<?xml version="1.0" encoding="utf-8"?>
<Return xmlns="http://www.irs.gov/efile" xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance" xsi:schemaLocation="http://www.irs.gov/efile" returnVersion="2022v5.0">
  <ReturnHeader binaryAttachmentCnt="0">
    <ReturnTs>2023-10-25T08:32:27-05:00</ReturnTs>
    <TaxPeriodEndDt>2022-12-31</TaxPeriodEndDt>
    <PreparerFirmGrp>
      <PreparerFirmEIN>042620388</PreparerFirmEIN>
      <PreparerFirmName>
        <BusinessNameLine1Txt>COLES &amp; BODOIN LLP</BusinessNameLine1Txt>
      </PreparerFirmName>
      <PreparerUSAddress>
        <AddressLine1Txt>75 SECOND AVENUE</AddressLine1Txt>
        <CityNm>NEEDHAM</CityNm>
        <StateAbbreviationCd>MA</StateAbbreviationCd>
        <ZIPCd>02494</ZIPCd>
      </PreparerUSAddress>
    </PreparerFirmGrp>
    <ReturnTypeCd>990EZ</ReturnTypeCd>
    <TaxPeriodBeginDt>2022-01-01</TaxPeriodBeginDt>
    <Filer>
      <EIN>043403232</EIN>
      <BusinessName>
        <BusinessNameLine1Txt>SAIL BOSTON INC</BusinessNameLine1Txt>
      </BusinessName>
      <BusinessNameControlTxt>SAIL</BusinessNameControlTxt>
      <PhoneNum>6174397700</PhoneNum>
      <USAddress>
        <AddressLine1Txt>88 BLACK FALCON AVENUE 202</AddressLine1Txt>
        <CityNm>BOSTON</CityNm>
        <StateAbbreviationCd>MA</StateAbbreviationCd>
        <ZIPCd>02210</ZIPCd>
      </USAddress>
    </Filer>
    <BusinessOfficerGrp>
      <PersonNm>MICHAEL E MOONEY</PersonNm>
      <PersonTitleTxt>PRESIDENT</PersonTitleTxt>
      <PhoneNum>6174392342</PhoneNum>
      <SignatureDt>2023-08-24</SignatureDt>
      <DiscussWithPaidPreparerInd>1</DiscussWithPaidPreparerInd>
    </BusinessOfficerGrp>
    <SigningOfficerGrp>
      <PersonFullName>
        <PersonFirstNm>MICHAEL</PersonFirstNm>
        <PersonLastNm>MOONEY</PersonLastNm>
      </PersonFullName>
      <SSN>999009999</SSN>
    </SigningOfficerGrp>
    <IRSResponsiblePrtyInfoCurrInd>0</IRSResponsiblePrtyInfoCurrInd>
    <PreparerPersonGrp>
      <PreparerPersonNm>GREGORY ARPINO CPA</PreparerPersonNm>
      <PTIN>P01287140</PTIN>
      <PhoneNum>7814551400</PhoneNum>
      <PreparationDt>2023-08-24</PreparationDt>
    </PreparerPersonGrp>
    <AdditionalFilerInformation>
      <TrustedCustomerGrp>
        <TrustedCustomerCd>2</TrustedCustomerCd>
        <AuthenticationAssuranceLevelCd>AAL1</AuthenticationAssuranceLevelCd>
        <IdentityAssuranceLevelCd>IAL1</IdentityAssuranceLevelCd>
      </TrustedCustomerGrp>
    </AdditionalFilerInformation>
    <TaxYr>2022</TaxYr>
    <BuildTS>2023-04-26 12:10:37Z</BuildTS>
  </ReturnHeader>
  <ReturnData documentCnt="4">
    <IRS990EZ documentId="RetDoc1234200001" referenceDocumentId="RetDoc1051800001 RetDoc2278000001">
      <MethodOfAccountingAccrualInd>X</MethodOfAccountingAccrualInd>
      <ScheduleBNotRequiredInd>X</ScheduleBNotRequiredInd>
      <WebsiteAddressTxt>WWW.SAILBOSTON.COM</WebsiteAddressTxt>
      <Organization501c3Ind referenceDocumentId="RetDoc1039100001">X</Organization501c3Ind>
      <TypeOfOrganizationCorpInd>X</TypeOfOrganizationCorpInd>
      <GrossReceiptsAmt>0</GrossReceiptsAmt>
      <InfoInScheduleOPartIInd>X</InfoInScheduleOPartIInd>
      <TotalRevenueAmt>0</TotalRevenueAmt>
      <FeesAndOtherPymtToIndCntrctAmt>1750</FeesAndOtherPymtToIndCntrctAmt>
      <OtherExpensesTotalAmt>1582</OtherExpensesTotalAmt>
      <TotalExpensesAmt>3332</TotalExpensesAmt>
      <ExcessOrDeficitForYearAmt>-3332</ExcessOrDeficitForYearAmt>
      <NetAssetsOrFundBalancesBOYAmt>-68699</NetAssetsOrFundBalancesBOYAmt>
      <OtherChangesInNetAssetsAmt>0</OtherChangesInNetAssetsAmt>
      <NetAssetsOrFundBalancesEOYAmt>-72031</NetAssetsOrFundBalancesEOYAmt>
      <InfoInScheduleOPartIIInd>X</InfoInScheduleOPartIIInd>
      <CashSavingsAndInvestmentsGrp>
        <BOYAmt>50312</BOYAmt>
        <EOYAmt>46980</EOYAmt>
      </CashSavingsAndInvestmentsGrp>
      <Form990TotalAssetsGrp>
        <BOYAmt>50312</BOYAmt>
        <EOYAmt>46980</EOYAmt>
      </Form990TotalAssetsGrp>
      <SumOfTotalLiabilitiesGrp>
        <BOYAmt>119011</BOYAmt>
        <EOYAmt>119011</EOYAmt>
      </SumOfTotalLiabilitiesGrp>
      <NetAssetsOrFundBalancesGrp>
        <BOYAmt>-68699</BOYAmt>
        <EOYAmt>-72031</EOYAmt>
      </NetAssetsOrFundBalancesGrp>
      <InfoInScheduleOPartIIIInd>X</InfoInScheduleOPartIIIInd>
      <PrimaryExemptPurposeTxt>TO ORGANIZE AND CONDUCT EVENTS IN CELEBRATION OF THE VISIT OF TALL SHIPS FROM AROUND THE WORLD TO BOSTON.</PrimaryExemptPurposeTxt>
      <ProgramSrvcAccomplishmentGrp>
        <DescriptionProgramSrvcAccomTxt>TO ORGANIZE AND CONDUCT EVENTS IN CELEBRATION OF THE VISIT OF TALL SHIPS FROM AROUND THE WORLD TO BOSTON.</DescriptionProgramSrvcAccomTxt>
        <GrantsAndAllocationsAmt>0</GrantsAndAllocationsAmt>
        <ProgramServiceExpensesAmt>0</ProgramServiceExpensesAmt>
      </ProgramSrvcAccomplishmentGrp>
      <TotalProgramServiceExpensesAmt>0</TotalProgramServiceExpensesAmt>
      <InfoInScheduleOPartIVInd>X</InfoInScheduleOPartIVInd>
      <OfficerDirectorTrusteeEmplGrp>
        <PersonNm>MICHAEL E MOONEY</PersonNm>
        <TitleTxt>PRESIDENT, TREASURER</TitleTxt>
        <AverageHrsPerWkDevotedToPosRt>0.00</AverageHrsPerWkDevotedToPosRt>
        <CompensationAmt>0</CompensationAmt>
        <EmployeeBenefitProgramAmt>0</EmployeeBenefitProgramAmt>
        <ExpenseAccountOtherAllwncAmt>0</ExpenseAccountOtherAllwncAmt>
      </OfficerDirectorTrusteeEmplGrp>
      <OfficerDirectorTrusteeEmplGrp>
        <PersonNm>CHERYL CRONIN</PersonNm>
        <TitleTxt>CLERK</TitleTxt>
        <AverageHrsPerWkDevotedToPosRt>0.00</AverageHrsPerWkDevotedToPosRt>
        <CompensationAmt>0</CompensationAmt>
        <EmployeeBenefitProgramAmt>0</EmployeeBenefitProgramAmt>
        <ExpenseAccountOtherAllwncAmt>0</ExpenseAccountOtherAllwncAmt>
      </OfficerDirectorTrusteeEmplGrp>
      <OfficerDirectorTrusteeEmplGrp>
        <PersonNm>PATRICK B MOSCARITOLO</PersonNm>
        <TitleTxt>DIRECTOR</TitleTxt>
        <AverageHrsPerWkDevotedToPosRt>0.00</AverageHrsPerWkDevotedToPosRt>
        <CompensationAmt>0</CompensationAmt>
        <EmployeeBenefitProgramAmt>0</EmployeeBenefitProgramAmt>
        <ExpenseAccountOtherAllwncAmt>0</ExpenseAccountOtherAllwncAmt>
      </OfficerDirectorTrusteeEmplGrp>
      <OfficerDirectorTrusteeEmplGrp>
        <PersonNm>ALISON NOLAN</PersonNm>
        <TitleTxt>DIRECTOR</TitleTxt>
        <AverageHrsPerWkDevotedToPosRt>0.00</AverageHrsPerWkDevotedToPosRt>
        <CompensationAmt>0</CompensationAmt>
        <EmployeeBenefitProgramAmt>0</EmployeeBenefitProgramAmt>
        <ExpenseAccountOtherAllwncAmt>0</ExpenseAccountOtherAllwncAmt>
      </OfficerDirectorTrusteeEmplGrp>
      <OfficerDirectorTrusteeEmplGrp>
        <PersonNm>THOMAS A KERSHAW</PersonNm>
        <TitleTxt>DIRECTOR</TitleTxt>
        <AverageHrsPerWkDevotedToPosRt>0.00</AverageHrsPerWkDevotedToPosRt>
        <CompensationAmt>0</CompensationAmt>
        <EmployeeBenefitProgramAmt>0</EmployeeBenefitProgramAmt>
        <ExpenseAccountOtherAllwncAmt>0</ExpenseAccountOtherAllwncAmt>
      </OfficerDirectorTrusteeEmplGrp>
      <OfficerDirectorTrusteeEmplGrp>
        <PersonNm>FREDERICK W CLARK JR</PersonNm>
        <TitleTxt>DIRECTOR</TitleTxt>
        <AverageHrsPerWkDevotedToPosRt>0.00</AverageHrsPerWkDevotedToPosRt>
        <CompensationAmt>0</CompensationAmt>
        <EmployeeBenefitProgramAmt>0</EmployeeBenefitProgramAmt>
        <ExpenseAccountOtherAllwncAmt>0</ExpenseAccountOtherAllwncAmt>
      </OfficerDirectorTrusteeEmplGrp>
      <OfficerDirectorTrusteeEmplGrp>
        <PersonNm>SCOTT M FERSON</PersonNm>
        <TitleTxt>DIRECTOR</TitleTxt>
        <AverageHrsPerWkDevotedToPosRt>0.00</AverageHrsPerWkDevotedToPosRt>
        <CompensationAmt>0</CompensationAmt>
        <EmployeeBenefitProgramAmt>0</EmployeeBenefitProgramAmt>
        <ExpenseAccountOtherAllwncAmt>0</ExpenseAccountOtherAllwncAmt>
      </OfficerDirectorTrusteeEmplGrp>
      <OfficerDirectorTrusteeEmplGrp>
        <PersonNm>STEPHEN JOHNSTON</PersonNm>
        <TitleTxt>DIRECTOR</TitleTxt>
        <AverageHrsPerWkDevotedToPosRt>0.00</AverageHrsPerWkDevotedToPosRt>
        <CompensationAmt>0</CompensationAmt>
        <EmployeeBenefitProgramAmt>0</EmployeeBenefitProgramAmt>
        <ExpenseAccountOtherAllwncAmt>0</ExpenseAccountOtherAllwncAmt>
      </OfficerDirectorTrusteeEmplGrp>
      <OfficerDirectorTrusteeEmplGrp>
        <PersonNm>PAUL SACCO</PersonNm>
        <TitleTxt>DIRECTOR</TitleTxt>
        <AverageHrsPerWkDevotedToPosRt>0.00</AverageHrsPerWkDevotedToPosRt>
        <CompensationAmt>0</CompensationAmt>
        <EmployeeBenefitProgramAmt>0</EmployeeBenefitProgramAmt>
        <ExpenseAccountOtherAllwncAmt>0</ExpenseAccountOtherAllwncAmt>
      </OfficerDirectorTrusteeEmplGrp>
      <OfficerDirectorTrusteeEmplGrp>
        <PersonNm>DAVID COLELLA</PersonNm>
        <TitleTxt>DIRECTOR</TitleTxt>
        <AverageHrsPerWkDevotedToPosRt>0.00</AverageHrsPerWkDevotedToPosRt>
        <CompensationAmt>0</CompensationAmt>
        <EmployeeBenefitProgramAmt>0</EmployeeBenefitProgramAmt>
        <ExpenseAccountOtherAllwncAmt>0</ExpenseAccountOtherAllwncAmt>
      </OfficerDirectorTrusteeEmplGrp>
      <OfficerDirectorTrusteeEmplGrp>
        <PersonNm>DENISE KAIGLER</PersonNm>
        <TitleTxt>DIRECTOR</TitleTxt>
        <AverageHrsPerWkDevotedToPosRt>0.00</AverageHrsPerWkDevotedToPosRt>
        <CompensationAmt>0</CompensationAmt>
        <EmployeeBenefitProgramAmt>0</EmployeeBenefitProgramAmt>
        <ExpenseAccountOtherAllwncAmt>0</ExpenseAccountOtherAllwncAmt>
      </OfficerDirectorTrusteeEmplGrp>
      <OfficerDirectorTrusteeEmplGrp>
        <PersonNm>MARIANNA ACCOMANDO</PersonNm>
        <TitleTxt>DIRECTOR</TitleTxt>
        <AverageHrsPerWkDevotedToPosRt>0.00</AverageHrsPerWkDevotedToPosRt>
        <CompensationAmt>0</CompensationAmt>
        <EmployeeBenefitProgramAmt>0</EmployeeBenefitProgramAmt>
        <ExpenseAccountOtherAllwncAmt>0</ExpenseAccountOtherAllwncAmt>
      </OfficerDirectorTrusteeEmplGrp>
      <InfoInScheduleOPartVInd>X</InfoInScheduleOPartVInd>
      <ActivitiesNotPreviouslyRptInd>0</ActivitiesNotPreviouslyRptInd>
      <ChgMadeToOrgnzngDocNotRptInd>0</ChgMadeToOrgnzngDocNotRptInd>
      <OrganizationHadUBIInd>0</OrganizationHadUBIInd>
      <SubjectToProxyTaxInd>0</SubjectToProxyTaxInd>
      <OrganizationDissolvedEtcInd>0</OrganizationDissolvedEtcInd>
      <DirectIndirectPltclExpendAmt>0</DirectIndirectPltclExpendAmt>
      <MadeLoansToFromOfficersInd>0</MadeLoansToFromOfficersInd>
      <TaxImposedUnderIRC4911Amt>0</TaxImposedUnderIRC4911Amt>
      <TaxImposedUnderIRC4912Amt>0</TaxImposedUnderIRC4912Amt>
      <TaxImposedUnderIRC4955Amt>0</TaxImposedUnderIRC4955Amt>
      <EngagedInExcessBenefitTransInd>0</EngagedInExcessBenefitTransInd>
      <TaxImposedOnOrganizationMgrAmt>0</TaxImposedOnOrganizationMgrAmt>
      <TaxReimbursedByOrganizationAmt>0</TaxReimbursedByOrganizationAmt>
      <ProhibitedTaxShelterTransInd>0</ProhibitedTaxShelterTransInd>
      <StatesWhereCopyOfReturnIsFldCd>MA</StatesWhereCopyOfReturnIsFldCd>
      <BooksInCareOfDetail>
        <BusinessName>
          <BusinessNameLine1Txt>SAIL BOSTON INC</BusinessNameLine1Txt>
        </BusinessName>
        <USAddress>
          <AddressLine1Txt>88 BLACK FALCON AVENUE NO 202</AddressLine1Txt>
          <CityNm>BOSTON</CityNm>
          <StateAbbreviationCd>MA</StateAbbreviationCd>
          <ZIPCd>02210</ZIPCd>
        </USAddress>
        <PhoneNum>6174397700</PhoneNum>
      </BooksInCareOfDetail>
      <ForeignFinancialAccountInd>0</ForeignFinancialAccountInd>
      <ForeignOfficeInd>0</ForeignOfficeInd>
      <DonorAdvisedFndsInd>0</DonorAdvisedFndsInd>
      <OperateHospitalInd>0</OperateHospitalInd>
      <TanningServicesProvidedInd>0</TanningServicesProvidedInd>
      <RelatedOrganizationCtrlEntInd>0</RelatedOrganizationCtrlEntInd>
      <TransactionWithControlEntInd>0</TransactionWithControlEntInd>
      <PoliticalCampaignActyInd>0</PoliticalCampaignActyInd>
      <LobbyingActivitiesInd>0</LobbyingActivitiesInd>
      <SchoolOperatingInd>0</SchoolOperatingInd>
      <TrnsfrExmptNonChrtblRltdOrgInd>0</TrnsfrExmptNonChrtblRltdOrgInd>
      <PartVIOfCompOfHghstPdEmplTxt>NONE</PartVIOfCompOfHghstPdEmplTxt>
      <PartVIHghstPdCntrctProfSrvcTxt>NONE</PartVIHghstPdCntrctProfSrvcTxt>
      <FiledScheduleAInd>1</FiledScheduleAInd>
    </IRS990EZ>
    <IRS990ScheduleA documentId="RetDoc1039100001">
      <PubliclySupportedOrg509a2Ind>X</PubliclySupportedOrg509a2Ind>
      <GiftsGrantsContrisRcvd509Grp>
        <CurrentTaxYearMinus2YearsAmt>25</CurrentTaxYearMinus2YearsAmt>
        <TotalAmt>25</TotalAmt>
      </GiftsGrantsContrisRcvd509Grp>
      <GrossReceiptsNonUnrltBusGrp>
        <CurrentTaxYearMinus4YearsAmt>6250</CurrentTaxYearMinus4YearsAmt>
        <CurrentTaxYearMinus3YearsAmt>28532</CurrentTaxYearMinus3YearsAmt>
        <TotalAmt>34782</TotalAmt>
      </GrossReceiptsNonUnrltBusGrp>
      <Total509Grp>
        <CurrentTaxYearMinus4YearsAmt>6250</CurrentTaxYearMinus4YearsAmt>
        <CurrentTaxYearMinus3YearsAmt>28532</CurrentTaxYearMinus3YearsAmt>
        <CurrentTaxYearMinus2YearsAmt>25</CurrentTaxYearMinus2YearsAmt>
        <TotalAmt>34807</TotalAmt>
      </Total509Grp>
      <AmountsRcvdDsqlfyPersonGrp>
        <TotalAmt>0</TotalAmt>
      </AmountsRcvdDsqlfyPersonGrp>
      <SubstantialContributorsAmtGrp>
        <CurrentTaxYearMinus4YearsAmt>1250</CurrentTaxYearMinus4YearsAmt>
        <TotalAmt>1250</TotalAmt>
      </SubstantialContributorsAmtGrp>
      <SubstAndDsqlfyPrsnsTotGrp>
        <CurrentTaxYearMinus4YearsAmt>1250</CurrentTaxYearMinus4YearsAmt>
        <TotalAmt>1250</TotalAmt>
      </SubstAndDsqlfyPrsnsTotGrp>
      <PublicSupportTotal509Amt>33557</PublicSupportTotal509Amt>
      <GrossInvestmentIncome509Grp>
        <CurrentTaxYearMinus3YearsAmt>81</CurrentTaxYearMinus3YearsAmt>
        <TotalAmt>81</TotalAmt>
      </GrossInvestmentIncome509Grp>
      <InvestmentIncomeAndUBTIGrp>
        <CurrentTaxYearMinus3YearsAmt>81</CurrentTaxYearMinus3YearsAmt>
        <TotalAmt>81</TotalAmt>
      </InvestmentIncomeAndUBTIGrp>
      <TotalSupportCalendarYearGrp>
        <CurrentTaxYearMinus4YearsAmt>6250</CurrentTaxYearMinus4YearsAmt>
        <CurrentTaxYearMinus3YearsAmt>28613</CurrentTaxYearMinus3YearsAmt>
        <CurrentTaxYearMinus2YearsAmt>25</CurrentTaxYearMinus2YearsAmt>
        <TotalAmt>34888</TotalAmt>
      </TotalSupportCalendarYearGrp>
      <PublicSupportCY509Pct>0.96180</PublicSupportCY509Pct>
      <PublicSupportPY509Pct>0.58330</PublicSupportPY509Pct>
      <InvestmentIncomeCYPct>0.00230</InvestmentIncomeCYPct>
      <ThirtyThrPctSuprtTestsCY509Ind>X</ThirtyThrPctSuprtTestsCY509Ind>
    </IRS990ScheduleA>
    <IRS990ScheduleO documentId="RetDoc1051800001">
      <SupplementalInformationDetail>
        <FormAndLineReferenceDesc>FORM 990-EZ, PART I, LINE 16 - OTHER EXPENSES</FormAndLineReferenceDesc>
        <ExplanationTxt>DESCRIPTION: INSURANCE. AMOUNT: 1,547. DESCRIPTION: MA FILING FEES. AMOUNT: 35. TOTAL TO FORM 990-EZ, LINE 16: 1,582.</ExplanationTxt>
      </SupplementalInformationDetail>
      <SupplementalInformationDetail>
        <FormAndLineReferenceDesc>FORM 990-EZ, PART II, LINE 26 - OTHER LIABILITIES</FormAndLineReferenceDesc>
        <ExplanationTxt>DESCRIPTION: ACCOUNTS PAYABLE AND ACCRUED EXPENSES. BEG. OF YEAR AMOUNT: 119,011. END OF YEAR AMOUNT: 119,011.</ExplanationTxt>
      </SupplementalInformationDetail>
    </IRS990ScheduleO>
    <TransferPrsnlBnftContractsDecl documentId="RetDoc2278000001">
      <DeclarationDesc>THE ORGANIZATION DID NOT, DURING THE YEAR, RECEIVE ANY FUNDS, DIRECTLY,OR INDIRECTLY, TO PAY PREMIUMS ON A PERSONAL BENEFIT CONTRACT.THE ORGANIZATION, DID NOT, DURING THE YEAR, PAY ANY PREMIUMS, DIRECTLY,OR INDIRECTLY, ON A PERSONAL BENEFIT CONTRACT.</DeclarationDesc>
    </TransferPrsnlBnftContractsDecl>
  </ReturnData>
</Return>
