn
Find this cruise to book →
$7415from / pp
ACL American Legend
American Cruise Lines Cruises
New York → Boston
⚓ Calls 27 Jul 20277 nights10 portsDeparts 2027 Jul 25
View itinerary · 10 ports
7 days, one-way from New York to Boston
  1. 25 JulDeparting from New York, NYC Manhattan-Brooklyn
  2. 25 JulNew York, NYC Manhattan-Brooklyn
  3. 26 JulLong Island New York, Sag Harbor, Port Jefferson
  4. 27 JulOld Saybrook CT, Connecticut
  5. 27 JulOld Saybrook CT, Connecticut
  6. 27 JulOld Saybrook CT, Connecticut
  7. 28 JulNew London CT, Connecticut, Mystic Seaport
  8. 29 JulNewport RI, Rhode Island
  9. 31 JulPlymouth MA, Massachusetts
  10. 01 AugArriving in Boston, Massachusetts
Find this cruise to book →
$7415from / pp
ACL American Maverick
American Cruise Lines Cruises
Boston → New York
⚓ Calls 31 Oct 20276 nights11 portsDeparts 2027 Oct 26
View itinerary · 11 ports
6 days, one-way from Boston to New York
  1. 26 OctDeparting from Boston, Massachusetts
  2. 26 OctBoston, Massachusetts
  3. 27 OctPlymouth MA, Massachusetts
  4. 27 OctCape Cod Canal, Massachusetts
  5. 28 OctNewport RI, Rhode Island
  6. 29 OctNew London CT, Connecticut, Mystic Seaport
  7. 30 OctLong Island New York, Sag Harbor, Port Jefferson
  8. 31 OctOld Saybrook CT, Connecticut
  9. 31 OctOld Saybrook CT, Connecticut
  10. 31 OctOld Saybrook CT, Connecticut
  11. 01 NovArriving in New York, NYC Manhattan-Brooklyn
Find this cruise to book →
$7835from / pp
ACL American Glory
American Cruise Lines Cruises
New York → Boston
⚓ Calls 17 May 20287 nights10 portsDeparts 2028 May 15
View itinerary · 10 ports
7 days, one-way from New York to Boston
  1. 15 MayDeparting from New York, NYC Manhattan-Brooklyn
  2. 15 MayNew York, NYC Manhattan-Brooklyn
  3. 16 MayLong Island New York, Sag Harbor, Port Jefferson
  4. 17 MayOld Saybrook CT, Connecticut
  5. 17 MayOld Saybrook CT, Connecticut
  6. 17 MayOld Saybrook CT, Connecticut
  7. 18 MayNew London CT, Connecticut, Mystic Seaport
  8. 19 MayNewport RI, Rhode Island
  9. 21 MayPlymouth MA, Massachusetts
  10. 22 MayArriving in Boston, Massachusetts
Find this cruise to book →
$6350from / pp
ACL American Glory
American Cruise Lines Cruises
Boston → New York
⚓ Calls 27 May 20286 nights11 portsDeparts 2028 May 22
View itinerary · 11 ports
6 days, one-way from Boston to New York
  1. 22 MayDeparting from Boston, Massachusetts
  2. 22 MayBoston, Massachusetts
  3. 23 MayPlymouth MA, Massachusetts
  4. 23 MayCape Cod Canal, Massachusetts
  5. 24 MayNewport RI, Rhode Island
  6. 25 MayNew London CT, Connecticut, Mystic Seaport
  7. 26 MayLong Island New York, Sag Harbor, Port Jefferson
  8. 27 MayOld Saybrook CT, Connecticut
  9. 27 MayOld Saybrook CT, Connecticut
  10. 27 MayOld Saybrook CT, Connecticut
  11. 28 MayArriving in New York, NYC Manhattan-Brooklyn
Find this cruise to book →
$6350from / pp
ACL American Glory
American Cruise Lines Cruises
New York → Boston
⚓ Calls 31 May 20287 nights10 portsDeparts 2028 May 29
View itinerary · 10 ports
7 days, one-way from New York to Boston
  1. 29 MayDeparting from New York, NYC Manhattan-Brooklyn
  2. 29 MayNew York, NYC Manhattan-Brooklyn
  3. 30 MayLong Island New York, Sag Harbor, Port Jefferson
  4. 31 MayOld Saybrook CT, Connecticut
  5. 31 MayOld Saybrook CT, Connecticut
  6. 31 MayOld Saybrook CT, Connecticut
  7. 01 JunNew London CT, Connecticut, Mystic Seaport
  8. 02 JunNewport RI, Rhode Island
  9. 04 JunPlymouth MA, Massachusetts
  10. 05 JunArriving in Boston, Massachusetts
Find this cruise to book →
$6350from / pp
ACL American Glory
American Cruise Lines Cruises
Boston → New York
⚓ Calls 10 Jun 20286 nights11 portsDeparts 2028 Jun 05
View itinerary · 11 ports
6 days, one-way from Boston to New York
  1. 05 JunDeparting from Boston, Massachusetts
  2. 05 JunBoston, Massachusetts
  3. 06 JunPlymouth MA, Massachusetts
  4. 06 JunCape Cod Canal, Massachusetts
  5. 07 JunNewport RI, Rhode Island
  6. 08 JunNew London CT, Connecticut, Mystic Seaport
  7. 09 JunLong Island New York, Sag Harbor, Port Jefferson
  8. 10 JunOld Saybrook CT, Connecticut
  9. 10 JunOld Saybrook CT, Connecticut
  10. 10 JunOld Saybrook CT, Connecticut
  11. 11 JunArriving in New York, NYC Manhattan-Brooklyn
Find this cruise to book →
$6350from / pp
ACL American Legend
American Cruise Lines Cruises
New York → Boston
⚓ Calls 12 Jun 20287 nights10 portsDeparts 2028 Jun 10
View itinerary · 10 ports
7 days, one-way from New York to Boston
  1. 10 JunDeparting from New York, NYC Manhattan-Brooklyn
  2. 10 JunNew York, NYC Manhattan-Brooklyn
  3. 11 JunLong Island New York, Sag Harbor, Port Jefferson
  4. 12 JunOld Saybrook CT, Connecticut
  5. 12 JunOld Saybrook CT, Connecticut
  6. 12 JunOld Saybrook CT, Connecticut
  7. 13 JunNew London CT, Connecticut, Mystic Seaport
  8. 14 JunNewport RI, Rhode Island
  9. 16 JunPlymouth MA, Massachusetts
  10. 17 JunArriving in Boston, Massachusetts
Find this cruise to book →
$7415from / pp
ACL American Legend
American Cruise Lines Cruises
Boston → New York
⚓ Calls 22 Jun 20286 nights11 portsDeparts 2028 Jun 17
View itinerary · 11 ports
6 days, one-way from Boston to New York
  1. 17 JunDeparting from Boston, Massachusetts
  2. 17 JunBoston, Massachusetts
  3. 18 JunPlymouth MA, Massachusetts
  4. 18 JunCape Cod Canal, Massachusetts
  5. 19 JunNewport RI, Rhode Island
  6. 20 JunNew London CT, Connecticut, Mystic Seaport
  7. 21 JunLong Island New York, Sag Harbor, Port Jefferson
  8. 22 JunOld Saybrook CT, Connecticut
  9. 22 JunOld Saybrook CT, Connecticut
  10. 22 JunOld Saybrook CT, Connecticut
  11. 23 JunArriving in New York, NYC Manhattan-Brooklyn
Find this cruise to book →
$7415from / pp
ACL American Legend
American Cruise Lines Cruises
New York → Boston
⚓ Calls 26 Jun 20287 nights10 portsDeparts 2028 Jun 24
View itinerary · 10 ports
7 days, one-way from New York to Boston
  1. 24 JunDeparting from New York, NYC Manhattan-Brooklyn
  2. 24 JunNew York, NYC Manhattan-Brooklyn
  3. 25 JunLong Island New York, Sag Harbor, Port Jefferson
  4. 26 JunOld Saybrook CT, Connecticut
  5. 26 JunOld Saybrook CT, Connecticut
  6. 26 JunOld Saybrook CT, Connecticut
  7. 27 JunNew London CT, Connecticut, Mystic Seaport
  8. 28 JunNewport RI, Rhode Island
  9. 30 JunPlymouth MA, Massachusetts
  10. 01 JulArriving in Boston, Massachusetts
Find this cruise to book →
$7415from / pp
ACL American Legend
American Cruise Lines Cruises
Boston → New York
⚓ Calls 27 Jul 20286 nights11 portsDeparts 2028 Jul 22
View itinerary · 11 ports
6 days, one-way from Boston to New York
  1. 22 JulDeparting from Boston, Massachusetts
  2. 22 JulBoston, Massachusetts
  3. 23 JulPlymouth MA, Massachusetts
  4. 23 JulCape Cod Canal, Massachusetts
  5. 24 JulNewport RI, Rhode Island
  6. 25 JulNew London CT, Connecticut, Mystic Seaport
  7. 26 JulLong Island New York, Sag Harbor, Port Jefferson
  8. 27 JulOld Saybrook CT, Connecticut
  9. 27 JulOld Saybrook CT, Connecticut
  10. 27 JulOld Saybrook CT, Connecticut
  11. 28 JulArriving in New York, NYC Manhattan-Brooklyn
Find this cruise to book →
$7415from / pp
ACL American Legend
American Cruise Lines Cruises
New York → Boston
⚓ Calls 31 Jul 20287 nights10 portsDeparts 2028 Jul 29
View itinerary · 10 ports
7 days, one-way from New York to Boston
  1. 29 JulDeparting from New York, NYC Manhattan-Brooklyn
  2. 29 JulNew York, NYC Manhattan-Brooklyn
  3. 30 JulLong Island New York, Sag Harbor, Port Jefferson
  4. 31 JulOld Saybrook CT, Connecticut
  5. 31 JulOld Saybrook CT, Connecticut
  6. 31 JulOld Saybrook CT, Connecticut
  7. 01 AugNew London CT, Connecticut, Mystic Seaport
  8. 02 AugNewport RI, Rhode Island
  9. 04 AugPlymouth MA, Massachusetts
  10. 05 AugArriving in Boston, Massachusetts
Find this cruise to book →
$7415from / pp

Itineraries and prices change — always confirm with the cruise line before booking. Some links are affiliate links that may earn us a commission at no extra cost to you.